The Genus Psychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

Calixto, Nivea O.; Pinto, Meri Emili F.; Ramalho, Suelem D.; Burger, Marcela C. M.; Bobey, Antonio F.; Young, Maria Claudia Marx; Bolzani, Vanderlan S.; Pinto, Angelo C.

doi:10.5935/0103-5053.20160149

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Reviews • J. Braz. Chem. Soc. 27 (8) • Aug 2016 • https://doi.org/10.5935/0103-5053.20160149 copy

The Genus Psychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Psychotria genus (Rubiaceae) is featured into the angiosperm, being the most speciose genus comprising approximately 1600 species. The available references demonstrate that Psychotria has several uses on traditional medicine including spiritual and cultural purposes, and presents great potential on pharmacological properties, especially the one related to neurodegenerative diseases. Despite its wide biological properties, this genus has shown complex phylogenetic analysis due to lack of chemotaxonomic information. In recent years, the interest in these plants has increased considerably and many active compounds have been isolated. Phytochemical investigations described in the literature confirmed the indole alkaloids as the major compounds and besides that, another particular chemical constituent are cyclic peptides, known as cyclotides. This present review will cover the relevant literature from 1962 until 2015, and outlines the current data on taxonomy, chemotaxonomy, traditional uses, pharmacological properties, chemical composition and ecological approach from Psychotria genus.

Keywords:
Psychotria; alkaloids; chemotaxonomy; ethnopharmacology; phytochemistry

1. Introduction

It is believed that about 80% of the population worldwide, especially Asian and African countries use plants and herbal medicines as a source of medicinal agents and primary health care. Traditional medicine is an important form of health care for many people and covers a wide variety of therapies and practices, which vary from country to country.¹1 http://www.who.int/medicines/areas/traditional/en, accessed in May 2016.
http://www.who.int/medicines/areas/tradi... Many useful drugs were inspired from plants sources and nature continues to be a major source of new structural leads, and effective drug development.²2 Cragg, G. M.; Newman, D. J.; Biochim. Biophys. Acta 2013, 1830, 3670. Thus, based on this estimates it is of great importance the proper identification and classification of plant species.

The genus Psychotria belongs to the Rubiaceae family (subfamily Rubioideae, tribe Psychotrieae) and is the most speciose angiosperm genera (flowering plants) comprising approximately 1600 species. These species are mostly shrubs, although are known, vines, herbaceous and epiphytes, widely distributed in tropical and pantropical countries.³3 Hamilton, C. W.; Ann. Mo. Bot. Gard. 1989, 76, 67.^,⁴4 Taylor, C. M.; Opera Bot. Belg. 1996, 7, 261. In South America countries the leaves of P. viridis is largely used by Amazon indigenous peoples as a component of the hallucinogenic drink "ayahuasca". This tea has been used for medicinal, spiritual and cultural purposes since pre-Columbian times.⁵5 McKenna, D. J.; Towers, G. H. N.; Abbot, F. J.; J. Ethnopharmacol. 1984, 10, 195.

6 Elisabetsky, E.; Castilhos, Z. C.; Int. J. Crude Drug Res. 1990, 28, 49.

7 Carlini, E. A.; Pharmacol., Biochem. Behav. 2003, 75, 501.^-⁸8 Tupper, K. W.; Int. J. Drug Policy 2008, 19, 297. Some other plants from the genus Psychotria (leaves, roots and rhizomes) have been widely used in traditional medicines for treating bronchial and gastrointestinal disorders such as cough, bronchitis, ulcer and stomachache. Also, they are commonly used for infections of the female reproductive system.⁹9 Perry, L. M.; Medicinal Plants of East and Southeast Asia: Attributed Properties; The MIT Press: Cambridge, USA, 1980.

Besides the variety of ethnopharmacology uses the taxonomy of Psychotria genus is very complex and a comprehensive phylogenetic analysis of this genus lack diagnostic characters. Until now, schizocarps and bacterial leaf nodules have been used for recognizing formal groups in Psychotrieae, but a robust phylogeny of the tribe, including their evolution and taxonomic value have not been described.¹⁰10 Razafimandimbison, S. G.; Taylor, C. M.; Wikström, N.; Pailler, T.; Khodabandeh, A.; Bremer, B.; Am. J. Bot. 2014, 101, 1102.

An increasing number of phytochemical studies have been investigated in Psychotria plants in the last decade contributing significantly to the ethnobotanical, pharmacological and chemotaxonomic studies in addition to the molecular phylogenetic analysis.¹¹11 Nepokroeff, M.; Bremer, B.; Sytsma, K.; Syst. Bot. 1999, 24, 5. The genus Psychotria can be characterized as an abundant source of indole, monoterpene indole, quinoline and isoquinoline alkaloids as well as flavonoids, coumarins, terpenoids and cyclic peptides that might be responsible for a wide range of biological activities (cytotoxicity, analgesics, antivirals, antifungals and modulators of the activity of the central nervous system) found on those species.¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.^,¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.

The purpose of this review is to provide an update of the recent ethnopharmacology, taxonomy, chemotaxonomy, chemical approach, pharmacological and ecological properties of the extracts and isolated compounds identified in some plants belonging to the genus Psychotria.

2. Method

In the present review, information on Psychotria genus was gathered via searching scientific databases including PubMed, Elsevier, Google Scholar, Scopus, Web of Science, Cybase and SciFinder by using the keyword Psychotria.

In order to retrieve the available literature pertaining to this genus and concisely illustrate it using an informative graph, a SciFinder search was performed in September 2015. Figure 1 shows the number of articles retrieved when using the keyword Psychotria for year, which demonstrate the relevance of this genus. It is remarkable the large increase in publications in recent years; whereas in 1995 had been described about 10 scientific papers, in 2014 more than 50 scientific papers have been published on Psychotria genus and this number continues to increase in 2015.

Figure 1
Results of SciFinder search for Psychotria genus publications up to 2015.

3. Taxonomy and Chemotaxonomic Approach of Genus Psychotria

The tribes Palicoureeae and Psychotrieae include about 91% of the species of the Psychotrieae alliance and about 24% of Rubiaceae as a whole. Members of these groups of plants are very important components of various terrestrial ecosystems throughout the tropics. The tribe Psychotrieae is well established, but the same does not occur for their genera. The Amaracarpus Blume, Calycosia A. Gray, Dolianthus C. H. Wright, Hedstromia A. C. Sm., and Hydnophytum Jack genera, for example, were nested within Psychotria L. rendering the latter genus paraphyletic.¹⁰10 Razafimandimbison, S. G.; Taylor, C. M.; Wikström, N.; Pailler, T.; Khodabandeh, A.; Bremer, B.; Am. J. Bot. 2014, 101, 1102.

Before 2014, the relationships between among most members of tribes Psychotrieae and Palicoureae were still unknown partly, due to the poor or lack of sampling from some biodiversity hotspots. Schizocarpous fruits and bacterial nodules were used for recognizing authentic groups, but the evolution and taxonomic value of these characters have not been addressed based on a broadened sampling of the tribe.

In 2014, a robust phylogenetic study was done for establishing new generic circumscriptions between these tribes. Razafimandimbison et al.¹⁰10 Razafimandimbison, S. G.; Taylor, C. M.; Wikström, N.; Pailler, T.; Khodabandeh, A.; Bremer, B.; Am. J. Bot. 2014, 101, 1102. established that Psychotria includes all its allied genera, rendering the tribe Psychotrieae monogeneric. It was confirmed the paraphyly of Psychotria, because the genera Amaracarpus, Calycosia, Camptopus, represented by its type C. mannii (= P. camptopus), Dolianthus, Hydnophytum, Grumilea Gaertn., represented by the type G. nigra (= Psychotria nigra), Mapouria, and all the WIOR genera (Apomuria, Cremocarpon, Psathura, Pyragra, and Trigonopyren) are nested within a broadly defined Psychotria.¹⁰10 Razafimandimbison, S. G.; Taylor, C. M.; Wikström, N.; Pailler, T.; Khodabandeh, A.; Bremer, B.; Am. J. Bot. 2014, 101, 1102.

A great variety of species of plants belonging to the genus Psychotria have been phytochemically investigated and several compounds have been isolated and identified. Thus, the phytochemical approach, which involves a range of compounds, became a very useful tool to understand and establish the chemotaxonomy of Psychotria. In this context, different classes of organic compounds have been reported.¹¹11 Nepokroeff, M.; Bremer, B.; Sytsma, K.; Syst. Bot. 1999, 24, 5.

Analysis of the chemical profile of some species like P. borucana contributed to the taxonomic rearrangement, which was grouped together with P. ipecac in Carapichea genus.¹⁴14 Bernhard, M.; Fasshuber, H.; Robien, W.; Brecker, L.; Greger, H.; Biochem. System. Ecol. 2011, 39, 232. The comparative study of 57 methanol extracts of Psychotria clearly showed a distinct chemical separation of P. borucana due to the bigger accumulation of alkaloids type dopamine-iridoid rather than alkaloids type tryptamine-iridoid, which is commonly found in other species. In this context stands out the borucoside alkaloid (1), which was first described in this species.¹⁴14 Bernhard, M.; Fasshuber, H.; Robien, W.; Brecker, L.; Greger, H.; Biochem. System. Ecol. 2011, 39, 232.

As an example, the species Psychotria acuminata was renamed to Palicourea acuminata (Benth.) and from methanol extract of its leaves and stem bark, were isolated several alkaloids type tryptamine-iridoids. Among those structures, lagamboside (2) is a novelty because represents an unusual pattern of N-glycosylation and a iridoid closely related to the unusual alkaloid vallesiachotamine (3).¹⁵15 Borhidi, A.; Acta Bot. Hung. 2011, 53, 241. Also, the co-occurrence of another rare alkaloid, the bahienoside B (4), comprising two iridoids structures, is of great interest and contributes to the chemotaxonomy of this species (Figure 2).¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.

Figure 2
The structures from Psychotria genus.

Besides the alkaloids, some other secondary metabolites also can be used as taxonomic markers. Vomifoliol (5), for example, is a megastigmane sesquiterpene that has been reported on Psychotria gitingensis from the Philippines. This compound has an α,β-unsaturated ketone that might be responsible for the observed orange spots in Dragendorff's test.¹⁷17 Tan, M. A.; Eusebio, J. A.; Alejandro, G. J. D.; Biochem. Syst. Ecol. 2012, 45, 20. It is well established that certain compounds can give false-positive alkaloid reactions with Dragendorff's spray reagent.¹⁸18 Habib, A. A.; J. Pharm. Sci. 1980, 69, 37.

Although P. gitingensis from Philipines did not present alkaloids, is highly recommended to verify the absence of alkaloids in species collected in other regions.

4. Traditional Uses of Psychotria Species

Plants from the genus Psychotria (leaves, roots, barks and rhizomes) are commonly used in traditional medicines for treating bronchial and gastrointestinal disorders such as cough, bronchitis, ulcer and stomachache. Also they are used for infections of the female reproductive system.⁹9 Perry, L. M.; Medicinal Plants of East and Southeast Asia: Attributed Properties; The MIT Press: Cambridge, USA, 1980.^,¹⁹19 Lajis, N. H.; Mahmud, Z.; Toia, R. F.; Planta Med. 1993, 59, 383.^,²⁰20 Formagio, A. S. N.; Volobuff, C. R. F.; Santiago, M.; Cardoso, C. A. L.; Vieira, M. C.; Pereira, Z. V.; Antioxidants 2014, 3, 745.P. poeppigiana is a native plant widely used in Latin America for the treatment of a variety of diseases, particularly gastrointestinal disorders, stomachaches and fever.²¹21 Gupta, M. P.; Solís, P. N.; Calderón, A. L.; Guionneau-Sinclair, F.; Correa, M.; Galdames, C.; Guerra, C.; Espinosa, A.; Alvenda, G. I.; Robles, G.; Ocampo, R.; J. Ethnopharmacol. 2005, 96, 389. In Panama, this plant is also used in traditional medicine for the treatment of dyspnea.²²22 Joly, L. G.; Guerra, S.; Séptimo, R.; Solís, P. N.; Correa, M.; Gupta, M.; Levy, S.; Sandberg, F.; J. Ethnopharmacol. 1987, 20, 145.P. colorata is a plant commonly found in Amazon region of Brazil, which is used as painkiller for earache and abdominal pain by traditional rural communities.²³23 Moura, L. T. S.; Maruo, V. M.; Rev. Cient. Eletr. Med. Vet. 2014, 23, 1. Available at http://faef.revista.inf.br/imagens_arquivos/arquivos_destaque/RlVaBqh06nvKOOw_2014-8-11-8-36-16.pdf, accessed in May 2016.
http://faef.revista.inf.br/imagens_arqui...

In Tamil Nadu (India) several tribes use the leaves, flowers and fruits from P. nudiflora Wt. & Arn. and P. nilgiriensis Deb. & Gan for rheumatism treatment.²⁴24 Sutha, S.; Mohan, V. R.; Kumaresan, S.; Murugan, C.; Athiperumalsami, T.; Indian J. Tradit. Know. 2010, 9, 502. Other applications are anti-emetic and against snakebites in Central and South America countries.²⁵25 Watt, J. M.; Breyer-Brandwijk, M. G.; The Medicinal and Poisonous Plants of Southern and Eastern Africa, 2nd ed.; E. & S. Livingstone: London, United Kingdom, 1962.^,²⁶26 Otero, R.; Núñez, V.; Barona, J.; Fonnegra, R.; Jiménez, S. L.; Osorio, R. G.; Saldarriaga, M.; Díaz, A.; J. Ethnopharmacol. 2000, 73, 233. In S. Tomé and Príncipe (Africa), P. subobliqua is used to treat toothaches and mouth inflammation.²⁷27 Madureira, M. C.; Paiva, J. A.; Fernandes, A. F.; Gonçalves, A.; Catalão, C.; Fernandes, C.; Atalaia, J.; Vieira, J.; Gaspar, V.; Pontes, S.; Gino, S.; Costa, S.; Estudo Etnofarmacológico de Plantas Medicinais de S. Tomé e Príncipe; Ed. Ministério da Saúde STP/Fundação Calouste Gulbenkian: Lisboa, Portugal, 2008.^,²⁸28 Currais, A.; Chiruta, C.; Goujon-Svrzic, M.; Costa, G.; Santos, T.; Batista, M. T.; Paiva, J.; Madureira, M. C.; Maher, P.; J. Ethnopharmacol. 2014, 155, 830.

P. ipecacuanha (Brot.) Stokes is another species important on traditional medicine. It has an important history as emetic, expectorant, amebicide and also in the treatment of dysenteries.²⁹29 Saint-Hilaire, A.; Plantas Usuais dos Brasileiro; Código Comunicação: Belo Horizonte, Brasil, 2009. Besides the properties already described, some Psychotria species are also used against microbial infections (malaria, amoebiasis, viral and venereal diseases), cardiovascular and mental disorders.³⁰30 Khan, M. R.; Kihara, M.; Omoloso, A. D.; Fitoterapia 2001, 72, 818.^,³¹31 Agripino, D. G.; Lima, M. E. L.; Silva, M. R.; Meda, C. I.; Bolzani, V. S.; Cordeiro, I.; Young, M. C. M.; Moreno, P. R. H.; Biota Neotrop. 2004, 4, 1.

In South America countries (Brazil, Peru and Ecuador) some species from the genus Psychotria are largely used by Amazon indigenous people as a component of the hallucinogenic drink "ayahuasca" which means "soul wine", used in religious ceremonies.⁵5 McKenna, D. J.; Towers, G. H. N.; Abbot, F. J.; J. Ethnopharmacol. 1984, 10, 195.

6 Elisabetsky, E.; Castilhos, Z. C.; Int. J. Crude Drug Res. 1990, 28, 49.

7 Carlini, E. A.; Pharmacol., Biochem. Behav. 2003, 75, 501.^-⁸8 Tupper, K. W.; Int. J. Drug Policy 2008, 19, 297. "Ayahuasca's" psychoactive effects are similar to LSD (lysergic acid diethylamide) and psilocybin.⁸8 Tupper, K. W.; Int. J. Drug Policy 2008, 19, 297. The" ayahuasca" tea usually incorporates the leaves of P. viridis and bark of Banisteriopsis caapi, which are rich in N,N-dimethyltryptamine (a non-selective serotonin agonist, 5-HT) and β-carboline alkaloids, respectively.³²32 Freedland, C. S.; Mansbach, R. S.; Drug Alcohol Depend. 1999, 54, 183.

33 Gambelunghe, C.; Aroni, K.; Rossi, R.; Moretti, L.; Bacci, M.; Biomed. Chromatogr. 2008, 22, 1056.^-³⁴34 Pic-Taylor, A. P.; Motta, L. G.; Morais, J. A.; Melo Jr., W.; Santos, A. F. A.; Campos, L. A.; Mortari, M. R.; von Zuben, M. V.; Caldas, E. D.; Behav. Processes 2015, 118, 102. A qualitative empirical study made by Anja and Rolf³⁵35 Anja, L-V.; Rolf, V.; J. Psychoact. Drugs 2014, 46, 63. explored the ritual use of "ayahuasca" in the treatment of addictions. The recently findings indicate that "ayahuasca" can serve as a therapeutic tool which catalyze neurological and psychological processes that support recovery from substance dependencies.

Some Psychotria species distributed in China are used in folk medicines for swelling and relieving muscles, activating collaterals and strengthening bones and muscles.³⁶36 Lu, Q.; Wang, J.; Luo, J.; Wang, X.; Shan, S.; Kong, L.; Nat. Prod. Res. 2014, 28, 1659.P. henryi is one of these species that has been used in traditional Chinese medicine for invigorating spleen to eliminate dampness and for regulating qi-flowing to relieve pain.³⁷37 Liu, Y.; Wang, J.-S.; Wang, X.-B.; Kong, L.-Y.; Fitoterapia 2013, 86, 178.

5. Chemical Constituents of Genus Psychotria

In recent years, the interest in plants from Psychotria genus has increased considerably, since it is an abundant source of several interesting natural products as alkaloids (major compounds), coumarins, flavonoids, terpenoids, tannins and cyclic peptides (Tables 1 and 2).

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Table 1
Compounds identified from Psychotria species^a aPsychotria species are organized in alphabetical order;

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Table 2
Cyclic peptides identified from Psychotria species

5.1. Alkaloids

Several classes of alkaloids found on Psychotria genus is already described in the literature and some others are still under investigation (Figure 3).

Figure 3
The structures of alkaloids from Psychotria species.

A phytochemical study of P. umbellata Thonn. resulted in the isolation of psychollatine (umbellatine) (6) and other three psychollatine-derived monoterpene indole alkaloids: 3,4-dehydro-18,19-β-epoxy-psychollatine (7), N4-[1-((R)-2-hydroxypropyl)]-psychollatine (8), and N4-[1-((S)-2-hydroxypropyl)]-psychollatine (9).⁸⁶86 Kerber, V. A.; Passos, C. S.; Verli, H.; Fett-Neto, A. G.; Quirion, J. P.; Henriques, A. T.; J. Nat. Prod. 2008, 71, 697.^,⁸⁸88 Kerber, V. A.; Passos, C. S.; Klein-Junior, L. C.; Quirion, J.-C.; Pannecoucke, X.; Salliot-Maire, I.; Henriques, A. T.; Tetrahedron Lett. 2014, 55, 4798. Two β-carboline alkaloids (harmane (10) and strictosidinic acid (11)) were isolated from the leaves and stems of P. barbiflora DC.⁹⁵95 Valadão, A. L. C.; Abreu, C. M.; Dias, J. Z.; Arantes, P.; Verli, H.; Tanuri, A.; Aguiar, R. S.; Molecules 2015, 20, 11474. Ipecac alkaloids are secondary metabolites produced in the medicinal plant P. ipecacuanha and emetine (12) is the main alkaloid found in syrup of Ipecac.⁹⁶96 Porto, D. D.; Matsuura, H. N.; Vargas, L. R. B.; Henriques, A. T.; Fett-Neto, A. G.; Nat. Prod. Commun. 2014, 9, 629. From the leaves and twigs of P. henryi, a new dimeric indole alkaloid, named psychohenin (13), was isolated.⁹⁷97 Matsuura, H. N.; Fett-Neto, A. G.; Nat. Prod. Res. 2013, 27, 402. Studies describe the presence of a monoterpene indole alkaloid, brachycerine (14), in the leaves and inflorescences of P. brachyceras.⁴²42 Kerber, V. A.; Gregianini, T. S.; Paranhos, J. T.; Schwambach, J.; Farias, F.; Fett, J. P.; Fett-Neto, A. G.; Zuanazzi, J. A. S.; Quirion, J. C.; Elizabetsky, E.; Henriques, A. T.; J. Nat. Prod. 2001, 64, 677.^,⁹⁷97 Matsuura, H. N.; Fett-Neto, A. G.; Nat. Prod. Res. 2013, 27, 402. From the leaves of P. leiocarpa Cham. & Schltdl. was obtained the major indole alkaloid N,β-D-glucopyranosyl vincosamide (15).⁶²62 Henriques, A. T.; Lopes, S. O.; Paranhos, J. T.; Gregianini, T. S.; Von Poser, G. L.; Fett-Neto, A. G.; Schripsema, J.; Phytochemistry 2004, 65, 449.^,⁹⁸98 Iniyavan, M.; Sangeetha, D.; Saravanan, S.; Parimelazhagan, T.; Food Sci. Biotechnol. 2012, 21, 1421. Psychotriasine (16) was isolated from the leaves of P. calocarpa. This compound is the first example of a dimeric tryptamine-related alkaloid that contains a free N-methyltryptamine unit in the molecule.⁴⁴44 Zhou, H.; He, H.-P.; Wang, Y.-H.; Hao, X.-J.; Helv. Chim. Acta 2010, 93, 1650. Two tryptamine-related alkaloids, psychotrimine (17) and psychopentamine (18), were isolated from the leaves of P. rostrata.⁷⁷77 Takayama, H.; Mori, I.; Kitajima, M.; Aimi, N.; Lajis, N. H.; Org. Lett. 2004, 6, 2945. The crude extracts from the roots and branches of P. prunifolia led to the isolation of several alkaloids such as 10-hydroxyisodeppeaninol (19), 10-hydroxyantirhine N-oxide (20), 14-oxoprunifoleine (21) and strictosamide (22).⁷⁴74 Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Ribeiro, L. C.; Carvalho, B. G.; Silva, C. C.; Schuquel, I. T. A.; Santin, S. M. O.; Nakamura, C. V.; Britta, E. A.; Miranda, N.; Iglesias, A. H.; Delprete, P. G.; J. Braz. Chem. Soc. 2012, 23, 355. From the leaves of P. pilifera was isolated the compound psychotripine (23), a trimeric pyrroloindoline derivative with a hendecacyclic system bearing a hexahydro-1,3,5-triazine unit.⁷³73 Li, X.-N.; Zhang, Y.; Cai, X.-H.; Feng, T.; Liu, Y.-P.; Li, Y.; Ren, J.; Zhu, H.-J.; Luo, X.-D.; Org. Lett. 2011, 13, 5896. The aerial parts of P. stachyoides led the isolation of two monoterpene indole alkaloids, stachyoside (24) and nor-methyl-23-oxo-correantoside (25).⁸²82 Pimenta, A. T. A.; Braz-Filho, R.; Delprete, P. G.; Bezerra, E. S.; Silveira, E. R.; Lima, M. A. S.; Magn. Reson. Chem. 2010, 48, 734. From the leaves of P. suterella Mull. Arg. were obtained three indole monoterpene alkaloids, lyaloside (26), naucletine (27) and strictosamide (22).⁸⁴84 van de Santos, L.; Fett-Neto, A. G.; Kerber, V. A.; Elisabetsky, E.; Quirion, J. C.; Henriques, A. T.; Biochem. Syst. Ecol. 2001, 29, 1185. From the leaves of P. nuda was isolated a major compound named strictosamide (22).⁷¹71 Farias, F. M.; Konrath, E. L.; Zuanazzi, J. A. S.; Henriques, A. T.; Biochem. Syst. Ecol. 2009, 36, 919.P. klugii yielded two new benzoquinolizidine alkaloids, klugine (28), and 7'-o-demethylisocephaeline (29), together with the previously known cephaeline (30), isocephaeline (31), and 7-o-methylipecoside (32).⁵⁸58 Muhammad, I.; Dunbar, D. C.; Khan, S. I.; Tekwani, B. L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L. A.; J. Nat. Prod. 2003, 66, 962. Two bis(monoterpenoid) indole alkaloid glucosides, bahienoside A (33) and bahienoside B (4), together with the known compounds 5α-carboxystrictosidine (34), angustine (35), strictosamide (22), and vallesiachotamine (3), were isolated from the aerial parts of P. bahiensis.³⁹39 Paul, J. H. A.; Maxwell, A. R.; Reynolds, W. F.; J. Nat. Prod. 2003, 66, 752. Dimethyltryptamine (36) was identified in the leaves of P. viridis, known for its ethnobotanical use as a hallucinogen.⁹¹91 Blackledge, R. D.; Taylor, C. M.; Microgram J. 2003, 1, 18.P. lyciiflora and P. oleoides, led to the isolation of several pyrrolidinoindoline alkaloids. Two dimers, the known meso-chimonanthine (37), N_b-desmethyl-meso-chimonanthine (38), and hodgkinsine (39), have been isolated from P. lyciiflora. Hodgkinsine (39), quadrigemine C (40), isopsychotridine B (41), psychotridine (42), quadrigemine I (43), oleoidine (44) and caledonine (45) were obtained from P. oleoides.⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. From the aerial parts of P. glomerulata were isolated three quinoline alkaloids such as glomerulatine A (46), B (47) and C (48).⁵³53 Solis, P. N.; Ravelo, A. G.; Palenzuela, J. A.; Gupta, M. P.; Gonzalez, A.; Phillipson, J. D.; Phytochemistry 1997, 44, 963. From extracts of the leaves and the roots of P. correae were obtained isodolichantoside (49) and the alkaloids correantoside (50), 10-hydroxycorreantoside (51), correantine A (52), B (53), and C (54), and 20-epi-correantine B (55).⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.P. forsteriana afforded three alkaloids (−)-calycanthine (56), iso-calycanthine (57), and meso-chimonanthine (38), a dimeric indole isomeric.⁵⁰50 Adjibadé, Y.; Weniger, B.; Quirion, J. C.; Kuballa, B.; Cabalion, P.; Anton, R.; Phytochemistry 1991, 31, 317.

5.2. Terpenoids

The phytochemical study on P. yunnanensis allowed the isolation of four norisoprenoids (58-61) and one monoterpenic acid (62). From the aerial parts of this plant a new type of sesquiterpene derived from acorane, possessing rare spirobicyclic carbon skeleton, known as psycacoraone A, was identified (63).³⁶36 Lu, Q.; Wang, J.; Luo, J.; Wang, X.; Shan, S.; Kong, L.; Nat. Prod. Res. 2014, 28, 1659.^,⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.

From the leaves of P. cadigensis, an endemic species from Philippines, were isolated three nor-sesquiterpenes: vomifoliol (5), loliolide (61) and isololiolide (64). This was the first time that the phytochemical study of this species was described in the literature.⁴³43 Tan, M. A.; Panghulan, G. F. M.; Uy, M. M.; Takayama, H.; Am. J. Essent. Oils Nat. Prod. 2014, 1, 18. In P. vellosiana Benth. was reported the presence of squalene (65), lupeol (66), a mixture of sitosterol (67) and stigmasterol (68) obtained from the aerial parts of the plant. Also according to the authors this is the first time that squalene was described on the genus.⁸⁹89 Moreno, B. P.; Fiorucci, L. L. R.; Carmo, M. R. B.; Sarragiotto, M. H.; Baldoqui, D. C.; Biochem. Syst. Ecol. 2014, 56, 80. From the floral essential oil of P. eurycarpa Standl. were obtained some components such as linalool (69) and α-terpineol (70).⁴⁹49 Setzer, W. N.; Noletto, J. A.; Haber, W. A.; J. Essent. Oil-Bear Plants 2006, 9, 28. The extract from leaves and roots of P. stachyoides Benth. provided β-sitosterol (71) and stigmasterol glucosides (72) (Figure 4).¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.

Figure 4
The structures of terpenoids from Psychotria species.

5.3. Flavonoids

P. carthagenensis, P. leiocarpa, P. capillacea and P. deflexa were investigated in order to found total phenolics, flavonoids, condensed tannins and flavonols in their composition. Among these species, the highest flavonoid concentration was found in P. carthagenensis and P. capillacea extracts.²⁰20 Formagio, A. S. N.; Volobuff, C. R. F.; Santiago, M.; Cardoso, C. A. L.; Vieira, M. C.; Pereira, Z. V.; Antioxidants 2014, 3, 745. Similar studies were done for P. hainanensis and P. nilgiriensis fruit and, both demonstrated highest total flavonoid content.⁵⁴54 Li, H.-F.; Huang, J.; Liu, M.-S.; Zhang, X.-P.; Chin. J. Exp. Tradit. Med. Formulae 2011, 19, 125.^,⁹⁸98 Iniyavan, M.; Sangeetha, D.; Saravanan, S.; Parimelazhagan, T.; Food Sci. Biotechnol. 2012, 21, 1421. From leaves of P. spectabilis were isolated quercetin (73) and quercetrin (74).¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565. Two flavonoid glycosides, from P. rubra, were identified as 6-hydroxy-luteolin-7-o-rutinoside (75) and luteolin-7-o-rutinoside (76).⁷⁹79 Lu, H.-X.; Liu, L.-Y.; Li, D.-P.; Li, J.-Z.; Xu, L.-C.; Biochem. Syst. Ecol. 2014, 57, 133. Recently, the chemical study of P. serpens allowed the isolation of rutin (77), quercetin (73), tamarixetin-3-o-rutinoside (78) and kaempferol (79)⁸¹81 Lin, C.-H.; Wu, A.-Z.; Zhong, Y.; Wang, Y.-W.; Peng, G.-T.; Su, X.-J.; Liu, B.-X.; Deng, Y.; Zhu, C.-C.; Zhang, C.-X.; J. Cancer Res. Updates 2015, 3, 60. (Figure 5).

Figure 5
The structures of flavonoids from Psychotria species.

5.4. Coumarins

The phytochemical investigation of P. vellosiana aerial parts yielded the scopoletin (80).⁸⁹89 Moreno, B. P.; Fiorucci, L. L. R.; Carmo, M. R. B.; Sarragiotto, M. H.; Baldoqui, D. C.; Biochem. Syst. Ecol. 2014, 56, 80. From leaves of P. spectabilis were isolated coumarin (81), umbelliferone (82), and psoralene (83) (Figure 6).¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.

Figure 6
The structures of coumarins from Psychotria species.

5.5. Tannins

A study realized for P. carthagenensis, P. leiocarpa, P. capillacea and P. deflexa showed not only high flavonoid concentration in the extracts, but also the presence of condensed tannins.²⁰20 Formagio, A. S. N.; Volobuff, C. R. F.; Santiago, M.; Cardoso, C. A. L.; Vieira, M. C.; Pereira, Z. V.; Antioxidants 2014, 3, 745.^,⁹⁸98 Iniyavan, M.; Sangeetha, D.; Saravanan, S.; Parimelazhagan, T.; Food Sci. Biotechnol. 2012, 21, 1421. For P. reevesii Wall. was realized a screening based on color reactions, high performance liquid chromatography (HPLC) analytical and nuclear magnetic resonance (NMR) spectroscopy. The obtained results revealed the presence of condensed tannins.⁹⁹99 Phan, M. G.; Ha, V. S.; Phan, T. S.; Vietnam J. Chem. 2007, 45, 628.

5.6. Cyclic peptides

Besides the presence of traditional secondary metabolites, another main chemical constituents are cyclic peptides, especially cyclotides. This peptide group is characterized by a peculiar cyclic structure with approximately 30 amino acids residues with cyclic cystine motif (CCK), conferring them a remarkable stability. All cyclotides sequences described in the literature from Psychotria species are presented on Table 2.¹⁰⁰100 Mulvenna, J. P.; Wang, C.; Craik, D. J.; Nucleic Acids Res. 2006, 34, D192.^,¹⁰¹101 Wang, C. K.; Kaas, Q.; Chiche, L.; Craik, D. J.; Nucleic Acids Res. 2008, 36, D206.

6. Pharmacological Properties of Psychotria Species

6.1. Neurodegenerative diseases

As previously demonstrated on section 4, plants from Psychotria genus commonly affect the central nervous system. Recently, several Psychotria alkaloids, mainly monoterpene indoles and β-carboline alkaloids have been reported for their inhibitory properties against acetylcholinesterase and monoamine oxidase proteins, which are enzymatic targets related with neurodegenerative diseases.⁶⁰60 Passos, C. S.; Simões-Pires, C. A.; Nurisso, A.; Soldi, T. C.; Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Marcourt, L.; Gottfried, C.; Carrupt, P. A.; Henriques, A. T.; Phytochemistry 2013, 86, 8.^,¹⁰²102 Hellinger, R.; Koehbach, J.; Puigpinoś, A.; Clark, R. J.; Tarrago, T.; Giralt, E.; Gruber, C. W.; J. Nat. Prod. 2015, 78, 1073. Alkaloidal fractions of Psychotria suterella and Psychotria laciniata as well as two monoterpene indole alkaloids isolated from these fractions were evaluated against monoamine oxidases (MAO-A and MAO-B) obtained from rat brain mitochondria.⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611. The monoterpene indole alkaloids lyaloside (26) and strictosamide (22) exhibited inhibitory effect on MAO-A (IC₅₀ 50.04 and 132.5 µg mL^-1, respectively) and MAO-B (IC₅₀ 306.6 and 162.8 µg mL^-1, respectively).⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.^,⁶⁰60 Passos, C. S.; Simões-Pires, C. A.; Nurisso, A.; Soldi, T. C.; Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Marcourt, L.; Gottfried, C.; Carrupt, P. A.; Henriques, A. T.; Phytochemistry 2013, 86, 8.^,⁸⁴84 van de Santos, L.; Fett-Neto, A. G.; Kerber, V. A.; Elisabetsky, E.; Quirion, J. C.; Henriques, A. T.; Biochem. Syst. Ecol. 2001, 29, 1185. These data confirm the previous study made by McKenna et al.⁵5 McKenna, D. J.; Towers, G. H. N.; Abbot, F. J.; J. Ethnopharmacol. 1984, 10, 195. which also demonstrated inhibition of MAO by alkaloids compounds present in hallucinogenic "ayahuasca" drink.

Some other effects on the central nervous system involving acetylcholinesterase (AChE), butilcolinesterase (BChE) have also been reported for various other alkaloids of Psychotria sp. The β-carboline quaternary alkaloids prunifoleine (84) and 14-oxoprunifoleine (21) inhibited the enzymes AChE by a non-competitive mode of inhibition, although inhibited both BChE and MAO by a time-dependent mode of inhibition. In addition, the monoterpene indole alkaloids angustine (36), vallesiachotamine lactone (85) and vallesiachotamine (3) also inhibited BChE and MAO.⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.^,⁶⁰60 Passos, C. S.; Simões-Pires, C. A.; Nurisso, A.; Soldi, T. C.; Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Marcourt, L.; Gottfried, C.; Carrupt, P. A.; Henriques, A. T.; Phytochemistry 2013, 86, 8. The monoterpene indole alkaloid strictosidinic acid (11) isolated from the leaves of Psychotria myriantha Mull. Arg. reduced levels of serotonin (5-HT) and DOPA C, a metabolite of dopamine neurotransmitter from the MAO action in rat hippocampus inhibiting probably the precursor enzyme of the biosynthesis of 5-HT. A reduction of 83.5% in 5-HT levels was observed after intra-hippocampal injection (20 µg µL^-1). In addition, decreased levels of DOPA C suggests that strictosidinic acid (11) have action on the dopaminergic system by inhibiting MAO, which was confirmed by enzymatic assay in rat brain mitochondria. After treatment by intraperitoneal route (10 mg kg^-1), a reduction of 63.4% in 5-HT levels and 67.4% in DOPA C values were observed.⁶⁹69 Farias, F. M.; Passos, C. S.; Arbo, M. D.; Barros, D. M.; Gottfried, C.; Steffen, V. M.; Henriques, A. T.; Fitoterapia 2012, 83, 1138.^,⁷¹71 Farias, F. M.; Konrath, E. L.; Zuanazzi, J. A. S.; Henriques, A. T.; Biochem. Syst. Ecol. 2009, 36, 919. This monoterpene glycosylated indole alkaloid also showed peripheral analgesic and antipyretic activities on mice.⁷⁰70 Simões-Pires, C. A.; Farias, F. M.; Marston, A.; Queiroz, E. F.; Chaves, C. G.; Henriques, A. T.; Hostettmann, K.; Nat. Prod. Commun. 2006, 1, 1101.^,¹⁰⁵105 Reanmongkol, W.; Sudhadhirasakul, S.; Kongsang, J.; Tanchong, M.; Kitti, J.; Pharm. Biol. 2000, 38, 68. Those findings suggest that species from genus Psychotria might be an interesting source for new MAO inhibitors.

The peptide cyclopsichotride A (Table 2), isolated from the extract of P. longipes inhibited the interaction of neurotensin radiolabeled with their membrane receptors on HT-29 cells (intestinal colon carcinoma) and stimulated the increase of calcium intracellular in two different cell lines not expressing neurotensin receptors. It suggests that this compound might be an antagonist of these types of receptors as well as also being able to act via other receptors.⁶⁵65 Witherup, K. M.; Bogusky, M. J.; Anderson, P. M.; Ramjit, H.; Ransom, R. W.; Wood, T.; Sardana, M.; J. Nat. Prod. 1994, 57, 1619.

Studies made by Hellinger and co-workers¹⁰⁴104 Koehbach, J.; Attah, A. F.; Berger, A.; Hellinger, R.; Kutchan, T. M.; Carpenter, E. J.; Rolf, M.; Sonibare, M. A.; Moody, J. O.; Wong, G. K.; Dessein, S.; Greger, H.; Gruber, C. W.; Biopolymers 2013, 100, 438. described the bioactivity-guided isolation of a cyclotide from P. solitudinum as an inhibitor of a serine-type protease, namely, the human prolyl oligopeptidase (POP). It yielded the isolated peptide psysol 2 (Table 2), which exhibited an IC₅₀ of 25 µmol L^-1. The enzyme POP plays an important role in memory and learning processes, and it is currently being considered as a therapeutic target for some psychiatric and neurodegenerative diseases, such as schizophrenia and Parkinson's disease.

6.2. Antioxidant and analgesic properties

The monoterpene indole alkaloids psychollatine (6) and brachycerine (14) isolated from P. umbellata and P. brachyceras, respectively, presented antioxidant and antimutagenic activity.⁴²42 Kerber, V. A.; Gregianini, T. S.; Paranhos, J. T.; Schwambach, J.; Farias, F.; Fett, J. P.; Fett-Neto, A. G.; Zuanazzi, J. A. S.; Quirion, J. C.; Elizabetsky, E.; Henriques, A. T.; J. Nat. Prod. 2001, 64, 677.^,¹⁰⁶106 Fragoso, V.; Nascimento, N. C.; Moura, D. J.; Silva, A. C. R.; Richter, M. F.; Saffi, J.; Fett-Neto, A. G.; Toxicol. In Vitro 2008, 22, 559.^,¹⁰⁷107 Nascimento, N. C.; Fragoso, V.; Moura, D. J.; Silva, A. C. R.; Fett-Neto, A. G.; Saffi, J.; Environ. Mol. Mutagen. 2007, 48, 728. In the study made by Both et al.,⁸⁷87 Both, F. L.; Farias, F. M.; Nicoláo, L. L.; Misturini, J.; Henriques, A. T.; Elisabetsky, E.; Rev. Bras. Pl. Med. 2002, 5, 41. it was described the analgesic properties of isodolichantoside (49) isolated from P. umbellata. These same analgesic properties have also been reported to alkaloid hodgkinsine (39) isolated from another Psychotria species, P. colorata which is in agreement with the previous study made by Amador et al.¹⁰⁸108 Amador, T. A.; Verotta, L.; Nunes, D. S.; Elisabetsky, E.; Planta Med. 2000, 66, 770 and Elisabetsky et al.,¹⁰⁹109 Elisabetsky, E.; Amador, T. A.; Albuquerque, R. R.; Nunes, D. S.; Carvalho, A. C. T.; J. Ethnopharmacol. 1995, 48, 77. which reported the alkaloid analgesic activity of leaves and flower extracts.

The alkaloid fraction from the ethanol extracts of flowers and leaves of P. colorata consisted primarily of a mixture of pyrrolidinoindoline alkaloids quadrigemine C (40), calycanthine (56), isocalycanthine (57) which showed analgesic activity by inhibiting the interaction of naloxone [H₃] with proteins of the cell membrane and also inhibiting the activity of the enzyme adenylate cyclase in rat. Thus, this suggests an action in opiodergic system since alkaloids did not inhibit the interaction of GMP [H₃]-pnp (guanylyl imidodiphosphate) with the proteins during the Tail-flick analgesic test.⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392.^,⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.^,¹¹⁰110 Amador, T. A.; Elisabetsky, E.; Souza, D. O.; Neurochem. Res. 1996, 21, 97.

6.3. Anti-inflammatory activity

Ten Psychotria species were collected in the Brazilian Atlantic Forest (P. pubigera, P. ruelliifolia, P. suterela, P. stachyoides, P. capitata, P. glaziovii, P. leiocarpa, P. nuda, P. racemosa and P. vellosiana) in order to check if they could inhibit the production of nitric oxide (NO) in macrophages and if they have free-radical scavenging properties. From the evaluated extracts for in vitro anti-inflammatory activity, P. suterela, P. stachyoides and P. capitata were the most active in inhibiting macrophage NO production. Interestingly 5,6-dihydro-β-carboline alkaloids were found in all of the ten species evaluated, besides, indol alkaloids were also detected in P. nuda and P. suterela.¹¹¹111 Moraes, T. M.; Araújo, M. H.; Bernardes, N. R.; Oliveira, D. B.; Lasunskaia, E. B.; Muzitano, M. F.; Cunha, M.; Planta Med. 2011, 77, 964.

6.4. Anti-protozoal activity

The alkaloids klugine (28), cephaelin (30) and isocephaeline (31) isolated from P. klugii presented in vitro leishmanicidal activity, being active against Leishmania donavani. In addition, the alkaloids 30 and 31 exhibited a potent antimalarial activity against W2 and D6 strains of Plasmodium falciparum.⁵⁸58 Muhammad, I.; Dunbar, D. C.; Khan, S. I.; Tekwani, B. L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L. A.; J. Nat. Prod. 2003, 66, 962. The alkaloids obtained from P. prunifolia (Kunth) also showed leishmanicidal activity. These alkaloids, 14-oxoprunifoleine (21) and strictosamide (22) showed selective activity against Leishmania amazonensis, with IC₅₀ values of 16.0 and 40.7 µg mL^-1, respectively, although they showed no effect on epimastigotes forms of T. cruzi.⁷⁴74 Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Ribeiro, L. C.; Carvalho, B. G.; Silva, C. C.; Schuquel, I. T. A.; Santin, S. M. O.; Nakamura, C. V.; Britta, E. A.; Miranda, N.; Iglesias, A. H.; Delprete, P. G.; J. Braz. Chem. Soc. 2012, 23, 355.

The compound 1-hydroxybenzoisochromanquinone (psychorubrin) (86) and benz[g]isoquinoline-5,10-dione (87) isolated from the roots and stems of P. camponutans by a bioguided fractionation showed inhibition against resistant Plasmodium falciparum strains in in vitro assays.⁴⁵45 Solis, P. N.; Lang'at, C.; Gupta, M. P.; Kirby, G. C.; Warhurst, D. C.; Phillipson, J. D.; Planta Med. 1995, 61, 62.

6.5. Antiviral activity

Ipecac alkaloids are secondary metabolites produced in the medicinal plant P. ipecacuanha. This species is known as a traditional herbal medicine, which was introduced to western medicine over 300 years ago and the syrup is commonly used as emetic for the treatment of patients who ingested poisons. Emetine (12) is one of the active compounds found in the syrup and the main alkaloid of Ipecac, which possesses a monoterpenoid-tetrahydroisoquinoline skeleton and is formed by condensation of dopamine and secologanin.⁵⁶56 Moller, M.; Herzer, K.; Wenger, T.; Herr, I.; Wink, M.; Oncol. Rep. 2007, 18, 737. Ementine (12) was evaluated as an antiviral agent against human immunodeficiency virus (HIV). It inhibited HIV-1 replication by interfering with reverse transcriptase activity and the obtained results showed that in cellular models reduced about 80% of HIV-1 infection. It also blocked HIV-1 infection of RT M184V mutant in in vitro reactions with isolated HIV-1RT and intravirion.⁹⁵95 Valadão, A. L. C.; Abreu, C. M.; Dias, J. Z.; Arantes, P.; Verli, H.; Tanuri, A.; Aguiar, R. S.; Molecules 2015, 20, 11474.

Six acetone subfractions of ethanolic extract from P. serpens significantly suppressed Herpes simplex virus type 1 replication on Vero cells. The viability of cells was not significantly decreased as well as deoxyribonucleic acid (DNA), ribonucleic acid (RNA) and protein synthesis were unaffected showing that inhibitory mechanism of viral replication was not through cytotoxicity and/or blocking of Vero cells growth.¹¹²112 Kuo, Y. C.; Chien, C. C.; Tsai, W. J.; Ho, Y. H.; Antiviral Res. 2001, 51, 95.

6.6. Cytotoxic activity

Some other bioactive compounds from the polypyrrolidinoindoline alkaloid family have been described as cytotoxic agents. The compounds quadrigemine A (88), quadrigemine B (89), isopsychotridine C (90) and psychotridine (42) isolated from P. forsteriana leaves showed cytotoxic activity in rat hepatoma cell line (HTC strain) and were more potent than vincristine, an anti-tumor agent.⁵¹51 Roth, A.; Kuballa, B.; Bounthanh, C.; Caballion, P.; Sévenet, T.; Beck, J. P.; Anton, R.; Planta Med. 1986, 5, 450.^,⁷⁶76 Mahmud, Z.; Musa, M.; Ismail, N.; Lajis, N. H.; Int. J. Pharmacol. 1993, 31, 142. These same compounds also inhibited the aggregation of washed human platelets induced by adenosine diphosphate (ADP), collagen and thrombin.¹¹³113 Beretz, A.; Roth-Georger, A.; Corre, G.; Kuballa, B.; Anton, R.; Cazenave, J. P.; Planta Med. 1985, 4, 300. In addition, the compounds vatine (91), vatamine (92) and vatamidine (93) exhibited strong cytotoxic activity in rat hepatoma cells and in human leukemia cells.⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.

The bioguided fractionation of P. serpens allowed the isolation of the triterpenoid ursolic acid (94), which showed cytotoxicity in leukemic cells P-388, L-1210 and A-549 human lung carcinoma. It also showed moderate cytotoxicity in human colon tumor cells (HCT-8) and breast cancer cells (MCF-7).⁸⁰80 Lee, K.-H.; Lin, Y.-M.; Wu, T.-S.; Zhang, D.-C.; Yamagishi, T.; Hayashi, T.; Hall, I. H.; Chang, J.-J.; Wu, R.-Y.; Yang, T.-H.; Planta Med. 1988, 54, 308.

From Psychotria sp. Zhang et al.¹¹⁴114 Zhang, C.-X.; Zhang, D-M.; Chen, M.-F.; Guan, S.-Y.; Yao, J.-H.; He, X.-X.; Lei, L.-F.; Zhong, Y.; Wang, Z.-F.; Ye, W.-C.; Planta Med. 2013, 79, 978. isolated six new triterpenoid saponins called psychotrianosides A-F (95-100) and some other two compounds already known psychotrianoside G (101) and ardisianoside D (102). In vitro assays showed that the evaluated compounds reduced the viability of tumor cell lines like MDA-MB-231, MCF-7 and HepG2, and inhibited the growth of multi-drug resistant strains such MCF-7/ADM and HepG2/ADM. Among the evaluated saponins, the psychotrianoside C (97) showed the most potent cytotoxic effect and also induced cell death by apoptosis.

The alkaloid emetine (12) presented cytotoxic and apoptosis effects in leukemia cell lines via mitochondrial pathway.⁵⁶56 Moller, M.; Herzer, K.; Wenger, T.; Herr, I.; Wink, M.; Oncol. Rep. 2007, 18, 737.^,¹¹⁵115 Moller, M.; Wink, M.; Planta Med. 2007, 73, 1389. When tested with cisplatin (standard chemotherapeutic agent) it increased levels of apoptosis, inducing the expression of several proapoptotic genes and inhibiting expression of survival factors.⁵⁶56 Moller, M.; Herzer, K.; Wenger, T.; Herr, I.; Wink, M.; Oncol. Rep. 2007, 18, 737.

The alkaloid psychotripine (23), a trimeric pyrroloindoline derivative with a hendecacyclic system bearing a hexahydro-1,3,5-triazine unit, was isolated from the leaves of P. pilifera. This compound was evaluated for cytotoxicity in five different tumor cell lines, HL-60 (leukemia), SMMC-7721 (liver cancer), A-549 (lung cancer), MCF-7 (breast cancer) and SW480 (colon cancer) although did not present any significant activity (IC₅₀ > 40 mmol L^-1).⁷³73 Li, X.-N.; Zhang, Y.; Cai, X.-H.; Feng, T.; Liu, Y.-P.; Li, Y.; Ren, J.; Zhu, H.-J.; Luo, X.-D.; Org. Lett. 2011, 13, 5896.

The 1-hydroxybenzoisochromanquinone (psychorubrin) (86) isolated from P. rubra showed cytotoxic effect on tumor lineage KB. In addition, some other naphthoquinones derived from structural modifications exhibited cytotoxic activity higher than the natural product psychorubrin, thus demonstrating the importance of structure-activity study.⁷⁸78 Hayashi, T.; Smith, F. T.; Lee, K.-H.; J. Med. Chem. 1987, 30, 2005.

From the species P. leptothyrsa, six cyclotides were isolated (Psyle A-F) (see Tables 1 and 2), however only the cyclotides psyle A, C and E showed a potent cytotoxic effect (IC₅₀ = 0.64 > 10 µmol L^-1) in breast cancer cell lines resistant (MCF-7/ADR) or not (MCF-7). It was demonstrated that the presence of cyclotides in MCF-7/ADR cell line significantly increased the cytotoxicity induced by doxorubicin (IC₅₀ = 0.39-0.76 µmol L^-1), revealing a chemosensitization effect of these compounds, as well as being promising against resistant breast cancer cell lines.⁶⁴64 Gerlach, S. L.; Burman, R.; Bohlin, L.; Mondal, D.; Goransson, U.; J. Nat. Prod. 2010, 73, 1207.^,¹¹⁶116 Gerlach, S. L.; Rathinakumar, R.; Chakravarty, G.; Goransson, U.; Wimley, W. C.; Darwin, S. P.; Mondal, D.; Biopolymers 2010, 94, 617.

6.7. Bactericidal and antifungal activity

The compound quadrigemine B (89) isolated from P. rostrata showed bactericidal activity against Escherichia coli and Staphylococcus aureus.⁷⁶76 Mahmud, Z.; Musa, M.; Ismail, N.; Lajis, N. H.; Int. J. Pharmacol. 1993, 31, 142. From the leaves of the same species were isolated some other alkaloids like psychotrimine (17) and psychopentamine (18), which showed anti-bactericidal activity against resistant gram-positive bacteria Bacillus subtilis and S. aureus.⁷⁷77 Takayama, H.; Mori, I.; Kitajima, M.; Aimi, N.; Lajis, N. H.; Org. Lett. 2004, 6, 2945.^,¹¹⁷117 Schallenberger, M. A.; Newhouse, T.; Baran, P. S.; Romesberg, F. E.; J. Antibiot. 2010, 63, 685.

In a study made by Moraes et al.,¹¹¹111 Moraes, T. M.; Araújo, M. H.; Bernardes, N. R.; Oliveira, D. B.; Lasunskaia, E. B.; Muzitano, M. F.; Cunha, M.; Planta Med. 2011, 77, 964. ten Psychotria species (P. pubigera, P. ruelliifolia, P. suterela, P. stachyoides, P. capitata, P. glaziovii, P. leiocarpa, P. nuda, P. racemosa and P. vellosiana) were evaluated for antimycobacterial activity, in an attempt to find new antituberculosis agents. From the evaluated extracts the species P. pubigera, P. ruelliifolia and P. stachyoides were the most active against Mycobacterium.

From P. spectabilis were isolated two diterpenes, solidagenone (103) and deoxysolidagenone (104), three coumarins, coumarin (81), umbelliferone (82) and psoralene (83), which exhibited antifungal activity against the filamentous fungi Cladosporium cladosporioides (Fresen) de Vries and Cladosporium sphaerospermum Penzig. Further evaluations of compounds 103 and 83 showed selective cytotoxicity against Rad 52Y mutant yeast strain of Saccharomyces cerevisiae.¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.

6.8. Other activities

The indole pyrrolidine alkaloids like psycholeine (105) and quadrigemine C (40) isolated from P. oleoides were subjected to the interaction study with radiolabeled somatostatin ([125 I] N-Tyr-SRIF), inhibition of the enzyme adenylate cyclase and somatostatin secretion of growth hormone (GH) by the rat pituitary cells. Psycholeine (105) presented antagonistic properties at the SRIF receptor with an IC₅₀ of 10^-5 mol L^-1.⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.^,¹¹⁸118 Rasolonjanahary, R.; Sévenet, T.; Voegelein, F. G.; Kordon, C.; Eur. J. Pharmacol. 1995, 285, 19.

7. Ecological Approach of Psychotria Species

The production of secondary metabolites may also help the plants to develop and grow in the environment. The monoterpene indole alkaloid brachycerine (14), an antioxidant glucosidic indole alkaloid, is involved in the defense of P. brachyceras Muell. Arg. against the osmotic/oxidative stress, contributing to the detoxification of hydroxyl radicals and superoxide anions. It was demonstrated that the agents responsible for inducing osmotic stress agents such as sodium chloride, sorbitol and polyethylene glycol lead to the alkaloid accumulation in leaves. Some other agents responsible for inducing oxidative stress such as exposure to aluminum, silver and abscisic acid also increased the amount of brachycerine (14). Nascimento et al.¹¹⁹119 Nascimento, N. C.; Menguer, P. K.; Henriques, A. T.; Fett-Neto, A. G.; Plant Physiol. Biochem. 2013, 73, 33. described that brachycerine in not herbivore deterrent, but is involved in defense by modulating oxidative stress.

The major indole alkaloid N,β-D-glucopyranosyl vincosamide (15) from leaves of P. leiocarpa Cham. & Schltdl. showed broad antioxidant activity and may act against oxidative stress generated upon wounding, UV exposure and perhaps other environmental stresses.⁹⁷97 Matsuura, H. N.; Fett-Neto, A. G.; Nat. Prod. Res. 2013, 27, 402.

The study made by Matsuura and Fett-Neto⁹⁷97 Matsuura, H. N.; Fett-Neto, A. G.; Nat. Prod. Res. 2013, 27, 402. showed the antioxidant effect of GPV (N,β-D-glucopyranosyl vincosamide) (15) when evaluated in vitro tests against singlet oxygen, superoxide and hydroxyl radicals and in situ tests against hydrogen peroxide. It was demonstrated that this alkaloid protects the plant P. leiocarpa indirectly against oxidative stress generated in injury, exposure to UV rays and other environmental damage, although not directly against herbivory.⁹⁶96 Porto, D. D.; Matsuura, H. N.; Vargas, L. R. B.; Henriques, A. T.; Fett-Neto, A. G.; Nat. Prod. Commun. 2014, 9, 629.

Psychotria plants are rich in secondary metabolites that could be toxic against Sitophilus zeamais (Coleoptera: Curculionidae) and Spodoptera frugiperda (Lepidoptera: Noctuidae) for maize protection. The study made by Tavares et al.¹²⁰120 Tavares, W. S.; Grazziotti, G. H.; Souza Jr., A. A.; Sousa Freitas, S.; Consolaro, H. N.; Ribeiro, P. E.; Zanuncio, J. C.; J. Food Prot. 2013, 76, 1892. demonstrated that extracts (leaves or stems) from P. hoffmannseggiana, P. capitata and P. goyazensis were significantly toxic to these type of insects involving the following parameters such as hatching rate, weight, length, repellence and mortality.

Figure 7
The structures from Psychotria species.

The extract from the leaves of P. microphylla showed to be very toxic to the young forms of Clarias gariepinus, important species of catfish from Africa. The toxicity of the extract was time and dose-dependent. This extract may be useful in aquaculture to eradicate predators and competitors of wild fishpond in farmed ponds or stocking hatchery fish species commercially cultivated.¹²¹121 Orji, O. U.; Ibiam, U. A.; Aja, P. M.; Int. J. Biol. Sci. 2014, 3, 038.

Species such as P. gabriellae and P. douarrei presented the ability to accumulate high amounts of nickel in their sprouts. Metabolites were identified in complexes with Ni including Ni-malonate from P. douarrei and the levels for some metabolites were found to correlate with the leaf Ni concentration.¹²²122 Merlot, S.; Hannibal, L.; Martins, S.; Martinelli, L.; Amir, H.; Lebrun, M.; Thomine, S.; J. Exp. Bot. 2014, 65, 1551.^,¹²³123 Callahan, D. L.; Roessner, U.; Dumontet, V.; Livera, A. M.; Doronila, A.; Baker, A. J. M.; Kolev, S. D.; Phytochemistry 2012, 81, 80. Studies conducted by Grison et al.¹²⁴124 Grison, C.; Escande, V.; Petit, E.; Garoux, L.; Boulangerd, C.; Grison, C.; RSC Adv. 2013, 3, 22340. demonstrated the use of biomass obtained from P. douarrei enriched by nickel a catalyst type Lewis acid in organic synthesis as an alternative source of nickel used in the synthesis of antifungal compound monastrol, thus showing its potential to be used in Green Chemistry.

8. Conclusions

As demonstrated in our methods an increasing number of publications revealed a significant interest in Psycothria genus in recently years, due to their traditional uses and pharmacological activities. This review presents the main traditional uses as long as pharmacological properties, phytochemistry, chemotaxonomy and ecological approach.

The genus Psychotria presents a complex taxonomy and its phytochemical approach became a very useful tool to understand and establish the chemotaxonomy. Several classes of natural products are described for this genus, although, this study highlights the importance of some alkaloids and cyclic peptides, which are involved on central nervous system and neurodegenerative diseases.

FAPESP has sponsored the publication of this article.

Acknowledgments

The authors are also grateful to CEPID-FAPESP grant No. 2010/52327-5 and 2013/07600-3, SISBIOTA-CNPq-FAPESP grant No. 2010/52327-5, FAPESP grant No. 2015/09533-7, CNPq and CAPES for scholarships and financial support.

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Publication Dates

Publication in this collection
Aug 2016

History

Received
10 Mar 2016
Accepted
10 May 2016

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Specie and synonymia ^b bthe synonym were obtained from references and reference 94.	Compound	Reference
P. acuminate Synonymia: Palicourea acuminata (Benth.) Borhidi; = Psychotria cuspidata Bredem. ex Schult.	strictosidinic acid (11)	¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.
	strictosidine	¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.
	palicoside	¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.
	bahienoside B (4)	¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.
	5α-carboxystrictosidine (34)	¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.
	desoxycordifoline	¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.
	lagamboside (2)	¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.
	vallesiachotamine (3)	¹⁶16 Berger, A.; Fasshuber, H.; Schinnerl, J.; Brecker, L.; Greger, H.; Phytochem. Lett. 2012, 5, 558.
P. adenophylla Wall. Synonymia: Grumilea adenophylla (Wall); = Psychotria connata Kurz; = Psychotria siamensis Ridl.; = Uragoga adenophylla (Wall.) Kuntze.	bauerenol	³⁸38 Dan, S.; Dan, S. S.; Fitoterapia 1986, 57, 445.
	bauerenol acetate	³⁸38 Dan, S.; Dan, S. S.; Fitoterapia 1986, 57, 445.
	friedelin	³⁸38 Dan, S.; Dan, S. S.; Fitoterapia 1986, 57, 445.
	betulin	³⁸38 Dan, S.; Dan, S. S.; Fitoterapia 1986, 57, 445.
	betulinic acid	³⁸38 Dan, S.; Dan, S. S.; Fitoterapia 1986, 57, 445.
	α-amyrin	³⁸38 Dan, S.; Dan, S. S.; Fitoterapia 1986, 57, 445.
	ursolic acid (94)	³⁸38 Dan, S.; Dan, S. S.; Fitoterapia 1986, 57, 445.
	β-sitosterol (71)	³⁸38 Dan, S.; Dan, S. S.; Fitoterapia 1986, 57, 445.
P. bahiensis DC Synonymia: Declieuxia psychotrioide DC.; = Palicourea didymocarpa (A. Rich. ex DC.) Griseb.; = Psychotria cuspidata var. bahiensis (DC.) Müll. Arg; = Psychotria didymocarpos (A. Rich ex DC.) Lemée; = Psychotria diplosphaerica Müll. Arg.; = Ronabea didymocarpos A. Rich. ex DC.; = Uragoga bahiensis (DC.) Kuntze.	bahienoside A (33)	³⁹39 Paul, J. H. A.; Maxwell, A. R.; Reynolds, W. F.; J. Nat. Prod. 2003, 66, 752.
	bahienoside B (4)	³⁹39 Paul, J. H. A.; Maxwell, A. R.; Reynolds, W. F.; J. Nat. Prod. 2003, 66, 752.
	5α-carboxystrictosidine (34)	³⁹39 Paul, J. H. A.; Maxwell, A. R.; Reynolds, W. F.; J. Nat. Prod. 2003, 66, 752.
	angustine (35)	³⁹39 Paul, J. H. A.; Maxwell, A. R.; Reynolds, W. F.; J. Nat. Prod. 2003, 66, 752.
	strictosamide (22)	³⁹39 Paul, J. H. A.; Maxwell, A. R.; Reynolds, W. F.; J. Nat. Prod. 2003, 66, 752.
	vallesiachotamine (3)	³⁹39 Paul, J. H. A.; Maxwell, A. R.; Reynolds, W. F.; J. Nat. Prod. 2003, 66, 752.
P. barbiflora DC Synonymia: Psychotria hoffmannseggiana (Willd. ex Schult.) Müll. Arg.	harmane (10)	⁴⁰40 Oliveira, A. M.; Lemos, R. P. L.; Conserva, L. M.; Biochem. Syst. Ecol. 2013, 50, 339.
	strictosidinic acid (11)	⁴⁰40 Oliveira, A. M.; Lemos, R. P. L.; Conserva, L. M.; Biochem. Syst. Ecol. 2013, 50, 339.
P. beccarioides Wernham Synonymia: Psychotria leptothyrsa Miq.	psychotridine (42)	⁴¹41 Hart, N. K.; Johns, S. R.; Lamberton, J. A.; Summons, R. E.; Aust. J. Chem. 1974, 27, 639.
P. borucana (Ant. Molina) C. M. Taylor & W. Burger Synonymia: Carapichea affinis (Standl.) L. Andersson	cephaeline (30)	¹⁴14 Bernhard, M.; Fasshuber, H.; Robien, W.; Brecker, L.; Greger, H.; Biochem. System. Ecol. 2011, 39, 232.
	emetine (12)	¹⁴14 Bernhard, M.; Fasshuber, H.; Robien, W.; Brecker, L.; Greger, H.; Biochem. System. Ecol. 2011, 39, 232.
	ipecoside	¹⁴14 Bernhard, M.; Fasshuber, H.; Robien, W.; Brecker, L.; Greger, H.; Biochem. System. Ecol. 2011, 39, 232.
	6-o-methylipecoside	¹⁴14 Bernhard, M.; Fasshuber, H.; Robien, W.; Brecker, L.; Greger, H.; Biochem. System. Ecol. 2011, 39, 232.
	6-o-methyl-trans-cephaeloside	¹⁴14 Bernhard, M.; Fasshuber, H.; Robien, W.; Brecker, L.; Greger, H.; Biochem. System. Ecol. 2011, 39, 232.
	borucoside (1)	¹⁴14 Bernhard, M.; Fasshuber, H.; Robien, W.; Brecker, L.; Greger, H.; Biochem. System. Ecol. 2011, 39, 232.
P. brachyceras Müll. Arg. Synonymia: Uragoga brachyceras (Müll. Arg.) Kuntze.	brachycerine (14)	⁴²42 Kerber, V. A.; Gregianini, T. S.; Paranhos, J. T.; Schwambach, J.; Farias, F.; Fett, J. P.; Fett-Neto, A. G.; Zuanazzi, J. A. S.; Quirion, J. C.; Elizabetsky, E.; Henriques, A. T.; J. Nat. Prod. 2001, 64, 677.
P. cadigensis Merr.	vomifoliol (5)	⁴³43 Tan, M. A.; Panghulan, G. F. M.; Uy, M. M.; Takayama, H.; Am. J. Essent. Oils Nat. Prod. 2014, 1, 18.
	loliolide (61)	⁴³43 Tan, M. A.; Panghulan, G. F. M.; Uy, M. M.; Takayama, H.; Am. J. Essent. Oils Nat. Prod. 2014, 1, 18.
	isololiolide (64)	⁴³43 Tan, M. A.; Panghulan, G. F. M.; Uy, M. M.; Takayama, H.; Am. J. Essent. Oils Nat. Prod. 2014, 1, 18.
P. calocarpa Kurz Synonymia: Psychotria viridiflora var. undulata Kurz; = Uragoga picta Kuntze.	psychotriasine (16)	⁴⁴44 Zhou, H.; He, H.-P.; Wang, Y.-H.; Hao, X.-J.; Helv. Chim. Acta 2010, 93, 1650.
P. camponutans (Dwyer & M. V. Hayden) Hammel Synonymia: Notopleura camponutans (Dwyer & M. V. Hayden) C. M. Taylor.	1-hydroxybenzoisochromanquinone (psychorubrin) (86) benz[g]isoquinoline-5,10-dione (87)	⁴⁵45 Solis, P. N.; Lang'at, C.; Gupta, M. P.; Kirby, G. C.; Warhurst, D. C.; Phillipson, J. D.; Planta Med. 1995, 61, 62. ⁴⁵45 Solis, P. N.; Lang'at, C.; Gupta, M. P.; Kirby, G. C.; Warhurst, D. C.; Phillipson, J. D.; Planta Med. 1995, 61, 62.
P. colorata (Willd. ex Roem. & Schult) Müll. Arg. Synonymia: Cephaelis amoena Bremek; = Cephaelis colorata Willd. ex. Roem.; = Cephaelis glabrescens (Müll. Arg.) Standl.; = Psychotria calviflora Steyerm.; = Psychotria glabrescens Müll. Arg.; = Psychotria megapontica Müll Arg.; = Uragoga colorata (Willd. ex Schult) Kuntze; = Uragoga glabrescens Müll. Arg.) Kuntze; = Uragoga megapontica (Müll. Arg.) Kuntze.	8-8a, 8'-8'a tetradehydroisocalycanthine 3a(R), 3a'(R)	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
	calycanthine (56)	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
	isocalycanthine (57)	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
	(+)-chimonanthine	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
	meso-chimonanthine (37) N_b-desmethyl-meso-chimonanthine (38)	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165. ⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
	hodgkinsine (39)	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
	quadrigemine B (89)	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
	quadrigemine C (40)	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
	psychotridine (42)	⁴⁶46 Verotta, L.; Pilati, T.; Tatò, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Nat. Prod. 1998, 61, 392. ^, ⁴⁷47 Verotta, L.; Peterlongo, F.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S.; J. Chromatogr. A 1999, 41, 165.
P. correae (Dwyer & M. V. Hayden) C. M. Taylor Synonymia: Cephaelis correae Dwyer & M. V. Hayden.	isodolichantoside (49)	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	correantoside (50)	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	correantine A (52)	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	correantine B (53)	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	20-epi-correantine B (55)	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	correantine C (54)	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	10-hydroxycorreantoside (51)	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	megastigm-5-ene-3,9-diol	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	S(+)-dehydrovomifoliol	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	lutein	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	rotungenic acid	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	clethric acid	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	daucosterol	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	stigmasterol glucoside (72)	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	cerebroside B_1b	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
	cerebroside	⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.
P. euricarpa Standl. Synonymia: Palicourea eurycarpa (Standl.) C. M. Taylor.	linalool	⁴⁹49 Setzer, W. N.; Noletto, J. A.; Haber, W. A.; J. Essent. Oil-Bear Plants 2006, 9, 28.
	methyl salicylate	⁴⁹49 Setzer, W. N.; Noletto, J. A.; Haber, W. A.; J. Essent. Oil-Bear Plants 2006, 9, 28.
P. forsteriana A. Gray Synonymia: Psychotria forsteriana var. vitiensis A. Gray; = Uragoga forsteriana (A. Gray) Drake.	calycanthine (56)	⁵⁰50 Adjibadé, Y.; Weniger, B.; Quirion, J. C.; Kuballa, B.; Cabalion, P.; Anton, R.; Phytochemistry 1991, 31, 317.
	iso-calycanthine (57)	⁵⁰50 Adjibadé, Y.; Weniger, B.; Quirion, J. C.; Kuballa, B.; Cabalion, P.; Anton, R.; Phytochemistry 1991, 31, 317.
	meso-chimonanthine (37)	⁵⁰50 Adjibadé, Y.; Weniger, B.; Quirion, J. C.; Kuballa, B.; Cabalion, P.; Anton, R.; Phytochemistry 1991, 31, 317.
	quadrigemine A (88)	⁵¹51 Roth, A.; Kuballa, B.; Bounthanh, C.; Caballion, P.; Sévenet, T.; Beck, J. P.; Anton, R.; Planta Med. 1986, 5, 450.
	quadrigemine B (89)	⁵¹51 Roth, A.; Kuballa, B.; Bounthanh, C.; Caballion, P.; Sévenet, T.; Beck, J. P.; Anton, R.; Planta Med. 1986, 5, 450.
	psychotridine (42)	⁵¹51 Roth, A.; Kuballa, B.; Bounthanh, C.; Caballion, P.; Sévenet, T.; Beck, J. P.; Anton, R.; Planta Med. 1986, 5, 450.
	isopsychotridine B (41)	⁵¹51 Roth, A.; Kuballa, B.; Bounthanh, C.; Caballion, P.; Sévenet, T.; Beck, J. P.; Anton, R.; Planta Med. 1986, 5, 450.
	quadrigemine G	⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.
	quadrigemine H	⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.
	hodgkinsine (39) isopsychotridine C (90)	⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.
	isopsychotridine D	⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.
	isopsychotridine E	⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.
	vatine (91)	⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.
	vatamine (92)	⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.
	vatamidine (93)	⁵²52 Adjibadé, Y.; Saad, H.; Kuballa, B.; Beck, J. P.; Sévenet, T.; Cabalion, P.; Anton, R.; J. Ethnopharmacol. 1990, 29, 127.
P. gitingensis Elmer Synonymia: Grumilea similis (Elmer) Merr.; = Grumilea versicolor (Elmer) Merr.; = Psychoria lucida Merr.; = Psychotria similis Elmer; = Psychotria versicolor Elmer.	vomifoliol (5)	¹⁷17 Tan, M. A.; Eusebio, J. A.; Alejandro, G. J. D.; Biochem. Syst. Ecol. 2012, 45, 20.
P. glomerulata (Donn.Sm.) Steyerm. Synonymia: Cephaelis glomerulata Donn. Sm.; = Palicourea glomerulata (Donn. Sm.) Borhidi.	glomerulatine A (46)	⁵³53 Solis, P. N.; Ravelo, A. G.; Palenzuela, J. A.; Gupta, M. P.; Gonzalez, A.; Phillipson, J. D.; Phytochemistry 1997, 44, 963.
	glomerulatine B (47)	⁵³53 Solis, P. N.; Ravelo, A. G.; Palenzuela, J. A.; Gupta, M. P.; Gonzalez, A.; Phillipson, J. D.; Phytochemistry 1997, 44, 963.
	glomerulatine C (⁴⁸48 Achenbach, H.; Lottes, M.; Waibel, R.; Karikas, G. A.; Correa, M. D. A.; Gupta, M. P.; Phytochemistry 1995, 38, 1537.)	⁵³53 Solis, P. N.; Ravelo, A. G.; Palenzuela, J. A.; Gupta, M. P.; Gonzalez, A.; Phillipson, J. D.; Phytochemistry 1997, 44, 963.
P. haianensis H. L. Li	β-sitosterol (71)	⁵⁴54 Li, H.-F.; Huang, J.; Liu, M.-S.; Zhang, X.-P.; Chin. J. Exp. Tradit. Med. Formulae 2011, 19, 125.
	stearic acid	⁵⁴54 Li, H.-F.; Huang, J.; Liu, M.-S.; Zhang, X.-P.; Chin. J. Exp. Tradit. Med. Formulae 2011, 19, 125.
	quercetin (73)	⁵⁴54 Li, H.-F.; Huang, J.; Liu, M.-S.; Zhang, X.-P.; Chin. J. Exp. Tradit. Med. Formulae 2011, 19, 125.
	rutin (77)	⁵⁴54 Li, H.-F.; Huang, J.; Liu, M.-S.; Zhang, X.-P.; Chin. J. Exp. Tradit. Med. Formulae 2011, 19, 125.
	daucosterol	⁵⁴54 Li, H.-F.; Huang, J.; Liu, M.-S.; Zhang, X.-P.; Chin. J. Exp. Tradit. Med. Formulae 2011, 19, 125.
P. henryi H. Lév.	psychohenin (13)	⁵⁵55 Liu, Y.; Wang, J.-S.; Wang, X.-B.; Kong, L.-Y.; J. Asian Nat. Prod. Res. 2014, 16, 29.
P. ipecacuanha (Brot.) Stokes Synonymia: Carapichea ipecacuanha (Brot.) L. Anderson.	emetine (12)	⁵⁶56 Moller, M.; Herzer, K.; Wenger, T.; Herr, I.; Wink, M.; Oncol. Rep. 2007, 18, 737.
	cephaeline (30)	⁵⁷57 Nomura, T.; Quesada, A. L.; Kutchan, T. M.; J. Biol. Chem. 2008, 283, 34650.
	ipecoside	⁵⁷57 Nomura, T.; Quesada, A. L.; Kutchan, T. M.; J. Biol. Chem. 2008, 283, 34650.
P. klugii Standl.	klugine (28)	⁵⁸58 Muhammad, I.; Dunbar, D. C.; Khan, S. I.; Tekwani, B. L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L. A.; J. Nat. Prod. 2003, 66, 962.
	7'-o-demethylisocephaeline (29)	⁵⁸58 Muhammad, I.; Dunbar, D. C.; Khan, S. I.; Tekwani, B. L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L. A.; J. Nat. Prod. 2003, 66, 962.
	cephaeline (30)	⁵⁸58 Muhammad, I.; Dunbar, D. C.; Khan, S. I.; Tekwani, B. L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L. A.; J. Nat. Prod. 2003, 66, 962.
	isocephaeline (31)	⁵⁸58 Muhammad, I.; Dunbar, D. C.; Khan, S. I.; Tekwani, B. L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L. A.; J. Nat. Prod. 2003, 66, 962.
	7-o-methylipecoside (32)	⁵⁸58 Muhammad, I.; Dunbar, D. C.; Khan, S. I.; Tekwani, B. L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L. A.; J. Nat. Prod. 2003, 66, 962.
	emetine (12)	⁵⁸58 Muhammad, I.; Dunbar, D. C.; Khan, S. I.; Tekwani, B. L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L. A.; J. Nat. Prod. 2003, 66, 962.
P. laciniata Vell. Synonymia: Psychotria kleinii L. B. Sm. & Downs; = Uragoga laciniata (Vell.) Kuntze.	strictosamide (22)	⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.
	lyaloside (26)	⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.
	vallesiachotamine (3)	⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.
	angustine (35)	⁶⁰60 Passos, C. S.; Simões-Pires, C. A.; Nurisso, A.; Soldi, T. C.; Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Marcourt, L.; Gottfried, C.; Carrupt, P. A.; Henriques, A. T.; Phytochemistry 2013, 86, 8.
	vallesiachotamine lactone (85)	⁶⁰60 Passos, C. S.; Simões-Pires, C. A.; Nurisso, A.; Soldi, T. C.; Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Marcourt, L.; Gottfried, C.; Carrupt, P. A.; Henriques, A. T.; Phytochemistry 2013, 86, 8.
	pauridianthoside	⁶⁰60 Passos, C. S.; Simões-Pires, C. A.; Nurisso, A.; Soldi, T. C.; Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Marcourt, L.; Gottfried, C.; Carrupt, P. A.; Henriques, A. T.; Phytochemistry 2013, 86, 8.
P. leiocarpa Cham. & Schltdl. Synonymia: Psychotria constricta Müll. Arg.; = Psychotria extratropica Müll. Arg.; = Psychotria lagoensis Müll. Arg.; = Psychotria nitidula Cham. & Schltdl.; = Psychotria psilogyne Müll. Arg.; = Psychotria tenella Müll. Arg.	asperuloside	⁶¹61 Lopes, S. O.; Poser, G. L. V.; Kerber, V. A.; Farias, F. M.; Konrath, E. L.; Moreno, P.; Sobral, M. E.; Zuanazzi, J. A. S.; Henriques, A. T.; Biochem. Syst. Ecol. 2004, 32, 1187.
	deacetylasperuloside	⁶¹61 Lopes, S. O.; Poser, G. L. V.; Kerber, V. A.; Farias, F. M.; Konrath, E. L.; Moreno, P.; Sobral, M. E.; Zuanazzi, J. A. S.; Henriques, A. T.; Biochem. Syst. Ecol. 2004, 32, 1187.
	N,b-D-glucopyranosyl vincosamide (15)	⁶²62 Henriques, A. T.; Lopes, S. O.; Paranhos, J. T.; Gregianini, T. S.; Von Poser, G. L.; Fett-Neto, A. G.; Schripsema, J.; Phytochemistry 2004, 65, 449.
	bicyclogermacrene	⁶³63 Andrade, J. M. M.; Biegelmeyer, R.; Xavier, C. A. G.; Bordignon, S. A. L.; Moreno, P. R. H.; Zuanazzi, J. A. S.; Henriques, A. T.; Apel, M. A.; Chem. Nat. Compd. 2010, 46, 649.
	germacrene	⁶³63 Andrade, J. M. M.; Biegelmeyer, R.; Xavier, C. A. G.; Bordignon, S. A. L.; Moreno, P. R. H.; Zuanazzi, J. A. S.; Henriques, A. T.; Apel, M. A.; Chem. Nat. Compd. 2010, 46, 649.
P. leptothyrsa Miq. Synonymia: Psychotria beccarii (K. Schum.) K. Schum.; = Psychotria beccarioides Wernham; = Psychotria montana var. gracillima Wernham; = Psychotria pedicellata Valeton; = Psychotria rugosa Valeton; = Psychotria salmoneiflora K. Schum.; = Psychotria schraderbergiensis Valeton; Uragoga beccarii (K. Schum.) Kuntze.	psyles A-F	⁶⁴64 Gerlach, S. L.; Burman, R.; Bohlin, L.; Mondal, D.; Goransson, U.; J. Nat. Prod. 2010, 73, 1207.
P. longipes Müll. Arg. Synonymia: Psychotria vellosiana Benth.	cyclopsychotride A	⁶⁵65 Witherup, K. M.; Bogusky, M. J.; Anderson, P. M.; Ramjit, H.; Ransom, R. W.; Wood, T.; Sardana, M.; J. Nat. Prod. 1994, 57, 1619.
P. lyciiflora (Baill.) Schltr. Synonymia: Uragoga lyciiflora Baill.	meso-chimonanthine (37)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838.
	hodgkinsine (39)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838.
	N_b-desmethyl-meso-chimonanthine (38)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838.
P. malayana Jack Synonymia: Chassalia expansa Miq.; = Grumilea aurantiaca (Wall.) Miq.; = Psychotria aurantiaca Wall.; = Psychotria stipulacea Wall.; = Uragoga malayana (Jack) Kuntze	(+)-chimonanthine	⁶⁷67 Hadi, S.; Asnawati, D.; Ersalena, V.F.; Azwari, A.; Rahmawati, K. P.; J. Pure Appl. Chem. Res. 2014, 3, 108.
	(−)-chimonanthine	⁶⁷67 Hadi, S.; Asnawati, D.; Ersalena, V.F.; Azwari, A.; Rahmawati, K. P.; J. Pure Appl. Chem. Res. 2014, 3, 108.
	meso-chimonanthine (37)	⁶⁷67 Hadi, S.; Asnawati, D.; Ersalena, V.F.; Azwari, A.; Rahmawati, K. P.; J. Pure Appl. Chem. Res. 2014, 3, 108.
	calycanthine (56)	⁶⁷67 Hadi, S.; Asnawati, D.; Ersalena, V.F.; Azwari, A.; Rahmawati, K. P.; J. Pure Appl. Chem. Res. 2014, 3, 108.
	hodgkinsine (39)	⁶⁷67 Hadi, S.; Asnawati, D.; Ersalena, V.F.; Azwari, A.; Rahmawati, K. P.; J. Pure Appl. Chem. Res. 2014, 3, 108.
	2-ethyl-6-methylpyrazine	⁶⁷67 Hadi, S.; Asnawati, D.; Ersalena, V.F.; Azwari, A.; Rahmawati, K. P.; J. Pure Appl. Chem. Res. 2014, 3, 108.
	3-methyl-1,2,3,4-tetrahydro-gamma-carboline	⁶⁷67 Hadi, S.; Asnawati, D.; Ersalena, V.F.; Azwari, A.; Rahmawati, K. P.; J. Pure Appl. Chem. Res. 2014, 3, 108.
P. mariniana (Cham. & Schltdl.) Fosberg Synonymia: Coffea mariniana Cham. & Schltdl.; = Psychotria hawaiiensis var. glabrithyrsa Fosberg; = Straussia mariniana (Cham. & Schltdl.) A. Gray	β-sitosterol (71)	⁶⁸68 Gonzalez, J.; Dieck, T.; Rev. Latinoam. Quim. 1996, 24, 7.
	betulin	⁶⁸68 Gonzalez, J.; Dieck, T.; Rev. Latinoam. Quim. 1996, 24, 7.
	lupeol (66)	⁶⁸68 Gonzalez, J.; Dieck, T.; Rev. Latinoam. Quim. 1996, 24, 7.
	ursolic acid (94)	⁶⁸68 Gonzalez, J.; Dieck, T.; Rev. Latinoam. Quim. 1996, 24, 7.
	asperuloside	⁶⁸68 Gonzalez, J.; Dieck, T.; Rev. Latinoam. Quim. 1996, 24, 7.
P. myriantha Müll. Arg.	strictosidinic acid (11)	⁶⁹69 Farias, F. M.; Passos, C. S.; Arbo, M. D.; Barros, D. M.; Gottfried, C.; Steffen, V. M.; Henriques, A. T.; Fitoterapia 2012, 83, 1138.
P. myriantha Müll. Arg.	myrianthosine	⁷⁰70 Simões-Pires, C. A.; Farias, F. M.; Marston, A.; Queiroz, E. F.; Chaves, C. G.; Henriques, A. T.; Hostettmann, K.; Nat. Prod. Commun. 2006, 1, 1101.
P. nuda (Cham. & Schltdl.) Wawra Synonymia: Cephaelis nuda Cham. & Schltdl.; = Psychotria brasiliensis Vell.; = Psychotria hirtipes Müll. Arg.; = Psychotria involucellaris Müll. Arg.; = Psychotria multicolor Müll. Arg.; = Psychotria obfuscata Müll. Arg.; = Suteria brasiliensis (Vell.) Mart.; = Suteria macrantha Gardner; = Uragoga brasiliensis (Vell.) Kuntze; = Uragoga hirtipes (Müll. Arg.) Kuntze.	srictosamide (22)	⁷¹71 Farias, F. M.; Konrath, E. L.; Zuanazzi, J. A. S.; Henriques, A. T.; Biochem. Syst. Ecol. 2009, 36, 919.
P. oleoides (Baill.) Schltr. Synonymia: Uragoga oleoides Baill.	hodgkinsine (39)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
	quadrigemine C (40)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
	isopsychotridine A	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
	isopsychotridine B (41)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
	psychotridine (42)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
	quadrigemine I (43)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
	oleoidine (44)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
	caledonine (45)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
	psycholeine (105)	⁶⁶66 Jannic, V.; Gueritte, F.; Laprevote, O.; Serani, L.; Martin, M.-T.; Sevenet, T.; Potier, P.; J. Nat. Prod. 1999, 62, 838. ^, ⁷²72 Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guénard, D.; Potier, P.; J. Nat. Prod. 1992, 55, 923.
P. pilífera Hutch.	psychotripine (23)	⁷³73 Li, X.-N.; Zhang, Y.; Cai, X.-H.; Feng, T.; Liu, Y.-P.; Li, Y.; Ren, J.; Zhu, H.-J.; Luo, X.-D.; Org. Lett. 2011, 13, 5896.
P. prunifolia (Kunth) Steyerm. Synonymia: Cephaelis microcephala Wild. ex Schult.; = Cephaelis prunifolia Kunth; = Psychotria xanthocephala Müll. Arg.; = Tapogomea prunifolia (Kunth) Poir.; = Uragoga fuscostipulata Kuntze; =Uragoga microcephala (Wild. Ex Schult) Kutze; = Uragoga prunifolia (Kunth) Kuntze; = Uragoga xanthocephala (Müll. Arg.) Kuntze.	10-hydroxyisodeppeaninol (19)	⁷⁴74 Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Ribeiro, L. C.; Carvalho, B. G.; Silva, C. C.; Schuquel, I. T. A.; Santin, S. M. O.; Nakamura, C. V.; Britta, E. A.; Miranda, N.; Iglesias, A. H.; Delprete, P. G.; J. Braz. Chem. Soc. 2012, 23, 355. ^, ⁷⁵75 Faria, E. O.; Kato, L.; Oliveira, C. M. A.; Carvalho, B. G.; Silva, C. C.; Sales, L. S.; Schuquel, I. T. A.; Silveira-Lacerda, E. P.; Delprete, P. G.; Phytochem. Lett. 2010, 3, 113.
	10-hydroxy-antirhirine	⁷⁴74 Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Ribeiro, L. C.; Carvalho, B. G.; Silva, C. C.; Schuquel, I. T. A.; Santin, S. M. O.; Nakamura, C. V.; Britta, E. A.; Miranda, N.; Iglesias, A. H.; Delprete, P. G.; J. Braz. Chem. Soc. 2012, 23, 355. ^, ⁷⁵75 Faria, E. O.; Kato, L.; Oliveira, C. M. A.; Carvalho, B. G.; Silva, C. C.; Sales, L. S.; Schuquel, I. T. A.; Silveira-Lacerda, E. P.; Delprete, P. G.; Phytochem. Lett. 2010, 3, 113.
	10-hydroxyantirhine N-oxide (20)	⁷⁴74 Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Ribeiro, L. C.; Carvalho, B. G.; Silva, C. C.; Schuquel, I. T. A.; Santin, S. M. O.; Nakamura, C. V.; Britta, E. A.; Miranda, N.; Iglesias, A. H.; Delprete, P. G.; J. Braz. Chem. Soc. 2012, 23, 355. ^, ⁷⁵75 Faria, E. O.; Kato, L.; Oliveira, C. M. A.; Carvalho, B. G.; Silva, C. C.; Sales, L. S.; Schuquel, I. T. A.; Silveira-Lacerda, E. P.; Delprete, P. G.; Phytochem. Lett. 2010, 3, 113.
	14-oxoprunifoleine (21)	⁷⁴74 Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Ribeiro, L. C.; Carvalho, B. G.; Silva, C. C.; Schuquel, I. T. A.; Santin, S. M. O.; Nakamura, C. V.; Britta, E. A.; Miranda, N.; Iglesias, A. H.; Delprete, P. G.; J. Braz. Chem. Soc. 2012, 23, 355. ^, ⁷⁵75 Faria, E. O.; Kato, L.; Oliveira, C. M. A.; Carvalho, B. G.; Silva, C. C.; Sales, L. S.; Schuquel, I. T. A.; Silveira-Lacerda, E. P.; Delprete, P. G.; Phytochem. Lett. 2010, 3, 113.
	prunifoleine (84)	⁷⁴74 Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Ribeiro, L. C.; Carvalho, B. G.; Silva, C. C.; Schuquel, I. T. A.; Santin, S. M. O.; Nakamura, C. V.; Britta, E. A.; Miranda, N.; Iglesias, A. H.; Delprete, P. G.; J. Braz. Chem. Soc. 2012, 23, 355. ^, ⁷⁵75 Faria, E. O.; Kato, L.; Oliveira, C. M. A.; Carvalho, B. G.; Silva, C. C.; Sales, L. S.; Schuquel, I. T. A.; Silveira-Lacerda, E. P.; Delprete, P. G.; Phytochem. Lett. 2010, 3, 113.
	strictosamide (22)	⁷⁴74 Kato, L.; Oliveira, C. M. A.; Faria, E. O.; Ribeiro, L. C.; Carvalho, B. G.; Silva, C. C.; Schuquel, I. T. A.; Santin, S. M. O.; Nakamura, C. V.; Britta, E. A.; Miranda, N.; Iglesias, A. H.; Delprete, P. G.; J. Braz. Chem. Soc. 2012, 23, 355. ^, ⁷⁵75 Faria, E. O.; Kato, L.; Oliveira, C. M. A.; Carvalho, B. G.; Silva, C. C.; Sales, L. S.; Schuquel, I. T. A.; Silveira-Lacerda, E. P.; Delprete, P. G.; Phytochem. Lett. 2010, 3, 113.
P. rostrata Blume Synonymia: Chassalia rostrata (Blume) Miq.; = Polyozus acuminata Blume; = Polyozus latifolia Blume; = Uragoga rostrata (Blume) Kuntze.	quadrigemine B	⁷⁶76 Mahmud, Z.; Musa, M.; Ismail, N.; Lajis, N. H.; Int. J. Pharmacol. 1993, 31, 142.
	psychotrimine (17)	⁷⁷77 Takayama, H.; Mori, I.; Kitajima, M.; Aimi, N.; Lajis, N. H.; Org. Lett. 2004, 6, 2945.
	psychopentamine (18)	⁷⁷77 Takayama, H.; Mori, I.; Kitajima, M.; Aimi, N.; Lajis, N. H.; Org. Lett. 2004, 6, 2945.
P. rubra (Willd. ex Schult.) Müll. Arg. Synonymia: Psychotria hoffmannseggiana (Willd. Ex Schult.) Müll. Arg.	helenalin	⁷⁸78 Hayashi, T.; Smith, F. T.; Lee, K.-H.; J. Med. Chem. 1987, 30, 2005.
	psychorubrin (86)	⁷⁸78 Hayashi, T.; Smith, F. T.; Lee, K.-H.; J. Med. Chem. 1987, 30, 2005.
	psyrubrin A	⁷⁹79 Lu, H.-X.; Liu, L.-Y.; Li, D.-P.; Li, J.-Z.; Xu, L.-C.; Biochem. Syst. Ecol. 2014, 57, 133.
	6-hydroxy-luteolin-7-o-rutinoside (75)	⁷⁹79 Lu, H.-X.; Liu, L.-Y.; Li, D.-P.; Li, J.-Z.; Xu, L.-C.; Biochem. Syst. Ecol. 2014, 57, 133.
	luteolin-7-o-rutinoside (76)	⁷⁹79 Lu, H.-X.; Liu, L.-Y.; Li, D.-P.; Li, J.-Z.; Xu, L.-C.; Biochem. Syst. Ecol. 2014, 57, 133.
	6α-hydroxygeniposide	⁷⁹79 Lu, H.-X.; Liu, L.-Y.; Li, D.-P.; Li, J.-Z.; Xu, L.-C.; Biochem. Syst. Ecol. 2014, 57, 133.
P. serpens L. Synonymia: Grumilea serpens (L.) K. Schum.; = Psychotria scandens Hook. & Arn.; = Psychotria serpens var. latifolia Pit.; = Uragoga serpens (L.) Kuntze.	ursolic acid (94)	⁸⁰80 Lee, K.-H.; Lin, Y.-M.; Wu, T.-S.; Zhang, D.-C.; Yamagishi, T.; Hayashi, T.; Hall, I. H.; Chang, J.-J.; Wu, R.-Y.; Yang, T.-H.; Planta Med. 1988, 54, 308.
	rutin (77)	⁸¹81 Lin, C.-H.; Wu, A.-Z.; Zhong, Y.; Wang, Y.-W.; Peng, G.-T.; Su, X.-J.; Liu, B.-X.; Deng, Y.; Zhu, C.-C.; Zhang, C.-X.; J. Cancer Res. Updates 2015, 3, 60.
	quercetin (73)	⁸¹81 Lin, C.-H.; Wu, A.-Z.; Zhong, Y.; Wang, Y.-W.; Peng, G.-T.; Su, X.-J.; Liu, B.-X.; Deng, Y.; Zhu, C.-C.; Zhang, C.-X.; J. Cancer Res. Updates 2015, 3, 60.
	tamarixetin-3-o-rutinoside (78)	⁸¹81 Lin, C.-H.; Wu, A.-Z.; Zhong, Y.; Wang, Y.-W.; Peng, G.-T.; Su, X.-J.; Liu, B.-X.; Deng, Y.; Zhu, C.-C.; Zhang, C.-X.; J. Cancer Res. Updates 2015, 3, 60.
	kaempferol (79)	⁸¹81 Lin, C.-H.; Wu, A.-Z.; Zhong, Y.; Wang, Y.-W.; Peng, G.-T.; Su, X.-J.; Liu, B.-X.; Deng, Y.; Zhu, C.-C.; Zhang, C.-X.; J. Cancer Res. Updates 2015, 3, 60.
P. spectabilis Steyerm. Synonymia: Cephaelis duckei Standl.	deoxysolidagenone (104)	¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.
	solidagenone (103)	¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.
	coumarin (81)	¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.
	umbelliferone (82)	¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.
	psoralene (83)	¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.
	quercetin (73)	¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.
	quercetrin (74)	¹³13 Benevides, P. J. C.; Young, M. C. M.; Bolzani, V. S.; Pharm. Biol. 2004, 42, 565.
P. stachyoides Benth. Synonymia: Psychotria hygrophiloides Benth.; = Psychotria mesotropa Müll. Arg.; = Psychotria purpurascens Müll. Arg.; = Uragoga hygrophilodes (Benth.) Kuntze; = Uragoga mesotropa (Müll. Arg.) Kuntze; = Uragoga purpurascens (Müll. Arg.) Kuntze; = Uragoga stachyoides (Benth.) Kuntze.	stachyoside (24)	⁸²82 Pimenta, A. T. A.; Braz-Filho, R.; Delprete, P. G.; Bezerra, E. S.; Silveira, E. R.; Lima, M. A. S.; Magn. Reson. Chem. 2010, 48, 734.
	nor-methyl-23-oxo-correantoside (25)	⁸²82 Pimenta, A. T. A.; Braz-Filho, R.; Delprete, P. G.; Bezerra, E. S.; Silveira, E. R.; Lima, M. A. S.; Magn. Reson. Chem. 2010, 48, 734.
	correantosine E	⁸²82 Pimenta, A. T. A.; Braz-Filho, R.; Delprete, P. G.; Bezerra, E. S.; Silveira, E. R.; Lima, M. A. S.; Magn. Reson. Chem. 2010, 48, 734.
	correantosine F	⁸²82 Pimenta, A. T. A.; Braz-Filho, R.; Delprete, P. G.; Bezerra, E. S.; Silveira, E. R.; Lima, M. A. S.; Magn. Reson. Chem. 2010, 48, 734.
	N-demethylcorreantoside	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
	bizantionoside B	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
	α-amyrin	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
	alizarine methyl-ether	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
	rubiadine	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
	scopoletin (80)	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
	barbinevic acid	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
	daucosterol	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
	stigmasterol glucoside (72)	¹²12 Pimenta, A. T. A.; Uchôa, D. E. A.; Braz-Filho, R.; de Souza, E. B.; Silveira, E. R.; Lima, M. A. S.; J. Braz. Chem. Soc. 2011, 22, 2216.
P. suerrensis Donn. Sm.	harmane (10)	⁸³83 Murillo, R.; Castro, V.; Ing. Cienc. Quim. 1998, 18, 61.
P. suterella Müll. Arg. Synonymia: Psychotria estrellana Müll. Arg.; = Psychotria estrellana var. lanceolata Müll. Arg.; = Suteria parviflora Gardner; = Uragoga estrellana (Müll. Arg.) Kuntze; = Uragoga suterella (Müll. Arg.) Kuntze.	lyaloside (26)	⁸⁴84 van de Santos, L.; Fett-Neto, A. G.; Kerber, V. A.; Elisabetsky, E.; Quirion, J. C.; Henriques, A. T.; Biochem. Syst. Ecol. 2001, 29, 1185. ^, ⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.
	strictosamide (22)	⁸⁴84 van de Santos, L.; Fett-Neto, A. G.; Kerber, V. A.; Elisabetsky, E.; Quirion, J. C.; Henriques, A. T.; Biochem. Syst. Ecol. 2001, 29, 1185. ^, ⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.
	naucletine (27)	⁸⁴84 van de Santos, L.; Fett-Neto, A. G.; Kerber, V. A.; Elisabetsky, E.; Quirion, J. C.; Henriques, A. T.; Biochem. Syst. Ecol. 2001, 29, 1185. ^, ⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.
	vallesiachotamine (3)	⁸⁴84 van de Santos, L.; Fett-Neto, A. G.; Kerber, V. A.; Elisabetsky, E.; Quirion, J. C.; Henriques, A. T.; Biochem. Syst. Ecol. 2001, 29, 1185. ^, ⁵⁹59 Passos, C. S.; Soldi, T. C.; Abib, R. T.; Apel, M. A.; Simões-Pires, C.; Marcourt, L.; Gottfried, C.; Henriques, A. T.; J. Enzyme Inhib. Med. Chem. 2013, 28, 611.
	cyclotide PS-1	⁸⁵85 Gruber, C. W.; Elliott, A. G.; Ireland, D. C.; Delprete, P. G.; Dessein, S.; Göransson, U.; Trabi, M.; Wang, C. K.; Kinghorn, A. B.; Robbrecht, E.; Craik, D. J.; Plant Cell 2008, 20, 2471.
P. umbellata Vell. Synonymia: Psychotria brachyopoda (Müll. Arg.) Britton	psychollatine umbellatine (6)	⁸⁶86 Kerber, V. A.; Passos, C. S.; Verli, H.; Fett-Neto, A. G.; Quirion, J. P.; Henriques, A. T.; J. Nat. Prod. 2008, 71, 697. ^, ⁸⁷87 Both, F. L.; Farias, F. M.; Nicoláo, L. L.; Misturini, J.; Henriques, A. T.; Elisabetsky, E.; Rev. Bras. Pl. Med. 2002, 5, 41. ⁸⁶86 Kerber, V. A.; Passos, C. S.; Verli, H.; Fett-Neto, A. G.; Quirion, J. P.; Henriques, A. T.; J. Nat. Prod. 2008, 71, 697. ^, ⁸⁸88 Kerber, V. A.; Passos, C. S.; Klein-Junior, L. C.; Quirion, J.-C.; Pannecoucke, X.; Salliot-Maire, I.; Henriques, A. T.; Tetrahedron Lett. 2014, 55, 4798.
	3,4-dehydro-18,19-β-epoxy-psychollatine (7)	⁸⁸88 Kerber, V. A.; Passos, C. S.; Klein-Junior, L. C.; Quirion, J.-C.; Pannecoucke, X.; Salliot-Maire, I.; Henriques, A. T.; Tetrahedron Lett. 2014, 55, 4798.
	N₄-[1-((R)-2-hydroxypropyl)]-psycholatine (8) N₄-[1-((S)-2-hydroxypropyl)]-psycholatine (9)	⁸⁸88 Kerber, V. A.; Passos, C. S.; Klein-Junior, L. C.; Quirion, J.-C.; Pannecoucke, X.; Salliot-Maire, I.; Henriques, A. T.; Tetrahedron Lett. 2014, 55, 4798.
P. vellosiana Benth. Synonymia: Cephaelis attenuata Miq.; = Coffea sessilis Vell.; = Psychotria caloneura Müll. Arg.; = Psychotria hancorniifolia Benth; = Psychotria longipes Müll. Arg.; = Psychotria sororopanenensis Standl. & Steyerm.; = Psychotria velutipes Müll. Arg.; Uragoga caloneura (Müll. Arg.) Kuntze; Uragoa hancornifolia (Benth.) Kuntze; Uragoga interjecta (Müll. Arg.) Kuntze; Uragoga janeirensis (Müll. Arg.) Kuntze; Uragoga longipes (Müll. Arg.) Kuntze; = Uragoga pachyneura (Müll. Arg.) Kuntze.	squalene (65)	⁸⁹89 Moreno, B. P.; Fiorucci, L. L. R.; Carmo, M. R. B.; Sarragiotto, M. H.; Baldoqui, D. C.; Biochem. Syst. Ecol. 2014, 56, 80.
	lupeol (66)	⁸⁹89 Moreno, B. P.; Fiorucci, L. L. R.; Carmo, M. R. B.; Sarragiotto, M. H.; Baldoqui, D. C.; Biochem. Syst. Ecol. 2014, 56, 80.
	stigmasterol (68)	⁸⁹89 Moreno, B. P.; Fiorucci, L. L. R.; Carmo, M. R. B.; Sarragiotto, M. H.; Baldoqui, D. C.; Biochem. Syst. Ecol. 2014, 56, 80.
	sitosterol (67)	⁸⁹89 Moreno, B. P.; Fiorucci, L. L. R.; Carmo, M. R. B.; Sarragiotto, M. H.; Baldoqui, D. C.; Biochem. Syst. Ecol. 2014, 56, 80.
	scopoletin (80)	⁸⁹89 Moreno, B. P.; Fiorucci, L. L. R.; Carmo, M. R. B.; Sarragiotto, M. H.; Baldoqui, D. C.; Biochem. Syst. Ecol. 2014, 56, 80.
P. viridis Ruiz & Pav. Synonymia: Palicourea viridis (Ruiz & Pav.) Schult.; = Psychotria glomerata Kunth; = Psychotria microdesmia Oerst.; = Psychotria trispicata Griseb.; = Uragoga glomerata (Kunth) Kuntze; = Uragoga microdesmia (Oerst.) kuntze; = Uragoga trispicata (Griseb.) Kuntze; Uragoga viridis (Ruiz & Pav.) Kuntze.	harmine	⁹⁰90 Callaway, J. C.; Brito, G. S.; Neves, E. S.; J. Psychoact. Drugs 2005, 37, 145.
	harmaline	⁹⁰90 Callaway, J. C.; Brito, G. S.; Neves, E. S.; J. Psychoact. Drugs 2005, 37, 145.
	tetrahydroharmine	⁹⁰90 Callaway, J. C.; Brito, G. S.; Neves, E. S.; J. Psychoact. Drugs 2005, 37, 145.
	N, N-dimethyltryptamine (36)	⁹¹91 Blackledge, R. D.; Taylor, C. M.; Microgram J. 2003, 1, 18. ^, ⁹⁰90 Callaway, J. C.; Brito, G. S.; Neves, E. S.; J. Psychoact. Drugs 2005, 37, 145. ^, ⁹²92 Reyna, V. P.; Torpoco, C. V.; Bol. Soc. Quim. Peru 1994, 60, 21.
P. yunnanensis Hutch. Synonymia: Psychotria kwangsiensis H. L. Li.	blumenol A	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	drummondol	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	(−)-loliolide	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	(6S)-menthiafolic acid	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	salicylic acid	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	resorcinol	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	4-hydroxybenzoic acid	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	vanillic acid	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	syringic acid	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	ethyl protocatechuate	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	3-hydroxy-1-(3,5-dimetoxy-4-hydroxyphenyl)propan-1-one	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	β-hydroxypropiovanillone	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	(+)-syringaresinol	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	2-(4-hydroxy-3-metoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	(−)-butin	⁹³93 Lu, Q.; Wang, J.; Kong, L.; Biochem. Syst. Ecol. 2014, 52, 20.
	psycacoraone A (63)	³⁶36 Lu, Q.; Wang, J.; Luo, J.; Wang, X.; Shan, S.; Kong, L.; Nat. Prod. Res. 2014, 28, 1659.

Name	Sequence	Plant	Reference
Cyclopsychotride A	-SIPCGESCVFIP-CTVTALLGCSCKSKV-CYKN	P. longipes	⁶⁵65 Witherup, K. M.; Bogusky, M. J.; Anderson, P. M.; Ramjit, H.; Ransom, R. W.; Wood, T.; Sardana, M.; J. Nat. Prod. 1994, 57, 1619.
PS-1	GFIPCGETCIWDKTCHAAG---CSCSVANICVRN	P. suterella	⁸⁵85 Gruber, C. W.; Elliott, A. G.; Ireland, D. C.; Delprete, P. G.; Dessein, S.; Göransson, U.; Trabi, M.; Wang, C. K.; Kinghorn, A. B.; Robbrecht, E.; Craik, D. J.; Plant Cell 2008, 20, 2471.
Psyle A	GIA-CGESCVFLG-CFIPG---CSCKSKV-CYFN	P. leptothyrsa	⁶⁴64 Gerlach, S. L.; Burman, R.; Bohlin, L.; Mondal, D.; Goransson, U.; J. Nat. Prod. 2010, 73, 1207.
Psyle B	GIP-CGETCVAFG-CWIPG—--CSCKDKL-CYYD	P. leptothyrsa	⁶⁴64 Gerlach, S. L.; Burman, R.; Bohlin, L.; Mondal, D.; Goransson, U.; J. Nat. Prod. 2010, 73, 1207.
Psyle C	--KLCGETCFKFK-CYTPG---CSCSYFP-CK--	P. leptothyrsa	⁶⁴64 Gerlach, S. L.; Burman, R.; Bohlin, L.; Mondal, D.; Goransson, U.; J. Nat. Prod. 2010, 73, 1207.
Psyle D	GIP-CGESCVFIP-CTVTALLGCSCQNKV-CYRD	P. leptothyrsa	⁶⁴64 Gerlach, S. L.; Burman, R.; Bohlin, L.; Mondal, D.; Goransson, U.; J. Nat. Prod. 2010, 73, 1207.
Psyle E	GVIPCGESCVFIP-CISSVLG-CSCKNKV-CYRD	P. leptothyrsa	⁶⁴64 Gerlach, S. L.; Burman, R.; Bohlin, L.; Mondal, D.; Goransson, U.; J. Nat. Prod. 2010, 73, 1207.
Psyle F	GVIPCGESCVFIP-CITAAVG-CSCKNKV-CYRD	P. leptothyrsa	⁶⁴64 Gerlach, S. L.; Burman, R.; Bohlin, L.; Mondal, D.; Goransson, U.; J. Nat. Prod. 2010, 73, 1207.
Psybra 1	GLPICGETCTLGT-CNTPG---CTCSWPI-CTKN	P. brachiata	¹⁰³103 Sacconnay, L.; Ryckewaert, L.; Passos, C. S.; Guerra, M. C.; Kato, L.; Oliveira, C. M. A. O.; Henriques, A.; Carrupt, P.-A.; Simões-Pires, C.; Nurisso, A.; Planta Med. 2015, 81, 517.
Psyde f1^a aPartial structure; Cys residues are highlighted in gray.	---XC--XCX----CNTSG---CTCK-WX-CTRX	P. deflexa	¹⁰³103 Sacconnay, L.; Ryckewaert, L.; Passos, C. S.; Guerra, M. C.; Kato, L.; Oliveira, C. M. A. O.; Henriques, A.; Carrupt, P.-A.; Simões-Pires, C.; Nurisso, A.; Planta Med. 2015, 81, 517.
Psyde f2^a aPartial structure; Cys residues are highlighted in gray.	---XCXESCWTSN-CFTSP---CXCX-HP-CTRX	P. deflexa	¹⁰³103 Sacconnay, L.; Ryckewaert, L.; Passos, C. S.; Guerra, M. C.; Kato, L.; Oliveira, C. M. A. O.; Henriques, A.; Carrupt, P.-A.; Simões-Pires, C.; Nurisso, A.; Planta Med. 2015, 81, 517.
Psypoe 1	GSVICGETCFTTV-CNTPG---CYCGAYX-CTRN	P. poeppigiana	¹⁰³103 Sacconnay, L.; Ryckewaert, L.; Passos, C. S.; Guerra, M. C.; Kato, L.; Oliveira, C. M. A. O.; Henriques, A.; Carrupt, P.-A.; Simões-Pires, C.; Nurisso, A.; Planta Med. 2015, 81, 517.
Psysol 1^a aPartial structure; Cys residues are highlighted in gray.	---XC--XCX----CYTPG---CTCGSYFVCNX-	P. solitudinum	¹⁰³103 Sacconnay, L.; Ryckewaert, L.; Passos, C. S.; Guerra, M. C.; Kato, L.; Oliveira, C. M. A. O.; Henriques, A.; Carrupt, P.-A.; Simões-Pires, C.; Nurisso, A.; Planta Med. 2015, 81, 517.
Psysol 2	GLPICGESCVGGT-CNTPG---CTCTWPV-CTRN	P. solitudinum	104
Psysue 1^a aPartial structure; Cys residues are highlighted in gray.	---XC--XCX----CXIAG---CSCSSALLCVX-	P. suerensis	¹⁰³103 Sacconnay, L.; Ryckewaert, L.; Passos, C. S.; Guerra, M. C.; Kato, L.; Oliveira, C. M. A. O.; Henriques, A.; Carrupt, P.-A.; Simões-Pires, C.; Nurisso, A.; Planta Med. 2015, 81, 517.
Psysue 2^a aPartial structure; Cys residues are highlighted in gray.	---XC--XCX----CXIAG---CSCSSALLCVX-	P. suerensis	¹⁰³103 Sacconnay, L.; Ryckewaert, L.; Passos, C. S.; Guerra, M. C.; Kato, L.; Oliveira, C. M. A. O.; Henriques, A.; Carrupt, P.-A.; Simões-Pires, C.; Nurisso, A.; Planta Med. 2015, 81, 517.

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