Brief Review on <i>Piper aduncum</i> L., its Bioactive Metabolites and its Potential to Develop Bioproducts

Conflicts of Interest: The authors declare no conflict of interest. Funders had no role in the design of the study; in the collection, analyses and interpretation of data; in the writing of the manuscript, nor in the decision to publish the results.

Figures (3)
Tables (1)

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Figure 1
Piper aduncum L. (Piperaceae) or pimenta-de-macaco in Brazilian Portuguese.

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Figure 2
Chemical constituents isolated from P. aduncum: 1: dillapiole (4,5-methyl-1-nodioxy-2,3-dimethoxy-allyl-benzene); 2: pseudo-dilla-2-piole (2,3-methylenodioxy-4,5- dimethoxy-allyl-benzene); 3: 3-(3’,7’-dimethyl-2’,6’-octa-dienyl)-4-methoxy-methyl benzoate; 4: 3-(3’,7’-dimethyl-2’,6’-octa-dienyl)-4-methoxy-benzoic acid; 5: 3-(6’-hydroxy-3’,7’-dimethyl-2’,7’-octa-dienyl)-4-methoxy- methyl benzoate; 6: 3-(2’-hydroxy-3’-methyl-3’-butenyl)-4-hydroxy-methyl benzoate; 7: 4-methoxy-3,5-bis(3’-methyl-2’-butenyl)-benzoic acid; 8: nervonic acid (4-hydroxy-3,5-bis(3-methyl-2-butenyl) benzoic acid); 9: 3,5-bis(3-methyl-2-butenyl)-4-methoxy-methyl benzoate; 10: 4-hydroxy-3-(3-methyl-2-butenoyl)-5-(3-methyl-2-butenyl)-benzoic acid; 11: 4-hydroxy-3,5-bis(3’-methyl-2’-butenyl)-11-methyl benzoate; 12: 4-hydroxy-3-(3-methyl-2-butenyl)-methyl benzoate; 13: 1-(1-methylethyl)-4-methyl-3-cyclohexanol 3,5-bis(3-methyl-2-butenyl)-4-hydroxy-benzoate; 14: 1-(1-methylethyl)-4-methyl-3-cyclohexanol 3,5-bis(3-methyl-2-butenyl)-4-methoxy-benzoate; 15: 2,2-dimethyl-8-(3’-methyl-2’-butenyl)-2H-chromeno-6-carboxylic acid; 16: 2,2-dimethyl-8-(3’-methyl-2’-butenyl)-2H-chromeno-6-methyl carboxylate; 17: 2,2-dimethyl-2H-chromeno-6-methyl carboxylate; 18: 2,2-dimethyl-2H-chromeno-6-carboxylic acid ; 19: 8-hydroxy-2,2-dimethyl-2H-chromeno-6-methyl carboxylate; 20: (6S)-2-trans-6- hydroxy-2,6-dimethyl-2,7-octadienoate; 21: 2’,6’-dihydroxy-4’-methoxy-dihydrochalcone; 22: 2’,4,6’-trihydroxy-4’-methoxy-dihydrochalcone; 23: 2’, 6’-dihydroxy-4’-methoxy-chalcone; 24: 2’-hydroxy-4’,6’-dimethoxy-dihydrochalcone; 25: 2’,4-dihydroxy-4’,6’,3-trimethoxy-dihydro-chalcone; 26: 2’,4-dihydroxy-4’,6’-dimethoxy-dihydrochalcone; 27: sakuranetin; 28: 5-hydroxy-7-methoxy-flavone; 29: 7-hydroxy-5-methoxy-dihydro-flavone; 30: piperaduncina A (3-(1-[2,4-dihydroxy-6-methoxy-3-(3-phenylpropanol)-phenyl]-3-methyl-2- butenyl)-4-hydroxy-methyl benzoate); 31: piperaduncina B (4-hydroxy-3-[2,3-dihidro-2-(1-hydroxy-1-methyl-ethyl)-6-hydroxy-4-methoxy-7-(3-phenyl-propanoil)-benzo[b]furan-3-il] methyl benzoate); 32: piperaduncina C (bis-[a, b-dihidro-2’,6’-dihydroxy-4’-methoxy-chalcone-5’-il] methane) [²³23 Pohlit AM, Pinto ACS, Mause R. Piper aduncum L.: Planta Pluripotente e Fonte de Substâncias fonte de Substâncias Fitoquímicas Importantes [Piper aduncum L.: Pluripotente Plant and Important Phytochemical Substance Source]. Rev. Fitos 2006; 2(1): 7-18.].

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Figure 3
Main chemical constituents found in the EOs of P. aduncum (Piperaceae) [¹1 Valadares ACF, Alves CCF, Alves JM, Deus IPB, Filho JGO, Santos TCL, et al. Essential oils from Piper aduncum inflorescences and leaves: chemical composition and antifungal activity against Sclerotinia sclerotiorum. An. Acad. Bras. Ciênc. 2018; 90(3): 2691-99., ²2 Oliveira GL, Cardoso SK, Júnior CRL, Vieira TM, Guimarães EF, Figueiredo LS, et al. Chemical study and larvicidal activity against Aedes aegypti of essential oil of Piper aduncum L. (Piperaceae). An. Acad. Bras. Ciênc. 2013; 85(04):1227-34., ⁵5 Monzote L, Scull R, Cos P, Setzer WN. Essential oil from Piper aduncum: chemical analysis, antimicrobial assessment, and literature review. Medicines 2017;4(3):49.]: terpinene-4-ol (1); piperitone (2); β-caryophyllene (3); α-humulene (4); germacrene D (5); myristicin (6); dillapiole (7); α-pinene (8); β-pinene (9); 1,8-cineole (10); trans-ocimene (11); camphor (12) and viridiflorol (13).

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Table 1
Previously described biological activities of P. aduncum L [²³23 Pohlit AM, Pinto ACS, Mause R. Piper aduncum L.: Planta Pluripotente e Fonte de Substâncias fonte de Substâncias Fitoquímicas Importantes [Piper aduncum L.: Pluripotente Plant and Important Phytochemical Substance Source]. Rev. Fitos 2006; 2(1): 7-18.].

Figure 2 Chemical constituents isolated from P. aduncum: 1: dillapiole (4,5-methyl-1-nodioxy-2,3-dimethoxy-allyl-benzene); 2: pseudo-dilla-2-piole (2,3-methylenodioxy-4,5- dimethoxy-allyl-benzene); 3: 3-(3’,7’-dimethyl-2’,6’-octa-dienyl)-4-methoxy-methyl benzoate; 4: 3-(3’,7’-dimethyl-2’,6’-octa-dienyl)-4-methoxy-benzoic acid; 5: 3-(6’-hydroxy-3’,7’-dimethyl-2’,7’-octa-dienyl)-4-methoxy- methyl benzoate; 6: 3-(2’-hydroxy-3’-methyl-3’-butenyl)-4-hydroxy-methyl benzoate; 7: 4-methoxy-3,5-bis(3’-methyl-2’-butenyl)-benzoic acid; 8: nervonic acid (4-hydroxy-3,5-bis(3-methyl-2-butenyl) benzoic acid); 9: 3,5-bis(3-methyl-2-butenyl)-4-methoxy-methyl benzoate; 10: 4-hydroxy-3-(3-methyl-2-butenoyl)-5-(3-methyl-2-butenyl)-benzoic acid; 11: 4-hydroxy-3,5-bis(3’-methyl-2’-butenyl)-11-methyl benzoate; 12: 4-hydroxy-3-(3-methyl-2-butenyl)-methyl benzoate; 13: 1-(1-methylethyl)-4-methyl-3-cyclohexanol 3,5-bis(3-methyl-2-butenyl)-4-hydroxy-benzoate; 14: 1-(1-methylethyl)-4-methyl-3-cyclohexanol 3,5-bis(3-methyl-2-butenyl)-4-methoxy-benzoate; 15: 2,2-dimethyl-8-(3’-methyl-2’-butenyl)-2H-chromeno-6-carboxylic acid; 16: 2,2-dimethyl-8-(3’-methyl-2’-butenyl)-2H-chromeno-6-methyl carboxylate; 17: 2,2-dimethyl-2H-chromeno-6-methyl carboxylate; 18: 2,2-dimethyl-2H-chromeno-6-carboxylic acid ; 19: 8-hydroxy-2,2-dimethyl-2H-chromeno-6-methyl carboxylate; 20: (6S)-2-trans-6- hydroxy-2,6-dimethyl-2,7-octadienoate; 21: 2’,6’-dihydroxy-4’-methoxy-dihydrochalcone; 22: 2’,4,6’-trihydroxy-4’-methoxy-dihydrochalcone; 23: 2’, 6’-dihydroxy-4’-methoxy-chalcone; 24: 2’-hydroxy-4’,6’-dimethoxy-dihydrochalcone; 25: 2’,4-dihydroxy-4’,6’,3-trimethoxy-dihydro-chalcone; 26: 2’,4-dihydroxy-4’,6’-dimethoxy-dihydrochalcone; 27: sakuranetin; 28: 5-hydroxy-7-methoxy-flavone; 29: 7-hydroxy-5-methoxy-dihydro-flavone; 30: piperaduncina A (3-(1-[2,4-dihydroxy-6-methoxy-3-(3-phenylpropanol)-phenyl]-3-methyl-2- butenyl)-4-hydroxy-methyl benzoate); 31: piperaduncina B (4-hydroxy-3-[2,3-dihidro-2-(1-hydroxy-1-methyl-ethyl)-6-hydroxy-4-methoxy-7-(3-phenyl-propanoil)-benzo[b]furan-3-il] methyl benzoate); 32: piperaduncina C (bis-[a, b-dihidro-2’,6’-dihydroxy-4’-methoxy-chalcone-5’-il] methane) [²³23 Pohlit AM, Pinto ACS, Mause R. Piper aduncum L.: Planta Pluripotente e Fonte de Substâncias fonte de Substâncias Fitoquímicas Importantes [Piper aduncum L.: Pluripotente Plant and Important Phytochemical Substance Source]. Rev. Fitos 2006; 2(1): 7-18.].

Type of activity	Organism under evaluation	Derivative under evaluation
Antibacterial	Actinobacillus actinomycetemcomitans	Alcoholic extract
	Bacillus cereus	Ethanolic extract
	Bacillus subtilis	Alcoholic extract, dichloromethane extract, petroleum ether extract, active chemical constituents 1, 3, 5-15,19, 21-23, 27, 30-32
	Enterococcus faecalis	Ethanolic extract
	Escherichia coli	Alcoholic extract, petroleum ether extract, dichloromethane extract, active chemical constituent 19
	Fusobacterium nucleatum	Alcoholic extract
	Micrococcus luteus	Petroleum ether extract, dichloromethane extract, active chemical constituents 5-8, 10, 12, 13, 15, 19, 21, 22, 30-32,34-36, 38
	Mycobacterium intracellulare	Alcoholic extract, active chemical constituents 7, 8,15, 21, 23
	Neisseria gonorrhoeae	Hydroalcoholic extract
	Prevotella intermedia	Alcoholic extract
	Pseudomonas aeruginosa	Active chemical constituents 7, 8, 15, 21, 23
	Staphylococcus aureus	Alcoholic extract, active chemical constituents 7, 8, 15, 21, 23, 27
	Staphylococcus epidermidis	Ethanolic extract
	Streptococcus pyogenes	Ethanolic extract
	Streptococcus sanguis	Ethanolic extract
	Xanthomonas compestris	Active chemical constituent 2
	Xanthomonas carotae	Active chemical constituent 2
Antifungal	Alternaria brassicicoli	Active chemical constituent 2
	Alternaria chrysanthemi	Active chemical constituent 2
	Aspergillus flavus	Alcoholic extract
	Aspergillus fumigatus	Alcoholic extract
	Candida albicans	Alcoholic extract, active chemical constituents 7, 8,15, 21, 23
	Cladosporium herbarum	Active chemical constituent 2
	Cladosporium sphaerospermum	Active chemical constituents 16, 17, 19, 21 e 37
	Cladosporium cladosporioides	Active chemical constituents 16, 17, 19, 21 e 37
	Cryptococcus neoformans	Alcoholic extract, active chemical constituents 7, 8,15, 21, 23
	Erysiphe graminus	Active chemical constituent 2
	Helminthosporum carbonum	Active chemical constituent 2

	Penicillium oxalicum	Petroleum ether extract, active chemical constituents 15 and 19
	Pyrenochaeta terrestris	Active chemical constituent 2
	Saccharomyces cerevisiae	Alcoholic extract, active chemical constituent 4, 16-19
	Trichophyton mentagrophytes	Alcoholic extract
Antioxidant	DPPH	Hydroalcoholic extract
Antitumor	Saccharomyces cerevisiae	Active chemical constituent 4
Antiviral	Poliovirus	Methanolic extract
KB cell/carcinoma	Homo sapiens (human cells)	Dichloromethane extract, active chemical constituents 27, 30, 31, 38
Cytotoxic	Murino	Active chemical constituents 21 and 22
Inseticidal	Tribolium casteneum	Active chemical constituent 1
	Cerotoma tingomarianus	Active chemical constituent 1
	Choristoneura rosaceana	Active chemical constituent 1
Inhibition of epoxidase activity	-	Active chemical constituent 1
Inhibition of p450 3A4 cytochrome	-	Active chemical constituent 1
Larvicidal	Aedes atropalpus	Active chemical constituent 1
Antileishmanial	s Leishmania amazonensi	active chemical constituent 23
	Leishmania braziliensis	Active chemical constituents 21 and 22
	Leishmania tropica	Active chemical constituents 21 and 22
	Leishmania infantum	Active chemical constituents 21 and 22
Molluscoidal	Biomphalaria glabrata	Petroleum ether extract, active chemical constituents 1, 7-10, 15, 19, 22

[1] Editor-in-Chief: Paulo Vitor Farago

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Brief Review on Piper aduncum L., its Bioactive Metabolites and its Potential to Develop Bioproducts

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