Analysis of the chemical constituents of <i>Thompson</i> atemoya seed oil

Venceslau, Adneia de Fátima Abreu; Mendonça, Andressa Campos; Benedick, Lilian Aparecida Zampieri; Thomasi, Sérgio Scherrer; Nunes, Cleiton Antônio; Pinto, Luciana Matos Alves

doi:10.1590/0100-29452021015

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Processing • Rev. Bras. Frutic. 43 (6) • 2021 • https://doi.org/10.1590/0100-29452021015 copy

Analysis of the chemical constituents of Thompson atemoya seed oil

Análise dos constituintes químicos do óleo de semente de atemoia Thompson

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

The objective of this study was to characterize the chemical composition in extracts of atemoya (var. Thompson) seed oil by spectrometric methods. The following extraction methods were performed: chemical extraction using hexane, mechanical extraction using a press, and partitioned extraction. The composition of each of the extracts was analysed by gas chromatography-mass spectrometry (GC-MS), and more than 100 compounds were identified. The major constituents of the hexane extraction were (Z)-hexadec-9-enal (49.42%) and triolein (23.28%), and the mechanically obtained extract contained elaidic acid (66.11%) and stearic acid (8.81%). In the partitioned extraction, the hydromethanolic fraction contained dihydroxyacetone (19.16%), 3-deoxy-d-mannoic lactone (16.34%), 5-hydroxymethylfurfural (10.77%), and 3-propanediol, 2-(hydroxymethyl)-2-nitro (9.89%); the hexane fraction contained gamma-sitosterol (31.73%), erucic acid (14.64%), stigmasterol (13.30%) and triolein (10.90%); the chloroform fraction contained gamma-sitosterol (22.11%), vaccenic acid (15.49%), triolein (14.65%) and stigmasterol (10.65%); and the ethyl acetate fraction contained (Z)-icos-9-enoic acid (31.28%), beta-sitosterol (16.29%), pentadecanoic acid (11.53%) and eicosanoic acid (8.01%).

Index terms
Annona atemoya; characterization; extraction; GC-MS

Sociedade Brasileira de Fruticultura Via de acesso Prof. Paulo Donato Castellane, s/n , 14884-900 Jaboticabal SP Brazil, Tel.: +55 16 3209-7188/3209-7609 - Jaboticabal - SP - Brazil
E-mail: rbf@fcav.unesp.br

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[1] Luciana Matos Alves Pinto E-mail:luca@ufla.br

Extração	Massa obtida (g)	Produção (%)
1 r extracção ** ASO H	23,881	15,92
2 nd extracção *** P	22.562	14,97
3 rd particionado extracção	6,714	3,73
ASO HM	2,173	32,37
*** HEX	0,466	6,94
ASO CHLO	1,107	16,49
ASO ACE	0,255	3,80

Compound	**** (%)	Molecular Formula	Chemical Classification	Bioactivity
(Z)-hexadec-9-enal	49.42	C₁₆H₃₀O	Fatty aldehyde	Pheromone(TEAL et al., 1981)
2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate	23.28	C₅₇H₁₀₄O₆	Triacylglycerol	Adjuvant treatment for brain tumours(KIM al., 2016** KIM HJ.; KIM YW.; CHOI SH.; CHO BM.; BANDU R.; AHN HS.; KIM KP. Triolein emulsion infusion into the carotid artery increases brain permeability to anticancer agents. Neurosurgery, Baltimore, v.78, n.5, p.726-733, 2016. )
(3E,12Z)-nonadeca-1,3,12-triene-5,14-diol	3.90	C₁₉H₃₄O₂	Not applicable	Antidiabetic and antilipidaemic(AHMADI et al., 2017 AHMADI, A.; KHALILI, M.; MASHAEE, F.; NAHRI-NIKNAFIS, B. The effects of solvent polarity on hypoglycemic and hypolipidemic activities of Vaccinium arctostaphylos l. Unripe fruits. Pharmaceutical Chemistry Journal, New York, v.50, n.11, p.746-752, 2017/02/01 2017. )
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodec ahydro-1H-cyclopenta[a]phenanthren-3-ol	3.36	C₂₉H₅₀O	Gamma-sitosterol	Phytosterol(LIUet al., 2012 LIU, F.; CHEN, J.; SHI, F.; WANG, T.; WATANABE, G.; TAYA ,K. Phytosterol additive boosts adrenal response to ACTH in male Japanese quail (Coturnix coturnix japonica). Endocrine, Houndsmills, v.41, n.2, p.338-341, 2012. ) ********* useful candidate for COVID-19(CHOWDHURY, 2020 CHOWDHURY, P. In silico investigation of phytoconstituents from Indian medicinal herb ‘Tinospora cordifolia (giloy)’ against SARS-CoV-2 (COVID-19) by molecular dynamics approach. Journal of Biomolecular Structure and Dynamics, New York, p.1-18, 2020. ; LUOet al.,2020 LUO, L.; JIANG, J.; WANG, C.; FITZGERALD, M.; HU, W.; ZHOU, Y.; ZHANG, H.; CHEN, S. Analysis on herbal medicines utilized for treatment of COVID-19. Acta Pharmaceutica Sinica B, Amsterdam, v.10, n.7, p.1192-1204, 2020. ; MAURYA et al., 2020 MAURYA, V.K.; KUMAR, S.; BHATT, M.L.B.; SAXENA, S.K. Antiviral activity of traditional medicinal plants from Ayurveda against SARS-CoV-2 infection. Journal of Biomolecular Structure and Dynamics, Guilderland, p.1-17, 2020. ; NARKHEDE al., 2020 NARKHEDE, R.R.; PISE, A.V.; CHEKE, R.S.; SHINDE. S;D. Recognition of natural products as potential inhibitors of COVID-19 Main Protease (Mpro): in-silico evidences. Natural Products and Bioprospecting, Heidelberg, v.10, n.5, p.297-306, 2020. ; WANG et al., 2020 WANG, J.; ZHANG, X.; OMARINI, A.N.; LI, B. Virtual screening for functional foods against the main protease of SARS-CoV-2. Journal of Food Biochemistry, Oxford, 2020. Disponível em: https://doi.org/10.1111/jfbc.13481. )
Decane	2.09	C₁₀H₂₂	Decane	Marker/mechanism in ****** and * apnoea, obstructive(AOKIet al., 2017 AOKI, T.; NAGAOKA,T.; KOBAYASHI, N.; KURAHASHI, M.; TSUJI, C.; TAKIGUCHI, H.; TOMOMATSU, K. OGUMA,T.; KOBAYASHI, N.; MAGATANI, K.; TAKEDA, S.; ASANO,K.; ABE, T. Editor's highlight: prospective analyses of volatile organic compounds in obstructive sleep apnea patients. Toxicological Sciences: an Official Journal of the Society of Toxicology, London, v.156, n.2, p.362-374, 2017. ; MALLAMPATIet al., 2010** MALLAMPATI, R.; PATLOLLA, R.R.; AGARWAL, S.; BABU, R.J.; HAYDEN, P.; KLAUSNER, M.; SINGH, M.S. Evaluation of EpiDerm full thickness-300 (EFT-300) as an in vitro model for skin irritation: studies on aliphatic hydrocarbons. Toxicology In Vitro, Oxford, v.24, n.2, p.669-676, 2010. )
1-methyl-3-methylidene-8-propan-2-yltricyclo[4.4.0.02,7]decane	1.82	C₁₅H₂₄	Sesquiterpene	Antibacterial(AJIBOYE al.,2016 AJIBOYE, T.O.; MOHAMMED, A.O.; BELO, S.A.; YUSUF I.I.; IBITOYE, O.B.; MURITALA H.F.; ONAJOBI, B. Antibacterial activity of Syzygium aromaticum seed: Studies on oxidative stress biomarkers and membrane permeability. Microbial Pathogenesis, London, v.95, p.208-215, 2016. ) Sesquiterpene contributing the ***** and aroma of wine(DUEHOLM et al., 2019** DUEHOLM, B.; DREW, D.P.; SWEETMAN, C.; SIMONSEN, H.T. In planta and in silico characterization of five sesquiterpene synthases from Vitis vinifera (cv. Shiraz) berries. Planta, Berlin, v.249, n.1, p.59-70, 2019. )
(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17- dodecahydro-1H-cyclopenta[a]phenanthren-3-ol	1.65	C₂₉H₄₈O	Phytosterol	Phytosterol(ULBRICHT, 2016 ULBRICHT, C.E. An Evidence-based systematic review of beta-sitosterol, sitosterol (22,23- dihydrostigmasterol, 24-ethylcholesterol) by the natural standard research collaboration. Journal of Dietary Supplements, New York, v.13, n.1, p.35-92, 2016. )and anti-nociceptive(WALKERet al., 2017 WALKER, C.I.B.; OLIVEIRA, S.M.; TONELLO, R.; ROSSATO, M.F.; DA SILVA BRUM, E.; FERREIRA, J.; TREVISAN, G. Anti-nociceptive effect of stigmasterol in mouse models of acute and chronic pain. Naunyn-Schmiedeberg's Archives of Pharmacology, Berlin, v.390, n.11, p.1163-1172, 2017. ) Potentially useful candidates for COVID-19(HUANGet al.,2020 HUANG, Y.; ZHENG, W.J.; NI, Y.S.; LI, M.S.; CHEN, J.K.; LIU, X.H.; TAN, X.H.; LI, J.Q. Therapeutic mechanism of Toujie Quwen granules in COVID-19 based on network pharmacology. BioData Mining, London, v.13, n.1, p.15, 2020. ; KAR al.,2020 KAR, P., SHARMA, N.R.; SINGH, B.; SEN, A.; ROY, A. Natural compounds from Clerodendrum spp. as possible therapeutic candidates against SARS-CoV-2: An in silico investigation. Journal of Biomolecular Structure and Dynamics, New York, v,39, p.4774-4785, 2020. ; LUOet al., 2020 LUO, L.; JIANG, J.; WANG, C.; FITZGERALD, M.; HU, W.; ZHOU, Y.; ZHANG, H.; CHEN, S. Analysis on herbal medicines utilized for treatment of COVID-19. Acta Pharmaceutica Sinica B, Amsterdam, v.10, n.7, p.1192-1204, 2020. ; ZHENJIE al., 2020)
Ethyl-octadec-9-******	1.58	C₂₀H₃₈O₂	Not applicable	Antitumoural, pheromone and biomarker excessive alcohol chronic use(CASTILLOet al., 2012 CASTILLO, C.; CHEN, H.. GRAVES, C.; MAISONNASSE, A.; CONTE, Y.; PLETTNER, E. Biosynthesis of ethyl oleate, a primer pheromone, in the honey bee (Apis mellifera L.). Insect Biochemistry and Molecular Biology, Oxford, 42, n.6, p.404-416, 2012. ; GONZáLEZ-ILLáN al., 2011 GONZÁLEZ-ILLÁN, F.; OJEDA-TORRES, G.; DÍAZ-VÁZQUEZ, L.M.; ROSARIO, O. Detection of fatty acid ethyl esters in skin surface lipids as biomarkers of ethanol consumption in alcoholics, social drinkers, light drinkers, and teetotalers using a methodology based on microwave-assisted extraction followed by solid-phase microextraction and gas chromatography-mass spectrometry. Journal of Analytical Toxicology, Oxford, v.35, n.4, p.232-237, 2011. ; MANOSROI al., 2012 MANOSROI, A.; JANTRAWUT, P.; SAINAKHAM ,M.; MANOSROI, W.; MANOSROI, J. Anticancer activities of the extract from Longkong (Lansium domesticum) young fruits. Pharmaceutical Biology, Lisse, v.50, n.11, p.1397-1407, 2012. ; POLITIet al., 2011** POLITI, L.; MARI, F.; FURLANETTO, S.; DEL BRAVO, E.; BERTOL, E. Determination of fatty acid ethyl esters in hair by GC-MS and application in a population of cocaine users. Journal of Pharmaceutical and Biomedical Analysis, Oxford, v.54, n.5, p.1192-1195, 2011. )
[(E)-10,13,13-trimethyltetradec-11-enyl]acetate	1.47	C₁₉H₃₆O₂	Not applicable	No activities listed.
(5-formyl-5,9-dimethyl-14-tetracyclo [11.2.1.01,10.04,9] hexadecanyl)methyl acetate	1.31	C₂₂H₃₄O₃	Not applicable	No activities listed.
Undecane	1.22	C₁₁H₂₄	Undecane	Pheromone(LENZ et al., 2013 LENZ, E.L.; KRASNEC, M.O.; BREED, M.D. Identification of undecane as an alarm pheromone of the ant formica argentea. Journal of Insect Behavior, Dordrecht, v.26, n.1, p.101-108, 2013. ; YAMAGATA et al., 2005 YAMAGATA, N.; FUJIWARA-TSUJII, N.; YAMAOKA, R.; MIZUNAMI, M. Pheromone communication and the mushroom body of the ant, Camponotus obscuripes (Hymenoptera: Formicidae). Naturwissenschaften, Berlin, v.92, n.11, p.532-536, 2005. )
(3E,12Z)-nonadeca-1,3,12-triene-5,14-diol	1.15	C₁₉H₃₄O₂	Not applicable	No activities listed.
3-O-(2,2-dimethylpropyl)1-O-tridecyl propanedioate	0.90	C₂₁H₄₀O₄	Not applicable	No activities listed.
[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dode cahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate	0.90	C₃₁H₅₂O₂	Steroid ester	Antioxidant, antitumoural, anti-diarrhoeal, analgesic, anti-diabetic, antiproliferative, *********** and anti-inflammatory(EL-SHAZLY al., 2012 EL-SHAZLY, A.; EL-SAYED, A.; FIKREY, E. Bioactive secondary metabolites from Salix tetrasperma Roxb. Zeitschrift fu¨r Naturforschung. C, A Journal of Biosciences, Berlin. v.67, n.7-8, p.353-359, 2012. ; ISLAM, 2020 ISLAM, M.T. Chemical profile and biological activities of Sonneratia apetala (Buch.-Ham.). Advances in Traditional Medicine, Singapore, v.20, n.2, p.123-132, 2020. ; OGUNLAKINet al.,2020 OGUNLAKIN, A.D.; SONIBARE, M.A.; JABEEN, A. Antiproliferative and ameliorative effects of Tetracera potatoria and its constituent. Advances in Traditional Medicine, South Korea, 2020. ( ; STEFANIet al., 2019 STEFANI, T.; GARZA-GONZÁLEZ, E.; RIVAS-GALINDO, V.M.; RIOS, M.Y.; ALVAREZ, L.; CAMACHO-CORONA, M.D.R. Hechtia glomerata Zucc: phytochemistry and activity of its extracts and major constituents against resistant bacteria. Molecules, Basel, v.24, n.19, 2019. )
2-butyloctan-1-ol	0.85	C₁₂H₂₆O	Alkyl alcohol	Antioxidant, anti-inflammatory and pheromone(AHMED et al., 2017 AHMED, A.; AKBAR, S.; SHAH, W.A. Chemical composition and pharmacological potential of aromatic water from Salix caprea inflorescence. Chinese Journal of Integrative Medicine, Beijing, 2017. Disponível em: DOI:10.1007/s11655-017-2781-5 DOI:10.1007/s11655-017-2781-5... ; TANG et al., 2016 TANG, R.; ZHANG, F.; KONE, N.G.; CHEN, J-H.; ZHU, F.; HAN, R-C.; LEI, C-L.; KENIS, M.; HUANG, L-Q.; WANG, C-Z. Identification and testing of oviposition attractant chemical compounds for Musca domestica. Scientific Reports, London, v.6, n.1, p.33017, 2016. )
(3S)-17-(5,6-dimethylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren -3-ol	0.83	C₂₈H₄₈O	Phytosterol	Adjuvant in determination of sitosterolemia, synthesis vitamins D(KOMBA et al., 2019 KOMBA, S.; KOTAKE-NARA, E.; TSUZUKI, W. Simultaneous synthesis of vitamins D(2), D(4), D(5), D(6), and D(7) from commercially available phytosterol, ß-Sitosterol, and identification of each vitamin D by HSQC NMR. Metabolites, Basel, v.9, n.6, p.107, 2019. ; LEEet al.,2020** LEE, J.H.; SONG, Y.; JUN, S-H,; SONG, S.H.; SHIN, C.H.; KI, C-S.; LEE, K.; SONG, J. High prevalence of increased sitosterol levels in hypercholesterolemic children suggest underestimation of sitosterolemia incidence. PLoS One, San Francisco, v.15, n.8, p.e0238079, 2020. )
(1S,6S,7S,8S)-1-methyl-3-methylidene-8-propan-2-yltricyclo[4.4.0.02,7]decane (1S,6S,7S,8S)-1-methyl-3-methylidene-8-propan-2-yltricyclo[4.4.0.02,7]decane	0.80	C₁₅H₂₄	Sesquiterpene	Pheromone and antimicrobial(FLATH et al., 1994 FLATH, R.A., CUNNINGHAM, R.T.; MON, T.R.; JOHN, J.O. Additional male mediterranean fruitfly (Ceratitis capitata wied.) Attractants from Angelica seed oil (Angelica archangelica L.). Journal of Chemical Ecology, New York, v.20, n.8, p.1969-1984, 1994. ; JELIAZKOVA et al., 2018 JELIAZKOVA, E.; ZHELJAZKOV, V.D.; KACÁNIOVA, M.; ASTATKIE, T.; TEKWANI, B.L. Sequential elution of essential oil constituents during steam distillation of hops (Humulus lupulus L.) and influence on oil yield and antimicrobial activity. Journal of Oleo Science, Tokyo, v.67, n.7, p.871-883, 2018. )
(1Z,6Z,8S)-1-methyl-5-methylidene-8-propan-2-ylcyclodeca-1,6-diene	0.80	C₁₅H₂₄	Sesquiterpene	Anti-inflammatory, anti-oedematogenic, antiproliferative, antileishmanial, antibacterial, antifungal and antioxidant(OLIVEIRA-TINTINO et al., 2018 OLIVEIRA-TINTINO, C.D.M.; PESSOA, R.T.; FERNANDES, M.N.M.; ALCÂNTARA, I.S.; DA SILVA, B.A.F.; DE OLIVEIRA, M.R.C.; MARTINS, A.O.B.P.B.; DA SILVA, M.D.S.; TINTINO, S.R.; RODRIGUES, F.F.G.; DA COSTA, J.G.M.; DE LIMA, S.G.; KERNTOPF, M.R.; DA SILVA, T.G.; DE MENEZES, I.R.A. Anti-inflammatory and anti-edematogenic action of the Croton campestris A. St.-Hil (Euphorbiaceae) essential oil and the compound ß-caryophyllene in vivo models. Phytomedicine, Stuttgart, v.41, p.82-95, 2018. ; SIQUEIRAet al., 2015 SIQUEIRA, C.A.; SERAIN, A.F.; PASCOAL, A.C.; ANDREAZZA, N.L.; DE LOURENÇO, C.C.; RUIZ, A.L.; DE CARVALHO, J.E.; DE SOUZA, A.C.; MESQUITA, J.T.; TEMPONE, A.G.; SALVADOR, M.J. Bioactivity and chemical composition of the essential oil from the leaves of Guatteria australis A.St.-Hil. Natural Product Research, Milton Park, v.29, n.20, p.1966-1969, 2015. )
(2Z)-2,6-dimethylocta-2,7-diene-1,6-diol	0.80	C₁₀H₁₈O₂	Not applicable	No activities listed.

Compound	Area (%)	Molecular Formula	Chemical Classification	Bioactivity
(E)-octadec-9-enoic acid	66.11	C₁₈H₃₄O₂	Long-chain fatty acid	Potential biomarker in biological age(ZHAO et al., 2020 ZHAO, Y.; WANG, B.; WANG, G.; HUANG, L.; YIN, T,; LI, X.; WANG, Q.; JING, J.; ZHANG, Y.. Functional interaction between plasma phospholipid fatty acids and insulin resistance in leucocyte telomere length maintenance. Lipids in Health and Disease, London, v.19, n.1, p.11, 2020. )
Octadecanoic acid	8.81	C₁₈H₃₆O₂	Straight ***** fatty acid	Immunoregulatory and anti-inflammatory(CALDER, 1998 CALDER, P. C. Immunoregulatory and anti-inflammatory effects of n-3 polyunsaturated fatty acids. Brazilian Journal of Medical and Biological Research, Raipur, v.31, p. 467-490, 1998. )
(Z)-icos-9-en-1-ol	6.67	C₂₀H₄₀O	Not applicable	No activities listed.
Hexadecanoic acid	3.76	C₁₆H₃₂O₂	******** chain fatty acid	Antitumoural, anti-inflammatory(HARADAet al.,2002 HARADA, H.; YAMASHITA, U.; KURIHARA, H.; FUKUSHI, E.; KAWABATA, J.; KAMEI, Y. Antitumor activity of palmitic acid found as a selective cytotoxic substance in a marine red alga. Anticancer Research, Athens, v.22, n.5, p.2587-2590, 2002. ; JOSHI-BARVE al.,2007 JOSHI-BARVE, S.; BARVE, S.S.; AMANCHERLA, K.; GOBEJISHVILI, L.; HILL, D.; CAVE, M.; HOTE, P.; MCCLAIN, C.J. Palmitic acid induces production of proinflammatory cytokine interleukin-8 from hepatocytes. Hepatology, Baltimore, v.46, n.3, p.823-830, 2007. ) * be successful as anti-COVID-19 agent(ELFIKY, 2020 ELFIKY, A.A. Natural products may interfere with SARS-CoV-2 attachment to the host cell. Journal of Biomolecular Structure and Dynamics, Guilderland, p.1-10, 2020. )
(1S,6S,7S,8S)-1-methyl-3-methylidene-8-propan-2-yltricyclo[4.4.0.02,7]decane (1S,6S,7S,8S)-1-methyl-3-methylidene-8-propan-2-yltricyclo[4.4.0.02,7]decane	2.85	C₁₅H₂₄	Sesquiterpene	Antibacterial(AJIBOYEet al., 2016 AJIBOYE, T.O.; MOHAMMED, A.O.; BELO, S.A.; YUSUF I.I.; IBITOYE, O.B.; MURITALA H.F.; ONAJOBI, B. Antibacterial activity of Syzygium aromaticum seed: Studies on oxidative stress biomarkers and membrane permeability. Microbial Pathogenesis, London, v.95, p.208-215, 2016. ) ************ contribute the flavour and aroma of wine(DUEHOLM et al., 2019 DUEHOLM, B.; DREW, D.P.; SWEETMAN, C.; SIMONSEN, H.T. In planta and in silico characterization of five sesquiterpene synthases from Vitis vinifera (cv. Shiraz) berries. Planta, Berlin, v.249, n.1, p.59-70, 2019. )
(E)-octadec-9-en-1-ol	2.24	C₁₈H₃₆O	Fatty alcohol	No ********** listed.
(1S,6S,7S,8S)-1-methyl-3-methylidene-8-propan-2-yltricyclo[4.4.0.02,7]decane (1S,6S,7S,8S)-1-methyl-3-methylidene-8-propan-2-yltricyclo[4.4.0.02,7]decane	1.31	C₁₅H₂₄	Sesquiterpene	Pheromone and antimicrobial(FLATH al., 1994 FLATH, R.A., CUNNINGHAM, R.T.; MON, T.R.; JOHN, J.O. Additional male mediterranean fruitfly (Ceratitis capitata wied.) Attractants from Angelica seed oil (Angelica archangelica L.). Journal of Chemical Ecology, New York, v.20, n.8, p.1969-1984, 1994. ; JELIAZKOVAet al., 2018** JELIAZKOVA, E.; ZHELJAZKOV, V.D.; KACÁNIOVA, M.; ASTATKIE, T.; TEKWANI, B.L. Sequential elution of essential oil constituents during steam distillation of hops (Humulus lupulus L.) and influence on oil yield and antimicrobial activity. Journal of Oleo Science, Tokyo, v.67, n.7, p.871-883, 2018. )
(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carbaldehyde	1.24	C₂₀H₃₀O	Diterpenoid	No activities listed.
(3E,12Z)-nonadeca-1,3,12-triene-5,14-diol	1.02	C₁₉H₃₄O₂	Not applicable	** activities listed.
2-[(9Z,12Z)-octadeca-9,12-dienoxy]ethanol	0.97	C₂₀H₃₈O₂	Not applicable	No activities listed.
Heptacos-1-ene	0.92	C₂₇H₅₄	Fatty Acyl	Pheromone(EVISONet al., 2012 EVISON, S.E.; FERREIRA, R.S.; D'ETTORRE, P.; FRESNEAU, D.; POTEAUX, C. Chemical signature and reproductive status in the facultatively polygynous ant pachycondyla verenae. Journal of Chemical Ecology, New York, v.38, n.11, p.1441-1449, 2012. )
(1Z,6Z,8S)-1-methyl-5-methylidene-8-propan-2-ylcyclodeca-1,6-diene	0.83	C₁₅H₂₄	Sesquiterpene	Anti-inflammatory, anti-oedematogenic, antiproliferative, antileishmanial, antibacterial, antifungal and antioxidant(OLIVEIRA-TINTINOet al., 2018 OLIVEIRA-TINTINO, C.D.M.; PESSOA, R.T.; FERNANDES, M.N.M.; ALCÂNTARA, I.S.; DA SILVA, B.A.F.; DE OLIVEIRA, M.R.C.; MARTINS, A.O.B.P.B.; DA SILVA, M.D.S.; TINTINO, S.R.; RODRIGUES, F.F.G.; DA COSTA, J.G.M.; DE LIMA, S.G.; KERNTOPF, M.R.; DA SILVA, T.G.; DE MENEZES, I.R.A. Anti-inflammatory and anti-edematogenic action of the Croton campestris A. St.-Hil (Euphorbiaceae) essential oil and the compound ß-caryophyllene in vivo models. Phytomedicine, Stuttgart, v.41, p.82-95, 2018. ; SIQUEIRAet al., 2015 SIQUEIRA, C.A.; SERAIN, A.F.; PASCOAL, A.C.; ANDREAZZA, N.L.; DE LOURENÇO, C.C.; RUIZ, A.L.; DE CARVALHO, J.E.; DE SOUZA, A.C.; MESQUITA, J.T.; TEMPONE, A.G.; SALVADOR, M.J. Bioactivity and chemical composition of the essential oil from the leaves of Guatteria australis A.St.-Hil. Natural Product Research, Milton Park, v.29, n.20, p.1966-1969, 2015. )
5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane	0.75	C₂₀H₃₂	Diterpene	Human metabolite and anti-allergic(CHEENPRACHAet al., 2006 CHEENPRACHA, S.; YODSAOUE, O.; KARALAI, C.K.; PONGLIMANONT, C.; SUBHADHRASAKU, S.; TEWTRAKULB, S.; KANJANA-OPAS, A. Potential anti-allergic ent-kaurene diterpenes from the bark of Suregada multiflora. Phytochemistry, New York, v.67, n. 24, p. 2630-2634, 2006. ; LINGWOOD and SIMONS, 2010 LINGWOOD, D.; SIMONS, K. Lipid rafts as a membrane-organizing principle. Science, London, v.327, n.5961, p.46-50, 2010. )
(S,1Z,6Z)-8-isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene	0.61	C₁₅H₂₄	Sesquiterpene	Anti-inflammatory, anti-oedematogenic, antiproliferative, antileishmanial, antibacterial, antifungal and antioxidant(OLIVEIRA-TINTINOet al., 2018 OLIVEIRA-TINTINO, C.D.M.; PESSOA, R.T.; FERNANDES, M.N.M.; ALCÂNTARA, I.S.; DA SILVA, B.A.F.; DE OLIVEIRA, M.R.C.; MARTINS, A.O.B.P.B.; DA SILVA, M.D.S.; TINTINO, S.R.; RODRIGUES, F.F.G.; DA COSTA, J.G.M.; DE LIMA, S.G.; KERNTOPF, M.R.; DA SILVA, T.G.; DE MENEZES, I.R.A. Anti-inflammatory and anti-edematogenic action of the Croton campestris A. St.-Hil (Euphorbiaceae) essential oil and the compound ß-caryophyllene in vivo models. Phytomedicine, Stuttgart, v.41, p.82-95, 2018. ; SIQUEIRAet al., 2015 SIQUEIRA, C.A.; SERAIN, A.F.; PASCOAL, A.C.; ANDREAZZA, N.L.; DE LOURENÇO, C.C.; RUIZ, A.L.; DE CARVALHO, J.E.; DE SOUZA, A.C.; MESQUITA, J.T.; TEMPONE, A.G.; SALVADOR, M.J. Bioactivity and chemical composition of the essential oil from the leaves of Guatteria australis A.St.-Hil. Natural Product Research, Milton Park, v.29, n.20, p.1966-1969, 2015. )
(S,1Z,6Z)-8-isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene	0.48	C₁₅H₂₄	Sesquiterpene	Anti-inflammatory, anti-oedematogenic, antiproliferative, antileishmanial, antibacterial, ******** and antioxidant(OLIVEIRA-TINTINO al.,2018 OLIVEIRA-TINTINO, C.D.M.; PESSOA, R.T.; FERNANDES, M.N.M.; ALCÂNTARA, I.S.; DA SILVA, B.A.F.; DE OLIVEIRA, M.R.C.; MARTINS, A.O.B.P.B.; DA SILVA, M.D.S.; TINTINO, S.R.; RODRIGUES, F.F.G.; DA COSTA, J.G.M.; DE LIMA, S.G.; KERNTOPF, M.R.; DA SILVA, T.G.; DE MENEZES, I.R.A. Anti-inflammatory and anti-edematogenic action of the Croton campestris A. St.-Hil (Euphorbiaceae) essential oil and the compound ß-caryophyllene in vivo models. Phytomedicine, Stuttgart, v.41, p.82-95, 2018. ; SIQUEIRAet al., 2015 SIQUEIRA, C.A.; SERAIN, A.F.; PASCOAL, A.C.; ANDREAZZA, N.L.; DE LOURENÇO, C.C.; RUIZ, A.L.; DE CARVALHO, J.E.; DE SOUZA, A.C.; MESQUITA, J.T.; TEMPONE, A.G.; SALVADOR, M.J. Bioactivity and chemical composition of the essential oil from the leaves of Guatteria australis A.St.-Hil. Natural Product Research, Milton Park, v.29, n.20, p.1966-1969, 2015. )
(S,1Z,6Z)-8-isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene	0.38	C₁₅H₂₄	Sesquiterpene	Anti-inflammatory, anti-oedematogenic, antiproliferative, antileishmanial, antibacterial, antifungal and antioxidant(OLIVEIRA-TINTINO al., 2018 OLIVEIRA-TINTINO, C.D.M.; PESSOA, R.T.; FERNANDES, M.N.M.; ALCÂNTARA, I.S.; DA SILVA, B.A.F.; DE OLIVEIRA, M.R.C.; MARTINS, A.O.B.P.B.; DA SILVA, M.D.S.; TINTINO, S.R.; RODRIGUES, F.F.G.; DA COSTA, J.G.M.; DE LIMA, S.G.; KERNTOPF, M.R.; DA SILVA, T.G.; DE MENEZES, I.R.A. Anti-inflammatory and anti-edematogenic action of the Croton campestris A. St.-Hil (Euphorbiaceae) essential oil and the compound ß-caryophyllene in vivo models. Phytomedicine, Stuttgart, v.41, p.82-95, 2018. ; ****** et al., 2015)
(2E,4E)-deca-2,4-dienal	0.35	C₁₀H₁₆O	Aldehyde	No activities listed.
(1R,2S,6S,7S,8S)-1,3-dimethyl-8-propan-2-yltricyclo[4.4.0.02,7]dec-3-ene	0.29	C₁₅H₂₄	Sesquiterpene	Antioxidant, anti-inflammatory, and anticancer(KETHA et al., 2020 KETHA, A.; VEDULA, G.S.; SASTRY, A.V.S.. In vitro antioxidant, anti-inflammatory, and anticancer activities of methanolic extract and its metabolites of whole plant Cardiospermum canescens Wall. Future Journal of Pharmaceutical Sciences, New Cairo, v.6, n.1, p.11, 2020. )
(S,1Z,6Z)-8-isopropyl-1-methyl-5-methylenecy	0.20	C₁₅H₂₄	Sesquiterpene	Anti-inflammatory, anti-oedematogenic, antiproliferative, antileishmanial, antibacterial, antifungal and antioxidant(OLIVEIRA-TINTINO et al.,2018 OLIVEIRA-TINTINO, C.D.M.; PESSOA, R.T.; FERNANDES, M.N.M.; ALCÂNTARA, I.S.; DA SILVA, B.A.F.; DE OLIVEIRA, M.R.C.; MARTINS, A.O.B.P.B.; DA SILVA, M.D.S.; TINTINO, S.R.; RODRIGUES, F.F.G.; DA COSTA, J.G.M.; DE LIMA, S.G.; KERNTOPF, M.R.; DA SILVA, T.G.; DE MENEZES, I.R.A. Anti-inflammatory and anti-edematogenic action of the Croton campestris A. St.-Hil (Euphorbiaceae) essential oil and the compound ß-caryophyllene in vivo models. Phytomedicine, Stuttgart, v.41, p.82-95, 2018. ; SIQUEIRA al., 2015** SIQUEIRA, C.A.; SERAIN, A.F.; PASCOAL, A.C.; ANDREAZZA, N.L.; DE LOURENÇO, C.C.; RUIZ, A.L.; DE CARVALHO, J.E.; DE SOUZA, A.C.; MESQUITA, J.T.; TEMPONE, A.G.; SALVADOR, M.J. Bioactivity and chemical composition of the essential oil from the leaves of Guatteria australis A.St.-Hil. Natural Product Research, Milton Park, v.29, n.20, p.1966-1969, 2015. )

Compound	Area (%)	Molecular Formula	Chemical Classification	Bioactivity
Dihydroxyacetone	19.16	C₃H₆O₃	Monosaccharide	Treatment of vitiligo, antifungal, photoprotector(FESQ et al., 2001 FESQ, H.; BROCKOW, K.; STROM, K.; MEMPEL, M.; RING, J.; ABECK, D. Dihydroxyacetone in a new formulation--a powerful therapeutic option in vitiligo. Dermatology, Basel, v.203, n.3, p.241-243, 2001. ; FUSARO and RICE, 2005 FUSARO, R.M.; RICE, E.G. The maillard reaction for sunlight protection.Annals of the New York Academy of Sciences, New York, v.1043, p.174-183, 2005. ; STOPIGLIAet al., 2011 STOPIGLIA, C.D.; VIEIRA, F.J.; MONDADORI, A.G.; OPPE, T.P.; SCROFERNEKER, M.L. In vitro antifungal activity of dihydroxyacetone against causative agents of dermatomycosis. Mycopathologia, Dordrecht, v.171, n.4, p.267-271, 2011. )
3,5-dihydroxy-6-(hydroxymethyl)oxan-2-one	16.34	C₆H₁₀O₅	Not applicable	Antimicrobial activity(SHOBANA et al., 2009 SHOBANA, S. GOPALAKRISHNAN, V.; MOHANDASS, R. Antibacterial activity of garlic varieties (ophioscordon and sativum) on enteric pathogens. Current Research Journal of Biological Sciences, New York, v.1, n.3, p.123-126, 2009. )
5-hydroxymethylfurfural	10.77	C₆H₆O₃	Aldehyde	Antioxidant, antiproliferative(ZHAO et al.,2013 ZHAO, L.; CHEN, J.; SU, J.; LI, L.; HU, S.; LI, B.; ZHANG, X.; XU, Z.; CHEN, T. In vitro antioxidant and antiproliferative activities of 5-hydroxymethylfurfural. Journal of Agricultural and Food Chemistry, Washington, v.61, n.44, p.10604-10611, 2013. ) Potentially used to ***** hypoxemia in COVID-19 patients(WOYKE et al.,2020** WOYKE S.; RAUCH S.; STRÖHLE M.; GATTERER H. Modulation of Hb-O2 affinity to improve hypoxemia in COVID-19 patients. Clinical Nutrition, Edinburgh, v.40, n.1, p.38-39, 2021 )
2-(hydroxymethyl)-2-nitropropane-1,3-diol	9.89	C₄H₉NO₅	Propylene Glycol	Antimicrobial(AMPONINet al., 2020 AMPONIN, D.E.; PRZYBEK-SKRZYPECKA, J.; ZYABLITSKAYA, M.; TAKAOKA, A.; SUH, L.H.; NAGASAKI, T.; TROKEL, S.L.; PAIK, D.C. Ex vivo anti-microbial efficacy of various formaldehyde releasers against antibiotic resistant and antibiotic sensitive microorganisms involved in infectious keratitis. BMC Ophthalmology, London, v.20, n.1, p.28, 2020. ; BEIERet al.,2008 BEIER, R.C.; DUKE, S.E.; ZIPRIN, R.L.; HARVEY, R.B.; HUME, M.E; POOLE, T.L.; SCOTT, H.M.; HIGHFIELD, L.D.; ALALI, W.Q.; ANDREWS, K.; ANDERSON, R.C.; NISBET, D.J. Antibiotic and disinfectant susceptibility profiles of Vancomycin-Resistant Enterococcus faecium (VRE) isolated from community wastewater in Texas. Bulletin of Environmental Contamination and Toxicology, New York, v.80, n.3, p.188-194, 2008. )
4-hydroxy-3-methylbutan-2-one	6.68	C₅H₁₀O₂	Beta-hydroxy ketone	Hypoglycaemic, antiviral, anti-inflammatory, antioxidant, and anti-apoptotic(AVETISYANet al.,1982 AVETISYAN, A.A.; DZHANDZHAPANYAN, A.N.; GALSTYAN, A.V.; KARAGEZ, S.KH.; VOTYAKOV, V.I.; KHLYUSTOV, S.V.; VLADYKO, G.V; KLIMOVICH, V.YA.; KOROBCHENKO, L.V.; SHASHIKHINA, M.N.; ZHAVRID, S.V. Research on unsaturated lactones. 75. Antiviral activity of some lactones. Pharmaceutical Chemistry Journal, London, 16, n. 8, p. 580-582, 1982/08/01 1982. ; HAFEZ et al., 2020 HAFEZ, M.H.; ELBLEHI, S.S.; EL-SAYED, Y.S. Date palm fruit extract ameliorated pancreatic apoptosis, endocrine dysfunction and regulatory inflammatory cytokines in Streptozotocin-induced diabetes in rats. Environmental Science and Pollution Research, Landsberg, v.27, n.34, p.43322-43339, 2020. )
6-oxoheptanoic acid	5.37	C₇H₁₂O₃	Oxo fatty acid	** activities listed.
4-hydroxyoxolan-2-one	4.19	C₄H₆O₃	Lactone	C4 chiral synthon for the synthesis of chiral pharmaceuticals and nutraceuticals such as HIV inhibitors, synthetic statins, and L-carnitine(LEE; PARK, 2009 LEE, S-H.; PARK, O-J. Uses and production of chiral 3-hydroxy-?-butyrolactones and structurally related chemicals. Applied Microbiology and Biotechnology, New York, v.84, n.5, p.817-828, 2009. )
3-hydroxyoxolan-2-one	3.37	C₄H₆O₃	Lactone	Antibacterial(MURUGAN al., 2013** MURUGAN, K.; SEKAR, K.; SANGEETHA, S.; RANJITHA, S.; SOHAIBANI, SA. Antibiofilm and quorum sensing inhibitory activity of Achyranthes aspera on cariogenic Streptococcus mutans: An in vitro and in silico study. Pharmaceutical Biology, London, v.51, n.6, p.728-736, 2013. )
1-(2-hydroxypropoxy)propan-2-ol	3.25	C₆H₁₄O₃	Solvent	Larvicidal(SHENG al.,2020** SHENG, Z.; JIAN, R.; XIE, F.; CHEM, B.; ZHANG, K.; LI, D.; CHEM W.; HUANG, C.; ZHANG, T. Screening of larvicidal activity of 53 essential oils and their synergistic effect for the improvement of deltamethrin efficacy against Aedes albopictus. Industrial Crops and Products, Amsterdam, v.145, p.112131, 2020. )
1-(2-methyltetrazol-5-yl)ethenyl acetate	3.20	C₆H₈N₄O₂	Solvent	** activities listed.
5,5-dimethyl-1,3-oxazolidine-2,4-dione	2.98	C₅H₇NO₃	Oxazole	Pancreatic stone dissolution and anticonvulsant(NODA al., 1984 NODA, A.; SHIBATA, T.; HAYAKAWA, T.; KONDO, T.; NAGAI, K.; HAMANO, H. Pancreatic stone dissolution with dimethadione (DMO). II. Roentgenological follow-up study in canine experimental pancreatic stones. Nihon Shokakibyo Gakkai Zasshi, Tokyo, v.81, n.2, p.254-262, 1984. ; OKAMOTO al., 1977 OKAMOTO, M.; ROSENBERG, H.C.; BOISSE, N.R. Evaluation of anticonvulsants in barbiturate withdrawal. The Journal of Pharmacology and Experimental Therapeutics, Baltimore, v.202, n.2, p.479-489, 1977. )
2,3-dihydroxypropyl acetate	2.97	C₅H₁₀O₄	Glyceride	Potential ****** repellent(GADDAGUTI al., 2016 GADDAGUTI, V.; VENKATESWARA, R.; RAO, P. Potential mosquito repellent compounds of Ocimum species against 3N7H and 3Q8I of Anophelesgambiae. 3 Biotech, Berlin, v.6, n.1, p.26, 2016. )
3-methylideneoxolane-2,5-dione	2.65	C₅H₄O₃	Transferase	In vitro cytotoxic activity against human breast tumours(POUDEL et al., 2015 POUDEL, A.; SATYAL, P.; SETZER, W.N. Composition and bioactivities of the leaf essential oil of Ficus religiosa Linn. American Journal of Essential Oils and Natural Products, New Delhi, v.2, n.3, p.16-17, 2015. )
3,5-dihydroxy-6-methyl-2,3-dihydropyran-4-one	1.70	C₆H₈O₄	Pyrone	Antioxidant(MOZAFARI et al., 2018 Mozafari, A.A.; Vafaee, Y.; Shahyad, M. Phytochemical composition and in vitro antioxidant potential of Cynodon dactylon leaf and rhizome extracts as affected by drying methods and temperatures. Journal of Food Science and Technology, Mysore, v.55, n.6, p.2220-2229, 2018. )
Pent-4-enoic acid	1.62	C₅H₈O₂	Fatty Acids, Unsaturated	Marker/mechanism * liver and Reye syndrome(GHONGHADZEet al., 2017 GHONGHADZE, M.; ANTELAVA, N.; LILUASHVILI, K.; OKUJAVA, M.; PACHKORIA, K. Action of L-carnitine, corvitin and their combination on functional state of liver in experimental model of Reye Syndrome in rats. Georgian Medical News, Tbilisi, n.263, p.105-111, 2017. ; TANG et al., 1995** TANG, W.; BOREL, A.G.; FUJIMIYA, T.; ABBOTT, F.S. Fluorinated analogues as mechanistic probes in valproic acid hepatotoxicity: hepatic microvesicular steatosis and glutathione status. )
Furan-2-ylmethanol	1.60	C₅H₆O₂	Furan	Marker/******* inadenoma, dermatitis, allergic contact, dermatitis, irritant, kidney neoplasms and respiratory hypersensitivity(FRANKO al., 2012 FRANKO, J.; JACKSON, L.G.; HUBBS, A.; KASHON, M.; MEADE, B.J.; ANDERSON, S.E. Evaluation of furfuryl alcohol sensitization potential following dermal and pulmonary exposure: enhancement of airway responsiveness. Toxicological Sciences, Orlando, v.125, n.1, p.105-115, 2012. ; SPALDING al.,2000** SPALDING, J.W.; FRENCH, J.E.; STASIEWICZ, S.; FUREDI-MACHACEK, M.; CONNER, F.; TICE, R.R.; TENNANT, R.W. Responses of transgenic mouse lines p53(+/-) and Tg.AC to agents tested in conventional carcinogenicity bioassays. Toxicological Science, Orlando, v.53, n.2, p.213-223, 2000. )
Furan-2-carbaldehyde	1.32	C₅H₄O₂	Furaldehyde	Agrochemical(BADAWY, 2008 BADAWY, M.E.I. Chemical modification of chitosan: synthesis and biological activity of new heterocyclic chitosan derivatives. Polymer International, New York, v.57, n.2, p.254-261, 2008. )
5-oxo-2-propylhexanal	1.11	C₉H₁₆O₂	Not applicable	No ********** listed.
2,5-dimethyloxolane-3,4-dione	0.97	C₆H₈O₃	Not applicable	No activities listed.

Compound	Area (%)	Molecular Formula	Chemical Classification	Bioactivity
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodec ahydro-1H-cyclopenta[a]phenanthren-3-ol	31.73	C₂₉H₅₀O	Gamma-sitosterol	Phytosterol(LIU; CHEN; SHI; WANGet al., 2012 LIU, F.; CHEN, J.; SHI, F.; WANG, T.; WATANABE, G.; TAYA ,K. Phytosterol additive boosts adrenal response to ACTH in male Japanese quail (Coturnix coturnix japonica). Endocrine, Houndsmills, v.41, n.2, p.338-341, 2012. ) Potentially useful candidate for COVID-19(CHOWDHURY, 2020 CHOWDHURY, P. In silico investigation of phytoconstituents from Indian medicinal herb ‘Tinospora cordifolia (giloy)’ against SARS-CoV-2 (COVID-19) by molecular dynamics approach. Journal of Biomolecular Structure and Dynamics, New York, p.1-18, 2020. ; LUOet al., 2020 LUO, L.; JIANG, J.; WANG, C.; FITZGERALD, M.; HU, W.; ZHOU, Y.; ZHANG, H.; CHEN, S. Analysis on herbal medicines utilized for treatment of COVID-19. Acta Pharmaceutica Sinica B, Amsterdam, v.10, n.7, p.1192-1204, 2020. ; **** al., 2020; NARKHEDE et al., 2020 NARKHEDE, R.R.; PISE, A.V.; CHEKE, R.S.; SHINDE. S;D. Recognition of natural products as potential inhibitors of COVID-19 Main Protease (Mpro): in-silico evidences. Natural Products and Bioprospecting, Heidelberg, v.10, n.5, p.297-306, 2020. ; WANG et al., 2020 WANG, J.; ZHANG, X.; OMARINI, A.N.; LI, B. Virtual screening for functional foods against the main protease of SARS-CoV-2. Journal of Food Biochemistry, Oxford, 2020. Disponível em: https://doi.org/10.1111/jfbc.13481. )
(Z)-docos-13-enoic acid	14.64	C₂₂H₄₂O₂	Fatty Acid, Unsaturated	Antimicrobial, antitumour and cardiac(ALTINOZ et al., 2018 ALTINOZ, M.A.; BILIR, A.; ELMACI, I. Erucic acid, a component of Lorenzo's oil and PPAR-d ligand modifies C6 glioma growth and toxicity of doxorubicin. Experimental data and a comprehensive literature analysis. Chemico-Biological Interactions, Amsterdam, v.294, p.107-117, 2018. ; SURESHet al.,2014 SURESH, A.; RAMASAMY, P.; THANGARAJ, R.; OSCAR, F.; BALDEV, E.; DHARUMADURAI, D.; THAJUDDIN, N. Microalgal fatty acid methyl ester a new source of bioactive compounds with antimicrobial activity. Asian Pacific Journal of Tropical Disease, Singapor, v.4, p.S979-S984, 2014 )
(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17- dodecahydro-1H-cyclopenta[a]phenanthren-3-ol	13.30	C₂₉H₄₈O	Phytosterol	Phytosterol(ULBRICHT, 2016 ULBRICHT, C.E. An Evidence-based systematic review of beta-sitosterol, sitosterol (22,23- dihydrostigmasterol, 24-ethylcholesterol) by the natural standard research collaboration. Journal of Dietary Supplements, New York, v.13, n.1, p.35-92, 2016. )and anti-nociceptive(WALKERet al., 2017 WALKER, C.I.B.; OLIVEIRA, S.M.; TONELLO, R.; ROSSATO, M.F.; DA SILVA BRUM, E.; FERREIRA, J.; TREVISAN, G. Anti-nociceptive effect of stigmasterol in mouse models of acute and chronic pain. Naunyn-Schmiedeberg's Archives of Pharmacology, Berlin, v.390, n.11, p.1163-1172, 2017. ) Potentially useful candidate for COVID-19(HUANGet al., 2020; KARet al.,2020 KAR, P., SHARMA, N.R.; SINGH, B.; SEN, A.; ROY, A. Natural compounds from Clerodendrum spp. as possible therapeutic candidates against SARS-CoV-2: An in silico investigation. Journal of Biomolecular Structure and Dynamics, New York, v,39, p.4774-4785, 2020. ; LUOet al.,2020 LUO, L.; JIANG, J.; WANG, C.; FITZGERALD, M.; HU, W.; ZHOU, Y.; ZHANG, H.; CHEN, S. Analysis on herbal medicines utilized for treatment of COVID-19. Acta Pharmaceutica Sinica B, Amsterdam, v.10, n.7, p.1192-1204, 2020. ; ZHENJIE al., 2020** ZHUANG, Z.; ZHONG, X.; ZHANG, H.; CHEN, H.; HUANG, B.; LIN, D.; WEN, J. Exploring the potential mechanism of shufeng jiedu capsule for treating COVID-19 by comprehensive network pharmacological approaches and molecular docking validation. Combinatorial Chemistry e High Throughput Screening, Hilversum, v.23, p.1-20, 2020. )
2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate	10.90	C₅₇H₁₀₄O₆	Fat unsaturated	Adjuvant treatment for brain tumours(KIMet al., 2016 KIM HJ.; KIM YW.; CHOI SH.; CHO BM.; BANDU R.; AHN HS.; KIM KP. Triolein emulsion infusion into the carotid artery increases brain permeability to anticancer agents. Neurosurgery, Baltimore, v.78, n.5, p.726-733, 2016. )
(3S)-17-(5,6-dimethylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren -3-ol	6.01	C₂₈H₄₈O	Phytosterol	Adjuvant determination of sitosterolemia, synthesis of vitamin D(KOMBA et al., 2019 KOMBA, S.; KOTAKE-NARA, E.; TSUZUKI, W. Simultaneous synthesis of vitamins D(2), D(4), D(5), D(6), and D(7) from commercially available phytosterol, ß-Sitosterol, and identification of each vitamin D by HSQC NMR. Metabolites, Basel, v.9, n.6, p.107, 2019. ; LEEet al.,2020** LEE, J.H.; SONG, Y.; JUN, S-H,; SONG, S.H.; SHIN, C.H.; KI, C-S.; LEE, K.; SONG, J. High prevalence of increased sitosterol levels in hypercholesterolemic children suggest underestimation of sitosterolemia incidence. PLoS One, San Francisco, v.15, n.8, p.e0238079, 2020. )
Hexadecanoic acid	5.12	C₁₆H₃₂O₂	Straight ***** fatty acid	Antitumour, anti-inflammatory(HARADAet al., 2002 HARADA, H.; YAMASHITA, U.; KURIHARA, H.; FUKUSHI, E.; KAWABATA, J.; KAMEI, Y. Antitumor activity of palmitic acid found as a selective cytotoxic substance in a marine red alga. Anticancer Research, Athens, v.22, n.5, p.2587-2590, 2002. ; JOSHI-BARVEet al., 2007 JOSHI-BARVE, S.; BARVE, S.S.; AMANCHERLA, K.; GOBEJISHVILI, L.; HILL, D.; CAVE, M.; HOTE, P.; MCCLAIN, C.J. Palmitic acid induces production of proinflammatory cytokine interleukin-8 from hepatocytes. Hepatology, Baltimore, v.46, n.3, p.823-830, 2007. ) Can be successful as an anti-COVID-19 agent(ELFIKY, 2020 ELFIKY, A.A. Natural products may interfere with SARS-CoV-2 attachment to the host cell. Journal of Biomolecular Structure and Dynamics, Guilderland, p.1-10, 2020. )
(11E,13Z)-octadeca-1,11,13-triene	3.35	C₁₈H₃₂	*** applicable	Antitumour(SWANTARA et al., 2019 SWANTARA, M.D.; RITA, W.S.; SUARTHA, N.; AGUSTINA, K.K. Anticancer activities of toxic isolate of Xestospongia testudinaria sponge. Veterinary World, Rajkot, v.12, n.9, p.1434-1440, 2019. )
2-[12-(oxiran-2-yl)dodecyl]oxirane	2.70	C₁₆H₃₀O₂	Not applicable	No activities listed.
Icosanoic acid	2.33	C₂₀H₄₀O₂	***** Acid	Antioxidant and antiproliferative(HARUENKITet al., 2010 HARUENKIT, R.; POOVARODOM. S.; VEARASILP, S.; NAMIESNIK, J.; SLIWKA-KASZYNSKA, M.; PARK, Y-S.; HEO, B-G.; CHO, J-Y.; JANG, H.G.; GORINSTEIN, S. Comparison of bioactive compounds, antioxidant and antiproliferative activities of Mon Thong durian during ripening. Food Chemistry, London, v.118, n.3, p.540-547, 2010. )
1,3-dihydroxypropan-2-yl hexadecanoate	2.03	C₁₉H₃₈O₄	Glyceride	Marker/mechanism in diabetes mellitus type 2(PICCOLOet al.,2016 PICCOLO, B.D.; GRAHAM, J.L.; STANHOPE, K.L.; FIEHN, O.; HAVEL, P.J.; ADAMS, S.H. Plasma amino acid and metabolite signatures tracking diabetes progression in the UCD-T2DM rat model. American Journal of Physiology. Endocrinology and Metabolism, Bethesda, v.310, n.11, p.E958-969, 2016. )
****** 8-(2-hexylcyclopropyl)octanoate	1.08	C₁₈H₃₄O₂	Not applicable	** activities listed.
5-(6-bromo-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)-3-methylidenepentane-1,2-diol	0.98	C₂₀H₃₅BrO₃	*** applicable	No activities listed.
(1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one	0.96	C₁₀H₁₆O	Bicyclic Monoterpene	Antifungal(BAIet al., 2020 BAI, L.; WANG, W.; HUA, J.; GUO, Z.; LUO, S. Defensive functions of volatile organic compounds and essential oils from northern white-cedar in China. BMC Plant Biology, London, v.20, n.1, p.500, 2020. )
N-(2-hydroxyethyl)octanamide	0.83	C₁₀H₂₁NO₂	Ethanolamine	Larvicidal(CHANDRASEKARANet al.,2018 CHANDRASEKARAN, R.; SEETHARAMAN, P.; KRISHNAN, M.; GNANASEKAR, S.; SIVAPERUMAL, S. Carica papaya (Papaya) latex: a new paradigm to combat against dengue and filariasis vectors Aedes aegypti and Culex quinquefasciatus (Diptera: Culicidae). 3 Biotech, Berlin, v.8, n.2, p.83, 2018. )
2-(dimethylamino)ethyl 2-methylprop-2-enoate	0.79	C₈H₁₅NO₂	Methacrylate	Used for drug delivery(XUet al.,2006 XU, F.J.; YUAN, S.; SIMO, P.; KANG, E.; NEOH, K.Antimicrobial surfaces of viologen-quaternized poly((2-dimethyl amino)ethyl methacrylate)-Si(100) hybrids from surface-initiated atom transfer radical polymerization. NanoBiotechnology, Totowa, v.2, n.3, p.123-134, 2006. )
Pentadecanal	0.76	C₁₅H₃₀O	Aldehyde	Antioxidant and cytotoxicity(SHAROPOV et al., 2020 SHAROPOV, F.; SATYAL, P.; WINK, M. The chemical composition and biological activities of essential oil from the leaves of philadelphus x purpureomaculatus lemoine. Pharmaceutical Chemistry Journal, New York, v.54, n.4, p.386-388, 2020. )
1,3-dihydroxypropan-2-yl hexadecanoate	0,71	C₁₉H₃₈O₄	Glyceride	Marker/mechanism in diabetes ****** type 2(PICCOLOet al.,2016** PICCOLO, B.D.; GRAHAM, J.L.; STANHOPE, K.L.; FIEHN, O.; HAVEL, P.J.; ADAMS, S.H. Plasma amino acid and metabolite signatures tracking diabetes progression in the UCD-T2DM rat model. American Journal of Physiology. Endocrinology and Metabolism, Bethesda, v.310, n.11, p.E958-969, 2016. )
1-hexadecyl-2,3-dihydro-1H-indene	0.68	C₂₅H₄₂	Not applicable	No activities listed.
6-ethyldecan-3-yloxy(trimethyl)silane	0.62	C₁₅H₃₄OSi	*** applicable	No activities listed.