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 linkcopy

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

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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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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)
(3E,12Z)-nonadeca-1,3,12-triene-5,14-diol	3.90	C₁₉H₃₄O₂	Not applicable	Antidiabetic and antilipidaemic(AHMADI et al., 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) ********* useful candidate for COVID-19(CHOWDHURY, 2020; LUOet al.,2020; MAURYA et al., 2020; NARKHEDE al., 2020; WANG et al., 2020)
Decane	2.09	C₁₀H₂₂	Decane	Marker/mechanism in ****** and *** apnoea, obstructive(AOKIet al., 2017; MALLAMPATIet al., 2010)
1-methyl-3-methylidene-8-propan-2-yltricyclo[4.4.0.02,7]decane	1.82	C₁₅H₂₄	Sesquiterpene	Antibacterial(AJIBOYE al.,2016) Sesquiterpene contributing the ******* and aroma of wine(DUEHOLM et al., 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)and anti-nociceptive(WALKERet al., 2017) Potentially useful candidates for COVID-19(HUANGet al.,2020; KAR al.,2020; LUOet al., 2020; ZHENJIE al., 2020)
Ethyl-octadec-9-******	1.58	C₂₀H₃₈O₂	Not applicable	Antitumoural, pheromone and biomarker excessive alcohol chronic use(CASTILLOet al., 2012; GONZáLEZ-ILLáN al., 2011; MANOSROI** al., 2012; POLITIet al., 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; YAMAGATA et al., 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; ISLAM, 2020; OGUNLAKINet al.,2020; STEFANIet al., 2019)
2-butyloctan-1-ol	0.85	C₁₂H₂₆O	Alkyl alcohol	Antioxidant, anti-inflammatory and pheromone(AHMED et al., 2017; TANG et al., 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; LEEet al.,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; JELIAZKOVA et al., 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; SIQUEIRAet al., 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)
Octadecanoic acid	8.81	C₁₈H₃₆O₂	Straight ***** fatty acid	Immunoregulatory and anti-inflammatory(CALDER, 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; JOSHI-BARVE al.,2007) * be successful as anti-COVID-19 agent(ELFIKY, 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) ************ contribute the flavour and aroma of wine(DUEHOLM et al., 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; JELIAZKOVAet al., 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)
(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; SIQUEIRAet al., 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; LINGWOOD and SIMONS, 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; SIQUEIRAet al., 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; SIQUEIRAet al., 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; ****** 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)
(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; SIQUEIRA** al., 2015)

Compound	Area (%)	Molecular Formula	Chemical Classification	Bioactivity
Dihydroxyacetone	19.16	C₃H₆O₃	Monosaccharide	Treatment of vitiligo, antifungal, photoprotector(FESQ et al., 2001; FUSARO and RICE, 2005; STOPIGLIAet al., 2011)
3,5-dihydroxy-6-(hydroxymethyl)oxan-2-one	16.34	C₆H₁₀O₅	Not applicable	Antimicrobial activity(SHOBANA et al., 2009)
5-hydroxymethylfurfural	10.77	C₆H₆O₃	Aldehyde	Antioxidant, antiproliferative(ZHAO et al.,2013) Potentially used to ******* hypoxemia in COVID-19 patients(WOYKE et al.,2020)
2-(hydroxymethyl)-2-nitropropane-1,3-diol	9.89	C₄H₉NO₅	Propylene Glycol	Antimicrobial(AMPONINet al., 2020; BEIERet al.,2008)
4-hydroxy-3-methylbutan-2-one	6.68	C₅H₁₀O₂	Beta-hydroxy ketone	Hypoglycaemic, antiviral, anti-inflammatory, antioxidant, and anti-apoptotic(AVETISYANet al.,1982; HAFEZ et al., 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)
3-hydroxyoxolan-2-one	3.37	C₄H₆O₃	Lactone	Antibacterial(MURUGAN** al., 2013)
1-(2-hydroxypropoxy)propan-2-ol	3.25	C₆H₁₄O₃	Solvent	Larvicidal(SHENG** al.,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; OKAMOTO al., 1977)
2,3-dihydroxypropyl acetate	2.97	C₅H₁₀O₄	Glyceride	Potential ****** repellent(GADDAGUTI al., 2016)
3-methylideneoxolane-2,5-dione	2.65	C₅H₄O₃	Transferase	In vitro cytotoxic activity against human breast tumours(POUDEL et al., 2015)
3,5-dihydroxy-6-methyl-2,3-dihydropyran-4-one	1.70	C₆H₈O₄	Pyrone	Antioxidant(MOZAFARI et al., 2018)
Pent-4-enoic acid	1.62	C₅H₈O₂	Fatty Acids, Unsaturated	Marker/mechanism *** liver and Reye syndrome(GHONGHADZEet al., 2017; TANG et al., 1995)
Furan-2-ylmethanol	1.60	C₅H₆O₂	Furan	Marker/******* inadenoma, dermatitis, allergic contact, dermatitis, irritant, kidney neoplasms and respiratory hypersensitivity(FRANKO al., 2012; SPALDING** al.,2000)
Furan-2-carbaldehyde	1.32	C₅H₄O₂	Furaldehyde	Agrochemical(BADAWY, 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) Potentially useful candidate for COVID-19(CHOWDHURY, 2020; LUOet al., 2020; **** al., 2020; NARKHEDE et al., 2020; WANG et al., 2020)
(Z)-docos-13-enoic acid	14.64	C₂₂H₄₂O₂	Fatty Acid, Unsaturated	Antimicrobial, antitumour and cardiac(ALTINOZ et al., 2018; SURESHet al.,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)and anti-nociceptive(WALKERet al., 2017) Potentially useful candidate for COVID-19(HUANGet al., 2020; KARet al.,2020; LUOet al.,2020; ZHENJIE** al., 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)
(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; LEEet al.,2020)
Hexadecanoic acid	5.12	C₁₆H₃₂O₂	Straight ***** fatty acid	Antitumour, anti-inflammatory(HARADAet al., 2002; JOSHI-BARVEet al., 2007) Can be successful as an anti-COVID-19 agent(ELFIKY, 2020)
(11E,13Z)-octadeca-1,11,13-triene	3.35	C₁₈H₃₂	*** applicable	Antitumour(SWANTARA et al., 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)
1,3-dihydroxypropan-2-yl hexadecanoate	2.03	C₁₉H₃₈O₄	Glyceride	Marker/mechanism in diabetes mellitus type 2(PICCOLOet al.,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)
N-(2-hydroxyethyl)octanamide	0.83	C₁₀H₂₁NO₂	Ethanolamine	Larvicidal(CHANDRASEKARANet al.,2018)
2-(dimethylamino)ethyl 2-methylprop-2-enoate	0.79	C₈H₁₅NO₂	Methacrylate	Used for drug delivery(XUet al.,2006)
Pentadecanal	0.76	C₁₅H₃₀O	Aldehyde	Antioxidant and cytotoxicity(SHAROPOV et al., 2020)
1,3-dihydroxypropan-2-yl hexadecanoate	0,71	C₁₉H₃₈O₄	Glyceride	Marker/mechanism in diabetes ******** type 2(PICCOLOet al.,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.