Analysis of the chemical constituents of Thompson atemoya seed oil

Análise dos constituintes químicos do óleo de semente de atemoia Thompson

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

Resumo

O objetivo deste trabalho foi caracterizar a composição química do óleo de semente de atemoia var. Thompson através de métodos espectrométricos. Foi realizada extração química utilizando hexano, extração mecânica utilizando prensa e uma extração particionada. A composição de cada uma das extrações foi analisada por CG/EM e mais de 100 compostos foram identificados. Os constituintes majoritários de cada extração foram hexano: (Z)-hexadec- 9-enal (49,42%) e trioleína (23,28%); prensa: ácido elaídico (66,11%) e ácido esteárico (8,81%). Na extração particionada, tem-se as frações hidrometanólica: diidroxiacetona (19,16%), lactona 3-desoxi-d-mannóica (16,34%), 5-hidroximetilfurfural (10,77%), 3-propanodiol, 2-(hidroximetil)-2-nitro (9,89%); hexânica: gama-sitosterol (31,73%), ácido erúcico (14,64%), estigmasterol (13,30%) e trioleína (10,90%); clorofórmica: gama-sitosterol (22,11%), ácido vacênico (15,49%), trioleína (14,65%) e estigmasterol (10,65%); acetato de etila: ácido (Z)- icos-9-enóico (31,28%), beta-sitosterol (16,29%), ácido pentadecanóico (11,53%) e ácido icosanóico (8,01%).

Termos para indexação
Annona atemoya; caracterização; extração; CG/EM

Introduction

The family Annonaceae comprises a large number of genera and species, with approximately 2500 species, and occurs in all primary and secondary tropical forests worldwide (COUVREUR et al., 2019). Atemoya is an interspecific hybrid fruit resulting from artificial crossing between cherimoya (Annona cherimola Mill.) and sugar apple (Annona squamosa L.). The first recorded crosses occurred in 1908, and there are also natural hybrids (MORTON, 1987). The fruits are known to have a pleasant aroma and flavour (BARON et al., 2018) and have been gaining market share. The fame of Annona goes far beyond flavour. Since the 1980s, the acetogenins of Annonaceae have been extensively studied due to their highly valuable pharmacological properties, such as antitumour activity (CAVÉ et al., 1997; CHANG et al., 1999; DURET et al., 1997; DURET et al., 1998; HOYE and ZHUANG, 1988; KAZMAN et al., 2020; NESKE et al., 2020; RUPPRECHT et al., 1986; SOUZA et al., 2008; VILA-NOVA et al., 2011; ZAFRA-POLO et al., 1998).

Extracts from various parts of Annonaceae plants have been shown to have significant antibacterial, antifungal, anti-inflammatory, antioxidant, and cytotoxic properties (COSTA et al., 2017; MA et al., 2017; TAECHOWISAN et al., 2016; TAMFU et al., 2019).

Regardless of the proportions and identity of the constituents in the total extract, they have the potential for biological activity (KRIMAT et al., 2017). The seeds are considered the plant component with the greatest diversity and richness of phytochemicals, including acetogenins, alkaloids and phenolic compounds (KAZMAN et al., 2020).

Different extraction methods give rise to different constituents. Hexane extracts constituents with low polarity, while mechanical extraction is considered an eco-friendly alternative with good yield (PETROPOULOS et al., 2018). Methanol allows the extraction of a greater number of compounds via the liquid-liquid partitioning process with solvents of increasing polarity (KRIM et al., 2020). The objective of this study was to determine the constituents of atemoya (var Thompson) seed oil obtained from different extraction methods by gas chromatographymass spectrometry (GC-MS) analysis.

Experimental part

Seed preparation and extractions

Fresh fruits of atemoya variety Thompson from the voucher specimen #30,249 deposited in the Herbarium of ESAL at Federal University of Lavras (UFLA) (98 Kg, around 480 fruits) have been collected from 30 different 12-year-old plants. Those fruits have been purchased from a farmer in the city of Lavras/MG/Brazil (21° 14′ South, 44° 59′ West) during the 2016/2017 harvest. The seeds were removed, washed in deionized water, dried in a forced-air oven at a temperature of 60-65 °C for 7 days and placed in hermetically sealed pots for subsequent extraction.

Part of the atemoya whole seeds (150 g) was crushed, sieved (150 mesh) and placed in hexane reflux (500 mL) for 24 hours at 100 °C (KOUBAA et al., 2017).

The solvent was removed by rotary evaporation, and the yield was calculated. The material obtained in this procedure was called ASOH (atemoya seed oil, ASO).

A second portion of the seeds (150 g) was also ground and evaluated for grain size (150 mesh).

Mechanical extraction with a bench screw press (Yoda - MQO001) was used to obtain the resulting material, which was called ASOP. At the end of the process, the yield was calculated (MAGALHÃES et al., 2020).

The third portion of the seeds was subjected to partitioned extraction. A total of 180 g of dried, ground, and sieved seeds (150 mesh) was placed in 500 mL of methanol. The seeds were left in contact with the methanol for 3 days at a temperature of 25 ± 2 °C. After filtration, the residue was extracted two more times, as previously described. The solvent was removed by rotary evaporation at 50 °C and lyophilized, leaving 6.714 g of crude extract (COSTA et al., 2017).

The crude extract was resuspended in methanol (20 mL) + ultrapure water (20 mL) and vigorously stirred at room temperature (25 ± 2 °C), and after 45 minutes of decantation, it was centrifuged for 10 minutes at 3500 xg. The supernatant was collected and called the hydromethanolic fraction (ASOHM). The precipitate was subjected to extraction with hexane (20 mL) with vigorous stirring at room temperature (25 ± 2 °C) and 15 minutes of decantation. This process was repeated 4 times, and centrifugation was performed for 10 minutes at 3500 xg. The supernatant was collected and called the hexane fraction (ASOHEX). A total of 20 mL of chloroform was added to the precipitate, followed by vigorous stirring at room temperature (25 ± 2 °C) and 15 minutes of decantation. This process was repeated 4 times, and then centrifugation was performed for 10 minutes at 3500 xg.

The supernatant was collected and called the chloroform fraction (ASO_CHLO). A total of 20 mL of ethyl acetate was added to the precipitate, followed by vigorous stirring at room temperature (25 ± 2 °C) and 15 minutes of decantation. This process was repeated 4 times, and at the end, there was no phase separation. The entire extract was collected and called the ethyl acetate fraction (ASO_ACE) (COSTA et al., 2017).

The elimination of all solvents was performed in an open amber flask protected from light in a desiccator until reaching constant weight. Finally, the samples were sent to the Analytical Centre of the Chemistry Institute of the University of Sao Paulo (USP) for analysis by GC-MS (QP2020 - Shimadzu). The analyses were performed using a capillary column (30 m x 0.25 mm x 0.25 μm, ZB-5HT, CarbolWAX). The injection conditions were 250 °C and 2.50 mL min^-1 for ASOH and ASOP and 320 °C and 3.00 mL min^-1 for ASO_HM, ASO_HEX, ASO_CHLO and ASO_ACE. The components of the ASO samples were identified through standard spectrum libraries for organic compounds, such as NIST107 and Wiley 229.

Results and discussion

The yield of each extraction is shown in Table 1, and the constituents identified in each extract by GC-MS and their biological activities are shown in Tables 2, 3, 4, 5, 6 and 7.

Table 1
ASO yield in each extraction

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

Table 2
Bioactive components of ASOH analysed by GC-MS.

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.

Table 3
Bioactive components of ASOP analysed by GC-MS.

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)

Table 4
Bioactive components of ASOHM analysed by GC-MS.

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.

Table 5
Bioactive components of ASOHEX analysed by GC-MS.

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.

Table 6
Bioactive components of ASOCHLO analysed by GC-MS.

Compound	**** (%)	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	22.11	C29H50O	Gamma-sitosterol	Phytosterol(LIU; CHEN; SHI; WANGet al., 2012) Potentially useful candidate for COVID-19(CHOWDHURY, 2020; LUOet al., 2020; MAURYA ** al., 2020; ******** ** al., 2020; **** et al., 2020)
(Z)-octadec-11-enoic acid	15.49	C18H34O2	Fatty Acid, Unsaturated	Anti-inflammatory(SALES-CAMPOS** al., 2013)
2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate	14.65	C57H104O6	Fats unsaturated	******** treatment for brain tumours(KIMet al., 2016)
(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	10.65	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; ZHENJIEet al., 2020)
(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	5.57	C28H48O	Phytosterol	Adjuvant in determination of sitosterolemia, synthesis of vitamin D(KOMBA et al., 2019; LEE** al., 2020)
Dodecyl 3-(3-dodecoxy-3-oxopropyl) sulfanylpropanoate	4.56	C30H58O4S	Propionate	Antioxidant(CHIEN; BOSS, 1972)
Hexadecanoic acid	4.23	C16H32O2	Straight chain fatty acid	Antitumour, anti-inflammatory(HARADA** al., 2002; JOSHI-BARVE** al.,2007) Can be successful as ** anti-COVID-19 agent(ELFIKY, 2020)
1,3-dihydroxypropan-2-yl hexadecanoate	3.48	C19H38O4	Glyceride	Marker/********* in diabetes ******** type 2(PICCOLOet al., 2016)
(9Z,12Z)-octadeca-9,12-dienoic acid	3.34	C18H32O2	Fatty Acids, Omega-6	Therapeutic use: Barth syndrome,dermatitis, fatty liver, hepatitis C, hypercholesterolemia, hyperlipidaemia, hypertriglyceridemia, lung neoplasms, neoplasm ************ and metastasis and anti-inflammatory(CHENet al., 2013; JANGet al., 2008; KOTHAPALLI et al., 2020; ******** et al.,2014; SHEU** al., 2002; TORIYAMA-BABAet al., 2001; YANOet al., 2007) Binding pocket in the locked structure of SARS-CoV-2 ***** protein(TOELZERet al.,2020)
Octadecanoic acid	3.14	C18H36O2	Straight ***** fatty acid	Immunoregulatory and anti-inflammatory(CALDER, 1998)
(9Z,12Z)-octadeca-9,12-dienoyl chloride	3.02	C18H31ClO	Not applicable	No ********** listed.
6-ethyldecan-3-yloxy(trimethyl)silane	1.62	C15H34OSi	Not applicable	No ********** listed.
1,3-dihydroxypropan-2-yl pentadecanoate	1.57	C18H36O4	Glyceride	Potentially used ** the detection of colorectal cancer(GOEDERTet al., 2014; MONLE e Oacute;Net al., 2009; PHUA** al.,2014; RITCHIE** al., 2010; SINHAet al., 2016; WEIRet al.,2013)
Octadecanamide	1.21	C18H37NO	Amide	Potentially used in the detection of colorectal cancer(GOEDERTet al., 2014; MONLEeOacute;N** al.,2009; PHUAet al.,2014; RITCHIEet al., 2010; SINHAet al., 2016; WEIRet al., 2013)
N-(2-hydroxyethyl)octanamide	1.20	C10H21NO2	Ethanolamine	Larvicidal(CHANDRASEKARANet al., 2018)
5,5-bis(heptylsulfanyl)pentane-1,2,3-triol	1.03	C19H40O3S2	Not applicable	No ********** listed.
(3-hexadecanoyloxy-2-trimethylsilyloxypropyl) hexadecanoate	0.86	C38H76O5Si	*** applicable	** activities listed.
3,5-di-tert-butylphenol	0.82	C14H22O	Phenol	** activities listed.
(Z)-docos-13-enamide	0.77	C22H43NO	Fatty Acids, Unsaturated	Antidepressant and anxiolytic-like *********** effect(LIet al., 2017)

Table 7
Bioactive components of ASOACE analysed by GC-MS.

Compound	**** (%)	Molecular Formula	Chemical Classification	Bioactivity
(Z)-icos-9-enoic acid	31.28	C20H38O2	Fatty acid derivative	Antioxidant and cardiovascular disease protection(BAILeAtilde;O et al., 2015)
(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-dodec ahydro-1H-cyclopenta[a]phenanthren-3-ol	16.29	C29H50O	Phytosterol	Antioxidant, ************* and induces apoptosis in MCF-7 cells(CHAI et al., 2008; HIDAYATHULLAet al., 2018) Potentially useful candidate *** COVID-19(CHOWDHURY, 2020; LUO et al.,2020; ****** et al., 2020; **** et al., 2020; ZHENJIEet al., 2020)
Pentadecanoic acid	11.53	C15H30O2	***** Acid	Potential natural agrochemical and antifungal(DING et al., 2019; MANILAL** al.,2010)
Eicosanoic acid	8.01	C20H40O2	Fatty Acid	Antioxidant and antiproliferative(HARUENKITet al., 2010)
(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	6.41	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; ZHENJIEet al., 2020)
(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	3.13	C28H48O	Phytosterol	Adjuvant in determination of sitosterolemia, synthesis ** vitamin D(KOMBA et al., 2019; LEEet al., 2020)
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one	2.86	C17H14O	Pentanone	Antioxidant(NASEERet al.,2015)
(9Z)-octadeca-9,17-dienal	2.63	C18H32O	*** applicable	Potential ********* MAO-A ********* (depression, anxiety, *** ********* impairments ** Alzheimer's and Parkinson's diseases)(******* et al., 2015)
(Z)-hexadec-7-enal	2.35	C16H30O	***** aldehyde	Pheromone(**** et al., 1981)
Dioctyl benzene-1,2-dicarboxylate	1.97	C24H38O4	******** Acid	Antitumour(ANGELINIet al.,2011; HABIB; KARIM, 2012; MARUYAMAet al., 1994)
[2-[2-[(E)-3-phenylprop-2-enoyl]oxyphenyl]phenyl] (E)-3-phenylprop-2-enoate	1.88	C30H22O4	Not applicable	No activities listed.
[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H- cyclopenta[a]phenanthren-3-yl] carbonochloridate	1.78	C28H45ClO2	Not applicable	Used in **** *********** liposomes(DEODHAR et al., 2020)
(9Z,12Z)-octadeca-9,12-dienoyl chloride	1.49	C18H31ClO	*** applicable	No activities listed.
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one	1.45	C17H14O	Pentanone	Antioxidant(NASEERet al., 2015)
(Z)-octadec-9-enamide	1.43	C18H35NO	Food Additives	Therapeutic use: amnesia and seizures(HEO et al., 2003; WU et al., 2003)
4-[[(E)-2-methoxyhexadec-4-enoxy]methyl]-2,2-dimethyl-1,3-dioxolane	1.27	C23H44O4	Not applicable	No activities listed.
1-acetyloxyethyl acetate	1.25	C6H10O4	Resins, synthetic	No activities listed.
2-hydroxyethyl acetate	1.15	C4H8O3	Ethylene Glycol	No activities listed.
Bicyclo[3.3.1]nonan-2-ol	0.99	C9H16O	Not applicable	No activities listed.

Table 1 shows the yield data for each extraction. As predicted, each extraction resulted in distinct constituents with diverse biological activities. These data are presented in detail for each constituent in Tables 2, 3, 4, 5, 6 and 7.

Each extraction presented 20 constituents, some of them with potential use for COVID-19 treatment. The four main constituents of the ASOH extraction were:

i) Cis-9-hexadecenal (49.42%), a fatty aldehyde classified as agrochemical/attractant mainly used as a pheromone (TEAL et al., 1981) and also used as insecticide against mosquito larvae (GOYAL et al., 2019). Goyal et al has found much lower percentages in Annona squamosa essential oils seeds (11.82 and 6.78%, respectively to methanolic and hexanic extraction);

ii) Triolein (23.28%), a triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is a component of Lorenzo’s oil and used as adjuvant treatment for brain tumors (KIM et al., 2016);

iii) E,E,Z-1,3,12-nonadecatriene-5,14-diol (3.90%) with antidiabetic and antilipidemic properties (AHMADI et al., 2017);

iv) Gamma-sitosterol (3.36%), a member of the class of phytosterols that is a poriferast-5-ene carrying a beta-hydroxy substituent at position 3. A percentage of 17.40% has been found in the seed extract of Annona squamosa (BHARDWAJ et al., 2014). Gammasitosterol is a potentially useful candidate for COVID-19 (CHOWDHURY, 2020; LUO et al., 2020; MAURYA et al., 2020; NARKHEDE et al., 2020; WANG et al., 2020).

The four main constituents of the ASO_P extraction were:

i) Elaidic acid (66.11%), the trans-isomer of oleic acid anion, and also a potential biomarker in biological age (ZHAO et al., 2020). Nwaehujor et al (2020) working with Annona muricata leaf found 8.61% of this compound (NWAEHUJOR et al., 2020);

ii) Stearic acid (8.81%), a saturated longchain fatty acid with immunoregulatory and antiinflammatory properties (CALDER, 1998). Annona squamosa pericarp oil has been shown to have 12.23% of this compound and anti-hepatoma effect (CHEN et al., 2020);

iii) Gadoleyl alcohol (6.67%) has no activities listed;

iv) Palmitic acid (3.76%), a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. It has antitumoral and anti-inflammatory properties (HARADA et al., 2002; JOSHI-BARVE et al., 2007). The palmitic acid can be a successful anti-COVID-19 agent (ELFIKY, 2020).

The crude hexanic extract from aerial parts of atemoya demonstrated 0.82% of this compound, cytotoxic and antimicrobial activity (RABÊLO et al., 2021).

The four main constituents of the ASOHM extraction were:

i) Dihydroxyacetone (19.16%), a ketotriose consisting of acetone bearing hydroxy substituents at positions 1 and 3. It is used in treatment of vitiligo, as antifungal, and photoprotector (FESQ et al., 2001; FUSARO and RICE, 2005; STOPIGLIA et al., 2011);

ii) 3-deoxy-d-mannoic lactone (16.34%) with antimicrobial activity (SHOBANA et al., 2009);

iii) 5-hydroxymethylfurfural (10.77%), a member of the class of furans. It has a role as an indicator of the product of the Maillard reaction, has antioxidant action, and is an antiproliferative (ZHAO et al., 2013). It can also have a potential use in improving hypoxemia in COVID-19 patients (WOYKE et al., 2020);

iv) 2-(hydroxymethyl)-2-nitropropane-1,3- diol (9.89 %), a propylene glycol used as microbicide and bacteriostat in disinfectants and industrial preservatives and as a disinfectant to control disease organisms in livestock and poultry areas on farms and equipment (AMPONIN et al., 2020; BEIER et al., 2008).

The four main constituents of the ASO_HEX extraction were:

i) Gamma-sitosterol (31.73%);

ii) Erucic acid (14.64%), a docosenoic acid having a cis- double bond at C-13 with antimicrobial, antitumor, and cardiac properties (ALTINOZ et al., 2018; SURESH et al., 2014);

iii) Stigmasterol (13.30%), a 3-beta-sterol and member of the phytosterols. It derives from a hydride of a stigmastane (ULBRICHT, 2016) and has antinociceptive action (WALKER et al., 2017). It can be a potentially useful candidate for COVID-19 (HUANG et al., 2020; KAR et al., 2020; LUO et al., 2020; ZHENJIE et al., 2020);

iv) Triolein (10.90 %).

The four main constituents of the ASOCHLO extraction were:mma-sitosterol (22.11%);Vaccenic acid (15.49%), an unsaturated fatty acid with anti-inflammatory properties (SALES-CAMPOS et al., 2013); (14.65%); Stigmasterol (10.65%).

The four main constituents of the ASO_ACE extraction were:

i) Gadoleic acid (31.28%), an icosenoic acid having a cis- double bond at position 9 with antioxidant properties and cardiovascular disease protection (BAILÃO et al., 2015);

ii) Beta-sitosterol (16.29%), a member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. It has antioxidant and antimicrobial properties, and induces apoptosis in MCF-7 cells (CHAI et al., 2008; HIDAYATHULLA et al., 2018). It is also a potentially useful candidate for COVID-19 (CHOWDHURY, 2020; LUO et al., 2020; MAURYA et al., 2020; WANG et al., 2020; ZHENJIE et al., 2020);

iii) Pentadecanoic acid (11.53%), a straightchain saturated fatty acid containing fifteen-carbon atoms.

It is a potential natural agrochemical and antifungal agent (DING et al., 2019; MANILAL et al., 2010);

iv) Eicosanoic acid (8.01%), a saturated long-chain fatty acid with a 20-carbon backbone with antioxidant and antiproliferative properties (HARUENKIT et al., 2010).

Among the parts of the atemoya (pulp, leaves and seeds), the seeds are the richest in phytochemicals, including anonaceous acetogenins, alkaloids and phenolic compounds (KAZMAN et al., 2020). In the ASOP, ASO_HEX, ASO_CHLO and ASO_ACE extractions the compound octadecanoic acid has been observed. This fatty acid also has been found in the study by Wu et al (2005), conducted with oil extraction from atemoya seeds harvested in China in 1996 (WU et al., 2005).

In a study with volatile components of atemoya leaves, Campos et al (2019) reported a considerable amount of hydrocarbon monoterpenes, oxygenated monoterpenes, hydrocarbon sesquiterpenes, oxygenated sesquiterpenes and other classes (CAMPOS et al., 2019).

Among these compounds, we emphasize the similar presence of copaene, germacrene D, beta-ylangen in the ASO_P extraction; and germacrene and n-decane in ASO_H.

Thus, the essential oil of atemoya leaves proved to be rich in monoterpenes and sesquiterpenes (CAMPOS et al., 2014; KUMAR et al., 2021).

For being a hybrid species, Annona atemoya has phytochemical components common to Annona squamosa and Annona cherimola, regardless of the parts of the plant from which their constituents are isolated. (KAZMAN et al., 2020).

The fatty acid profile found in Annona squamosa seeds has shown to have some components that were also found in Atemoya seed oil extractions. n-hexadecanoic acid; ergost-5-en-3-ol; stigmasta-5,22-dien-3-ol; gammasitosterol and octadecanoic acid (ASO_P, ASO_HEX, ASO_CHLO and ASO_ACE) (ZAHID et al., 2018).

Conclusion

In summary, this work presented an interesting analysis of the chemical composition of different extractions of atemoya seed oil (var. Thompson). Among the one hundred and fourteen compounds identified, 20 had antioxidant activity, 17 had anti-inflammatory activity, 10 had antibacterial activity, 9 had antifungal activity, 7 had antitumor activity, 4 had auxiliary activity in the treatment of cancer, 3 had larvicidal activity and 2 showed antidiabetic activity. Furthermore, 12 are potential adjuvants in coping with COVID-19. In addition, some compounds are pheromones, have auxiliary effects in neglected diseases, and act as biological biomarkers, among other important activities. The results have demonstrated that each method of extraction provides compounds with specific biological potential. Thus, these results give important information to aid in the selection of extraction methods when considering the desired constituents.

Acknowledgment

This study was funded in part by the Brazilian Federal Agency for the Support and Evaluation of Graduate Education (CAPES) - Finance Code 001.

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Publication Dates

• Publication in this collection
  07 Oct 2021
• Date of issue
  2021

History

• Received
  04 Mar 2021
• Accepted
  08 Sept 2021