Extração e caracterização química do óleo da semente de nim (Azadirachta indica)

Autores

DOI:

https://doi.org/10.20873/jbb.uft.cemaf.v11n4.16258

Palavras-chave:

Azadirachta indica a. juss , cromatografia gasosa, microextração em headspace de fase sólida, sohxlet

Resumo

A árvore nim (Azadirachta indica A. Juss) é conhecida por suas propriedades terapêuticas, pesticidas, fertilizantes e farmacológicas. Devido a esses atributos, essa árvore tem potencial econômico e continua sendo utilizada mundialmente. Para a extração do óleo foi utilizado o sistema Sohxlet, para a extração e caracterização dos voláteis foi utilizado o método HS-SPME/CG-EM e o perfil de ácidos graxos foi caracterizado por CG-DIC. O rendimento médio obtido do óleo foi de 23%. Foram detectados 34 compostos voláteis, dos quais 9 foram identificados pelo índice de Kovat: 2-metildecano, 3-metildecano, 4-metildecano, 2-metilundecano, 3-metilundecano, 3,4-dimetiltiofeno, 2,5-diol- 3-hexano, 1,2,3-trimetilbenzeno e buticiclohexano. Além dos voláteis no óleo, foram encontrados 7 ácidos graxos; ácido oleico, ácido linoleico, ácido palmítico e ácido esteárico, entre esses a maior concentração encontrada foi de ácido oleico e ácido linoleico. Diante da presença destes compostos químicos no óleo de nim, sugere-se, para investigações subsequentes, o isolamento e aplicação dos compostos organossulfurados como inseticidas. A extração do óleo das flores e sementes de nim com solventes menos prejudiciais ao meio ambiente, juntamente com sua aplicação, possibilita a avaliação de seu potencial pesticida. Além disso, é fundamental avaliar a influência do nim na população de abelhas, analisando casos de mortalidade e buscando soluções para evitar danos ambientais. Adicionalmente, destaca-se a viabilidade do óleo de nim como produto de limpeza industrial e hospitalar, explorando as propriedades antimicrobianas, antibacterianas e propriedades biodegradáveis.

Referências

Alba SL, García-Gonzáles C, Coronado OMA, Ayla BJR, Alpírez GM, Montes DGLNN. extraction methods and ap-plications of bioactive compounds from neem (Azadirachta indica): A mini-review. Mini-Reviews in Organic Chemis-try, v.20, n.7, p.644-654, 2023. https://doi.org/10.2174/1570193X19666220707125726

Aider FA, Kellouche A, Fellag H, Debras JF. Evaluation of the bio-insecticidal effects of the main fatty acids of olive oil on Callosobruchus maculatus F. (Coleoptera-Bruchidae) in cowpea (Vigna unguiculata (L.). Journal of Plant Diseases and Protection, v.123, p.235-245, 2016. https://doi.org/10.1007/s41348-016-0034-z

Ayalew AA. Chromatographic and spectroscopic determina-tion of solvent-extracted Lantana camara leaf oil. Journal of International Medical Research, v.48, n.10, p.1-12, 2020.

https://doi.org/10.1177/0300060520962344

Ayinde AA, Morakinyo OM, Sridhar MKC. Repellency and larvicidal activities of Azadirachta indica seed oil on Anop-heles gambiae in Nigeria. Heliyon, v.6, n.5, p. 1-7, 2020.

https://doi.org/10.1016/j.heliyon.2020.e03920

Baby AR, Freire TB, Marques GA, Rijo P, Lima FV, Carva-lho JCM, Rojas P, Magalhães WV, Velasco MVR, Moro-cho-Jácome AL. Azadirachta indica (Neem) as a potential natural active for dermocosmetic and topical products: a nar-rative review. Cosmetics, v. 9, n. 3, p.1-17, 2022. https://doi.org/10.3390 /cosmetics9030058

Balandrin MF, Lee SM, Klocke JA. Biologically active volatile organosulfur compounds from seeds of the neem tree, Aza-dirachta indica (Meliaceae). Journal of Agricultural and Fo-od Chemistry, v.36, n.5, p.1048–1054, 1988. https://doi.org/10.1021/jf00083a035

Barbosa LMP, Santos JO, Sousa RCM, Furtado JLB, Vidinha P, Garcia MAS, Vitorino HA, Dall’Oglio DF. Bioherbicide from Azadirachta indica seed waste: exploitation, efficient extraction of neem oil and allelopathic effect on senna occi-dentalis. Recycling, v. 8, n. 3, p.1-15, 2023. https://doi.org/10.3390/recycling 8030050

Beyecha Hundi̇e K, Abdi̇ssa D, Bekele Bayu A. Extraction, optimization, and characterization of neem seed oil via box-behnken design approach. Journal of the Turkish Chemical Society Section A: Chemistry, v.9, n.2, p.513-526, 2022.

https:// doi.org/10.18596/jotcsa.1039997

Breu W. Allium cepa L. (Onion) Part 1: Chemistry and analysis. Phytomedicine, v.3, n.3, p.293–306, 1996. https://doi.org/10.1016/S0944-7113(96)80069-9

Bukvicki DR, Tyagi AK, Gottardi DG, Veljic MM, Jankovic SM, Guerzoni ME et al. Assessment of the chemical com-position and in vitro antimicrobial potential of extracts of the liverwort scapania aspera. Natural Product Communications, v.8, n.9, p.1-4, 2013. https://doi.org/10.1177/1934578X1300800932

Cantrell MS, Seale JT, Arispe SA, McDougal OM. Determi-nation of Organosulfides from Onion Oil. Foods, v.9, n.7, p.884, 2020.

https://doi.org/10.3390/foods9070884

Carvalho AMS, Heimfarth L, Pereira EWM, Oliveira FS, Menezes IRA, Coutinho HDM et al. Phytol, a chlorophyll component, produces antihyperalgesic, anti-inflammatory, and antiarthritic effects: possible NFκB pathway involve-ment and reduced levels of the proinflammatory Cytokines TNF-α and IL-6. Journal of Natural Products, v.83, n.4, p.1107-1117, 2020. https://doi.org/10.1021/acs.jnatprod.9b01116

Casillas-vargas G, Ocasio-Malavé C, Medina S, Morales-Guzman C, Valle RG Del, Carballeira NM, Carballeira NM, Sanabria-Ríos DJ. Antibacterial fatty acids: An update of possible mechanisms of action and implications in the deve-lopment of the next-generation of antibacterial agents. Pro-gress in Lipid Research, v.82, p.1-10, 2021. https://doi.org/10.1016/j.plipres.2021.101093

Chaudhary MF, Ashraf A, Waseem M, Hayat S, Nadeem HU, Siddique MH et al. Neem oil. In: Inamuddin, Boddula R, Asiri AM (org.). Green Sustainable Process Chemical and Environmental. Elsevier, 2021. p.57-73.

Chinnasamy G, Chandrasekharan S, Koh TW, Bhatnagar S. Synthesis, characterization, antibacterial and wound healing efficacy of silver nanoparticles from Azadirachta indica. Frontiers in Microbiology, v.12, p.1-14, 2021. https://doi.org/10.3389/fmicb.2021.611560

Choi SM, Lee D-J, Kim J-Y, Lim S-T. Volatile composition and sensory characteristics of onion powders prepared by convective drying. Food Chemistry, v.231, p.386-392, 2017.

https://doi.org/10.1016/j.foodchem.2017.03.129

Desai SN, Jadhav AJ, Holkar CR, Pawar BG, Pinjari DV. Extraction and microencapsulation of Buchanania lanzan Spreng seed oil. Chemical Papers, v.76, n.6, p.3521-3530, 2022.

https://doi.org/10.1007/s11696-022-02116-0

Ebrahimi M, Safaralizade MH, Valizadegan O. Contact toxi-city of Azadirachta indica (Adr. Juss.), Eucalyptus camal-dulensis (Dehn.) and Laurus nobilis (L.) essential oils on mortality cotton aphids, Aphis gossypii Glover (Hem.: Aphididae). Archives of Phytopathology and Plant Protec-tion, v.46, n.18, p.2153–2162, 2013. https://doi.org/10.1080/03235408.2013 .774526

Fagbemi KO, Aina DA, Olajuyigbe OO. Soxhlet extraction versus hydrodistillation using the clevenger apparatus: A comparative study on the extraction of a volatile compound from Tamarindus indica seeds. The Scientific World Jour-nal, v.2021, p.1-8, 2021. https://doi.org/10.1155/2021/5961586

Fernandes SR, Barreiros L, Oliveira RF, Cruz A, Prudêncio C, Oliveira AI, Pinho C, Santos N, Morgado J. Chemistry, bioactivities, extraction and analysis of azadirachtin: State-of-the-art. Fitoterapia, v.134, p.141-150, 2019. https://doi.org/10.1016/j.fitote.2019.02.006

Ghosh S, Mali SN, Bhowmick DN, Pratap AP. Neem oil as natural pesticide: Pseudo ternary diagram and computational study. Journal of the Indian Chemical Society, v.98, n.7, p.1-7, 2021.

https://doi.org/10.1016/j.jics.2021.100088

Granado-Casas M, Mauricio D. Oleic acid in the diet and what it does: implications for diabetes and its complications. In: Watson RR, Preedy VR (ed.). Bioactive food as dietary in-terventions for diabetes. Academic Press. 2019. p.211-229.

https://doi.org/ 10.1016/ B978-0-12-813822-9.00014-X

Guchhait KC, Manna T, Barai M, Karmakar M, Nandi SK, Jana D, Dey A, Panda S, Raul P, Patra A, Bhattacharya R, Chatterjee S, Panda Ak, Ghosh C. Antibiofilm and antican-cer activities of unripe and ripe Azadirachta indica (neem) seed extracts. BMC Complementary Medicine and Therapi-es, v.22, n.1, p.1-18, 2022. https://doi.org/10.1186/s12906-022-03513-4

Gutbrod K, Romer J, Dörmann P. Phytol metabolism in plants. Progress in Lipid Research, v.74, p.1-17, 2019. https://doi.org/10.1016/j.plipres.2019.01.002

Hirondart M, Rombaut N, Fabiano-Tixier AS, Bily A, Chemat F. Comparison between pressurized liquid extraction and conventional soxhlet extraction for rosemary antioxidants, yield, Composition, and Environmental Footprint. Foods, v.9, n.5, p.1-14, 2020.

https://doi.org/10.3390/foods9050584

Hossain MA, Al-Toubi WAS, Weli AM, Al-Riyami QA, Al-Sabahi JN. Identification and characterization of chemical compounds in different crude extracts from leaves of Omani neem. JTUSCI, v.7, n.4, p.181-188, 2013. https://doi.org/10.1016/j.jtusci .2013.05.003

Islam MD T, Alencar MVOB de, Machado KC, Machado KC, Melo-Cavalcante A A de C, Sousa DP de et al. Phytol in a pharma-medico-stance. Chemico-Biological Interactions, v.240, p.60–73, 2015. https://doi.org/10.1016/j.cbi.2015.07.010

Islam MT, Ali ES, Uddin SJ, Shaw S, Islam Md A, Ahmed Md I et al. Phytol: A review of biomedical activities. Food and Chemical Toxicology, v.121, p.82-94, 2018. https://doi.org/ 10.1016/j.fct.2018.08.032

Islas JF, Acosta E, G-Buentello Z, Delgado-Gallegos JL, Moreno-Treviño MG, Escalante B et al. An overview of neem (Azadirachta indica) and its potential impact on health. Journal of Functional Foods, v.74, p.1-13, 2020. https://doi.org/10.1016/j.jff.2020.104171

Ismaila SS, Sani Y, Sani AA, Yakasai SM, Momoh H, Mohammed Sa’a. E. Determination of fatty acids and physi-cochemical properties of neem (Azadrachta Indica L) seed oil extracts. AJOL, v.8, n.1, p.149-160, 2022. https://doi.org/10.4314/dujo pas.v8i1a.16

Jeelani I et al. Pharmaceutical potential of constituents from Azadirachta indica and their specific role as anti-cancer agents. Current Bioactive Compounds, v.19, n.3, p.94-103, 2023. http://dx.doi.org/10.2174/1573407218666220818110059

Jishma P, Hussain N, Chellappan R, Rajendran R, Mathew J, Radhakrishnan EK. Strain-specific variation in plant growth promoting volatile organic compounds production by five different Pseudomonas spp. as confirmed by response of Vigna radiata seedlings. Journal of Applied Microbiology, v.123, n.1, p.204–216, 2017. https://doi.org/10.1111/jam.13474

Kaura SK, Gupta SK, Chowdhury JB. Morphological and oil content variation in seeds of Azadirachta indicates A. Juss. (Neem) from northern and western provenances of India. Plant Foods for Human Nutrition, v.52, p.293-298, 1998. https://doi.org/10.1023/A: 1008013424150

Keneni YG, Marchetti JM. Oil extraction from plant seeds for biodiesel production. AIMS Energy. v. 5, n. 2, p. 316-340, 2017.

https://doi.org/10.3934/energy.2017.2.316

Kilani-Morakchi S, Morakchi-Goudjil H, Sifi K. Azadirachtin-Based Insecticide: Overview, Risk Assessments, and Future Directions. Frontiers in Agronomy, v.3, p.1-13, 2021.

https://doi.org/10.3389/fagro.2021.676208

Kostik V, Memeti S, Bauer B. Fatty acid composition of edible oils and fats. Journal of Hygienic Engineering and Design. v.4, p.112-116, 2013.

Koul O. Biological activity of volatile di-n-propyl disulfide from seeds of neem, Azadirachta indica (Meliaceae), to two species of stored grain pests, Sitophilus oryzae (L.) and Tri-bolium castaneum (Herbst). Journal of Economic Entomo-logy, v.97, n.3, p.1142-1147, 2004. https://doi.org/10.1093/jee/97.3.1142

Kumar S, Singh N, Devi LS, Kumar S, Kamle M, Kumar P et al. Neem oil and its nanoemulsion in sustainable food pre-servation and packaging: Current status and future pros-pects. Journal of Agriculture and Food Research, v.7, p.1-9.

https://doi.org/10.1016/j.jafr.2021.100254

Kumar Tyagi A, Bukvicki D, Gottardi D, Veljic M, Guerzoni ME et al. Antimicrobial potential and chemical characteriza-tion of serbian liverwort (Porella arboris-vitae): SEM and TEM Observations. Evidence-Based Complementary and Alternative Medicine, v.2013, p.1-7, 2013. https://doi.org/10.1155/2013/382927

Lienard V, Seck D, Lognay G, Gaspar C, Severin M. Biologi-cal activity of Cassia occidentalis L. against Callosobruchus maculatus (F.) (Coleoptera: Bruchidae). Journal of Stored Products Research, v.29, n.4, p.311-318, 1993. https://doi.org/10.1016/0022-474X(93)90046-7

Loganathan T, Barathinivas A, Soorya C, Balamurugan S, Nagajothi TG, Ramya S, et al. Physicochemical, druggable, ADMET pharmacoinformatics and therapeutic potentials of azadirachtin - a prenol lipid (triterpenoid) from seed oil ex-tracts of Azadirachta indica A. Juss. Journal of Drug Deli-very and Therapeutics, v.11, n.5, p.33-46, 2021. https://doi.org/10.22270/jddt.v1 1i5.4981

López-Bascón MA, Luque de Castro MD. Soxhlet Extraction. In: Poole CF (org.). Liquid-Phase Extraction. Elsevier. 2020. p.27 https://doi.org/10.10 16/B978-0-12-816911-7.00011-6

Marangoni F, Agostoni C, Borghi C, Catapano AL, Cena H, Ghiselli A, Vecchia CL, Lercker G, Manzato E, Pirillo A, Riccardi G, Risé P, Visioli F, Poli A. Dietary linoleic acid and human health: Focus on cardiovascular and cardiometa-bolic effects. Atherosclerosis, v.292, p.90–98, 2020. https://doi.org/10.1016/j.atherosclerosis.2019 .11.018

Mohamadpoor M, Amini J, Ashengroph M, Azizi A. Evalua-tion of biocontrol potential of Achromobacter xylosoxidans strain CTA8689 against common bean root rot. Physiologi-cal and Molecular Plant Pathology, v.117, p.101769, 2022.

https://doi.org/10.1016/j.pmpp.2021.101769

Mubarak AM, Kulatilleke CP. Sulphur constituents of neem seed volatiles: A revision. Phytochemistry, v.29, n.10, p.3351-3352, 1990. https://doi.org/10.1016/0031-9422(90)80213-Z

Mulla M, Ahmed J, Alagarsamy S, K Habeebullah SF. Utili-zation of novel and rapid techniques for characterization of neem Azadirachta indica seed oil and palm oil blends. Inter-national Journal of Food Engineering, v.16, n.10, p.20200047, 2020.

https://doi.org/10.1515/ijfe-2020-0047

Neves EJM, Carpanezzi AA. The cultivation of neem (Aza-dirachta indica) for fruit production in Brazil. Colombo: Embrapa Forests, 8p. 2008.

Olofsson P, Hultqvist M, Hellgren LI, Holmdahl R. Phytol: A chlorophyll component with anti-inflammatory and metabo-lic properties. In: Jacob C, Kirsch G, Slusarenko A, Win-yard P, Burkholz T, (org.). Recent advances in redox active plant and microbial products: From basic chemistry to widespread applications in medicine and agriculture. Dor-drecht: Springer Netherlands. 2014. p.14.

Perera AGWU, Karunaratne MMSC, Chinthaka SDM. Bioac-tivity and volatile profiling of Azadirachta indica leaves for the management of maize weevil, Sitophilus zeamais (motsch.) infestations. JTFE, v.8, n.1, p.10-24, 2018. https://doi.org/10.31357/jtfe.v8i1 .3479

Perera WPRT, Liyanage JA, Dissanayake KGC, Gunathilaka H, Weerakoon WMTDN, Wanigasekara DN et al. Antiviral potential of selected medicinal herbs and their isolated natu-ral products. BioMed Research International, v.2021, p.1-18, 2021. https://doi.org/10.1155/2021/7872406

Ragunath C, Kumar YAS, Kanivalan I, Radhakrishnan S. Phytochemical screening and GC-MS analysis of bioactive constituents in the methanolic extract of Caulerpa racemosa (Forssk.) J. Agardh and Padina boergesenii Allender & Kraft. Current Applied Science And Technology, v.20, n.3, p.380-393, 2020.

Rana S, Saxena A. Medicinal chemistry of neem: A state of art. Kochi, Kerala, India: 1, 2023. https://doi.org/10.1063/5.0114567

Raza W, Ling N, Liu D, Wei Z, Huang Q, Shen Q. Volatile organic compounds produced by Pseudomonas fluorescens WR-1 restrict the growth and virulence traits of Ralstonia solanacearum. Microbiological Research, v.192, p.103-113, 2016.

https://doi.org/10.1016/j.mi cres.2016.05.014

Saha tchinda J-B, Tchebe TMF, Tchoukoua A, Yona AMC, Fauconnier ML, Kor M N, et al. Fatty acid profiles, antioxi-dant, and phenolic contents of oils extracted from Acacia polyacantha and Azadirachta indica (Neem) seeds using green solvents. Journal of Food Processing and Preserva-tion, v.45, n.2, p.1-13, 2021. https://doi.org/10.1111/jfpp.15115

Sarkar S, Singh RP, Bhattacharya G. Exploring the role of Azadirachta indica (neem) and its active compounds in the regulation of biological pathways: an update on molecular approach. 3 Biotech, v.11, n.4, p.178, 2021. https://doi.org/10.1007/s13205-021-02745-4

Satyal P, Craft JD, Dosoky NS, Setzer WN. The chemical compositions of the volatile oils of garlic (Allium sativum) and wild garlic (Allium vineale). Foods, v.6, n.8, p.63, 2017.

https://doi.org/10.3390/foods6080063

Shariare MH, Noor HB, Khan JH, Uddin J, Ahamad SR, Altamimi MA, Alanazi FK, Kazi M. Liposomal drug deli-very of Corchorus olitorius leaf extract containing phytol using design of experiment (DoE): In-vitro anticancer and in-vivo anti-inflammatory studies. Colloids and Surfaces B: Biointerfaces, v.199, p,1-11, 2021. https://doi.org/10.1016/j.colsurfb.2020.111543

Suganthy M, Gajendra CV. Chemical characterization of Strychnos nux-vomica L. leaves for biopesticide properties using GC-MS. International Journal of Chemical Studies, v.8, n.1, p.1112-1116, 2020. https://doi.org/10.22271/chemi.2020.v8.i1o.8398

Tesfaye B, Tefera T, Misikir O, Tsegaye G. Extraction and comparison of essential oil from neem seed by using soxhlet extraction and simple distillation methods. International Journal of Engineering Technologies and Management Re-search, v.5, n.9, p.74-81, 2018. https://doi.org/10.29121/ijetmr.v5.i9.2018 .291

Tesfaye B, Tefera T. Extraction of essential oil from neem seed by using soxhlet extraction methods. IJAEMS, v.3, n.6, p.646-650, 2017.

https://dx.doi.org/10.24001/ij aems.3.6.5

Tulashie SK, Adjei F, Abraham J, Addo E. Potential of neem extracts as natural insecticide against fall armyworm (Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctui-dae). Case Studies in Chemical and Environmental Engi-neering, v.4, p.1-7, 2021.

https://doi.org/10.1016 /j.cscee.2021.100130

Ungo-Kore HY, Ibrahim YKE, Tytler BA. Anti-dermatophytic activity of hexane extracts of Azadirachta indicates A. Juss. African Journal of Microbiology Research, v.13, n.26, p.421-429, 2019. https://doi.org/10.5897/AJMR2018.8819

Winnett V, Sirdaarta J, White A, Clarke FM, Cock IE. Inhibi-tion of Klebsiella pneumoniae growth by selected australian plants: natural approaches for the prevention and manage-ment of ankylosing spondylitis. Inflammopharmacology, v.25, p.223-235, 2017. https://doi.org/10.1007/s10787-017-0328-1

Yami AM, Ibrahim ME, Raji A. Extraction and characterizati-on of oil from neem and yellow oleander seeds for biodiesel production. European Journal of Materials Science and En-gineering, v.5, n.4, p.212-221, 2020. https://doi.org/10.36868/ejmse.2020.05.04.212

Zambiazi RC, Przybylski R, Zambiazi MW, Mendonça CB. Fatty acid composition of vegetable oils and fats. Bulletin of the Center for Food Research and Processing, v.25, n.1, p.111-120, 2007.

http://dx.doi.org/10.5380/cep.v25i1.8399

Zatelli A, Fondati A, Maroli M. The knowns and unknowns of the efficacy of neem oil (Azadirachta indica) used as a preventative measure against Leishmania sand fly vectors (Phlebotomus genus). Preventive Veterinary Medicine, v.202, p.1-5, 2022.

https://doi.org/10.1016/j.prevetmed.2022.105618

Zhang H, Mallik A, Zeng RS. Control of panama disease of banana by rotating and intercropping with chinese chive (Al-lium Tuberosum Rottler): role of plant volatiles. Journal of Chemical Ecology, v.39, n.2, p.243-252, 2013. https://doi.org/10.1007/s10886-013-0243-x

Zhao B, Li H, Lan T, Wu D, Chen Z. Characterization of the chemical composition of chinese Moringa oleifera seed oil. Journal of the American Oil Chemists' Society, v.96, n.5, p.523-533, 2019.

https://doi.org/10.1002/aocs.12203

Zhao Y, Smyth HE, Tao K, Henry RJ, Gilbert RG. Starch molecular structural features and volatile compounds affec-ting the sensory properties of polished australian wild rice. Foods, v.11, n.4, p.1-22, 2022.

https://doi.org/10.3390/foods11040511

Zheng L, Shen X, Wang Y, Liang J, Xu M, Fang X, Gang C, Guilliang C. Content and composition of phospholipids, fatty acids and sterols in commercial natural phospholipid excipients. Current Pharmaceutical Analysis, v.17, n.7, p.892-902, 2021.

https://doi.org/10.2174 /1573412916999200605162707

Journal of Biotechnology and Biodiversity

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15-12-2023

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Cabral, S. M., Silva, F. L. do N., Rodrigues, P. J., Rambo, M. K. D., Santos, J. R., Chaves, M. H., & Pinto, B. F. (2023). Extração e caracterização química do óleo da semente de nim (Azadirachta indica). Journal of Biotechnology and Biodiversity, 11(4), 170–181. https://doi.org/10.20873/jbb.uft.cemaf.v11n4.16258