Chemical profile, antibacterial activity and antibiotic-modifying effects of the fixed oil of Annona squamosa L. (Annonaceae)

Authors

DOI:

https://doi.org/10.3989/gya.0435251.2320

Keywords:

Annona squamosa, Antibacterial activity, CG-MS, Elaidic acid

Abstract


Annona squamosa Linn (Annonaceae) is a medicinal plant used to treat various ailments such as urinary infections, diarrhea, and fever. The aim of this study was to determine the chemical profile and evaluate the antibacterial and antibiotic-modifying activities of the fixed oil from A. squamosa seeds (OFSAs). The antibacterial activity was evaluated by determining the Minimum Inhibitory Concentration (MIC) and antibiotic modulation with aminoglycosides. The chemical analysis of the OFSAS identified 21 fatty acid esters, with elaidic acid being the major compound, comprising 38.06% of the oil. The MIC antibacterial assay showed inhibitory effects and the modulation with aminoglycoside antibiotics demonstrated enhanced antibacterial activity. Statistical analysis of the modulation assay was performed using two-way ANOVA followed by Tukey’s post hoc test, with ****p < 0.0001. The use of OFSAs represents a promising perspective for application in antibacterial therapy, with further research needed, particularly regarding its mechanisms of action.

Downloads

Download data is not yet available.

References

Albuquerque TN, Gomes JP, Campos ARN, Costa JD, Gregório M, Santana GRAC, Filho AAO, Fonseca ADT. 2024. Composição química e atividade antibacteriana do óleo comercial das sementes de romã (Punica granatum L.) frente a bactérias de origem alimentar. Caderno Pedagógico 21 (7), e5671. https://doi.org/10.54033/cadpedv21n7-121

Araújo ACJ, Freitas PR, Barbosa CRS, Muniz DF, Rocha JE, Silva ACA, Oliveira-Tintino CDM, Ribeiro-Filho J, Silva LE, Confortin C, Amaral W, Deschamps C, Barbosa-Filho JM, Lima NTR, Tintino SR, Coutinho HDM. 2020. GC-MS-FID Characterization and antibacterial activity of the Mikania cordifolia essential oil and limonene against MDR strains. Food Chem. Toxicol. 136, 111023. https://doi.org/10.1016/j.fct.2019.111023 PMid:31866146

Arora P, Garg M, Gera T, Vaid L, Sood P, Kaur L, Kaur P, Sahu SK. 2024. Antimicrobial activity of secondary metabolites in medicinal plants: An update. BIO Web Conf. 86, 01040. https://doi.org/10.1051/bioconf/20248601040

Bezerra AA. 2023. Evaluation of the insecticidal activity of Syagrus coronata (Mart.) Becc. oil against Sitophilus zeamais Motschulsky, 1855 (Coleoptera: Curculionidae). Dissertation (MSc in Biochemistry and Physiology), Univ. Fed. Pernambuco, Recife-PE.

Borba DRS. 2023. Evaluation of the antibacterial activity of endophytic fungus metabolite extracts from Pantanal against multidrug-resistant bacteria. Dissertation (MSc in Biotechnology), Univ. Fed. Rio Gd. Sul, Campo Grande-MS.

Bruno CMA, Almeida MR. 2021. Essential and vegetable oils: Raw materials for the manufacture of bioproducts in experimental organic chemistry. Quím. Nova 44 (7), 899-907.

Cabral MES, Dias DQ, Sales DL, Oliveira OP, Teles DA, Araujo Filho JA, Sousa JGG. 2013. Evaluations of the antimicrobial activities and chemical compositions of body fat from amphibians Leptodactylus macrosternum and Leptodactylus vastus in Northeastern Brazil. Evid.-Based Complement. Altern. Med. 2013, 913671. pp. 1-7. https://doi.org/10.1155/2013/913671 PMid:23710241 PMCid:PMC3655571

CLSI. 2015. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard. Wayne, USA.

Coutinho HDM, Costa JGM, Lima EO, Falcão-Silva VS, Siqueira-Júnior JP. 2008. Enhancement of the antibiotic activity against a multiresistant Escherichia coli by Mentha arvensis L. and chlorpromazine. Chemotherapy 54 (4), 328-330. https://doi.org/10.1159/000151267 PMid:18698137

Debbabi M, Zarrouk A, Bezine M, Meddeb W, Nury T, Badreddine A, Karym EM, Sghaier R, Bretillon L, Guyot S, Samadi M, Cherkaoui-Malki M, Nasser B, Mejri M, Ben-Hammou S, Hammami M, Lizard G. 2017. Comparison of the effects of main fatty acids in the Mediterranean diet (oleic acid, docosahexaenoic acid) and in hydrogenated oils (elaidic acid) on oxiapoptosis induced by 7-cetocholesterol in BV-2 microglial cells. Chem. Phys. Lipids 207, 151-170. https://doi.org/10.1016/j.chemphyslip.2017.04.002 PMid:28408132

Harahap D, Niaci S, Mardina V, Zaura B, Qanita I, Purnama A, Puspita K, Rizki DR, Iqhrammullah M. 2022. Antibacterial activities of seven ethnomedicinal plants from family Annonaceae. J. Adv. Pharm. Technol. Res. 13 (3), 222-227. https://doi.org/10.4103/japtr.japtr_111_22 PMid:35935693 PMCid:PMC9355059

Holanda LEG, Ramos CS, França Filho JR. 2023. Fatty acid profiles and antimicrobial activity from tropical

fruit seeds. J. Mex. Chem. Soc. 67 (2).

Lai Y, Gao Y, Lin J, Liu F, Yang L, Zhou J, Xue Y, Li Y, Chang Z, Li J, Chao T, Chen J, Cheng X, Gao X, Li X, Lu F, Chu Q, Wang W. 2024. Dietary elaidic acid enhances tumor antigen presentation and immunity to cancer via ACSL5. Cell Metab. 36 (4), 822-838.e8. https://doi.org/10.1016/j.cmet.2024.01.012 PMid:38350448

Liu H, Nan B, Yang C, Li X, Yan H, Yuan Y. 2022. Elaidic acid induced NLRP3 inflammasome activation via ERS-MAPK signaling pathways in Kupffer cells. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1867 (1), 159061. https://doi.org/10.1016/j.bbalip.2021.159061 PMid:34610469

Mancini A, Imperlini E, Nigro E, Montagnese C, Daniele A, Orrù S, Buono P. 2015. Biological and nutritional properties of palm oil and palmitic acid: Effects on health. Molecules 20 (9), 17339-17361. https://doi.org/10.3390/molecules200917339 PMid:26393565 PMCid:PMC6331788

Neto PPA, Silva CR, Santos RRL, Paiva AGC, Ximenes JC, Guimarães DVFS, Castro LMB, Moreira THG, Carvalho RRN, Barros FT. 2023. Consecutive bacterial resistance from the indiscriminate use of antibiotics: An integrative review. Arq. Ciênc. Saúde UNIPAR 27 (5), 3320-3330. https://doi.org/10.25110/arqsaude.v27i5.2023-076

Nonato CDA, Leite DOD, Carvalho NKG, Lima SG, Rodrigues FFG, Costa JGM. 2020. Chemical characterization and evaluation of antioxidant and antimicrobial properties of the pulp oil of fruits of Mauritia flexuosa L. Bol. Latinoam. Caribe Plantas Med. Aromát. 19 (4), 408-419. https://doi.org/10.37360/blacpma.20.19.4.28

Nugraha AS, Damayanti YD, Wangchuk P, Keller PA. 2019. Anti-infective and anticancer properties of the Annona species: Its ethnomedicinal uses, alkaloid diversity, and pharmacological activities. Molecules 24, 4419. https://doi.org/10.3390/molecules24234419 PMid:31816948 PMCid:PMC6930583

Ohmori H, Fujii K, Kadochi Y, Mori S, Nishiguchi Y, Fujiwara R, Kishi S, Sasaki T, Kuniyasu H. 2017. Elaidic acid, a trans fatty acid, enhances metastasis of colorectal cancer cells. Pathobiol. Infect. Dis. 84 (3), 144-151. https://doi.org/10.1159/000449205 PMid:27832659

Pinheiro AA. 2022. Chemical characterization, evaluation of antioxidant, hypoglycemic, and antimicrobial potential of Annona tomentosa R. E. Fr. (Annonaceae). Dissertation (MSc in Chemistry), Univ. Fed. Maranhão, São Luís-MA.

Pinto NCC, Silva JB, Menegati LM, Guedes MCMR, Marques LB, Silva TP, Melo RCN, Souza-Fagundes EM, Salvador MJ, Scio E. 2017. Cytotoxicity and bacterial membrane destabilization induced by Annona squamosa L. extracts. An. Acad. Bras. Ciênc. 89 (3), 2053-2073. https://doi.org/10.1590/0001-3765201720150702 PMid:28813096

Rangel J, Liberal Â, Catarino S, Costa JC, Romeiras MM, Fernandes Â. 2020. Phytochemical and bioactive potential of African Annonaceae species. Plants 9, 1326.

Santos LGP, Castro CMVA. 2023. Effects of Annona squamosa leaf extract on the insects Aedes aegypti, Nasutitermes corniger, and Sitophilus zeamais and the microcrustacean Hyalella sp. S. Afr. J. Bot. 162, 913-919. https://doi.org/10.1016/j.sajb.2023.10.002

Sawant SS, Gabhe SY, Singh KK. 2023. In vitro effect on Plasmodium falciparum and in vivo effect on Plasmodium berghei of Annomaal, an oily fraction obtained from Annona squamosa seeds. Molecules 28, 5472. https://doi.org/10.3390/molecules28145472 PMid:37513343 PMCid:PMC10383673

Shao F, Ford DA. 2014. Elaidic acid increases hepatic lipogenesis by mediating sterol regulatory element binding protein-1c activity in HuH-7 cells. Lipids 49 (5), 403-413. https://doi.org/10.1007/s11745-014-3883-x PMid:24481861 PMCid:PMC3999188

Sousa ABA, Ramalho FL, Camargo B. 2020. Prevalência de infecções nosocomiais ocasionadas por Klebsiella pneumoniae produtora de carbapenemase (KPC) em indivíduos hospitalizados. Braz. J. Health Rev. 3 (2), 1915-1932. https://doi.org/10.34119/bjhrv3n2-051

Sundaramahalingam MA, Karthikumar S, Rajaram SK, Samuel KJ, Shajahan S, Sivasubramanian V, Sivashanmugam P, Varalakshmi P, Syed A, Marraiki N, Elgorban AM, Vinoth Kumar R, Moorthy IG. 2021. An intensified approach for transesterification of biodiesel from Annona squamosa seed oil using ultrasound-assisted homogeneous catalysis reaction and its process optimization. Fuel 291, 120195. https://doi.org/10.1016/j.fuel.2021.120195

Xia J, Zhang X, Zhang Y, Wang Y, Li J, Wang X, Zhang W, Zhang L, Wang X. 2020. Protective effect of Se-methylselenocysteine on elaidic acid-induced inflammation in human arterial endothelial cells. J. Nutr. Sci. Vitaminol. 66 (6), 577-583. https://doi.org/10.3177/jnsv.66.577 PMid:33390400

Urban-Chmiel R, Marek A, Stępień-Pyśniak D, Wieczorek K, Dec M, Nowaczek A, Osek J. 2022. Antibiotic resistance in bacteria - A review. Antibiotics 11, 1079. https://doi.org/10.3390/antibiotics11081079 PMid:36009947 PMCid:PMC9404765

Yuan Y, Wang X, Li L, Wang Z, Li W, Pang Y, Yan H. 2024. Apoptosis mechanism induced by combined action of acrylamide and elaidic acid via endoplasmic reticulum stress injury. Food Chem. Toxicol. 189, 114733. https://doi.org/10.1016/j.fct.2024.114733 PMid:38740238

Downloads

Published

2025-06-30

How to Cite

1.
Donelardy A, Leite D, do Nascimento J, Nascimento L, Rodrigues F, Castro J, de Carvalho N, Mendes J, G-Rodrigues F, da Costa J. Chemical profile, antibacterial activity and antibiotic-modifying effects of the fixed oil of Annona squamosa L. (Annonaceae). Grasas aceites [Internet]. 2025Jun.30 [cited 2026Jul.27];76(2):2320. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/2320

Issue

Section

Research