Triterpenes, steroids and phenolic isolated from Minquartia guianensis Aubl. (Coulaceae) and antibacterial activity
Triterpenos, esteroides e fenólico isolados de Minquartia guianensis Aubl. (Coulaceae) e atividade antibacteriana
DOI:
https://doi.org/10.53660/CLM-920-23B61Palavras-chave:
NMR, β-amyrin, β-amyrone, Methyl gallate, PhytochemistryResumo
This work aimed to carry out a chemical study of Minquartia guianensis branches and leaves extracts (Coulaceae) and to evaluate their antibacterial potential. The collection of plant material was carried out at Reserva Ducke, Manaus, Amazonas. The plant material was dried, ground, and extracted with hexane (Hex) and methanol (MeOH). The extracts obtained were submitted to chromatographic analysis and showed characteristics mainly of terpenes and phenolics. The chemical fractionation of branches methanol extract allowed the isolation of the triterpenes: lupen-3-one, β-amyrone, lupeol, β-amyrin; the steroids: β-sitosterol and stigmasterol, and a phenolic derivative: methyl gallate. From the leaf’s methanol extract, the triterpene: taraxerol was identified. These same methanol extracts were active against gram-positive bacteria: Staphylococcus aureus and gram-negative bacteria: Aeromonas hydrophila and Pseudomonas fluorescens, with an inhibition percentage of 63 to 70%. Based on the results, this work contributed to the chemical and biological knowledge of the species M. guianensis, this being the first report of the substances: β-amyrin, β-amyrone and methyl gallate for the Coulaceae family.
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ABDEL-RAOUF, N.; AL-ENAZI, N. M.; AL-HOMAIDAN, A. A.; IBRAHEEM, I. B. M.; AL-OTHMAN, M. R.; HATAMLEH, A. A. Antibacterial β-amyrin isolated from Laurencia microcladia. Arabian J. Chem., v. 8, p. 32–37, 2015. DOI: 10.1016/j.arabjc.2013.09.033
ATANASOV, A. G.; ZOTCHEV, S. B.; DIRSCH, V. M.; SUPURAN, C. T. Natural products in drug discovery: advances and opportunities. Nat. Rev. Drug Disc., v. 20, p. 200–216, 2021. DOI: 10.1038/s41573-020-00114-z
BARBIERI, R.; COPPO, E.; MARCHESE, A.; DAGLIA, M.; SOBARZO-SÁNCHEZ, E.; NABAVI, S. F.; NABAVI, S. M. Phytochemicals for human disease: An update on plant-derivedcompounds antibacterial activity. Microbiol. Res., v. 196, p. 44–68, 2017. DOI: 10.1016/j.micres.2016.12.003
BI, X.; HAN, L.; QU T; MU, Y.; GUAN, P.; QU, X.; WANG, Z.; HUANG, X. Anti-Inflammatory effects, SAR, and action mechanism of monoterpenoids from Radix Paeoniae alba on LPS-stimulated RAW 264.7 cells. Molecules, v. 22, n. 5, p. 715, 2017. DOI: 10.3390/molecules22050715
BREZÁNI, V.; LELÁKOVÁ, V.; HASSAN, S. et al. Anti-infectivity against herpes simplex virus and selected microbes and anti-Inflammatory activities of compounds isolated from Eucalyptus globulus Labill. Viruses, v. 10, n. 7, p. 360, 2018. DOI: 10.3390/v10070360.
CHO, M.; SO, I.; CHUN, J. N.; JEON, J-H. The antitumor effects of geraniol: modulation of cancer hallmark pathways review. Int. J. Oncol., v. 48, n. 5, p. 1772-1782, 2016. DOI: 10.3892/ijo.2016.3427
CHUKWUNONSO, E.; VERONICA, B.; TOYO, P. Methicillinresistant Staphylococcus aureus: a mini review. Int. J. Med. Res. Hea. Sci., vol. 7, no. 1, p. 122–127, 2018.
CLSI. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved Standard-Tenth Edition. M07 A10. v. 35, p. 1-87, 2015.
CURSINO, L. M. C.; MESQUITA, A. S. S.; MESQUITA, D. W. O.; FERNANDES, C. C.; NUNEZ, C. V. Triterpenos das folhas de Minquartia guianensis Aubl. (Olacaceae). Acta. Amazonica, v. 39, n. 1, p. 181–186, 2009.
CURSINO, L. M. C.; NUNEZ, C. V.; DE PAULA, R. C.; NASCIMENTO, M. F. A.; DOS SANTOS, P. A. Triterpenes from Minquartia guianensis (Olacaceae) and in vitro antimalarial activity. Quimica Nova, v. 35, n. 11, p. 2165–2168, 2012.
DOGAN, G.; KARA, N.; BAGCI, E.; GUR, S. Chemical composition and biological activities of leaf and fruit essential oils from Eucalyptus camaldulensis. Zeitschrift für Naturforschung C.; v. 72, n. 11, p .483-489, 2017. DOI:10.1515/znc-2016-0033
FLORA DO BRASIL. http://floradobrasil.jbrj.gov.br/reflora/floradobrasil/FB19958, acessado em Fev 2023.
GHONIEM, E. M.; HENDAWY, G. R.; MOTELEB, T. M. A. Caracterização de Staphylococcus aureus resistente à vancomicina no National Liver Institute. Menoufia Med. J., vol. 27, p. 825–832, 2014.
JEPPESEN, P. B.; YRSKOG, S. E.; AGGER, A.; GREGERSEN, S.; COLOMBO, M.; XIAO, J.; HERMANSEN, K. Can stevioside in combination with a soy-based dietary supplement be a new useful treatment of type 2 diabetes? an in vivo study in the diabetic Goto-Kakizaki rat. Rev Diabet Stud., v. 3, n. 4, p. 189-199, 2006. DOI: 10.1900/RDS.2006.3.189
KHAMENEH, B.; IRANSHAHY, M.; SOHEILI, V.; FAZLY BAZZAZ, B. S. Review on plant antimicrobials: a mechanistic viewpoint. Antimicrob. Resist. Infect. Control. v. 8, p. 118, 2019 DOI: 10.1186/s13756-019-0559-6
KANG, M. S.; OH, J. S.; KANG, I. C.; HONG, S. J.; CHOI, C. H. Inhibitory effect of methyl gallate and gallic acid on oral bacteria. The J. Microb., v. 46, n. 6, p. 744-750, 2008. DOI 10.1007/sl12275-008-0235-7
KOAY, Y. C.; WONG, K. C.; OSMAN, H; ELDEEN, I. M. S; ASMAWI, M. Z. Chemical Constituents and Biological Activities of Strobilanthes crispus L. Rec. Nat. Prod., v. 7, n. 1, p. 59-64, 2013. EISSN:1307-6167
LISEWSKI A. M.; QUIROS J. P.; NG, C. L, ADIKESAVAN, A. K.; MIURA, K.; PUTLURI, N.; EASTMAN, R. T. et al. Supergenomic network compression and the discovery of EXP1 as a glutathione transferase inhibited by artesunate. Cell., v. 158, n. 4, p. 916-928. DOI: 10.1016/j.cell.2014.07.011
MANDAL, S. M.; ROY, A.; GHOSH, A.K.; HAZRA, T.K.; BASAK, A.; FRANCO, O. L. Challenges and future prospects of antibiotic therapy: from peptides to phage sutilization. Front. Pharmacol., v. 5, n. 5, p. 1–12, 2014. DOI: 10.3389/fphar.2014.00105
MARTINEZ, A. M.; GAMBIN, Y.; SIERECKI, Y. Thinking outside the bug: molecular targets and strategies to overcome antibiotic resistance. Inter. J. Mol. Sci., v. 20, n. 6, p. 1255–1277, 2019. DOI: 10.3390/ijms20061255.
PANDE, S.; KOST, C. Bacterial unculturability and the formation of Intercellular metabolic networks. Trends Microbiol., v. 25, n. 5, p. 1-13, 2017. ISSN 0966-842X.
PATIL, P.; SOUJANYA, B.; KIRAN, K. A. A review on lupeol: superficial triterpenoid from horticulture crops. Internat. J. Chem. Stud., v. 6, n. 3, p. 3301-3305, 2018. ISSN: 2349–8528
PEDROZA, L. S.; SALAZAR, M. G. M.; OSORIO, M. I. C.; FACHIN-ESPINAR, M. T.; PAULA, R. C.; NASCIMENTO, M. F. A.; OLIVEIRA, A. B.; NUNEZ, C. V. Estudo químico e avaliação da atividade antimalárica dos galhos de Piranhea trifoliata. Rev. Fitos, v. 14, n. 4, p. 476-491, 2020. DOI 10.32712/2446-4775.2020.905
RASMUSSEN, H. B.; CHRISTENSEN, S. B.; KVIST, L. P.; KHARAZMI, A.; HUANSI, A. G. Absolute configuration and antiprotozoal activity of Minquartynoic acid. J. Nat. Prod., v. 63, n. 9, p. 1295–1296, 2000. DOI: 10.1021/np990604k
SANTIAGO, C., PANG, E. L., LIM, K. H., LOH, H. S., TING, K. N. Inhibition of penicillin-binding protein 2a (PBP2a) in methicillin resistant Staphylococcus aureus (MRSA) by combination of ampicillin and a bioactive fraction from Duabanga grandiflora. BMC Complement. Altern. Med., v. 15, n. 1, p. 1, 2015. DOI: 10.1186/s12906-015-0699-z
SHAN, L. Y.; THING, T. C.; PING, T. S.; AWANG, K.; HASHIM N. M.; NAFIAH, M. A.; AHMAD, K. Cytotoxic, antibacterial and antioxidant activity of triterpenoids from Kopsia singapurensis Ridl. J. Chem. and Pharm. Res., v. 6, n. 5, p. 815-822, 2014. ISSN: 0975-7384
TAN, Y. P.; CHAN, E. W. C.; LIM, C. S. Y. Potent quorum sensing inhibition by methyl gallate isolated from leaves of Anacardium occidentale L. (cashew). Chiang Mai J. Sci. v. 42, n. 3, p. 650-656, 2015.
TENOVER, F. C. Mechanisms of antimicrobial resistance in bacteria. Am. J. Infect. Control., v. 34 p. 3–10, 2006. DOI: 10.1016/j.ajic.2006.05.219.
TOUANI, F. K.; SEUKEP, A. J.; DJEUSSI, D. E.; FANKAM, A. G.; NOUMEDEM, J. A.; KUETE, V. Antibiotic-potentiation activities of four Cameroonian dietary plants against multidrug-resistant Gram-negative bacteria expressing efflux pumps. BMC Complement. Altern. Med., v. 14, n. 258, 2014.
WANG, W.; GY, S.; WQ, H.; ZHAO, Y. Q. Advances in pharmacological effects of ginsenosides on cardiovascular diseases in the past 10 years. Chinese Herb. Medic., v. 47, p. 3736-3741, 2016.
YAGUI, M. Resistencia antimicrobiana: nuevo enfoque y oportunidad. Rev. Peru. Med. Exp. Sal. Púb., vol. 35, n. 1, p. 7-8, 2018. DOI: 10.17843/rpmesp.2018.351.3594
