Two antimicrobial compounds drimane sesquiterpene polygodial and 11-hydroxydrim-8-en-7-one from the stem bark of Drimys arfakensis Gibbs. (Winteraceae)
DOI:
https://doi.org/10.11113/mjfas.v14n1-2.955Keywords:
C. albicans, D. arfakensis, E. coli, polygodial, hydroxydrim-8-en-7-one, S. aureus (MRSA)Abstract
Antimicrobial-guided fractionation and isolation of the bioactive compounds from the stem bark of Drimys arfakensis Gibbs. were carried out. Two antimicrobial compounds were isolated. The sructures of the compounds were elucidated by spectroscopic methods such as 1H NMR, 13C NMR, 2-D NMR, ESI-MS and EI-MS. Based on the spectroscopic data, the two antimicrobial compounds were polygodial, 1 and and 11-Hydroxydrim-8-en-7-one, 2. . Compound 1 exhibited very strong activity against methicillin-resistant Staphylococcus aureus (MRSA) (B-1823), and yeast-like fungi Candida albicans (B-2219) with both having MIC values of 7.8 µg.mL-1. It also showed strong activity against gram negative bacteria Escherichia coli (B-1634 ) with MIC value of 31.2 µg.mL-1 . While compound 2 only possesses strong activity against S. aureus (MRSA), no activity against C. albicans and E. coli was observed. This is the first report on the antimicrobial activity of compound 2 and on the isolation of these two compounds from D. arfakensis Gibbs.References
Aves T. M. A., Ribeiro F. L., Kloos H., Zani C. L. 2001. Polygodial, the fungitoxic component from the Brazilian medicinal plant Polygonum punctatum. Mem. Inst. Oswaldo Cruz, 96, 831–833.
Eloff, J. N. 1998. A sensitive and quick microplate method to determine the minimum inhibitory concentration of plant extracts for bacteria. Planta Med., 64, 711–713.
Fattouch, S., Caboni, P., Coroneo, V., Tuberoso, C. I., Angioni, A., Dessi, S. 2007. Antimicrobial activity of Tunisian quince (Cydonia oblonga Miller) pulp and peel polyphenolic extracts. J. Agric. Food Chem., 55, 963–969.
Gatsing, D., Nkeugouapi, C. F. N., Nji-Nkah, B. F., Kuiate, J. R., Tchouanguep, F. M. 2010. Antibacterial activity, bioavailability and acute toxicity evaluation of the leaf extract of Alchornea cordifolia
(Euphorbiaceae). Int. J. Pharmacol., 6, 173–182.
Gibbs, L. S. 1917. A contribution to the phytogeography and flora of the Arfak mountains. London: Taylor and Francis.
Hamburger, M. O., Cordell, G. A. 1987. A direct bioautographic TLC assay for compounds possessing antibacterial activity. J. Nat. Prod., 50, 19–22.
Heywood, V. H. 1993. Flowering plants of the world. London: Andromeda Oxford Ltd.
Kubo, I., Fujita, K., Lee, S. H., Ha, T. J. 2005. Antibacterial activity of polygodial. Phytother. Res., 19, 1013–1017.
Lee, S. H, Lee, J. R., Lunde, C. S., Kubo, I. 1999 In vitro antifungal susceptibilities of Candida albicans and other fungal pathogens to polygodial, a sesquiterpene dialdehyde, Planta Med., 65, 205–208.
Lensee, O. N. 2002. Ethnobotanical study of traditional medicinal plants from Manokwari Regency, West Papua, Indonesia, Master’s thesis, James Cook University.
Malheiros, A., Cechinel, V., Schmitt, C., Santos, A., Scheidt, C., Calixto, J., Monache, F., Yunes, R. A. 2001. A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark. Phytochemistry, 57, 103–107.
Malheiros, A., Cechinel, V., Filho, V., Schmitt, C. B., Yunes, R.A., Escalante, A., Svetaz, L., Zacchino, S., Monache, F. D. 2005 Antifungal activity of drimane sesquiterpenes from Drimys brasiliensis using bioassay-guided fractionation. J. Pharm. Pharm. Sci., 8, 2, 335–339.
Santoso, B. B., Lensee, O. N., Sadsoeitoeboen, M. J., Sjamsul, A. A, Syah, Y. M. 2005. Screening for phytochemicals and antimicrobial activities of medicinal plants from Manokwari Regency. Jurnal Natural Indonesia, 5, 34–40.
Santoso, B. B., Lensee, O. N., Sadsoeitoeboen, M. J., Sjamsul, A. A., Yana, Y. M. 2007. Screening for cytotoxicity and antioxidant activities of medicinal plants from Manokwari Regency, Papua, Indonesia. Jurnal Natural Indonesia, 7, 23–28.
Silveira, A. C. O., Cludino, V. D., Yunes, R. A., Cechinel, V., Filho, V., Malheiros, A., Cordova, C. M. N., Bella cruz, A. 2012. Antibacterial activity and toxicity of Drimys brasiliensies. Lat. Am. J. Pharm., 31 (7), 93–40.
Vlad, P. F., Popa, D. P, Gorincoi, C. C., Coltsa, M. N., Mironov, G. N. 2000. Synthesis of 11-hydroxydrim-8(9)-en-7-one and 11,12-dihydroxydrim-8(9)-en-7-one from drim-8 (9)-en-7-one. Russ. Chem. Bull, 49, 1, 98–101.
Zhao, Z. Z., Chen, H. P., Feng, T., Li, Z. H., Liu, J. K. 2014. Four new sesquiterpenoids from cultures of the fungus Phellinidium sulphurascens. Nat. Prod. Bioprospect., 5, 1, 23–28.
