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Isolation and characterization of new secondary metabolites from Asphodelus microcarpus.

ABSTRACT: Phytochemical study of the ethanolic extract of Asphodelus microcarpus Salzm. et Viv. (Asphodelaceae) resulted in the isolation of two new compounds, methyl-1,4,5-trihydroxy-7-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate (1), and (1R) 3,10-dimethoxy-5-methyl-1H-1,4-epoxybenzo[h]isochromene (2) as well as three known compounds; 3,4-dihydroxy-methyl benzoate (3), 3,4-dihydroxybenzoic acid (4), and 6-methoxychrysophanol (5). Compound 1 showed a potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus aureus with IC50 values of 1.5 and 1.2 µg/mL, respectively. Compound 3 showed antileishmanial activity with an IC50 value of 33.2 µg/mL. Compound 2 is the first isochromene possessing a highly strained 1,4-epoxy moiety. The structure elucidation of isolated metabolites was carried out using spectroscopic data, the absolute configuration of 2 based on optical rotation and electronic circular dichroism experiments and calculations.

SUBMITTER: Ghoneim MM 

PROVIDER: S-EPMC5048751 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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Isolation and characterization of new secondary metabolites from <i>Asphodelus microcarpus</i>.

Ghoneim Mohammed M MM   Elokely Khaled M KM   El-Hela Atef A AA   Mohammad Abd Elsalam I AE   Jacob Melissa M   Cutler Stephen J SJ   Doerksen Robert J RJ   Ross Samir A SA  

Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents 20140211 7

Phytochemical study of the ethanolic extract of <i>Asphodelus microcarpus</i> Salzm. et Viv. (Asphodelaceae) resulted in the isolation of two new compounds, methyl-1,4,5-trihydroxy-7-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate (<b>1</b>), and (1<i>R</i>) 3,10-dimethoxy-5-methyl-1<i>H</i>-1,4-epoxybenzo[<i>h</i>]isochromene (<b>2</b>) as well as three known compounds; 3,4-dihydroxy-methyl benzoate (<b>3</b>), 3,4-dihydroxybenzoic acid (<b>4</b>), and 6-methoxychrysophanol (<b>5</b>). C  ...[more]

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