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Bioassay-guided studies on Bombax ceiba leaf extract: isolation of shamimoside, a new antioxidant xanthone C-glucoside

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Chemistry of Natural Compounds Aims and scope

Bioassay-guided isolation studies on the methanolic extract of the leaves of Bombax ceiba employing DPPH antioxidant assay led to the isolation of a new xanthone C-glucoside, shamimoside (2), along with three known constituents, mangiferin (1), stigma-5-en-3-O-β-glucoside, and β-amyrin. The structure of shamimoside has been elucidated through extensive spectroscopic methods, including 1D and 2D NMR experiments, as 4-C-β-D-glucopyranosyl-1,3,6,8-tetrahydroxy-7-O-(p-hydroxybenzoyl)-9H-xanthen-9-one (2). It is the first naturally occurring xanthone containing a benzoate moiety directly attached to an aromatic ring. Polar extracts and fractions demonstrated better antioxidant activity, and 1 was found to be more potent than 2 in this assay.

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Acknowledgment

One of the authors (Rehman S. Z.) is grateful to the Higher Education Commission Islamabad, Pakistan for financial support through the Merit Scholarship Scheme for Ph.D. Studies in Science and Technology (200 Scholarships).

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Authors and Affiliations

  1. International Center for Chemical and Biological Sciences, H. E. J. Research Institute of Chemistry, University of Karachi, 75270, Karachi, Pakistan

    Shaheen Faizi, Sadia Zikr-ur-Rehman, Aneela Naz, Ahsana Dar & Sabira Naqvi

  2. Department of Chemistry, Federal Urdu University of Arts, Sciences and Technology, Science Campus, Gulshan-e-Iqbal, 75300, Karachi, Pakistan

    Muhammad Ali Versiani

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  1. Shaheen Faizi
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  2. Sadia Zikr-ur-Rehman
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  3. Aneela Naz
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  4. Muhammad Ali Versiani
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  5. Ahsana Dar
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  6. Sabira Naqvi
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Correspondence to Muhammad Ali Versiani.

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Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2012, pp. 692–696.

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Faizi, S., Zikr-ur-Rehman, S., Naz, A. et al. Bioassay-guided studies on Bombax ceiba leaf extract: isolation of shamimoside, a new antioxidant xanthone C-glucoside. Chem Nat Compd 48, 774–779 (2012). https://doi.org/10.1007/s10600-012-0379-x

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  • DOI: https://doi.org/10.1007/s10600-012-0379-x

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