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    Resin Glycosides from the Herbal Drug Jalap (Ipomoea purga)
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    Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Mexico City 04510 D.F., Mexico
    *Tel: +52 55 5622-5288. Fax: +52 55 5622 5329. E-mail: [email protected]
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2011, 74, 5, 1148–1153
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    https://doi.org/10.1021/np200080k
    Published March 29, 2011
    Copyright © 2011 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    Three new resin glycosides, purginosides I and II (1 and 2) and purgin I (3), were isolated from the aerial parts of Ipomoea purga and purified by preparative-scale recycling HPLC from a chloroform-soluble extract. Their structures were established through NMR spectroscopy and mass spectrometry. Purginosides I and II (1 and 2) are partially acylated branched pentasaccharides derived from operculinic acid A, which is composed of one d-fucose, one d-glucose, and three l-rhamnose units. The site of the aglycon macrolactonization is at C-2 of the second saccharide (rhamnose). In both compounds 1 and 2, three different esterifying residues were located at C-2 of the second rhamnose unit and at C-2 (or C-3) and C-4 on the third rhamnose moiety. The acylating residues were characterized as trans-cinnamic, n-decanoic, and either (+)-(2S)-2-methylbutanoic or n-hexanoic acid. Purgin I (3) was found to be an ester-type dimer of operculinic acid A, acylated by n-dodecanoic, (+)-(2S)-2-methylbutanoic, and trans-cinnamic acids at the same oligosaccharide core positions found in compounds 1 and 2. The site of lactonization by the aglycon in unit A was placed at C-2 of the second saccharide. The position for the ester linkage for the monomeric unit B on the macrocyclic unit A was identified as C-4 of the terminal glucose. This is the first report on the isolation, purification, and structure elucidation of intact individual resin glycoside constituents from the herbal drug jalap.

    Copyright © 2011 The American Chemical Society and American Society of Pharmacognosy

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    Supporting Information

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    1H, 13C, COSY, TOCSY, HMQC, and HMBC NMR spectra as well as FABMS and ESIMS of natural products 1−3 and derivative 5 (Figures S1−S28). HMBC correlations for 1−3 (Figures S29 and S30). Structure for compounds 4 and 5 (Figure S31). This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2011, 74, 5, 1148–1153
    Click to copy citationCitation copied!
    https://doi.org/10.1021/np200080k
    Published March 29, 2011
    Copyright © 2011 The American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

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