Resin Glycosides from the Herbal Drug Jalap (Ipomoea purga)

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. Pur...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2011-05, Vol.74 (5), p.1148-1153
Hauptverfasser: Castañeda-Gómez, Jhon, Pereda-Miranda, Rogelio
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Sprache:eng
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Zusammenfassung: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np200080k