Resin Glycosides from the Roots of Operculina macrocarpa (Brazilian Jalap) with Purgative Activity

Analysis of the methanol-soluble resin glycosides from the roots of Operculina macrocarpa was assessed by generating NMR profiles of five glycosidic acids obtained through saponification, acetylation, and recycling HPLC purification. Operculinic acid H (1), two novel hexasaccharides, operculinic aci...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2019-06, Vol.82 (6), p.1664-1677
Main Authors: Lira-Ricárdez, Jesús, Pereda-Miranda, Rogelio, Castañeda-Gómez, Jhon, Fragoso-Serrano, Mabel, Simas, Rosineide Costa, Leitão, Suzana Guimarães
Format: Article
Language:English
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Summary:Analysis of the methanol-soluble resin glycosides from the roots of Operculina macrocarpa was assessed by generating NMR profiles of five glycosidic acids obtained through saponification, acetylation, and recycling HPLC purification. Operculinic acid H (1), two novel hexasaccharides, operculinic acids I (2) and J (3), the known purgic acid A (4), and a quinovopyranoside of (−)-(7R)-hydroxydecanoic acid, operculinic acid K (5), were isolated. Three intact resin glycosides related to 1, the novel macrocarposidic acids A (6) and B (7), in addition to the previously known macrocarposidic acid C (8), were also purified with isovaleroyl, tigloyl, and exogonoyl [(3S,9R)-3,6:6,9-diepoxydecanoyl] groups as esterifying residues. A selective intramolecular lactonization was produced to generate a macrocyclic artifact (17) during acetylation of 1, resembling the distinctive structure of the Convolvulaceous resin glycosides.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.9b00222