Jalapinoside, a macrocyclic bisdesmoside from the resin glycosides of Ipomea purga, as a modulator of multidrug resistance in human cancer cells.

Abstract

The first macrocyclic bisdesmoside resin glycoside, jalapinoside (4), was purified by preparative-scale recycling HPLC from the MeOH-soluble extracts of Ipomoea purga roots, the officinal jalap. Purgic acid C (3), a new glycosidic acid of ipurolic acid, was identified as 3-O-β-d-quinovopyranoside, 11-O-β-d-quinovopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-fucopyranosyl-(1→4)]-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-quinovopyranoside (3S,11S)-dihydroxytetradecanoic acid. The acylating residues of this core were acetic, (+)-(2S)-methylbutanoic, and dodecanoic acids. The site of lactonization was defined as C-3 of the second saccharide moiety. Reversal of multidrug resistance by this noncytotoxic compound was evaluated in vinblastine-resistant human breast carcinoma cells.

• Authors: Elihú Bautista, Mabel Fragoso-Serrano, Rogelio Pereda-Miranda
• Journal: Journal of natural products (J Nat Prod) Vol. 78 Issue 1 Pg. 168-72 (Jan 23 2015) ISSN: 1520-6025 [Electronic] United States
• PMID: 25536852 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents, Phytogenic
• Resins, Plant
• Saponins
• bisdesmoside
• jalapinoside
• Vinblastine

Topics

• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Chromatography, High Pressure Liquid
• Drug Resistance, Multiple (drug effects)
• Drug Resistance, Neoplasm (drug effects)
• Drug Screening Assays, Antitumor
• Female
• Humans
• Ipomoea (chemistry)
• Mexico
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Resins, Plant (chemistry)
• Saponins (chemistry, isolation & purification, pharmacology)
• Stereoisomerism
• Vinblastine (pharmacology)