Structural Investigation of Resin Glycosides from Ipomoea lonchophylla

• Published in: Journal of natural products (Washington, D.C.) D.C.), 1997-05, Vol.60 (5), p.467-471
• Main Authors: MacLeod, John K, Ward, Annemarie, Oelrichs, Peter B
• Format: Article
• Language: English
• Subjects: AGNEAU; Analytical, structural and metabolic biochemistry; Animals; Biological and medical sciences; Carbohydrate Sequence; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; CORDERO; dumb lamb syndrome; ESPECTROMETRIA; ESTER; ESTERES; ESTERS; ESTRUCTURA QUIMICA; Fatty acids; Fundamental and applied biological sciences. Psychology; GLICOSIDOS; GLYCOSIDE; GLYCOSIDES; Glycosides - chemistry; Glycosides - toxicity; HIDROLISIS; HYDROLYSE; HYDROLYSIS; IPOMOEA; LAMBS; Lipids; Magnetic Resonance Spectroscopy; METABOLITE; METABOLITES; METABOLITOS; Methylation; Mice; Molecular Sequence Data; Other biological molecules; PLANTAS TOXICAS; PLANTE TOXIQUE; Plants, Toxic - chemistry; POISONOUS PLANTS; QUEENSLAND; RESINAS; RESINE; RESINS; Resins, Plant - chemistry; Resins, Plant - toxicity; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; Spectrometry, Mass, Fast Atom Bombardment; STRUCTURE CHIMIQUE; SUBSTANCE TOXIQUE; SUSTANCIAS TOXICAS; TOXIC SUBSTANCES
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960693q

A fraction from Ipomoea lonchophylla, which was toxic to mice, contained an inseparable mixture of resin glycosides with differing numbers of C5 ester groups on the hexasaccharide chain. After alkaline hydrolysis of the esters, the structure of the major component (1) was elucidated using high-field NMR spectroscopy, mass spectrometry, chemical studies, and comparison with known resin glycosides. Compound 1 was identified as 3,11-dihydroxytetradecanoic acid 11-O-β-quinovopyranosyl-(1→2)-β-glucopyranosyl-(1→3)-[α-rhamnopyranosyl-(1→4)]-quinovopyranosyl-(1→2)-β-glucopyranosyl-(1→2)-β-fucopyranoside.