Structural investigation of resin glycosides from Ipomoea lonchophylla.
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-beta-quinovopyranosyl-(1-->2)-beta-glucopyranosyl-(1-->3)- [alpha-rhamnopyranosyl- (1-->4)]-quinovopyranosyl-(1-->2)-beta-glucopyranosyl-(1-->2)-beta -fucopyranoside.
MacLeod
J K
JK
Research School of Chemistry, Australian National University, Canberra, Australia. macleod@rsc.anu.edu.au
Ward
A
A
Oelrichs
P B
PB
D000818:Animals; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000737:chemistry* / Q000633:toxicity; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D051379:Mice; D008969:Molecular Sequence Data; D010947:Plants, Toxic / Q000737:chemistry*; D012116:Resins, Plant / Q000737:chemistry* / Q000633:toxicity; D016339:Spectrometry, Mass, Fast Atom Bombardment
D006027:Glycosides; D012116:Resins, Plant