Structural characterization, by two-dimensional NMR spectroscopy and fast-atom-bombardment mass spectrometry, of a highly acylated trirhamnoside from Mezzettialeptopoda (Annonaceae)
- 1 July 1990
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 68 (7) , 1044-1050
- https://doi.org/10.1139/v90-163
Abstract
The structure of Mezzettiaside 3, a highly acylated trisaccharide obtained from the stem bark of Mezzettialeptopoda, was determined by a combination of double-quantum-filtered {1H,1H} correlation spectroscopy, two-dimensional homonuclear Hartmann–Hahn, and 1H-detected {1H,13C} one-bond and multiple-bond shift correlation nuclear magnetic resonance experiments, in conjunction with fast-atom-bombardment mass spectrometry. Mezzettiaside 3 was found to be the α-(n-octyl)glycoside of 3,4-di-O-acetyl-L-rhamnopyranosyl-α(1 → 3)-2,4-di-O-acetyl-L-rhamnopyranosyl-α(1 → 3)-4-O-hexanoyl-L-rhamnopyranose. The heteronuclear multiple-bond correlation NMR technique proved to be invaluable in establishing the location of the O-acyl groups in this complex carbohydrate. Keywords: oligosaccharide, HMBC, HMQC, HOHAHA, FAB-MS.Keywords
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