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Novel octulosonic acid derivatives in the composite Smallanthus sonchifolius

✍ Scribed by Makiko Takenaka; Hiroshi Ono

Book ID
104252823
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
111 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Two novel octulosonic acid derivatives with a 6,8-dioxabicyclo[3.2.1]octane skeleton that are major water-soluble phenolic compounds were found in the roots of Smallanthus sonchifolius. The structures of these compounds were determined to be (1R,2S,3S,4R,5S,7R)-4-hydroxy-7-hydroxymethyl-3-[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyloxy]-6,8-dioxabicyclo[3.2.1]octan-5-carboxylic acid (4-O-caffeoyl-2,7-anhydro-D-glycero-b-D-galacto-oct-2-ulopyranosonic acid) and (1R,2S,3R,4R,5S,7R)-2,4-dihydroxy-7-hydroxymethyl-2,3-bis[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyloxy]-6,8-dioxabicyclo[3.2.1]octan-5-carboxylic acid (4,5-di-O-caffeoyl-2,7-anhydro-D-glycero-b-D-galacto-oct-2-ulopyranosonic acid) by MS, NMR and CD spectral analyses.

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Conformational analysis of isopropyliden
Conformational analysis of isopropylidene-protected C-glycosyl derivatives of 3-deoxy-d-manno-2-octulosonic acid (Kdo) in the solid state and in solution
✍ Martin Orbe; Kristina Luthman; Tommy WΓ₯glund; Alf Claesson; Ingeborg CsΓΆregh πŸ“‚ Article πŸ“… 1991 πŸ› Elsevier Science 🌐 English βš– 955 KB

The favoured conformations of a series of C-glycosyl derivatives of 4,5:7,8-di-O-isopropylidene-3deoxy-D-munno-2-octulosonic acid (Kdo) esters were analyzed by n.m.r. spectroscopy and in one instance by X-ray crystallography. The Kdo derivatives were found to adopt a skew-boat conformation (& + OS,)