Enzymatic degradation of the triterpenoid saponin helianthoside 2.
Helianthoside 2 (1), the main bisdesmosidic saponin of Helianthus annuus L. was converted to the products 2, 3 and 4 by several, optimized enzymatic hydrolysis methods. Monosaccharide units of the acylglycosidic at C-28 of the sapogenin bonded, linear chain oligosaccharide were cleaved, but the branched trisaccharide at C-3 of the aglycone are stable under the conditions used. Compounds 2 and 3 are new triterpenoid glycosides, which were characterized as 28-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (2) and 28-O-alpha-L-arabinopyranoside (3) of 3-O-[alpha-L-rhamnopyranosyl-(1-->3)][beta-D-xylopyranosyl-(1-->4)] beta-D-glucopyranoside of 3 beta,16 alpha-dihydroxy-olean-12-en-28-oic acid.
Bader
G
G
Institut für Pharmazie, Mathematisch-Naturwissenschaftliche Fakultät I, Humboldt-Universität zu Berlin, Germany.
Streich
S
S
Gründemann
E
E
Flatau
S
S
Hiller
K
K
D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry; D002853:Chromatography, Liquid; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D012503:Saponins / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry*
D002241:Carbohydrates; D012503:Saponins; D014315:Triterpenes; C109889:helianthoside 2