Novel glucoalkaloids from Rauwolfia cell cultures--acetylrauglucine and related glucosides.
From cell suspension cultures of Rauwolfia serpentina grown in an optimized production medium for the glucoalkaloid raucaffricine, a novel glucoalkaloid was isolated and identified as 17-O-acetyl-21-O-beta-D-glucopyranosyl-ajmaline (acetylrauglucine). This alkaloid is formed in very small amounts (less than 5 x 10(-4)%). The biogenetically related N alpha-demethylated base (acetyl-nor-rauglucine) and the deacetyl product rauglucine have also been detected in culture extracts. In addition 21(R)-(beta-D-glucopyranosyl)-hydroxy-sarpagan-17-al has been isolated and identified as an artifact which originates from raucaffricine.
Ruyter
C M
CM
Institut für Pharmazeutische Biologie, Universität München, Bundesrepublik Deutschland.
Schübel
H
H
Stöckigt
J
J
D000404:Ajmaline / Q000031:analogs & derivatives* / Q000302:isolation & purification; D002478:Cells, Cultured; D005960:Glucosides / Q000302:isolation & purification*; D006027:Glycosides / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D046948:Secologanin Tryptamine Alkaloids / Q000302:isolation & purification*; D013056:Spectrophotometry, Ultraviolet
D005960:Glucosides; D006027:Glycosides; D046948:Secologanin Tryptamine Alkaloids; C058592:17-acetylrauglucine; D000404:Ajmaline