Alkaloids ofRhinopetalum stenantherum. II. The structure of stenanthine and stenanthidine

Chemistry of Natural Compounds
1981.0

Abstract

From a methanolic extract of the epigeal part of Rhinopetalum stenantherum have been isolated β-chaconine (I) and the new glucoalkaloids stenanthine with mp 262-264°C [α]D 46.5°, C45H73NO15 (II), and stenanthidine with mp 269-271°C, [α]D -47.5°, C39H63NO11 (III). On the basis of the facts that partial hydrolysis of the trioside (II) formed the biosides (I) and (III), and that on the hydrolysis of the latter the monoside γ-chaconine was found, it may be assumed that stenanthine has the structure of solanidine 3-0-{[0-β-D-glucosyl-(1 → 6)]-[0-α-L-rhamnosyl-(1 → 4)]-D-glucoside}, and stenanthidine that of solanidine 3-0-[0-β-D-glucosyl-(1 → 6)-D-glucoside]. © 1982 Plenum Publishing Corporation.

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