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Malkanguniol, one of the polyalcohols from celastrus paniculatus willd

Authors
Publisher
Pergamon Press
Publication Date
Disciplines
  • Biology
  • Pharmacology

Abstract

PII: S0040-4039(01)95732-6 Tetrahedron Letters No, 11, PP 845 - 848, 1973. Pergamon Press. Printed in Great MALKANGUNIOL, ONE OF THE POLYALCOHOLS FROM CELASTRUS PANICULATUS H.J. den Hertog Jr and J.Th. Hackmann (t) Britain. WILLD. Twente Uhiversity of Technology, Enschede, The Netherlands and D.D. Nanavati"and Sukh Dev National Chemical Laboratory, Poona, India (Received in 1K 25 January 1973; accepted for publication 1 Wbruary 1973) In connection with pharmacological properties ascribed to the seeds of Celas- trus paniculatus Willd. (Hindi: Malkanguni), a plant mentioned in old Indian medi- cal literature, the composition of the components of these seeds has been studied. In 1938, Gunde and Hilditch 1) investigated the fat of the aril-free seeds of Celastrus paniculatus and, by extraction with 80% MeOH aq., segregated it into glY- ceride and non glyceride fractions. From the latter fraction, these authors iso- lated, after saponification and acetylation of the neutral part, a resinous product which on the basis of element analysis , was considered to be the tetra-acetate of a tetrahydroxylic alcohol with an approximate composition ClSH2SOS. The nature of this compound(s), however, could not be defined. Some years ago, a more detailed investigation of this polyalcohol mixture was undertaken, independently, by two different groups, in Indiaa) and in the Nether- lands3). We find that several polyhydric alcohols are present and now report on the structure of one of the major constituents. This compound, now called malkanguniol (I) is a crystalline solid, m.p. 171-172O [aID 32.94°(c:2,99)4) and analyses for C15H2605 (M+,m/e 286). The compound has no C=O (IR) or C=C bond (IR,NMR, negative tetranitromethane test) and is, thus, clearly a tricyclic polyalcohol. By D20 exchange and total acetylation (Ac20, py- ridine, reflux) to a tetraacetate IIII), m.p. 134-135O, [aID 25.0°(c:3.08); C23H340g, (M+, m/e 454; NMR, see

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