Advertisement

Chemistry of Natural Compounds

, Volume 22, Issue 5, pp 571–574 | Cite as

Triterpene glycosides of alfalfa. III. Medicoside I

  • A. E. Timbekova
  • N. K. Abubakirov
Article

Abstract

On the basis of chemical transformations and with the aid of physicochemical results, the structure of glycoside I isolated from the roots of the plantMedicago sativa has been established as hederagin 3-O-[O-α-L-arabinopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 2)-α-L-arabinopyranoside] 28-O-β-D-glucopyranoside. Compound (I), C52H84O22, mp 210–212°C, [α] D 21 +38.4° (c 1.48; methanol). Acid hydrolysis of (I) led to hederogenin (II) — C30H48O4, mp 326–330°C, [α] D 23 +84.2° (c 0.19; pyridine. The Hakomorimethylation of glycoside (I) yielded the permethylate (IV) — C65H11O22 [α] D 23 +41.6° (c 1.79; methanol). The GLC analysis of the products of the methanolysis of compound (IV) showed the presence of 3,4,6-tri-O-methyl-D-glucopyranose, 2,3,4,6-tetra-O-methyl-D-glucopyranose, 3,4-di-O-methyl-L-O-arabinopyranose, and 2,3,4-tri-o-methyl-L-arabinopyranose. The alkaline hydrolysis of glycoside I gave compound (III) with mp 230–233°C, [α] D 21 +35.2° (c 0.21; methanol), which was identified as medicoside C. Details of the PMR spectrum are given for compound (IV) and of the IR spectrum for compound (I).

Keywords

Glycoside Anomeric Proton Triterpene Glycoside Hederagenin Tungstophosphoric Acid 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. E. Timbekova and N. K. Abubakirov, Khim. Prir. Soedin., 451 (1984).Google Scholar
  2. 2.
    A. E. Timbekova and N. K. Abubakirov, Khim. Prir. Soedin., 805 (1985).Google Scholar
  3. 3.
    S. Hakomori, J. Biochem. (Tokyo),55, 205 (1964).PubMedPubMedCentralGoogle Scholar
  4. 4.
    J. M. Van der Veen, J. Org. Chem.,28, 564 (1963).CrossRefGoogle Scholar
  5. 5.
    W. Klyne, Biochem. J.,47, xli (1950).Google Scholar

Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • A. E. Timbekova
  • N. K. Abubakirov

There are no affiliations available

Personalised recommendations