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] 21D +38.4° (c 1.48; methanol). Acid hydrolysis of (I) led to hederogenin (II) — C30H48O4, mp 326–330°C, [α] 23D +84.2° (c 0.19; pyridine. The Hakomorimethylation of glycoside (I) yielded the permethylate (IV) — C65H11O22 [α] 23D +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] 21D +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).
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Institute of the Chemistry of Plant Substances of the Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 607–610, September–October, 1986.
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Timbekova, A.E., Abubakirov, N.K. Triterpene glycosides of alfalfa. III. Medicoside I. Chem Nat Compd 22, 571–574 (1986). https://doi.org/10.1007/BF00599263
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DOI: https://doi.org/10.1007/BF00599263