Medicinal foodstuffs. XVI. Sugar beet. (3): Absolute stereostructures of betavulgarosides II and IV, hypoglycemic saponins having a unique substituent, from the roots of Beta vulgaris L.

DOI: 10.1248/cpb.47.1717

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1717 - 1724 (1999)

Update date:2022-08-04

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Authors:

Murakami, Toshiyuki

Matsuda, Hisashi

Inadzuki, Masahiro

Hirano, Kazuhiro

Yoshikawa, Masayuki

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Article abstract of DOI:10.1248/cpb.47.1717

The absolute stereostructures of betavulgaroside II having a dioxolane- type substituent and betavulgaroside IV having an acetal-type substituent, which were isolated from the roots of Beta vulgaris L. (sugar beet, Chenopodiaceae) and exhibited hypoglycemic activity on glucose-loaded rats, were determined by the chemical correlations of betavulgarosides II and IV with a known saponin, momordin I. In these chemical correlations, the α-L- arabinopyranosyl moiety of momordin I was converted to a dioxolane-type substituent of betavulgaroside II or to an acetal-type substituent of betavulgaroside IV. Additionally, the 2'-diastereoisomer of betavulgaroside IV was synthesized from momordin I, and four acetal-type substituent analogues were also synthesized from L- and D-arabinose.

Full text of DOI:10.1248/cpb.47.1717

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