Issue 6, 1988

Starfish saponins. Part 34. Novel steroidal glycoside sulphates from the starfish Asterias amurensis

Abstract

A reinvestigation of the extracts from the starfish Asterias amurensis has led to the isolation of eight novel steroidal glycosides along with major amounts of the already reported glycoside B2(1), ovarian asterosaponin-1 (3), and ovarian asterosaponin-4 (4). Four novel compounds are ‘asterosaponins’ assigned as the asteroside A (8), B (9), C (10), and D (11), consisting of a Δ9(11)-3β,6α-dihydroxysteroidal moiety, a pentasaccharide portion attached at C-6, and a sulphate group at C-3. Asterosides A–C possess the same saccharide portion, β-D-quinovopyranosyl-(1 → 2)-β-D-galactopyranosyl-(1 → 4)-[β-D-quinovopyranosyl-(1 → 2)]-β-D-xylopyranosyl-(1 → 3)-β-D-quinovopyranosyl, already encountered in glycoside B-2, while the saccharide chain of asteroside D is identical with that of ovarian asterosaponin-4 (4) and differs from the previous one by the replacement of the galactose by glucose. Main differences among the novel ‘asterosaponins’ reside in the steroid side chains.

The second group of saponins consists of four new polyhydroxysteroidal xylopyranosides, designated amurensosides A–D (12)–(15). Three of them, A–C, are sulphated compounds.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 1337-1347

Starfish saponins. Part 34. Novel steroidal glycoside sulphates from the starfish Asterias amurensis

R. Riccio, M. Iorizzi, L. Minale, Y. Oshima and T. Yasumoto, J. Chem. Soc., Perkin Trans. 1, 1988, 1337 DOI: 10.1039/P19880001337

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements