ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Biologically Active Glycosides from Asteroidea, VI1,2). - Steroid Oligoglycosides from the Starfish Luidia maculata Müller et Troschel, 1. - Structures of a New Aglycone Sulfate and two New Oligoglycoside SulfatesFive already known aglycones, 3β,6α-dihydroxy-5α-pregn-9(11)-en-20-one (1), 3β,6α,20ξ-trihydroxy-5α-cholesta-9(11),24-dien-23-one (2), 3β,6α,20ξ-trihydroxy-5α-cholest-9(11)-en-23-one (3), 3β,6α-dihydroxy-5α-cholesta-9(11),24-dien-23-one (4), and 3β,6α-dihydroxy-5α-cholest-9(11)-en-23-one (5) were isolated from solvolysis products of the enzymatic hydrolyzate of an oligoglycoside mixture prepared from the starfish Luidia maculata Müller et Troschel. A new aglycone sulfate was also isolated from the enzymatic hydrolyzate, and two new oligoglycoside sulfates were obtained from the same glycoside mixture. The structures of the three sulfates were elucidated by chemical and spectroscopic evidence to be the monocalcium salt of bis [6α,20ξ-dihydroxy-3β-(sulfooxy)-5α-cholest-9(11)-en-23-one] (8), the monosodium salt of 6α-[(O-β-D-fucopyranosyl-(1 → 3)-O-β-D-fucopyranosyl-(1 → 2)-O-β-D-quinovopyranosyl-(1 → 4)-O-β-D-quinovopyranosyl-(1 → 2)]-O-β-D-xylopyranosyl-(1 → 3)-β-D-quinovopyranosyl)oxy]-20ξ-
Notes:
Fünf bereits bekannte Aglyca, 3β,6α-Dihydroxy-5α-pregn-9(11)-en-20-on (1), 3β,6α,20ξ-Trihydroxy-5α-cholesta-9(11),24-dien-23-on (2), 3β,6α,20ξ-Trihydroxy-5α-cholest-9(11)-en-23-on (3), 3β,6α-Dihydroxy-5α-cholesta-9(11),24-dien-23-on (4) und 3β,6α-Dihydroxy-5α-cholest-9(11)-en-23-on (5), ließen sich aus dem Solvolyseprodukt des enzymatischen Hydrolysats eines Oligoglycosidgemisches isolieren, das aus Seesternen Luidia maculata Müller et Troschel gewonnen wurde. Zusätzlich wurde ein neues Aglyconsulfat aus dem enzymatischen Hydrolysat einheitlich erhalten, und zwei neue Oligoglycosidsulfate konnten aus dem gleichen Ollgoglycosidgemisch isoliert werden. Auf Grund chemischer und spektroskopischer Beweise wurden die Strukturen der drei Sulfate als Monoclaciumsalz von Bis[6α,20ξ-dihydroxy-3β-(sulfooxy)-5α-cholest-9(11)-en-23-on] (8), Mononatriumsalz von 6α -[(O-β-D-Fucopyranosyl-(1 → 3)-O-β-D-Fucopyranosyl-(1 → 3)-O-β-D-fucopyranosyl-(1 → 2)-O-β-D-chinovopyranosyl-(1 → 4)-O-[β-D-chinovopyranosyl-(1 → 2)]-O-β-D-xylopyranosyl-(1 → 3)-β-D-chinovopyranosyl)oxy]-20ξ-hydroxy-3β-(sulfooxy)5α-cholest-9(11)-en-23-on (10) und Monoammoniumsalz von 6α-[(O-β-D-Fucopyranosyl-(1 → 2)-O-β-D-chinovopyranosyl-(1 → 4)-O-[β-D-chinovopyranosyl-(1 → 2)]- O-β-D-xylopyranosyl-(1 → 3)-β-D-chinovopyranosyl)oxy]-20ξ-hydroxy-3β-(sulfooxy)-5α-cholest-9(11)-en-23-on (11) ermittelt.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198319831206
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