Sixteen steroidal glycosides were isolated from the starfish C. tenuispina. The more polar components are 10 asterosaponins, consisting of a Δ9(11)-3β,6α-dihydroxysteroidal moiety, a pentasaccharide portion attached at C-6, and a sulfate group at C-3. New saponins are tenuispinosides A-C, (e.g., I). The 2nd group of polar glycosides consists of 2 new xylose saponins, possessing monosulfate polyhydroxysteroidal aglycons and 2 new 4-O-sulfated glucose saponins, assigned as coscinasterosides A-D. The less polar glycosides are the new nonsulfated xylosides, designated as coscinasterosides E (II) and F (III). The structures of the new saponins were detd. by extensive 1H- and 13C-NMR investigations, fast-atom bombardment mass spectroscopy, and comparison with known compds. The location of the sulfate ester functionalities in coscinasterosides A-D were assigned on comparison of their spectral data with those of the corresponding desulfated analogs. C. tenuispina Also contains 3 new monosulfated polyhydroxysteroids (IV-VI).
STARFISH SAPONINS .30. ISOLATION OF 16 STEROIDAL GLYCOSIDES AND 3 POLYHYDROXYSTEROIDS FROM THE MEDITERRANEAN STARFISH COSCINASTERIAS-TENUISPINA
RICCIO, Raffaele;
1986-01-01
Abstract
Sixteen steroidal glycosides were isolated from the starfish C. tenuispina. The more polar components are 10 asterosaponins, consisting of a Δ9(11)-3β,6α-dihydroxysteroidal moiety, a pentasaccharide portion attached at C-6, and a sulfate group at C-3. New saponins are tenuispinosides A-C, (e.g., I). The 2nd group of polar glycosides consists of 2 new xylose saponins, possessing monosulfate polyhydroxysteroidal aglycons and 2 new 4-O-sulfated glucose saponins, assigned as coscinasterosides A-D. The less polar glycosides are the new nonsulfated xylosides, designated as coscinasterosides E (II) and F (III). The structures of the new saponins were detd. by extensive 1H- and 13C-NMR investigations, fast-atom bombardment mass spectroscopy, and comparison with known compds. The location of the sulfate ester functionalities in coscinasterosides A-D were assigned on comparison of their spectral data with those of the corresponding desulfated analogs. C. tenuispina Also contains 3 new monosulfated polyhydroxysteroids (IV-VI).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
