Starfish saponins, LVI Three new asterosaponins from the starfish Goniopecten demonstrans

Citation
S. De Marino et al., Starfish saponins, LVI Three new asterosaponins from the starfish Goniopecten demonstrans, EUR J ORG C, (24), 2000, pp. 4093-4098
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
24
Year of publication
2000
Pages
4093 - 4098
Database
ISI
SICI code
1434-193X(200012):24<4093:SSLTNA>2.0.ZU;2-D
Abstract
Three new steroidal sulfate pentaglycosides (asterosaponins), goniopectenos ides A-C (1-3), were isolated from the polar extract of the starfish Goniop ecten demonstrans. The pentasaccharide moiety Linked to C-6 of 3 beta -sulf ated steroidal aglycones, consists of D-xylose, D-fucose, D-quinovose, and the unprecedented 3-O-methyl-D-quinovose. The three asterosaponins differ f rom each other in the side chains. Their structures were elucidated by exte nsive NMR experiments including H-1-H-1 (COSY, TOCSY, ROESY) and H-1-C-13 ( HMQC and HMBC) spectroscopy as well as chemical evidence. The isolated aste rosaponins have been found to significantly inhibit the settlement of the b iofouling marine brown macroalga Hincksia irregularis.