Glycosides from the North Atlantic sea cucumber Cucumaria frondosa V - Structures of five new minor trisulfated triterpene oligoglycosides, frondosides A₇-1, A₇-2, A₇-3, A₇-4, and isofrondoside C

Authors: Silchenko, Alexandra S.; Avilov, Sergey A.; Kalinovsky, Anatoly I.; Dmitrenok, Pavel S.; Kalinin, Vladimir I.; Morre, Jeffrey; Deinzer, Max L.; Woodward, Carl; Collin, Peter D.

Source: Canadian Journal of Chemistry, Volume 85, Number 9, September 2007 , pp. 626-636(11)

Publisher: NRC Research Press

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Abstract:

Seven highly polar trisulfated triterpene glycosides belonging to the frondoside A₇ group have been isolated from the North Atlantic sea cucumber Cucumaria frondosa. The structures of five new glycosides, frondosides A₇-1 (1), A₇-2 (2), A₇-3 (3), A₇-4 (4), and isofrondoside C (5) were elucidated, three of which contained lanostane aglycons without a lactone-ring. Three pairs of the glycosides proved to be isomers by virture of the positions of double bonds in the aglycons nuclei; two pairs of the glycosides differed from each other by the character of the oxygen functionality at C-22. The results from these studies provided the basis for postulating the biosynthetic pathways of norlanostane glycosides in the sea cucumber.Key words: Cucumaria frondosa, sea cucumbers, frondosides, triterpene glycosides.

Au départ de concombres de mer, Cucumaria frondosa, du nord l'Atlantique, on a isolé plusieurs glycosides de triterpène trisulfatés très polaires qui appartiennent au groupe frondoside A₇. On a élucidé les structures de cinq nouveaux glycosides, les frondosides A₇-1 (1), A-2 (2), A₇-3 (3), A₇-4 (4) et l'isofrondoside C (5), dont trois contiennent des aglycones de lanostane sans noyau lactonique. Trois paires de glycosides sont des isomères de position de doubles liaisons dans les noyaux des aglycones; les deux autres paires de glycosides diffèrent l'un de l'autre par le caractère de la fonctionnalité oxygène en C-22. Les résultats de ces études fournissent les bases nécessaires pour postuler les voies de biosynthèse des glycosides du norlanostane dans les concombres de mer.Mots-clés : Cucumaria frondosa, concombres de mer, frondosides, glycosides de triterpène.[Traduit par la Rédaction]

Document Type: Research article

Publication date: 2007-09-01

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Published since 1929, this monthly journal reports current research findings in all branches of chemistry. It includes the traditional areas of analytical, inorganic, organic, and physical-theoretical chemistry and newer interdisciplinary areas such as materials science, spectroscopy, chemical physics, and biological, medicinal and environmental chemistry. Full papers, preliminary communications and review articles are all welcomed.
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