Biosynthesis of drimane terpenoids in dorid molluscs: Pivotal role of 7- deacetoxyolepupuane in two species of Dendrodoris nudibranchs

Angelo Fontana, Maria Letizia Ciavatta, Tomofumi Miyamoto, Aldo Spinella, Guido Cimino

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Described in this paper is the biosynthesis of defensive drimanes in dorid nudibranchs. Two geographically distinct populations of molluscs belonging to the genus Dendrodoris have been studied. The de novo synthesis of 7-deacetoxyolepupuane (2) has been demonstrated by radiolabelled precursors in both species. The results of the studies are consistent with the pivotal role of 2 in the formation of the other drimanes both in the mantle and in the egg masses of the molluscs. The new drimane 6-β- acetoxypolygodial (7) is reported from the skin extract of the pacific Dendrodoris arborescens. Its structure elucidation was accomplished by NMR spectroscopy.

Original languageEnglish
Pages (from-to)5937-5946
Number of pages10
JournalTetrahedron
Volume55
Issue number18
DOIs
Publication statusPublished - Apr 30 1999

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Molluscs
Mollusca
Biosynthesis
Terpenes
Nuclear magnetic resonance spectroscopy
Ovum
Skin
Magnetic Resonance Spectroscopy
Population
7-deacetoxyolepupuane
drimane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Biosynthesis of drimane terpenoids in dorid molluscs : Pivotal role of 7- deacetoxyolepupuane in two species of Dendrodoris nudibranchs. / Fontana, Angelo; Ciavatta, Maria Letizia; Miyamoto, Tomofumi; Spinella, Aldo; Cimino, Guido.

In: Tetrahedron, Vol. 55, No. 18, 30.04.1999, p. 5937-5946.

Research output: Contribution to journalArticle

Fontana, Angelo ; Ciavatta, Maria Letizia ; Miyamoto, Tomofumi ; Spinella, Aldo ; Cimino, Guido. / Biosynthesis of drimane terpenoids in dorid molluscs : Pivotal role of 7- deacetoxyolepupuane in two species of Dendrodoris nudibranchs. In: Tetrahedron. 1999 ; Vol. 55, No. 18. pp. 5937-5946.
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