Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens

Gilles Goetz, Youichi Nakao, Paul J. Scheuer

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

The sacoglossan mollusk Elysia rufescens elaborates six cyclic depsipeptides, kahalalides A- F. Its green algal diet (Bryopsis sp.) contains kahalalide G, which is an acyclic analogue of kahalalide F. Further analysis of the molluskan extract revealed two new acyclic peptides, kahalalide H (1) and kahalalide J (2), which share only four amino acids (leucine, phenylalanine, serine, and valine) with kahalalide F. Both contain aspartic acid and 4-hydroxyproline residues, and kahalalide J (2) also contains lysine. They have in common a β-hydroxy fatty acid, 3-hydroxy-9- methyldecanoic, previously encountered in kahalalide E. For kahalalide H (1) we succeeded in determining the sequential positions of the antipodal D- and L-phenylalanine. In common with the acyclic constituent of the alga, kahalalide G, the new compounds lack significant cytotoxicity.

Original languageEnglish
Pages (from-to)562-567
Number of pages6
JournalJournal of Natural Products
Volume60
Issue number6
DOIs
Publication statusPublished - 1997 Jun
Externally publishedYes

Fingerprint

Mollusca
Phenylalanine
algae
phenylalanine
molluscs
depsipeptides
Bryopsis
Depsipeptides
hydroxy fatty acids
Hydroxy Acids
hydroxyproline
Hydroxyproline
Valine
aspartic acid
Cytotoxicity
Algae
Nutrition
valine
Aspartic Acid
Leucine

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens. / Goetz, Gilles; Nakao, Youichi; Scheuer, Paul J.

In: Journal of Natural Products, Vol. 60, No. 6, 06.1997, p. 562-567.

Research output: Contribution to journalArticle

Goetz, Gilles ; Nakao, Youichi ; Scheuer, Paul J. / Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens. In: Journal of Natural Products. 1997 ; Vol. 60, No. 6. pp. 562-567.
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