Cyclic peptides from an endophytic fungus obtained from a mangrove leaf (Kandelia candel)

J Nat Prod. 2007 Nov;70(11):1696-9. doi: 10.1021/np0605891. Epub 2007 Oct 19.

Abstract

Two new cyclic depsipeptides, 1962A (1) and 1962B (2), along with the three known cyclodipeptides cyclo-(Leu-Tyr) (3), cyclo-(Phe-Gly) (4), and cyclo-(Leu-Leu) (5) were isolated from the fermentation broth of the mangrove endophytic fungus (No. 1962) isolated from an old leaf of Kandelia candel collected in Hong Kong. Through spectroscopic experimentation, X-ray crystallographic analysis, and acid hydrolysis followed by chiral HPLC analysis, their structures were established to be 1962A, cyclo-(D-Leu-Gly-L-Tyr-L-Val-Gly-S-O-Leu) (1), and 1962B, cyclo-(D-Leu-Gly-L-Phe-L-Val-Gly-S-O-Leu) (2), respectively. Both of these new cyclo-depsipeptides were found to contain one d-amino acid. In the MTT bioassay, 1962A (1) showed weak activity against human breast cancer MCF-7 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Crystallography, X-Ray
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Depsipeptides / pharmacology
  • Drug Screening Assays, Antitumor
  • Female
  • Fungi / chemistry*
  • Hong Kong
  • Humans
  • Molecular Conformation
  • Molecular Structure
  • Peptides, Cyclic / chemistry
  • Plant Leaves / chemistry
  • Rhizophoraceae / microbiology
  • Stereoisomerism

Substances

  • Amino Acids
  • Depsipeptides
  • Peptides, Cyclic
  • cyclo-(D-Leu-Gly-L-Phe-L-Val-Gly-S-O-Leu)
  • cyclo-(D-Leu-Gly-L-Tyr-L-Val-Gly-S-O-Leu)