Cerebroside analogues from marine-derived fungus Aspergillus flavipes

J Asian Nat Prod Res. 2004 Dec;6(4):249-57. doi: 10.1080/1028602031000147384.

Abstract

From the mycelium of the marine-derived fungus Aspergillus flavipes, isolated from the sea anemone Anthopleura xanthogrammica, two new cerebroside analogues, namely flavicerebrosides A (1): [(2S,2'R,3R,4E,8E)-N-2'-hydroxyoctadecanoyl-1-O-beta--galactopyranosyl-9-methyl-4,8-sphingadienine], and B (2): [(2S,2'R,3R,3'E,4E,8E)-N-2'-hydroxy-3'-octadecenoyl-1-O-beta--galactopyranosyl-9-methyl-4,8-sphingadienine], together with two known glycosphingolipids cerebrosides D (3) and C (4), were isolated. Their structures were identified by means of extensive spectroscopic analysis (IR, UV, 2D NMR, MS, CD) and chemical degradation. All four compounds showed cytotoxic activity against the KB cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / pharmacology
  • Aspergillus / chemistry*
  • Cerebrosides / chemistry*
  • Cerebrosides / isolation & purification
  • Cerebrosides / pharmacology
  • Humans
  • KB Cells
  • Molecular Structure
  • Mycelium / chemistry
  • Sphingosine / analogs & derivatives*
  • Sphingosine / chemistry

Substances

  • Antineoplastic Agents
  • Cerebrosides
  • cerebroside C
  • cerebroside D
  • flavicerebroside A
  • flavicerebroside B
  • Sphingosine