A new benzofuran glycoside and indole alkaloids from a sponge-associated rare actinomycete, Amycolatopsis sp

Mar Drugs. 2014 Apr 22;12(4):2326-40. doi: 10.3390/md12042326.

Abstract

Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 1-3 were determined to be a new benzofuran glycoside and new indole alkaloids related to cyclopiazonic acids, a class that has previously only been reported in fungi. The absolute configurations of 1 and 3 were deduced by ECD calculations, whereas that of 2 was determined using the modified Mosher method. Amycolactam (3) displayed significant cytotoxicity against the gastric cancer cell line SNU638 and the colon cancer cell line HCT116.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinomycetales / isolation & purification
  • Actinomycetales / metabolism*
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Benzofurans / chemistry
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • HCT116 Cells
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification
  • Indole Alkaloids / pharmacology*
  • Indoles / chemistry
  • Indoles / isolation & purification
  • Indoles / pharmacology
  • Porifera / microbiology*
  • Pyrrolidinones / chemistry
  • Pyrrolidinones / isolation & purification
  • Pyrrolidinones / pharmacology
  • Secondary Metabolism

Substances

  • Antineoplastic Agents
  • Benzofurans
  • Glycosides
  • Indole Alkaloids
  • Indoles
  • Pyrrolidinones
  • amycolactam