Columbamides D and E: Chlorinated Fatty Acid Amides from the Marine Cyanobacterium Moorea bouillonii Collected in Malaysia

Org Lett. 2017 Aug 18;19(16):4231-4234. doi: 10.1021/acs.orglett.7b01869. Epub 2017 Aug 7.

Abstract

Two new chlorinated fatty acid amides, columbamides D (1) and E (2), along with apratoxins A and C and wewakazole, were isolated from the organic extract of a Moorea bouillonii sample from Sabah, Malaysia. Structure elucidation was accomplished by a combination of MS and NMR analyses. The total synthesis of all four stereoisomers of 1 was completed, and the absolute configuration was determined by chiral-phase HPLC and Marfey's analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amides / isolation & purification*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Aquatic Organisms
  • Cell Line, Tumor
  • Cyanobacteria / chemistry*
  • Drug Screening Assays, Antitumor / methods
  • Fatty Acids / chemistry
  • Fatty Acids / isolation & purification*
  • Halogenation
  • Humans
  • Malaysia
  • Molecular Conformation
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification
  • Stereoisomerism

Substances

  • Amides
  • Antineoplastic Agents
  • Fatty Acids
  • Peptides, Cyclic
  • wewakazole