Biseokeaniamides A, B, and C, Sterol O-Acyltransferase Inhibitors from an Okeania sp. Marine Cyanobacterium

J Nat Prod. 2017 Apr 28;80(4):1161-1166. doi: 10.1021/acs.jnatprod.7b00137. Epub 2017 Mar 15.

Abstract

Biseokeaniamides A, B, and C (1-3), structurally novel sterol O-acyltransferase (SOAT) inhibitors, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Biseokeaniamide B (2) exhibited moderate cytotoxicity against human HeLa cancer cells, and compounds 1-3 inhibited both SOAT1 and SOAT2, not only at an enzyme level but also at a cellular level. Biseokeaniamides (1-3) are the first linear lipopeptides that have been shown to exhibit SOAT-inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Caspase 3 / metabolism
  • Cyanobacteria / chemistry*
  • HeLa Cells
  • Humans
  • Lipopeptides / chemistry
  • Lipopeptides / isolation & purification*
  • Lipopeptides / pharmacology*
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sterol O-Acyltransferase / antagonists & inhibitors*

Substances

  • Antineoplastic Agents
  • Lipopeptides
  • biseokeaniamide A
  • biseokeaniamide B
  • biseokeaniamide C
  • Sterol O-Acyltransferase
  • Caspase 3