Malyngamide 2, an oxidized lipopeptide with nitric oxide inhibiting activity from a Papua New Guinea marine cyanobacterium

J Nat Prod. 2011 Jan 28;74(1):95-8. doi: 10.1021/np1005407. Epub 2010 Dec 14.

Abstract

A Papua New Guinea collection of the marine cyanobacterium cf. Lyngbya sordida yielded three known compounds as well as a new PKS-NRPS-derived malyngamide with anti-inflammatory and cytotoxic activity. Malyngamide 2 features an extensively oxidized cyclohexanone ring. Resolution of the ring core as a 6,8,9-triol rather then a 7,8,9-triol and relative configuration was based on chemical shift and bond geometry modeling in conjunction with homonuclear and heteronuclear coupling constants, NOE and ROE correlations, and other structural information. Malyngamide 2 exhibited anti-inflammatory activity in LPS-induced RAW macrophage cells (IC(50) = 8.0 μM) with only modest cytotoxicity to the mammalian cell line.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Cyanobacteria / chemistry
  • Drug Screening Assays, Antitumor
  • Lipopeptides / chemistry
  • Lipopeptides / isolation & purification*
  • Lipopeptides / pharmacology*
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Papua New Guinea

Substances

  • Antineoplastic Agents
  • Lipopeptides
  • Lipopolysaccharides
  • malyngamide 2
  • Nitric Oxide