Sceliphrolactam, a polyene macrocyclic lactam from a wasp-associated Streptomyces sp

Org Lett. 2011 Feb 18;13(4):752-5. doi: 10.1021/ol102991d. Epub 2011 Jan 19.

Abstract

A previously unreported 26-membered polyene macrocyclic lactam, sceliphrolactam, was isolated from an actinomycete, Streptomyces sp., associated with the mud dauber, Sceliphron caementarium. Sceliphrolactam's structure was determined by 1D- and 2D-NMR, MS, UV, and IR spectral analysis. Sceliphrolactam displays antifungal activity against amphotericin B-resistant Candida albicans (MIC = 4 μg/mL, 8.3 μM).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amphotericin B / pharmacology
  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Candida albicans / drug effects
  • Lactams, Macrocyclic / chemistry
  • Lactams, Macrocyclic / isolation & purification*
  • Lactams, Macrocyclic / pharmacology
  • Microbial Sensitivity Tests
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyenes / chemical synthesis*
  • Polyenes / chemistry
  • Polyenes / pharmacology
  • Streptomyces / chemistry*
  • Wasps / microbiology*

Substances

  • Antifungal Agents
  • Lactams, Macrocyclic
  • Polyenes
  • sceliphrolactam
  • Amphotericin B