Lumazine peptides penilumamides B-D and the cyclic pentapeptide asperpeptide A from a gorgonian-derived Aspergillus sp. fungus

J Nat Prod. 2014 Jul 25;77(7):1601-6. doi: 10.1021/np5001686. Epub 2014 Jul 8.

Abstract

Three new lumazine peptides, penilumamides B-D (2-4), and one known analogue, penilumamide (1), together with a new cyclic pentapeptide, asperpeptide A (5), were isolated from the gorgonian-derived fungus Aspergillus sp. XS-20090B15. Among them, 2 was obtained from the feeding culture with l-methionine of this strain. All structures were elucidated by spectroscopic methods and chemical derivatization. Compounds 1-4 are rare lumazine peptides, of which 1 and 3 are formed from 2 by oxidation of the l-methionine residue.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / pharmacology
  • Animals
  • Anthozoa / microbiology*
  • Aspergillus / chemistry*
  • Bacillus cereus / drug effects
  • Escherichia coli / drug effects
  • Methionine / analogs & derivatives
  • Methionine / chemistry
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nocardia / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligopeptides / chemistry
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Pseudomonas / drug effects
  • Pteridines / chemistry
  • Salmonella enterica / drug effects
  • Sesquiterpenes / pharmacology
  • Staphylococcus / drug effects
  • Vibrio / drug effects

Substances

  • Alkaloids
  • Oligopeptides
  • Peptides, Cyclic
  • Pteridines
  • Sesquiterpenes
  • asperpeptide A
  • penilumamide
  • penilumamide B
  • penilumamide C
  • penilumamide D
  • huperzine A
  • lumazine
  • Methionine