Expanding the strategies in natural product studies of marine-derived fungi: a chemical investigation of penicillium obtained from deep water sediment

J Nat Prod. 2004 Mar;67(3):362-7. doi: 10.1021/np030388m.

Abstract

Three previously unknown pentaketides, (+)-formylanserinone B (3), (-)-epoxyserinone A (4), and (+)-epoxyserinone B (5), along with two known fungal pigments, anserinones A (1) and B (2), were isolated and identified from a deep water (-4380 ft), marine-derived saltwater fungal culture. Two other minor constituents, hydroxymethylanserinone B (6) and deoxyanserinone B (7), were also isolated, but not completely purified. The structures of 3-7, each expanding the dense functionalization of the anserinones, were determined by dereplication and spectroscopic analysis. Bioactivity was explored in two separate cell-based assays. Leukemia selectivity was greatest with 2 and 3, while 1-3 exhibited modest activity against the MDA-MB-435 cell line.

Publication types

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

MeSH terms

  • Benzoquinones / chemistry
  • Benzoquinones / isolation & purification*
  • Benzoquinones / pharmacology
  • Biological Factors* / chemistry
  • Biological Factors* / isolation & purification
  • Biological Factors* / pharmacology
  • Drug Screening Assays, Antitumor
  • Fungi / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry*
  • Stereoisomerism
  • Tumor Cells, Cultured
  • Water Microbiology*

Substances

  • Benzoquinones
  • Biological Factors
  • anserinone A
  • anserinone B
  • epoxyserinone A
  • formylanserinone B