Dihydrothiophene-condensed chromones from a marine-derived fungus Penicillium oxalicum and their structure-bioactivity relationship

Bioorg Med Chem Lett. 2014 Jun 1;24(11):2433-6. doi: 10.1016/j.bmcl.2014.04.028. Epub 2014 Apr 18.

Abstract

Four dihydrothiophene-condensed chromones including two new compounds oxalicumones D-E (1-2) and known oxalicumones A-B (3-4), along with five other known chromones were isolated from a culture broth of the marine gorgonian-associated fungus Penicillium oxalicum SCSGAF 0023. The structures of 1-2 were elucidated by spectroscopic analysis. Eleven derivatives 3a-3i and 4a-4b were obtained from the acylation of 3 and 4, respectively. Compounds 1-4, 3a-3e, 3g-3h, and 4b showed significant cytotoxicity against several carcinoma cell lines with IC50 ≤ 10 μM. And their structure-bioactivity relationship was discussed.

Keywords: Cytotoxicity; Dihydrothiophene-condensed chromones; Penicillium oxalicum; Structure–bioactivity relationship.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Chromones / chemistry
  • Chromones / isolation & purification
  • Chromones / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • K562 Cells
  • MCF-7 Cells
  • Molecular Structure
  • Penicillium / chemistry*
  • Structure-Activity Relationship
  • Thiophenes / chemistry*
  • U937 Cells

Substances

  • Antineoplastic Agents
  • Chromones
  • Thiophenes