Thiodiketopiperazines from the marine-derived fungus Phoma sp. OUCMDZ-1847

J Nat Prod. 2014 Jan 24;77(1):132-7. doi: 10.1021/np400802d. Epub 2013 Dec 26.

Abstract

Three new thiodiketopiperazines, named phomazines A-C (1-3), along with 10 known analogues (4-13), were isolated from the fermentation broth of an endophytic fungus, Phoma sp. OUCMDZ-1847, associated with the mangrove plant Kandelia candel. The structures including the absolute configurations of the new compounds were unambiguously elucidated by spectroscopic, X-ray crystallographic, and Mosher's methods along with quantum ECD and (13)C NMR calculations. Compounds 2, 4, 5, 11, and 12 showed cytotoxicities against the HL-60, HCT-116, K562, MGC-803, and A549 cell lines with IC50 values in the range 0.05 to 8.5 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Ascomycota / chemistry*
  • China
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • K562 Cells
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Piperazines / chemistry
  • Piperazines / isolation & purification*
  • Piperazines / pharmacology
  • Rhizophoraceae / microbiology
  • Sulfur Compounds / chemistry
  • Sulfur Compounds / isolation & purification*
  • Sulfur Compounds / pharmacology

Substances

  • Antineoplastic Agents
  • Piperazines
  • Sulfur Compounds
  • phomazine A
  • phomazine B
  • phomazine C