4.7 Article

Prenylated Indole Diketopiperazines from the Marine-Derived Fungus Aspergillus versicolor

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 17, Pages 7895-7904

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo5010179

Keywords

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Funding

  1. National Natural Science Foundation of China [41176120, 21372208]
  2. National High Technology Research and Development Program of China [2013AA092901]
  3. NSFC-Shandong Joint Fund [U1406402]
  4. Program for New Century Excellent Talents in University [NCET-12-0499]
  5. State Oceanic Administration [2010418022-3]
  6. Program for Changjiang Scholars and Innovative Research Team in University [IRT0944]

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Seven new prenylated indole diketopiperazines, versicamides A-G (1-7) and a novel chemical derivative from 7, versicamide H (8), along with three known analogic diketopiperazines (9-11) were obtained from the marine-derived fungus Aspergillus versicolor HDN08-60. Their structures were determined by spectroscopic techniques, including 2D NMR, ECD calculations, and single-crystal X-ray diffraction analysis, together with the assistance of further chemical conversions. The cytotoxicities of 1-8 were tested against the HeLa, HCT-116, HL-60, and K562 cell lines, but only 8 exhibited moderate activity against HL-60 cells, with an IC50 value of 8.7 mu M. Further investigation with target screening showed that 8 exhibited selective PTK inhibitory activities.

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