Chrysamides A-C, Three Dimeric Nitrophenyl trans-Epoxyamides Produced by the Deep-Sea-Derived Fungus Penicillium chrysogenum SCSIO41001

Org Lett. 2016 Aug 5;18(15):3650-3. doi: 10.1021/acs.orglett.6b01699. Epub 2016 Jul 21.

Abstract

Three dimeric nitrophenyl trans-epoxyamides, chrysamides A-C (1-3), were obtained from the deep-sea-derived fungus Penicillium chrysogenum SCSIO41001. Their structures were characterized by spectroscopic analysis, electronic circular dichroism computations, and X-ray single-crystal diffraction analysis. Notably, compound 1 possesses a novel centrosymmetric dimer skeleton featuring an unprecedented 7-oxa-2,5-diazabicyclo[2.2.1]heptane ring system, which represents the first example of dimeric nitrophenyl trans-epoxyamide in nature. Compound 3 suppresses the production of proinflammatory cytokine interleukin-17. A possible biosynthetic pathway of 1-3 was proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amides / metabolism*
  • Bridged Bicyclo Compounds / chemistry
  • Bridged Bicyclo Compounds / metabolism*
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Conformation
  • Penicillium chrysogenum / chemistry*
  • Penicillium chrysogenum / metabolism
  • Piperazines / chemistry
  • Piperazines / metabolism*
  • Stereoisomerism

Substances

  • Amides
  • Bridged Bicyclo Compounds
  • Piperazines
  • chrysamide A
  • chrysamide B
  • chrysamide C