Penicamins A-L, Polyoxygenated Diterpenes from Penicillium camemberti JSB-7212

J Nat Prod. 2024 Oct 25;87(10):2441-2449. doi: 10.1021/acs.jnatprod.4c00700. Epub 2024 Oct 16.

Abstract

Penicamins A-L (1-12), 12 highly oxygenated novel diterpenes, were obtained from the fungus Penicillium camemberti JSB-7212. Compounds 1-12 share the same 7/6/5 tricyclic skeleton as valparane-type diterpenes but differ in the absolute configurations at C-7, C-11, and C-14, as well as in the oxidation levels at C-6 and C-8, which were determined through extensive spectroscopic data interpretation. Stereochemical assignments of compounds 1, 2, and 4-12 were established by single-crystal X-ray diffraction, and the absolute configuration of 3 was determined by analysis of the NOESY data and biogenetic consideration. Compounds 2 and 3 were immunosuppressive against lipopolysaccharide (LPS)-induced B cells, with IC50 values of 3.0 and 7.9 μM, respectively. They also moderately suppressed concanavalin A (ConA)-induced T cell proliferation, with IC50 values of 19 and 20 μM, respectively.

MeSH terms

  • Animals
  • B-Lymphocytes / drug effects
  • Crystallography, X-Ray
  • Diterpenes* / chemistry
  • Diterpenes* / isolation & purification
  • Diterpenes* / pharmacology
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / isolation & purification
  • Immunosuppressive Agents / pharmacology
  • Mice
  • Molecular Structure
  • Penicillium* / chemistry
  • T-Lymphocytes / drug effects

Substances

  • Diterpenes
  • Immunosuppressive Agents