Immunosuppressive Nor-isopimarane Diterpenes from Cultures of the Fungicolous Fungus Xylaria longipes HFG1018

J Nat Prod. 2020 Feb 28;83(2):401-412. doi: 10.1021/acs.jnatprod.9b00889. Epub 2020 Jan 21.

Abstract

Eighteen new nor-isopimarane diterpenes, xylarinorditerpenes A-R (1-18), along with two previously reported compounds, 14α,16-epoxy-18-norisopimar-7-en-4α-ol (19) and the labdane-type diterpene agatadiol (20), were isolated from cultures of the fungicolous fungus Xylaria longipes HFG1018 isolated from the wood-rotting basidiomycete Fomitopsis betulinus. The structure elucidation and relative configuration assignments of 1-18 were accomplished by interpretation of spectroscopic data and through computational methods. The absolute configurations of 1, 4, and 16 were determined by single-crystal X-ray diffraction. Compounds 1-16 possess an 18- or 19-nor-isopimarane skeleton, and compounds 17 and 18 possess an 18,19-dinor-isopimarane skeleton. Compounds 2-5, 9, 14, 19, and 20 showed immunosuppressive activity but were devoid of cytotoxicity against the cell proliferation by concanavalin A-induced T lymphocytes and lipopolysaccharide-induced B lymphocytes, with IC50 values varying from 1.0 to 27.2 μM and from 16.1 to 51.8 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes / chemistry*
  • Ascomycota / chemistry*
  • Basidiomycota
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Diterpenes / chemistry*
  • Diterpenes / pharmacology
  • Immunosuppressive Agents / chemistry*
  • Immunosuppressive Agents / pharmacology
  • Molecular Structure
  • Polyporales / chemistry
  • Xylariales / chemistry*

Substances

  • Abietanes
  • Diterpenes
  • Immunosuppressive Agents

Supplementary concepts

  • Piptoporus betulinus
  • Xylaria longipes