Taichunins E-T, Isopimarane Diterpenes and a 20- nor-Isopimarane, from Aspergillus taichungensis (IBT 19404): Structures and Inhibitory Effects on RANKL-Induced Formation of Multinuclear Osteoclasts

J Nat Prod. 2021 Sep 24;84(9):2475-2485. doi: 10.1021/acs.jnatprod.1c00486. Epub 2021 Aug 31.

Abstract

Fifteen new isopimarane-type diterpenes, taichunins E-S (1-15), and a new 20-nor-isopimarane, taichunin T (16), together with four known compounds were isolated from Aspergillus taichungensis (IBT 19404). The structures of these new compounds were determined by NMR and mass spectroscopy, and their absolute configurations were analyzed by NOESY and TDDFT calculations of ECD spectra. Taichunins G, K, and N (3, 7, and 10) completely inhibited the receptor activator of nuclear factor-κB ligand (RANKL)-induced formation of multinuclear osteoclasts in RAW264 cells at 5 μM, with 3 showing 92% inhibition at a concentration of 0.2 μM.

MeSH terms

  • Abietanes / isolation & purification
  • Abietanes / pharmacology*
  • Animals
  • Aspergillus / chemistry*
  • Biological Products / isolation & purification
  • Biological Products / pharmacology
  • Mice
  • Molecular Structure
  • Osteoclasts / drug effects*
  • RANK Ligand*
  • RAW 264.7 Cells
  • Taiwan

Substances

  • Abietanes
  • Biological Products
  • RANK Ligand
  • Tnfsf11 protein, mouse

Supplementary concepts

  • Aspergillus taichungensis