20- nor-Isopimarane and isopimarane diterpenoids produced by Aspergillus sp. WT03

Org Biomol Chem. 2023 Mar 1;21(9):1895-1902. doi: 10.1039/d3ob00005b.

Abstract

Five new uncommon 20-nor-isopimarane diterpenoids, aspewentins N-R (1-5), and three related known congeners (6-8), along with an isopimarane diterpenoid, sphaeropsidin C (9), were isolated from a Coptis chinensis Franch. rhizosphere soil-derived fungal strain, Aspergillus sp. WT03. The structures of compounds 1-9 were characterized based on the comprehensive analysis of the spectroscopic data, and their absolute configurations were elucidated by single crystal X-ray diffraction and time-dependent density functional theory (TDDFT)-ECD calculations. Compounds 1-5 represent rare examples of 20-nor-isopimarane analogues featuring a 1,2,3,4-tetrahydronaphthalene and 3,4-dihydronaphthalen-1(2H)-one moiety. The biosynthetic pathway of these diterpenoids was also proposed. Additionally, compounds 1, 3 and 4 showed moderate cytotoxic activity against MCF-7, A549 and HT-29 cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes
  • Antineoplastic Agents*
  • Aspergillus / chemistry
  • Diterpenes* / chemistry
  • Molecular Structure

Substances

  • Abietanes
  • Diterpenes
  • Antineoplastic Agents