Modified Fusicoccane-Type Diterpenoids from Alternaria brassicicola

J Nat Prod. 2020 Jun 26;83(6):1931-1938. doi: 10.1021/acs.jnatprod.0c00165. Epub 2020 Jun 10.

Abstract

Seven new modified fusicoccane-type diterpenoids (1-7), together with two known congeners (8 and 9), were obtained from Alternaria brassicicola. Their structures were elucidated from a combination of NMR and HRESIMS data and 13C NMR calculation as well as DP4+ probability analyses, and the absolute configurations of 1-5 were determined by ECD calculation and single-crystal X-ray diffraction (Cu Kα). Compounds 1-3 belong to a rare class of 16-nor-dicyclopenta[a,d]cyclooctane diterpenoids, and compounds 2 and 4 represent the first examples of fusicoccane-type diterpenoids featuring two previously undescribed tetracyclic 5/6/6/5 ring systems, while compound 5 features a previously undescribed tetracyclic 5/8/5/3 ring system. Compound 7 was moderately anti-inflammatory, and compounds 2, 3, 5, and 7 were weakly cytotoxic.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alternaria / chemistry*
  • Animals
  • Anti-Inflammatory Agents / pharmacology
  • Antibiotics, Antineoplastic / pharmacology
  • Cell Line, Tumor
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Drug Screening Assays, Antitumor
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • RAW 264.7 Cells
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Anti-Inflammatory Agents
  • Antibiotics, Antineoplastic
  • Diterpenes

Supplementary concepts

  • Alternaria brassicicola