Alterbrassinoids A-D: Fusicoccane-Derived Diterpenoid Dimers Featuring Different Carbon Skeletons from Alternaria brassicicola

Org Lett. 2019 Oct 18;21(20):8353-8357. doi: 10.1021/acs.orglett.9b03133. Epub 2019 Oct 1.

Abstract

Alterbrassinoids A-D (1-4), the first examples of fusicoccane-derived diterpenoid dimers furnished by forming an undescribed C-12-C-18' linkage, were isolated from modified cultures of Alternaria brassicicola. Compounds 1 and 2 represent unprecedented heterodimers, whereas 3 and 4 represent unprecedented homodimers, and 4 also features an undescribed anhydride motif. Their structures were assigned via spectroscopic methods, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Putative biosynthetic pathways and a bioactivity evaluation for 1-4 were discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alternaria / chemistry*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line
  • Cell Proliferation / drug effects
  • Diterpenes / chemical synthesis
  • Diterpenes / chemistry
  • Diterpenes / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Diterpenes
  • fusicoccane A