Guanacastane diterpenoids from the plant endophytic fungus Cercospora sp

J Nat Prod. 2014 Apr 25;77(4):873-81. doi: 10.1021/np4009688. Epub 2014 Feb 27.

Abstract

Cercosporenes A-F (1-6, respectively), six new guanacastane diterpenes, including a homodimer (5) and a heterodimer (6), were isolated from the crude extract of the fungus Cercospora sp., endophytic to the medicinal plant Fallopia japonica. The structures of 1-6 were elucidated by nuclear magnetic resonance experiments, and 4 and 5 were further confirmed by X-ray crystallography. The absolute configuration of 1 and 3 was assigned by electronic circular dichroism calculations, whereas that of 6 was deduced by the application of the circular dichroism exciton chirality method. In addition to its cytotoxicity against a panel of five human tumor cell lines, HeLa, A549, MCF-7, HCT116, and T24, heterodimer 6 also induced autophagy in HCT116 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / isolation & purification
  • Antineoplastic Agents* / pharmacology
  • Ascomycota / chemistry*
  • China
  • Circular Dichroism
  • Crystallography, X-Ray
  • Diterpenes* / chemistry
  • Diterpenes* / isolation & purification
  • Diterpenes* / pharmacology
  • Drug Screening Assays, Antitumor
  • Fallopia japonica / microbiology
  • HCT116 Cells
  • HeLa Cells
  • Humans
  • Molecular Conformation
  • Molecular Structure
  • Plant Leaves / microbiology
  • Plants, Medicinal / microbiology
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Diterpenes
  • cercosporene F