New terpenoids and triketides from culture of the fungus Botrysphaeria laricina

Fitoterapia. 2020 Nov:147:104758. doi: 10.1016/j.fitote.2020.104758. Epub 2020 Oct 15.

Abstract

Three new isopimarane-type diterpenoids, botrysphins G-I (1-3), a new muurolane-type sesquiterpenoid, 11,12-dihydroxylentideusether (4), and two new triketides, 4-dechlorobotrysphone C (5) and 4,5-dihydroxy-3-methoxy-6-undecanoyloxy-2-cyclohexen-1-one (6), together with one known diterpenoid, sphaeropsidin A (7), one sesquiterpenoid, lentideusether (8), and one triketide sphaeropsidone (9), were isolated from culture of the fungus Botrysphaeria laricina associated with the moss Rhodobryum umgiganteum. The structures of the new compounds were established on the basis of extensive spectroscopic techniques including HRMS and 1D and 2D NMR data. Compounds 1 and 2 exhibited NO inhibitory activity with IC50 values of 13.9 μM and 41.9 μM, respectively. At the same time, these two compounds showed quinone reductase inducing activity with 2.7-fold of induction for 1 at 12.5 μM and 1.6-fold for 2 at 25.0 μM.

Keywords: Botrysphaeria laricina; Diterpenoid; NO production inhibitory activity; Quinone reductase inducing activity; Sesquiterpenoid; Triketides.

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Bryophyta / microbiology
  • Cell Line, Tumor
  • China
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Enzyme Activators / isolation & purification
  • Enzyme Activators / pharmacology
  • Mice
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone)
  • Nitric Oxide / metabolism
  • Polyketides / isolation & purification
  • Polyketides / pharmacology*
  • RAW 264.7 Cells
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*

Substances

  • Diterpenes
  • Enzyme Activators
  • Polyketides
  • Sesquiterpenes
  • Nitric Oxide
  • NAD(P)H Dehydrogenase (Quinone)

Supplementary concepts

  • Botryosphaeria laricina