Thielavialides A-E, nor-spiro-azaphilones, and a bis-spiro-azaphilone from Thielavia sp. PA0001, an endophytic fungus isolated from aeroponically grown Physalis alkekengi

J Nat Prod. 2014 Jun 27;77(6):1467-72. doi: 10.1021/np500237h. Epub 2014 Jun 2.

Abstract

Four new nor-spiro-azaphilones, thielavialides A-D (1- 4), a new bis-spiro-azaphilone, thielavialide E (5), together with pestafolide A (6), were isolated from the endophytic fungal strain, Thielavia sp. PA0001, occurring in the healthy leaf tissue of aeroponically grown Physalis alkekengi. The structures and relative configurations of 1-5 were established on the basis of their MS and NMR data. Possible biosynthetic pathways to thielavialides A-E (1- 5) from pestafolide A (6), some involving a Favorskii-like rearrangement, are proposed.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Ascomycota / chemistry*
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Fungi / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Physalis / microbiology*
  • Pigments, Biological / chemistry
  • Pigments, Biological / isolation & purification*
  • Plant Leaves / microbiology
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*

Substances

  • Benzopyrans
  • Pigments, Biological
  • Spiro Compounds
  • azaphilone