Terreuspyridine: An Unexpected Pyridine-Fused Meroterpenoid Alkaloid with a Tetracyclic 6/6/6/6 Skeleton from Aspergillus terreus

Org Lett. 2020 Sep 4;22(17):7041-7046. doi: 10.1021/acs.orglett.0c02641. Epub 2020 Aug 25.

Abstract

Terreuspyridine (1), the first 3,5-demethylorsellinic acid (DMOA) derived meroterpenoid alkaloid, was isolated from the fungus Aspergillus terreus, which represents a new type of meroterpenoid possessing an unexpected tetracyclic 6/6/6/6 architecture. The structure of 1 with absolute configuration was determined by X-ray diffraction analysis. Biogenetically, it was proposed to be derived from the fusion of a DMOA-meroterpenoid and a glutamate. Terreuspyridine (1) exhibited moderate inhibitory activity against the BChE with an IC50 value of 16.4 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Aspergillus
  • Crystallography, X-Ray
  • Molecular Structure
  • Polycyclic Compounds / chemistry*
  • Polycyclic Compounds / isolation & purification
  • Pyridines / chemistry*
  • Pyridines / isolation & purification
  • Terpenes / chemistry
  • Terpenes / isolation & purification

Substances

  • Alkaloids
  • Polycyclic Compounds
  • Pyridines
  • Terpenes

Supplementary concepts

  • Aspergillus terreus