Isolation and structure elucidation of secopenitrem D, an indole alkaloid from Penicillium crustosum Thom

Angel Moldes-Anaya; Thomas Rundberget; Silvio Uhlig; Frode Rise; Alistair L Wilkins

doi:10.1016/j.toxicon.2010.11.020

Isolation and structure elucidation of secopenitrem D, an indole alkaloid from Penicillium crustosum Thom

Toxicon. 2011 Feb;57(2):259-65. doi: 10.1016/j.toxicon.2010.11.020. Epub 2010 Dec 8.

Authors

Angel Moldes-Anaya¹, Thomas Rundberget, Silvio Uhlig, Frode Rise, Alistair L Wilkins

Affiliation

¹ Section of Chemistry and Toxicology, National Veterinary Institute, P.O. Box 750 Sentrum, N-0106 Oslo, Norway. angel.moldes-anaya@vetinst.no

PMID: 21145337
DOI: 10.1016/j.toxicon.2010.11.020

Abstract

Chemical investigation of three isolates of Penicillium crustosum Thom cultures, one of which was derived from a recent dog poisoning investigation, has led to the isolation and structure elucidation of secopenitrem D (1). Penitrems A-F and roquefortine C were also present in the isolates analyzed. The structure of 1 was unambiguously assigned based on extensive 1D and 2D-NMR spectroscopic experiments, MS-aided structural studies and by comparison with structurally related congeners. Secopenitrem D lacks the C-16-C-18 ether linkage present in penitrems A-F.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromatography, High Pressure Liquid
Indole Alkaloids / chemistry*
Indole Alkaloids / isolation & purification
Molecular Conformation
Nuclear Magnetic Resonance, Biomolecular
Penicillium / chemistry*

Substances

Indole Alkaloids
secopenitrem D