Insights into the metabolomic capacity of podaxis and isolation of podaxisterols A-D, ergosterol derivatives carrying nitrosyl cyanide-derived modifications.

Guo H, Daniel JM, Seibel E, Burkhardt I, Conlon BH, Görls H, Vassão DG, Dickschat JS, Poulsen M, Beemelmanns C (2022) Insights into the metabolomic capacity of podaxis and isolation of podaxisterols A-D, ergosterol derivatives carrying nitrosyl cyanide-derived modifications. J Nat Prod 85(9), 2159-2167. (Review)

Abstract

Cultures of a termite-associated and a free-living member of the fungal genus Podaxis, revived from spores maintained in century-old herbarium collections, were analyzed for their insecticidal and antimicrobial effects. Their secondary metabolomes were explored to uncover possible adaptive mechanisms of termite association, and dereplication of LC-HRMS/MS data sets led to the isolation of podaxisterols A-D (1-4), modified ergosterol derivatives that result from a Diels-Alder reaction with endogenous nitrosyl cyanide. Chemical structures were determined based on HRMS/MS and NMR analyses as well as X-ray crystallography. The putative origin of the endogenous fungal nitrosyl cyanide and ergosterol derivatives is discussed based on results obtained from stable isotope experiments and in silico analysis. Our

Leibniz-HKI-Authors

Christine Beemelmanns
Jan-Martin Daniel
Huijuan Guo
Elena Seibel

Identifier

doi: 10.1021/acs.jnatprod.2c00380

PMID: 36040034