Insights into the Metabolomic Capacity of Podaxis and Isolation of Podaxisterols A-D, Ergosterol Derivatives Carrying Nitrosyl Cyanide-Derived Modifications
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Insights into the Metabolomic Capacity of Podaxis and Isolation of Podaxisterols A-D, Ergosterol Derivatives Carrying Nitrosyl Cyanide-Derived Modifications. / Guo, Huijuan; Daniel, Jan Martin; Seibel, Elena; Burkhardt, Immo; Conlon, Benjamin H.; Görls, Helmar; Vassão, Daniel Giddings; Dickschat, Jeroen S.; Poulsen, Michael; Beemelmanns, Christine.
In: Journal of Natural Products, Vol. 85, No. 9, 2022, p. 2159-2167.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Insights into the Metabolomic Capacity of Podaxis and Isolation of Podaxisterols A-D, Ergosterol Derivatives Carrying Nitrosyl Cyanide-Derived Modifications
AU - Guo, Huijuan
AU - Daniel, Jan Martin
AU - Seibel, Elena
AU - Burkhardt, Immo
AU - Conlon, Benjamin H.
AU - Görls, Helmar
AU - Vassão, Daniel Giddings
AU - Dickschat, Jeroen S.
AU - Poulsen, Michael
AU - Beemelmanns, Christine
N1 - Publisher Copyright: © 2022 American Chemical Society and American Society of Pharmacognosy.
PY - 2022
Y1 - 2022
N2 - 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 "omics"-driven analysis of this underexplored yet worldwide distributed fungal genus builds a foundation for studies on a potential metabolic adaptations to diverse lifestyles.
AB - 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 "omics"-driven analysis of this underexplored yet worldwide distributed fungal genus builds a foundation for studies on a potential metabolic adaptations to diverse lifestyles.
U2 - 10.1021/acs.jnatprod.2c00380
DO - 10.1021/acs.jnatprod.2c00380
M3 - Journal article
C2 - 36040034
AN - SCOPUS:85138078113
VL - 85
SP - 2159
EP - 2167
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 9
ER -
ID: 320759416