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Trends in Chromatography   Volumes    Volume 6 
Biogenesis of infractine alkaloids in Cortinarius infractus: Importance of 5-Hydroxytriptophane pathway in biogenesis of alkaloids in mushrooms
Ilia Brondz, Klaus Høiland
Pages: 23 - 30
Number of pages: 8
Trends in Chromatography
Volume 6 

Copyright © 2010 Research Trends. All rights reserved

Cortinarius infractus (Pers.: Fr.) Fr. (brown spored mushrooms in Agaricales, Basidiomycota) are characterized by an overall olivaceous color on the basidiocarp, globose to subglobose spores, and a more or less bitter taste. The bitter taste may be caused by the presence of the bitter indole alkaloid infractopicrine. C. infractus is classified into the subgenus Phlegmacium according to the traditional infrageneric systematic of Cortinarius. Secondary metabolites were analyzed using high performance liquid chromatography (HPLC) equipped with a diode array detector (DAD) and mass spectrometry (MS) with pneumatically assisted electrospray ionization EI source, and gas chromatography-MS with a supersonic beams (GC-MS with SMB). HPLC-MS recorded the presence of β-carboline-1-propionic acid, 6-hydroxy- β-carboline-1-propionic acid, 5-hydroxytryptophan, and infractopicrine in C. infractus. The fraction that tentatively included 5-hydroxytryptophan was collected and analyzed by GC-MS with SMB to verify the hypothesis that C. infractus contains β-carboline-1-propionic acid-like alkaloids. The recorded spectral data were consistent with previously published information [1-3]. The presence of 6-hydroxy-β-carboline-1-propionic acid and 5-hydroxytryptophan in C. infractus was recorded by direct measurement. The biogenesis of 5-hydroxytryptophan and 6-hydroxy-β-carboline-1-propionic acid from tryptophan in C. infractus is proposed and is explained in schemas. The biogenesis of alkaloids and toxins via the 5-hydroxytryptophan pathway in plants may have been underestimated because of the general belief that 5-hydroxytryptophan is a rare amino acid that is seldom found in living systems and that exists mainly as an intermediate transmitter in the nervous system.
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