Purpurolic acid, a new natural alkaloid from Claviceps purpurea (Fr.) Tul.
File(s)
Accepted version
Author(s)
Mantle, PG
Manzarpour, A
Roberts, A
Beaumont, C
Type
Journal Article
Abstract
A novel secondary metabolite from the sclerotia of Claviceps purpurea (Fr.) Tul. is described; the structure is based on ¹H and ¹³C NMR spectroscopy and electrospray mass spectrometry. It has an elemental composition C₁₀ H₁₆ N₂ O₇ and is comprised mainly of proline and alanine moieties, although without peptide linkage. Notably, these amino-acids are also components of the cyclic tripeptide side chain of several classic ergoline alkaloids. Designated as purpurolic acid, the new compound is the principal free amino-acid in ergot and its natural abundance exceeds that of the ergoline alkaloids with which it accumulates in parallel during parasitic development. In contrast, it does not accumulate in the fungus in axenic culture, even when ergotamine is synthesised. The extent to which the compound is a metabolite of other ergot fungi worldwide is unknown. Biological activity and metabolic significance also remain unknown, but purpurolic acid could become a biomarker for detection of ergot contamination in agricultural products of temperate latitudes.
Date Issued
2016-01
Date Acceptance
2015-10-16
Citation
Fungal Biology, 2016, 120 (1), pp.104-110
ISSN
1878-6146
Publisher
Elsevier
Start Page
104
End Page
110
Journal / Book Title
Fungal Biology
Volume
120
Issue
1
Copyright Statement
© 2015, Elsevier. All rights reserved. This manuscript is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/
Subjects
Ergot
Sclerotia
Parasitism
Biomarker
Ion-exchange chromatography
Preparative electrophoresis
Publication Status
Published
Date Publish Online
2015-11-12