Indole–diterpenoid profiles of Claviceps paspali and Claviceps purpurea from high‐resolution Fourier transform Orbitrap mass spectrometry. (30th July 2014)

• Record Type: Journal Article
• Authors: Uhlig, Silvio; Egge‐Jacobsen, Wolfgang; Vrålstad, Trude; Miles, Christopher O.
• Is Part Of: Rapid communications in mass spectrometry. Volume 28:Number 14(2014)
• Page Start: 1621
• Page End: 1634
• Publication Date: 2014-07-30
• Subjects: Mass spectrometry -- Periodicals; 543.65
• DOI: 10.1002/rcm.6938
• Languages: English
• ISSNs: 0951-4198

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <sec id="rcm6938-sec-0001" sec-type="section"> <title>RATIONALE</title> <p>The biological activities most commonly associated with indole–diterpenoids are tremorgenicity in mammals and toxicity in insects through modulation of ion channels. The neurotoxic effects of some analogues are the cause of syndromes such as 'ryegrass staggers' and 'Paspalum staggers' in cattle and sheep. Our purpose was to obtain and interpret mass spectra of some pure <italic>Claviceps</italic>‐related indole–diterpenoids (paspaline, paspalinine, paxilline, paspalitrems A and B) to facilitate identification of related compounds for which standards were not available.</p> </sec> <sec id="rcm6938-sec-0002" sec-type="section"> <title>METHODS</title> <p> <italic>C. paspali</italic>‐infected <italic>Paspalum dilatatum</italic> as well as <italic>C. purpurea</italic> sclerotia obtained from infected <italic>Phalaris arundinacea</italic> were extracted and the extracts separated via liquid chromatography. Low‐ and high‐resolution mass spectra were then obtained of known and potentially unknown indole–diterpenoids.</p> </sec> <sec id="rcm6938-sec-0003" sec-type="section"> <title>RESULTS</title> <p>At least 20 different indole–diterpenoids were detected in the <italic>C. paspali</italic> extract with molecular masses ranging from 405 Da (C<sub>28</sub>H<sub>40</sub>NO) to 517 Da (C<sub>32</sub>H<sub>40</sub>NO<sub>5</sub>). The <italic>C. purpurea</italic> sclerotia were shown to contain several indole–diterpenoids with molecular masses ranging from 405 Da (C<sub>28</sub>H<sub>40</sub>NO) to 419 Da (C<sub>28</sub>H<sub>38</sub>NO<sub>2</sub>).</p> </sec> <sec id="rcm6938-sec-0004" sec-type="section"> <title>CONCLUSIONS</title> <p>This study demonstrates for the first time that <italic>C. purpurea</italic> may also produce indole–diterpenoids. This might explain why grazing of <italic>Phalaris</italic> spp. is occasionally connected with a tremorgenic syndrome in cattle, called 'phalaris staggers'. Copyright © 2014 John Wiley & Sons, Ltd.</p> </sec> </abstract>