Publication Date:
2014-12-11
Description:
Hermidin ( 1 ), a piperidine-2,3-dione alkaloid, has been previously detected as a lipophilic constituent in Mercurialis perennis L. and other Mercurialis species. Because of strong electron-withdrawing effects of its carbonyl groups, an acidic H-atom is easily subtracted from 1 , whereas the latter shows high reactivity towards oxidation reactions or the attack of C-nucleophilic agents. To obtain a better understanding of possible chemical pathways upon extraction of root parts of M. perennis , the products obtained with different solvents from 1 were investigated. Extraction of M. perennis with aqueous MeOH or EtOH yielded a mixture of hermidin quinone ( 3 ), 5-hydroxy-4-methoxy-5-(alkoxycarbonyl)-1-methyl-3-pyrrolin-2-ones, 7 and 8 , and d , l - and meso -isochrysohermidins, 5 and 6 , all of them being investigated by GC/MS and LC/MS n . The latter compounds were supposedly formed by free-radical reactions, followed by spontaneous benzilic acid rearrangement and esterification. Furthermore, extraction of M. perennis with aqueous Me 2 CO produced an aldol condensation product, the known alkaloid speranskatine A ( 9a ), which was identified by NMR after chromatographic purification. In a similar manner, a CH 2 homolog of speranskatine A ( 10a ) was obtained as a novel compound when ethyl methyl ketone (=butan-2-one; EtCOMe) instead of Me 2 CO was used for extraction. Consequently, 1 easily undergoes artefact formation upon extraction of plant material with polar or slightly polar solvents.
Print ISSN:
0018-019X
Electronic ISSN:
1522-2675
Topics:
Chemistry and Pharmacology
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