92446-37-2Relevant academic research and scientific papers
Chemistry of hermidin: Insights from extraction experiments with the main Alkaloid of mercurialis perennis L. Tracked by GC/MS and LC/MSn
Lorenz, Peter,Conrad, Jürgen,Duckstein, Sarina,Kammerer, Dietmar R.,Stintzing, Florian C.
, p. 1606 - 1623 (2014)
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 electronwithdrawing 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/MSn. 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 Me2CO produced an aldol condensation product, the known alkaloid speranskatine A (9a), which was identified by NMR after chromatographic purification. In a similar manner, a CH2 homolog of speranskatine A (10a) was obtained as a novel compound when ethyl methyl ketone (=butan-2-one; EtCOMe) instead of Me2CO was used for extraction. Consequently, 1 easily undergoes artefact formation upon extraction of plant material with polar or slightly polar solvents.
