- Lipophilic constituents from aerial and root parts of Mercurialis perennis L
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Introduction - Dog's mercury (Mercurialis perennis L.) is a perennial herb used in remedies for medicinal purposes. The plant is supposed to contain potentially active substances but its constituents have only been rarely studied. Objective - Detailed studies on the phytochemical composition are of great interest to broaden the knowledge on the chemotaxonomy and pharmacognosy of M. perennis. Methodology - Chloroform and hexane extracts from roots and aerial parts were investigated using GC/MS and LC/MS. Results - The whole plant exhihited a broad spectrum of structurally diverse constituents, mainly alkaloids, terpenes, sterols and simple aromatic compounds. Closer inspection of the piperidine alkaloid hermidin revealed its inherent instability towards air oxygen. To obtain quantitative data on these alkaloids the synthesis of the more stable reference compound 4-methoxy-1-methylpyridine-2,6(1H,3H)-dione (MMPD) was required. In this study, MMPD was detected for the fi rst time as a genuine compound in Mercurialis. Hermidine quinone and hermidin dimers originating from hermidin via a free anionic radical reaction were also confi rmed by GC/MS. Moreover, volatile compounds such as benzylalcohol, 2-phenylethanol, 4-methoxy- and 3,4-dimethoxyphenol, (-)-cis- and (+)-trans-myrtanol, (-)-cis-myrtanal as well as squalene were predominantely present in Mercurialis roots. In contrast, aerial parts mainly contained phytol derivatives, sterols and tocopherols. By changing solvent polarity, lipid and wax-containing fractions were obtained. LC/MS-studies on hexane extracts showed the presence of several mixed triglycerides constituted by linolenic, linoleic, oleic, stearic and palmitic acids, as well as lutein, carotenes and pheophytins. Conclusions - The phytochemical data presented complement our knowledge on the rarely studied plant M. perennis and may broaden its use in future phytotherapy. Copyright
- Lorenz, Peter,Hradecky, Marc,Berger, Melanie,Bertrams, Julia,Meyer, Ulrich,Stintzing, Florian C.
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experimental part
p. 234 - 245
(2011/11/06)
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- Isolation, Structure, and Synthesis of Hermidin, a Chromogen from Mercurialis perennis L.
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Hermidin has been isolated from Mercurialis perennis L. as a colourless, crystalline compound, shown by synthesis to be 5-hydroxy-4-methoxy-1-methylpyridine-2,6(1H,3H)-dione (2), which in aqueous solution exist as a dihydroxy-4-methoxy-1-methylpyridin-2(1H)-one (3) or (4).Oxidation of hermidin with nitric acid affords 4-methoxy-1-methylpyridine-2,3,6-trione (16).When equimolecular amounts of the latter and hermidin in aqueous solution are mixed an immediate deep blue solution containing an ion-radical (17) results.Oxidation of hermidin by air in methanolic solution gives 5,5'-dihydroxy-4,4'-dimethoxy-1,1'-dimethyl-3,3'-bipyridine-2,2',6,6'-(1H,1'H,3H,3'H)-tetraone (18), and in pyridine solution 4,4'-dimethoxy-1,1'-dimethyl-3,3'-bipyridine-2,2',5,5',6,6'-hexaone (23).Knackmuss' conclusions on the oxidation of 3,6-dihydroxy-4-methylpyridin-2(1H)-one (26) have been re-interpreted. 3,4-Dihydroxy-5-methoxy-1-methylpyridin-2(1H)-one (7) has been synthesized.
- Swan, George A.
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p. 1757 - 1766
(2007/10/02)
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