The flavonoids of Tanacetum parthenium and T. vulgare and their anti-inflammatory properties
Introduction
As part of an investigation of the biological properties of flavonoids in the genus Tanacetum, we reported earlier the discovery of four 6-hydroxyflavonol methyl ethers in the surface extracts of leaf, flower and seed of feverfew, Tanacetum parthenium (L.) Schultz Bip. (Williams, Hoult, Harborne, Greenham, & Eagles, 1995). The anti-inflammatory activity of the major flavonoid, called tanetin, was found to be significant (Hoult et al., 1995), particularly because feverfew is currently used in the treatment of arthritis and migraine (Newell, Anderson, & Phillipson, 1996).
While the structures of the four flavonol methyl ethers of feverfew seemed to be securely based on EI-MS and UV spectral data, insufficient material was then available for confirmation by NMR. We have now isolated and separated larger amounts of these lipophilic constituents and here report the NMR results. These clearly show that in the earlier structures, the position of the A-ring methoxyl was incorrectly assigned to the 7- instead of the 6-position and that all four compounds are the respective 6-O-methyl ethers. At the same time, six other minor lipophilic flavonoids have been identified in feverfew tissues.
We also describe in this paper a parallel investigation of lipophilic flavonoids in the related composite plant, the tansy Tanacetum vulgare L. and report on their anti-inflammatory activities. Tansy is a well known medicinal plant, much used in the past, but is now contraindicated for deworming children because of the toxic monoterpene, α-thujone, present throughout the tissues (Newell et al., 1996). Previous investigations of tansy flowers have revealed the presence of quercetagetin 3,6,3′-trimethyl ether and 6-hydroxyluteolin 6,3′-dimethyl ether (Ognyanov, & Tochorova, 1983). A water-soluble apigenin 7-diglycoside has been found in the leaf of tansy (Khvorost, 1969). In this paper, we therefore record a comprehensive reinvestigation of lipophilic and water-soluble flavonoids in feverfew and tansy and describe some pharmacological properties of the main lipophilic constituents.
Section snippets
Structural revision of the major lipophilic flavonols of feverfew
A comparison of brief acetone washings of leaf, flower and seed of feverfew indicated that the seed contained a very similar profile of flavonoids as the leaf. The dried seeds were used to isolate sufficient material for NMR analyses. Thus, the seed washings were purified on polyamide and Sephadex to give three flavonol methyl ethers in a combined yield of 0.1%. These were identical in all respects (Rf, Rt, UV spectra and shifts) to the same compounds previously obtained from leaf washings
Plant material
Fresh leaves, flowers and seeds of T. parthenium (L.) Schultz Bip. and T. vulgare L. were collected from plants grown at the School of Plant Sciences, The University of Reading from seed supplied by the Botanic Gardens of Munich and Berlin-Dahlem, Germany, respectively. Voucher specimens have been deposited in the University of Reading Herbarium (RNG).
Isolation of lipophilic flavonoids from feverfew seed for NMR analysis
The flavonoids were removed from the surface of the seeds by covering with Me2CO and immediately decanting off the solvent (×3). The concentrated
Acknowledgements
We are grateful to Mrs. Jenny Greenham for experimental assistance and to John Eagles, Food Research Institute, Norwich, for EI-MS determinations.
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