Elsevier

Phytochemistry

Volume 51, Issue 3, June 1999, Pages 417-423
Phytochemistry

The flavonoids of Tanacetum parthenium and T. vulgare and their anti-inflammatory properties

https://doi.org/10.1016/S0031-9422(99)00021-7Get rights and content

Abstract

The lipophilic flavonoids in leaf and flower of Tanacetum parthenium and T. vulgaris have been compared. While those of T. parthenium are methyl ethers of the flavonols 6-hydroxykaempferol and quercetagetin, the surface flavonoids of T. vulgare are methyl ethers of the flavones scutellarein and 6-hydroxyluteolin. Apigenin and two flavone glucuronides are surprisingly present in glandular trichomes on the lower epidermis of the ray florets of T. parthenium. The opportunity has been taken to revise the structures of the four 6-hydroxyflavonol methyl ethers of T. parthenium based on NMR measurements. These are now shown to be uniformly 6- rather than 7-O-methylated. Tanetin, previously thought to be a new structure, is now formulated as the known 6-hydroxykaempferol 3,6,4′-trimethyl ether. The vacuolar flavonoids of both plants are dominated by the presence of apigenin and luteolin 7-glucuronides; nine other glycosides were present, including the uncommon 6-hydroxyluteolin 7-glucoside in T. vulgare. When the major flavonol and flavone methyl ethers of the two plants were tested pharmacologically, they variously inhibited the major pathways of arachidonate metabolism in leukocytes. There were significant differences in potency, with the tansy 6-hydroxyflavones less active than the feverfew 6-hydroxyflavonols as inhibitors of cyclo-oxygenase and 5-lipoxygenase.

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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