From Tanacetum parthenium

Williams, C.A. et al., A biologically active lipophilic flavonol from Tanacetum parthenium. Phytochemistry, 38, 267, 1995. 

Stimulation of macrophages by lipopolysaccharide (LPS) results in activation of members of MAPKs, ERKl and ERK2. The main sesquiterpene lactone from Tanacetum parthenium (Asteraceae), parthenolide (28), suppressed LPS-stimulated tyrosine phosphorylation of various proteins in RAW 264.7 cells. Of these proteins the MAPKs exhibited the most dramatic inhibition in response to parthenolide. 

Parthenolide, isolated from Tanacetum parthenium and other species, is a sesquiterpene lactone widely investigated for its anti-inflammatory activity [168,169,170]. Recent in vitro studies have shown that this compound inhibits the NF-kB pathway. A study on the effect of parthenolide in endotoxic shock in rodents showed that treatment with this compound stopped nitrotyrosine formation, PARP synthetase expression, and apoptosis. It also reduced iNOS mRNA content in the tissues studied. All these effects are brought about by the compound s inhibition of NF-kB [171]. In addition, parthenolide mimicked the effects of IkBoc in that it inhibited both NF-kB DNA binding activity as well as Mn-SOD expression, while simultaneously increasing paclitaxel-induced apoptosis of breast cancer cells [90]. 

Kelm and Nair detected the presence of parthenolide in the hexane extract of M. salicifolia fruits by HPLC [11]. Parthenolide (1) and a related compound, costunolide (2), had shown topoisomerase I (top-l) inhibitory activity (refer to Bioassay Procedures section, Topoisomerase inhibitory bioassays) against Saccharomyces cerevisiae mutant strains hypersensitive to top- poisons [12] (Table 1). The isolation of parthenolide from M. grandiflora [13, 14, 15] and M sieboldii spp. japonica and M. praecoissima a.r. praecoissima [16] is discussed in other studies as well. Costunolide was isolated from the trunk and root bark ether extracts of M sieboldii [17, 18]. Also, parthenolide and costunolide, were isolated from Tanacetum parthenium Asteraceae [19]. The extraction of these compounds by supercritical CO2 (SFCO2) and near critical propane from M. grandiflora has also been carried out [20]. 

Bohlmann F, Zdero C 1982 Naturally occurring terpene derivatives. Part 454. Sesquiterpene lactones and other constituents from Tanacetum parthenium. Phytochemistry 21 2543-2549... 

Feverfew (Tanacetum parthenium). Reprinted with permission from Sturdivant and Blakely. (1999). Medicinal Herbs in the Garden, Field, and Marketplace. Friday Flarbor, WA San Juan Naturals. Illustration by Peggy Sue McRae. 

In 1959-61, a Czech group [8,9] reported the isolation of a new sesquiterpene lactone from Chrysanthemum (Tanacetum) parthenium as part of a study of the sesquiterpene lactones of the Compositae family. They named it parthenolide. The initial structure for parthenolide was later revised [10,11] and the accepted structure for parthenolide today is represented by structure (1). Parthenolide is a germacranolide-type sesquiterpene lactone. The crystal structure for parthenolide has also been reported [12]. Extractions of C. (T.) parthenium grown in Mexico, known locally as santamaria, did not yield parthenolide [13], but a closely related compound was isolated and named santamarine (3). This suggests that regional variations in the chemical constituents may occur. 

More than 11,000 Sesquiterpenes have been isolated from natural sources [3]. Feverfew (Tanacetum parthenium (L.) Sch. Bip.,. Compositae) is a common herb utilized for fever, arthritis and migraine. The leaves of feverfew contain large amounts of sesquiterpene lactones. The chloroform extracts of fresh leaves and a commercial leaf product show dose-dependent inhibiting the production of throboxane B2 (TXB2) and leukotriene B4 (LTB4) in rat and human leukocytes. Sesquiterpene lactones isolated from the leaves of feverfew, such as parthenolide and tanaparthin-a-peroxide, demonstrate potent dual inhibitions of COX and LOX pathways with IC50 for COX at 6 17 pg/ml, and for LOX at 12 17 pg/ml, respectively [135],... 

Tanacetum parthenium Chrysanthemum parthenium) is known feverfew. "Feverfew" comes from the Latin fetrifugia meaning driver out of fevers and it has been used for centuries as an antipyretic. Traditionally, the leaves or infussions of the herb have long been used as a febrifuge and to relieve menstrual and rheumatic pain and migraine [11]. Nowadays standardized feverfew capsules containing the leaf extract are available in the market. 

Makhej a AN, B ailey JM. A platelet phospholipase inhibitor from the medicinal herb feverfew (Tanacetum parthenium). Prostaglandins LeukotMed 1982 8 653-660. 

Perhaps the most prominent example with respect to anti-secretive effects of STLs is related to the well-known anti migraine activity of feverfew (Tanacetum parthenium, Asteraceae). The main STL from this plant is parthenolide (PAR), structure 1 in Fig. (15), and it has been shown that PAR is a potent inhibitor of serotonin (5HT)-release from thrombocytes. Although it is not finally clarified to which extent this effect is involved along with the numerous other reported activities of PAR in the clinically proven efficacy of feverfew [71, 72], it should at least contribute to the overall effect. 

Widyarini S, Spinks N, Husband AJ, Reeve VE (2001) Isoflavonoid compounds from red clover Trifolium pratense) protect from inflammation and immune suppression induced by UV radiation. Photochem Photobiol 74(3) 465 70 Williams CA, Goldstone F, Greenham J (1996) Flavonoids, cinnamic acids and coumarins from the different tissues and medicinal preparations of Taraxacum officinale. Phytochemistry 42(1) 121-127 Williams CA, Harborne JB, Geiger H, Hoult JR (1999) The flavonoids of Tanacetum parthenium and T. vulgare and their anti-inflammatory properties. Phytochemistry 51(3) 417 23 Wink M (1999) Introduction biochemistry, role and biotechnology of secondary metabolites. In Wink M (ed) Biochemistry of plant secondary metabolism, vol 2, Annual plant reviews. CRC Press, Boca Raton, pp 1-16... 

---