Compositae sesquiterpene lactones

Key Word Index--/xem denticulata f pimatipariita Kitag. I. sonchifolia Hance Compositae sesquiterpene lactone glucoside guaianolide ixerin X ixerin Z cytotoxicity. 

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. 

The sesquiterpene lactone, lactucain C (67) isolated from Lactuca indica L. (family Compositae) showed moderate lowering of plasma glucose (A -22.74 12.53%) in vivo at a dose of 1.0 mM/kg in STZ-diabetic rats. ... 

A different cychzation reaction of 460, by treatment with iodine and silver oxide, gave l,6-dioxaspiro[3.4]octanes 469 (Scheme 130). This heterocychc core present in a series of sesquiterpenic lactones has interesting biological activity and is isolated as secondary metabolites from species of the Compositae family . 

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],... 

An Austrian study has re-confirmed the importance of testing with not only a mixture of Compositae and a mixture of sesquiterpene lactones, but also with additional plant extracts when there is continuing clinical suspicion of allergy to one of the Compositae (3). By using additional short ether extracts, the authors found two of five patients who had otherwise been overlooked. 

A. millefolium contains sesquiterpene lactones, polyacetylenes, coumarins, and flavonoids. Extracts have often been used in cosmetics in concentrations of 0.5-10%. A. millefolium was weakly genotoxic in Drosophila mela-nogaster. In provocative testing, patients reacted to a mix of Compositae that contained yarrow, as well as to yarrow itself. In clinical use, a formulation containing a 0.1% extract was not a sensitizer and alcoholic extracts of the dried leaves and stalks of the flower were not phototoxic (6). However, positive patch tests to A. millefolium have been reported (7). 

Plants Barley dust, lichens (o-usnic acid), hops (colophony), hetzil, sawdust, sesquiterpene lactones compositae, frullania spp.), tulips (tulipalin A), poison ivy (urushiol)... 

In Ebadi s Chapter 23, the plant family Compositae or Asteraceae is said to contain members that have antitumor action. Among the classes of compounds present are the sesquiterpene lactones (SQLs), associated with antitumor activity, for example, the substance known as parihenin. 

Paulsen, E., K.E. Andersen, and B.M. Hausen. 1993. Comp>ositae dermatitis in a Danish dermatology department in one year. I. Results of routine patch testing with the sesquiterpene lactone mix sujjplemented with aimed patch testing with extracts and sesquiterpene lactones of Compositae plants. Cemtact Dermat. 29(1) 6-10. 

Hausen, B.M., and P.E. Osmundsen. 1983. Contact allergy to parthenolide in Tanacetum parthenium (L.) Schulz-Bip. (feverfew, Asteraceae) and cross-reactions to related sesquiterpene lactone containing Compositae sjjecies. Acta Derm. Venereal. 63(4) 308-314. 

Mabry, T. J., Infraspecific variation of sesquiterpene lactones in Ambrosia (Compositae) Applications to evolutionary problems at the populational level, in Phytochemical Phylogeny (J. B. Harborne, ed.), 269-300, Academic Press, London, 1970. 

Sesquiterpene lactones, such as those in Compositae or Frullania Sulphur compounds Turpentine... 

Contact dermatitis to plants can mimic almost any other form of contact dermatitis, but in the United States most cases are easily recognized because poison ivy and its relatives are the leading cause of plant dermatitis. With experience, one can perhaps at least suspect the cause in those eruptions caused by the Compositae and other plants containing sesquiterpene lactones. Eruptions from sesquiterpene lactones are reported in woodcutters in the Pacific Northwest [4], in farmers in most of the United States [5], and in retail [6] and wholesale [7] florists and flower sellers [3]. 

Sesquiterpene-lactone mix is available from both Chemotechnique and Trolab and is part of the European standard series it will detect many reactions to Compositae and FruUania, but wiU also miss some... 

Ducombs G, Benezra C, Talaga P, et al. (1990) Patch testing with the sesquiterpene lactone mix a marker for contact allergy to Compositae and other sesquiterpene-lactone-containing plants. Contact Dermatitis 22 249-252... 

Paulsen E, Andersen KE, Carlsen L, Egsgaard H (1993) Carvone an overlooked contact allergen cross-reacting with sesquiterpene lactones Contact Dermatitis 29 138-143 Green C, Ferguson J (1994) Sesquiterpene lactone mix is not an adequate screen for Compositae dlergy. Contact Dermatitis 31 151-153 Reference deleted in press... 

Hausen BM, Breuer J, Weglewski J, Rucker G (1991) alpha Peroxyachifolid and other new sensitizing sesquiterpene lactones from yarrow (Achillea millefolium L., Compositae). Contact Dermatitis 24 274-280... 

Compositae (Asteraceae), the daisy family, are major causes of allergic dermatitis in plant handlers. Eczema is typically localised to the hands and typically affects women in their 40s and 50s (Ross et al. 1995). The sesquiterpene-lactone mix provides a useful diagnostic tool (Bangha and Eisner 1996), although it may not detect all Compositae-sensitive patients (Green and Ferguson 1994). 

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