Chrysanthemum lactone

Sumner H, Umit S, Knight DW, Hoult JRS. Chrysanthemum parthenium (L.) Bernh. Inhibition of 5-lipoxygenase and cyclooxygenase in leukocytes by feverfew Involvement of sesquiterpene lactones and other components. Biochem Pharmacol 1992 43 2313-2320. 

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. 

N.A. Chrysanthemum parthenium (L.) Berhn. Camphor, tannins, mucilage, sesquiterpene lactone.277 Treat fevers, migraine, arthritis, colds, indigestion, diarrhea, hysteria. 

Although the first survey listed 45 natural chlorinated sesquiterpene lactones, several such compounds were omitted in that coverage (1) and are described here. The novel sesquiterpene lactone chlorochrymorin (239) was isolated from Chrysanthemum morfolium (499), and the chlorohydrin graminichlorin (240) is found in Liatris graminifolia (500). The antibacterial AA-57 (241), which is related to pentalenolactone, is produced by a Streptomyces sp. (501). The plant Eupatorium chinense var. simplicifolium has yielded eupachifolin D (242) (502) (side-chain double bond stereochemistry revised (518)), and the new guaianolide andalucin (243) was characterized from Artemisia lanata (503). The previously known chlorohyssopifolins (1) have been studied for cytostatic activity, and the presence of one and even two chlorine atoms amplifies this activity (504). 

Osawa T, Suzuki A, Tamura S, Ohashi Y, Sasada Y (1973) Structure of Chlorochrymorin, a Novel Sesquiterpene Lactone from Chrysanthemum morifolium. Tetrahedron Lett 14 5135... 

Michefuscalide (sesquiterpene lactone) Tanacetum parthenium (Chrysanthemum parthenium) (feverfew) (Asteraceae) [herb] COX (12) (PGS, AA PGE,)... 

Numerous examples of [ 2 -I- 2] photocycloaddition of five-membered oxygen-containing heterocycles to alkenes have been reported, many of which have useful synthetic applications. The regiochemistry and stereochemistry of each adduct has not always been fully established. The lactone (311) undergoes photoaddition to cyclopentene to afford the cis,anti,cis adduct (312), whereas three stereoisomeric adducts were obtained with cyclohexene. Analogous additions of substituted lactones to alkenes have been employed in the syntheses of ( )-dihydrofomannosin acetate and cyclobutane analog of chrysanthemumic acid. The photoaddition of... 

E.3 ContactedlerpfensThc sesquiterpene lactones of the Asteraceae, e.g. chrysanthemums, asters and daisies, are well-known causes of contact allergic dermatitis. Patients with such allergies should avoid (and should be advised to avoid) herbs such as Artemisia (Mugwort), Chamomile, Yarrow (Achillea). Feverfew, Echinacea-inA Arnica because of cross-sensitisation. 

IsHiBASHi, H., H. Nakatani, T.S. So, T. Fujita, M. Ikeda Alkylative Lactonization of y,5-Unsaturated Esters with a-Chlorosulfides. A Concise Synthesis of the Mono-terpene Lactone from Chrysanthemum flosculosum. Heterocycles, 31, 215 (1990). 

Chrysanthemum (or Dendranthema X cultivar) is a special case, as one must test the patient for reactions to the plants to which the patient is exposed. I have seen one color of a variety produce a prominent reaction, while other colors of what is ostensibly the same variety are negative. Alantalactone is available as helenin (a mixture of alantolactone and isoalanto-lactone) [98] from Sigma and other chemical compa-... 

Sugai T, Takahashi Y, Okuno F (1980) Chrysanthemum dermatitis in Japan. Contact Dermatitis 6 155 Stampf J, Benezra C, Klecak G, et al. (1982) The sensitizing capacity of helenin and of two of its main constituents, the sesquiterpene lactones alantolactone and isoalantolactone a comparison of epicutaneous and intradermal sensitizing methods in different strains of guinea pig. Contact Dermatitis 8 16-24... 

Ecuador into the U.S. The active principals are pyrethrins I and II, cinerins I and II, and jasmolin I and II, collectively known as pyrethrins. Pyrethrins are used extensively in stock sprays, pet sprays, household sprays, aerosols, and food protection in warehouses. Pyrethrins are stable for long periods in water-based aerosols, in which modern emulsifiers are used. Dermatitis from natural pyrethrins usually occurs on parts of the body exposed to the spray. The substance is a moderately potent allergic sensitizer. Crossreactions occur among pyrethrum, chrysanthemum, shasta daisy, and ragweed oleo resin [31, 32]. Asthma and urticaria have also been reported as reactions to natural pyrethrin [33, 34]. In 1972, Mitchell et al. found that a sesquiterpene lactone, pyrethrosin, was the chief allergen in pyrethrin [35]. Contact dermatitis due to pyrethrum is usually mild, but bullous reactions have been reported [36]. In Denmark, positive patch-test reactions to pyrethrum were obtained in 1-2% of dermatitis patients [37]. 

Mitchell JC, Dupuis G, Towers GH (1972) Allergic contact dermatitis from pyrethrum (Chrysanthemum spp). The roles of pyrethrosin, a sesquiterpene lactone, and of pyrethrin II. Br J Dermatol 86 568-573... 

Sesquiterpene lactone present in, e.g., species of Chrysanthemum plants (helenin)... 

Generally, sesquiterpenes are less volatile than monoterpenes. Among the sesquiterpenes, the sesquiterpene lactones are widely distributed in terrestrial and marine organisms and are well known for their wide variety of biological activities. The anti-inflammatory activities of some medicinal plants are due to presence of one or more sesquiterpene lactones [89]. Parthenolide is responsible for the majority of the medicinal characteristics of this traditional herbal remedy. This sesquiterpene lactone can be found in several species, including Chrysanthemum parthenium, Leucanthemum parthenium, Pyrethrum parthenium, and Tanacetum parthenium [90]. 

Reported cases of contact allergic reactions to A. montana preparations are numerous and date from as early as 1844. Cross-reactivity with other plants is also reported (e.g., sunflower, Tagetes, Chrysanthemum). Sesquiterpene lactones, especially helenalin and its derivatives, are known sensitizers. " Data on the safety of Arnica Montana extract, which is made from the dried flower heads of A. montana, are lacking. Ithas an oral LD50 of >5 g/kg in rats, whereas in mice the LD50 was 123 mg/ kg p.o. An extract made from the dried plant showed mutagenic activity in the Ames test, an effect attributed to the flavonol content. ... 

By analogy with this type of intramolecular addition, the 3-lactone, capillarin (LXII) (Harada et al., i960 Bohlmann and Kleine, 1962b) might be visualized as arising from a structure related to frutescin (LXIII). Both of these compounds were isolated from the same chrysanthemum species (Bohlmann and Kleine, 1962 a, b). 

---