Allergens Sesquiterpene lactone

Chamomile is the vernacular name ot Anthemis genus and Matricaria recutita (German chamomile, pinhead). The former are more potent skin sensitizers (delayed-type) than the latter, presumably because they can contain a higher concentration of the sesquiterpene lactone, antheco-tullid. Cross-sensitivity with related allergenic sesquiterpene lactones in other plants is possible. 

As Tanacetum parthenium is rich in allergenic sesquiterpene lactones, such as parthenolide, it is not surprising that contact dermatitis has been observed (SEDA-11, 426). The most common adverse effect of oral feverfew is mouth ulceration. A more widespread inflammation of the oral mucosa and tongue, swelhng of the lips, and loss of taste have also been reported. 

Laurel oil obtained from the berries of L. nobilis is a potent skin sensitizer, owing to the presence of allergenic sesquiterpene lactones, and is usually seen in aromatherapists or their clients (12-14). 

A positive patch test reaction to U. dioica has been obtained in a patient who had developed edematous gingivostomatitis following the regular use of stinging nettle tea as a tonic the patient also had positive reactions to chamomile (Anthemis nobilis) and its allergens (sesquiterpene lactones) (2). 

More than 1000 species of Frullania are known in the world. Mitchell et al. (255) reported that F. riparia, F. kunzei, F. eboracensis, F. franciscana, F. inflata and F. bolanderi induced allergy. However, the active substances have not been isolated. Twenty-five Frullania species have been chemically analyzed and potentially allergenic sesquiterpene lactones have been found... 

In combination with sesquiterpene lactones, the chromenes and benzofurans are another group of defensive compounds that desert Invertebrates have to detoxify. Indeed, the success of many desert sunflower species Is In part due to their diverse secondary chemistry. Prenylated qulnones, on the other hand seem to be restricted to the Hydrophyllaceae and tropical trees. The qulnones are extremely active chemicals that exhibit Insecticidal activity at concentrations lower than many chromenes. The prenylated qulnones of Phacella are also potent cytotoxlns and allergens. 

Paulsen, E., Andersen, K., Carlsen, L., and Egsgaard, H. 1993. Carvone An overlooked contact allergen cross-reacting with sesquiterpene lactones Contact Dermatit. 29, 138-143. 

C15H20O2, Mr 232.32, colorless crystals, mp. 82 °C, bp. 275 °C, [a] 3 +197° (CHCI3), almost insoluble in water, soluble in alcohol and ether. The name of this tricyclic sesquiterpene lactone is derived from the Asteraceae ]nula helenium originally indigenous to Central Asia. H. was isolated for the first time from the essential oil of the roots (Inula oil). H. is also an older synonym for helenalin as well as the name for a metabolite from Penicillium funiculosum (ribonucleoprotein). Because of its a-methylene-y-lactone structure H. is a contact allergen. 

Fig. 3.17 The ehemieal struetures of sesquiterpene lactone matricin, an anti-inflammatory compound in chamomile and allergen anthecotulide. (Authors own work)...

Konishi T, Shimada Y, Nagao T, Okabe H, Konoshima T (2002) Antiproliferative sesquiterpene lactones from the roots of Inula helenium. Biol Pharm Bull 25(10) 1370-1372 Konovalov DA, Nesterova TA (2003). Phytochemical study of some Caucasian species of Asteraceae and the possibility of their allergenic properties. Vestnik VGU. Seriya Khimiya. Biologiya. Farmatsiya (2) 205-207 (in Russian)... 

Menage H du P, Ross JS, Norris PG, Hawk JLM, White IR (1995) Contact and photocontact sensitization in chronic actinic dermatitis sesquiterpene lactone mix is an important allergen. Br J Dermatol 132 543-547... 

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]. 

Paulsen E, Anderson KE, Carlsen L, Egsgaard H (1993) Carvone an overlooked contact allergen cross-reacting with sesquiterpene lactones Contact Derrmatitis 29 138-143 Peltonen L, Wickstrom G, Vaahtoranta M (1985) Occupational dermatoses in the food industry. Dermatosen 33 166-169 Piraccini BM, Bardazzi F, Vincenzi C, Tardio MP (1990) Occupational contact dermatitis due to coffee. Contact Dermatitis 23 114... 

Adams RM, Daly AD, Brancaccio RR, et al. (1990) AlstroemeriUy a new and potent allergen for florists. Dermatol Clin 8 73-76 Apted JH (1990) Contact dermatitis due to Alstroemeria (Peruvian lily). Australas J Dermatol 31 111-113 Bangha E, Eisner P (1996) Occupational contact dermatitis towards sesquiterpene lactones in a florist. Am J Contact Dermat 7 188-190... 

Katzenellenbogen I (1955) Caterpillar dermatitis as an occupational disease. Dermatologica 111 99 Knoche H, Ourisson G, Perold GW, Foussereau J, Maleville J (1969) Allergenic component of a liverwort a sesquiterpene lactone. Science 166 239-240... 

The allergen eudesmanolide sesquiterpene lactone was isolated from elecampane (Inula helenium L.). With dehydrocostuslactone and costunolide, it is a component of the (sesquiterpene) lactone-mix, used to detect sensitization to Compositae. 

Alleged allergenic monoterpenes and sesquiterpenes are citral (neral + geranial), limonene, geraniol, linalool, citronellol, and famesol. Among the sesquiterpene lactones, there are potent allergens [9]. 

Mitchell, J. C., B. Fritig, B. Singh, and G. H. N. Towers Allergenic Contact Dermatitis from Frullania and Compositae. The Role of Sesquiterpene Lactones. J. Invest. Derm. 54, 233 (1970). 

A new methodology for the synthesis of five-membered exo-a-methylene tricyclic lactones was elaborated by Minami at al. [44] and applied to a short synthesis of frullanolide (40), an allergenically active a-methylene-y-butyrolactone sesquiterpene (Scheme 19). In this synthesis, alkylation of the ethyl (diethoxy-... 

---