Contact allergy to resin acid hydroperoxides. Hapten binding via free radicals and epoxides.
For a better understanding of the mechanisms of contact allergic reactions, the patterns of cross-reactivity between different resin acid oxidation products were studied. The 13,14(alpha)-epoxide and the 13,14(beta)-epoxide of abietic acid and 15-hydroperoxydehydroabietic acid (15-HPDA) were shown in experimental sensitization studies to be contact allergens. Cross-reactivity was observed between the alpha- and beta-epoxides and also between the epoxides and the previously identified rosin allergen 15-hydroperoxyabietic acid (15-HPA). This indicates that 15-HPA may form an epoxide which then reacts with skin protein to generate the complete antigen. 15-HPA and 15-HPDA cross-reacted as well. This can be explained by the formation of similar alkoxy radicals from both hydroperoxides which further react with skin protein. Cross-reactivity patterns of the resin acid oxidation products indicate that 15-HPA may react with skin proteins either as a radical or as an epoxide, thus generating different antigens. The presence in rosin of the epoxides of abietic acid was also studied. The beta-epoxide was detected in gum rosin. Moreover, the epoxides elicited reactions in rosin-allergic individuals. Thus, the 13,14(beta)-epoxide of abietic acid was identified as a new, important rosin allergen.
Gäfvert
E
E
Department of Occupational Dermatology, National Institute of Occupational Health, Solna, Sweden.
Shao
L P
LP
Karlberg
A T
AT
Nilsson
U
U
Nilsson
J L
JL
D045784:Abietanes; D000818:Animals; D003429:Cross Reactions; D017449:Dermatitis, Allergic Contact / Q000209:etiology*; D004224:Diterpenes / Q000138:chemical synthesis / Q000276:immunology* / Q000378:metabolism; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000276:immunology* / Q000378:metabolism; D005260:Female; D005609:Free Radicals / Q000378:metabolism; D006168:Guinea Pigs; D006241:Haptens / Q000378:metabolism*; D006801:Humans; D007114:Immunization; D012116:Resins, Plant / Q000737:chemistry*; D012882:Skin Tests
D045784:Abietanes; D004224:Diterpenes; D004852:Epoxy Compounds; D005609:Free Radicals; D006241:Haptens; D012116:Resins, Plant; C087599:methyl 13,14-epoxyabietate; C013893:rosin