Rosin allergy: identification of a dehydroabietic acid peroxide with allergenic properties.
A peroxide of dehydroabietic acid was isolated from rosin using flash chromatography and preparative HPLC. It was identified by 1H-NMR and MS. In animal experiments, this peroxide cross-reacted with a previously identified allergen in rosin, 15-hydroperoxyabietic acid (15-HPA), despite differences in molecular weight and unsaturation. Both substances are able to react via a radical mechanism generating structurally similar molecules. In patch testing of patients, no reactions were observed to the peroxide. Low skin penetration of the peroxide could be the explanation for this. The peroxide seems of little clinical importance. The observed cross-reactivity is an indication of antigen generation via a radical mechanism. Only a few compounds that react with radical mechanisms to form antigens are described in the literature.
Gäfvert
E
E
Department of Occupational Dermatology, National Institute of Occupational Health, Solna, Sweden.
Nilsson
U
U
Karlberg
A T
AT
Magnusson
K
K
Nilsson
J L
JL
D045784:Abietanes; D000485:Allergens / Q000032:analysis / Q000633:toxicity*; D000818:Animals; D017449:Dermatitis, Allergic Contact / Q000209:etiology*; D004224:Diterpenes / Q000032:analysis / Q000633:toxicity*; D005260:Female; D006168:Guinea Pigs; D006801:Humans; D007114:Immunization; D008054:Lipid Peroxides / Q000633:toxicity*; D015394:Molecular Structure; D010328:Patch Tests; D010545:Peroxides; D012116:Resins, Plant / Q000633:toxicity*; D013638:Tars / Q000633:toxicity*
D045784:Abietanes; D000485:Allergens; D004224:Diterpenes; D008054:Lipid Peroxides; D010545:Peroxides; D012116:Resins, Plant; D013638:Tars; C055834:15-hydroperoxyabietic acid; C079707:bis(methyldehydroabietate-15-yl)peroxide; C013893:rosin