Limonene hydroperoxide analogues differ in allergenic activity

被引：60
作者：
Christensson, Johanna Brared [1 ,2 ]
Johansson, Staffan [1 ]
Hagvall, Lina [1 ]
Jonsson, Charlotte [1 ]
Borje, Anna [1 ]
Karlberg, Ann-Therese [1 ]
机构：
[1] Univ Gothenburg, Dept Chem, S-41296 Gothenburg, Sweden
[2] Sahlgrens Univ Hosp, Dept Dermatol, SE-41345 Gothenburg, Sweden
来源：
CONTACT DERMATITIS | 2008年 / 59卷 / 06期
关键词：
allergic contact dermatitis; autoxidation; fragrances; hydroperoxides; limonene; limonene hydroperoxides; local lymph node assay; patch testing; structure activity relationship;
D O I：
10.1111/j.1600-0536.2008.01442.x
中图分类号：
R392 [医学免疫学];
学科分类号：
100102 ;
摘要：
The fragrance terpene R-limonene is a very weak sensitizer but forms allergenic oxidation products upon contact with air. Oxidized (ox.) limonene is a frequent cause of contact allergy in clinical testing. This study investigates the sensitizing potencies of ox. and non-ox. limonene and of structurally closely related limonene hydroperoxides. The clinical importance of the difference in sensitizing potency of two hydroperoxides in autoxidized limonene was studied. Ox. and non-ox. limonene were investigated in the murine local lymph node assay (LLNA). Limonene hydroperoxides were investigated using a modified LLNA involving non-pooled lymph nodes and statistical calculations; patch testing of patients with known contact allergy to ox. limonene was performed. A marked increase in the sensitizing potency of ox. limonene compared with that of pure limonene was observed in the LLNA. One analogue, limonene-1-hydroperoxide, was a significantly more potent sensitizer than the other hydroperoxides and gave more positive test reactions in the allergic patients. The results support that hydroperoxides have a specific reactivity indicating that oxygen-centred radicals are important in hapten-protein complex formation of hydroperoxides. The primary oxidation products of ox. limonene, the hydroperoxides, have an important impact on the sensitizing capacity of the oxidation mixture.
引用
收藏
页码：344 / 352
页数：9
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