PMID- 19076885
OWN - NLM
STAT- MEDLINE
DCOM- 20090402
LR  - 20181201
IS  - 1600-0536 (Electronic)
IS  - 0105-1873 (Linking)
VI  - 59
IP  - 6
DP  - 2008 Dec
TI  - Limonene hydroperoxide analogues differ in allergenic activity.
PG  - 344-52
LID - 10.1111/j.1600-0536.2008.01442.x [doi]
AB  - BACKGROUND: 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. OBJECTIVES: 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. PATIENTS/METHODS: 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. RESULTS: 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. CONCLUSIONS: 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.
FAU - Christensson, Johanna Brared
AU  - Christensson JB
AD  - Dermatochemistry and Skin Allergy, Department of Chemistry, University of 
      Gothenburg, SE-412 96 Gothenburg, Sweden. jacpth01@geh.regionh.dk
FAU - Johansson, Staffan
AU  - Johansson S
FAU - Hagvall, Lina
AU  - Hagvall L
FAU - Jonsson, Charlotte
AU  - Jonsson C
FAU - Borje, Anna
AU  - Borje A
FAU - Karlberg, Ann-Therese
AU  - Karlberg AT
LA  - eng
PT  - Controlled Clinical Trial
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - England
TA  - Contact Dermatitis
JT  - Contact dermatitis
JID - 7604950
RN  - 0 (Cyclohexenes)
RN  - 0 (Perfume)
RN  - 0 (Solvents)
RN  - 0 (Terpenes)
RN  - 9MC3I34447 (Limonene)
RN  - BBX060AN9V (Hydrogen Peroxide)
SB  - IM
MH  - Adult
MH  - Aged
MH  - Animals
MH  - Cyclohexenes/*adverse effects
MH  - Dermatitis, Allergic Contact/*diagnosis/etiology
MH  - Female
MH  - Humans
MH  - Hydrogen Peroxide/*adverse effects
MH  - Limonene
MH  - Local Lymph Node Assay
MH  - Male
MH  - Mice
MH  - Middle Aged
MH  - Oxidation-Reduction
MH  - Patch Tests/methods
MH  - Perfume/*adverse effects
MH  - Solvents/*adverse effects
MH  - Terpenes/*adverse effects
EDAT- 2008/12/17 09:00
MHDA- 2009/04/03 09:00
CRDT- 2008/12/17 09:00
PHST- 2008/12/17 09:00 [entrez]
PHST- 2008/12/17 09:00 [pubmed]
PHST- 2009/04/03 09:00 [medline]
AID - COD1442 [pii]
AID - 10.1111/j.1600-0536.2008.01442.x [doi]
PST - ppublish
SO  - Contact Dermatitis. 2008 Dec;59(6):344-52. doi: 10.1111/j.1600-0536.2008.01442.x.