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Archives of Dermatological Research

, Volume 295, Issue 6, pp 229–235 | Cite as

Contact allergy to oak moss: search for sensitizing molecules using combined bioassay-guided chemical fractionation, GC-MS, and structure-activity relationship analysis

  • Guillaume Bernard
  • Elena Giménez-Arnau
  • Suresh Chandra Rastogi
  • Siri Heydorn
  • Jeanne Duus Johansen
  • Torkil Menné
  • An Goossens
  • Klaus Andersen
  • Jean-Pierre Lepoittevin
Original Paper

Abstract

In addition to pure synthetic fragrance materials several natural extracts are still in use in the perfume industry. Among them oak moss absolute, prepared from the lichen Evernia prunastri (L.) Arch., is considered a major contact sensitizer and is therefore included in the fragrance mix used for diagnosing perfume allergy. The process of preparing oak moss absolute has changed during recent years and, even though several potential sensitizers have been identified from former benzene extracts, its present constituents and their allergenic status are not clear. In the study reported here, we applied a method developed for the identification of contact allergens present in natural complex mixtures to oak moss absolute. The method is based on the combination of bioassay-guided chemical fractionation, gas chromatography-mass spectrometry analysis and structure-activity relationship studies. Our first results showed that atranol and chloroatranol, formed by transesterification and decarboxylation of the lichen depsides, atranorin and chloroatranorin, during the preparation of oak moss absolute, are strong elicitants in most patients sensitized to oak moss. Methyl-β-orcinol carboxylate, a depside degradation product and the most important monoaryl derivative of oak moss from an olfactory standpoint, was also found to elicit a reaction in most patients.

Keywords

Fragrance allergy Oak moss Atranol Chloroatranol Methyl-β-orcinol carboxylate 

Notes

Acknowledgements

The assistance of Mireille Huel for the synthesis of atranol and chloroatranol is gratefully acknowledged. This work was financially supported by the Fifth Framework Programme of the European Commission, under the Quality of Life and Management of Living Resources thematic programme, key action Environment and Health (Contract QLK4-CT-1999-01558: "Fragrance chemical allergy: a major environmental and consumer health problem in Europe"). Research participants: Jean-Pierre Lepoittevin, Elena Giménez-Arnau and Guillaume Bernard, University Louis Pasteur, Strasbourg, France; Ann-Therese Karlberg, Mihaly Matura, Anna Börje and Maria Sköld, National Institute for Working Life, Stockholm, Sweden; David Basketter and Grace Patlewicz, SEAC, Unilever Research, Bedford, UK; Torkil Menné, Jeanne Duus Johansen and Siri Heydorn, Department of Dermatology, Gentofte Hospital, University of Copenhagen, Denmark; Peter J. Frosch, Department of Dermatology and University of Witten/Herdecke, Dortmund, Germany; Ian White, Department of Contact Dermatitis and Occupational Dermatology, St. John's Institute of Dermatology, St. Thomas' Hospital, London, UK; Suresh Rastogi, National Environmental Research Institute, Roskilde, Denmark; Klaus E. Andersen, Department of Dermatology, Odense University Hospital, Denmark; Magnus Bruze and Cecilia Svedman, Department of Occupational Dermatology, University Hospital Malmö, Sweden; and An Goossens, Department of Dermatology, University Hospital KU Leuven, Belgium.

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Copyright information

© Springer-Verlag is a part of Springer Sciences + Business Media 2003

Authors and Affiliations

  • Guillaume Bernard
    • 1
  • Elena Giménez-Arnau
    • 1
  • Suresh Chandra Rastogi
    • 2
  • Siri Heydorn
    • 3
  • Jeanne Duus Johansen
    • 3
  • Torkil Menné
    • 3
  • An Goossens
    • 4
  • Klaus Andersen
    • 5
  • Jean-Pierre Lepoittevin
    • 1
  1. 1.Laboratoire de Dermatochimie, Clinique DermatologiqueCHUStrasbourgFrance
  2. 2.National Environmental Research InstituteRoskildeDenmark
  3. 3.Department of Dermatology, Gentofte HospitalUniversity of CopenhagenHellerupDenmark
  4. 4.Department of DermatologyUniversity Hospital, KU LeuvenLeuvenBelgium
  5. 5.Department of DermatologyUniversity HospitalOdense CDenmark

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