Pharmaceutisch Weekblad

, Volume 13, Issue 3, pp 119–122 | Cite as

Allergic contact dermatitis caused by naturally occurring quinones

  • Jean-Pierre Lepoittevin
  • Claude Benezra


Quinones play a major role in allergic contact dermatitis caused by plants. The principal allergens are benzoquinones or naphthoquinones but also compounds, such as catechols and other phenolic or flavonoid compounds, which are bioconverted intoortho-quinones orpara-quinones. The high electrophilic reactivity of these compounds toward nucleophilic residues of proteins associated with lipophilic properties may explain that they are strong sensitizers. The more important allergens are reported and their structure-activity relationship is discussed.


Allergens Bioflavonoids Catechols Dermatitis, contact Haptens Phenols Proteins Quinones 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Benezra C, Ducombs G, Sell Y, Foussereau J. Plant contact dermatitis. Toronto: B.C. Decker, 1985.Google Scholar
  2. 2.
    Hausen B. Woods injurious to human health. Berlin: Walter de Gruyter, 1981.Google Scholar
  3. 3.
    Polak L. Immunological aspects of contact sensitivity. Basle: Karger, 1980.Google Scholar
  4. 4.
    Benezra C, Maibach H. True cross-sensitization, false cross-sensitization and otherwise. Contact Dermatitis 1984;11:65–9.PubMedGoogle Scholar
  5. 5.
    Dupuis G, Benezra C. Allergic contact dermatitis to simple chemicals: A molecular approach. New York: Marcel Dekker, 1982.Google Scholar
  6. 6.
    Baer H, Watkins RC, Bowser RT. Delayed contact sensitivity to catechols and resorcinols. Immunochemistry 1966;3:479–85.CrossRefGoogle Scholar
  7. 7.
    Liberate DJ, Byers V, Dennick RG, Castagnoli N Jr. Regiospecific attack of nitrogen and sulfur nucleophiles on quinones derived from poison oak/ivy catechols (urushiols) and analogs as models for urushiolprotein conjugate formation. J Med Chem 1981;24:28–33.CrossRefPubMedGoogle Scholar
  8. 8.
    Pearson RG. Hard and soft acids and bases. J Am Chem Soc 1963;85:3533–39.CrossRefGoogle Scholar
  9. 9.
    Baer H, Watkins RC, Kurtz AP, Byck JS, Dawson CR. Delayed contact sensitivity to catechols. The relationship of side chain length to sensitizing potency of catechols chemically related to the active principles of poison ivy. J Immunol 1967;99:370–5.PubMedGoogle Scholar
  10. 10.
    Schildknecht H, Bayer I, Schmidt H. Struktur des Primelgiftstoffes. Z Naturforsch 1967;22b:36–41.Google Scholar
  11. 11.
    Woods B, Calnan CD. Toxic woods. Br J Dermatol 1976;(Suppl 13):34.Google Scholar
  12. 12.
    Benezra C, Stampf J-L, Barbier P, Ducombs G. Enantiospecificity in allergic contact dermatitis. Contact Dermatitis 1985;13:110–4.PubMedGoogle Scholar
  13. 13.
    Schultz KH, Garbe I, Hausen BM, Simatupang MH. The sensitizing capacity of naturally occurring quinones. Experimental studies in guinea pigs. Naphthylquinones and related compounds. Arch Dermatol Res 1977;258:41.CrossRefPubMedGoogle Scholar
  14. 14.
    Tezuka M, Takahashi C, Kuroyanagi M, Satake M, Yoshihira K, Natori S. New naphthoquinones fromDiospyros. Phytochemistry 1973;12:173–83.CrossRefGoogle Scholar
  15. 15.
    Marini-Bettolo GB, Casinovi CG, Galeffi G. A new class of quinones: sesquiterpenoid quinones ofMansonia altissima. Tetrahedron Lett 1965:4857–64.Google Scholar
  16. 16.
    Reynolds G, Rodriguez E. Prenylated hydroquinones: contact allergens from trichomes ofPhacelia minor andP. parryi. Phytochemistry 1981;20:1365–6.CrossRefGoogle Scholar
  17. 17.
    Lepoittevin JP, Benezra C, Asakawa Y. Allergic contact dermatitis toGinkgo biloba L. Relationship with urushiol. Arch Dermatol Res 1989;281:227–30.CrossRefPubMedGoogle Scholar

Copyright information

© Royal Dutch Association for Advancement of Pharmacy 1991

Authors and Affiliations

  • Jean-Pierre Lepoittevin
    • 1
  • Claude Benezra
    • 1
  1. 1.Laboratoire de DermatochimieClinique Dermatologique, CHRUStrasbourgFrance

Personalised recommendations