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Archives of Dermatological Research

, Volume 255, Issue 2, pp 111–121 | Cite as

Chrysanthemum allergy

III. Identification of the allergens
  • B. M. Hausen
  • K. H. Schulz
Article

Summary

Experimental and chemical studies in guinea pigs on contact allergy caused byChrysanthemum indicum L. (Chrysanthemum of the florists) led to the isolation of several sesquiterpene lactones.

From the crude extract of dried flowers 12 fractions were obtained of which four gave strong reactions on epicutaneous application to guinea pigs sensitized with an extract of C.indicum L.

One of these allergens was identified as a sesquiterpene lactone of the guaianolide type. It is identical to Arteglasin-A derived fromArtemisia douglasiana Bess.

The occurrence of Arteglasin-A inChrysanthemum indicum L. as well as its allergenic properties are described for the first time.

These findings give rise to the assumption that the other, as yet unidentified sesquiterpene lactones of this flower also belong to the guaianolide type.

Keywords

Public Health Crude Extract Lactone Chemical Study Sesquiterpene 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Zusammenfassung

Chemische Untersuchungen und experimentelle Teste an Meerschweinchen bezüglich der durch Chrysanthemen verursachten Kontaktallergie führten zur Isolierung mehrerer Sesquiterpenlaktone.

Aus dem Rohextrakt getrockneter Chrysanthemen wurden 12 Fraktionen isoliert, von denen vier im Epikutantest bei sensibilisierten Meerschweinchen eine stark positive Reaktion ergaben. Eins der Allergene wurde als Sesquiterpenlakton vom Guaianolid-Typ identifiziert. Es ist identisch mit Arteglasin-A ausArtemisia douglasiana Bess.

Sowohl das Vorkommen von Arteglasin-A inChrysanthemum indicum L. als auch seine allergene Wirkung werden hier das erste Mal beschrieben.

Die Untersuchungsbefunde lassen vermuten, daß die anderen bisher nicht identifizierten Sesquiterpenlaktone ebenfalls dem Guaianolid-Typ angehören.

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References

  1. 1.
    Hausen, B. M., Schulz, K. H.: Chrysanthemen-Allergie 1. Mitteilung. Berufs-Dermatosen21, 199–214 (1973)Google Scholar
  2. 2.
    Schulz, K. H., Hausen, B. M., Wallhöfer, L., Schmidt-Löffler, P.: Chrysanthemen-Allergie. 2. Experimentelle Untersuchungen zur Identifizierung der Allergene. Arch. Derm. Forsch.251, 235–244 (1975)Google Scholar
  3. 3.
    Yoshioka, H., Mabry, T. J., Timmermann, B. N.: Sesquiterpene lactones. University of Tokyo Press, 1973Google Scholar
  4. 4.
    Herz, W.: Pseudoguaianolides in Compositae. Nobel Symp.25, 153–172 (1974)Google Scholar
  5. 5.
    Romo, J., Romo de Vivar, A., Ortega, A.: Novel sesquiterpenes isolated in compositae. Recent Advanc. Phytochem.6, 21–29 (1973)Google Scholar
  6. 6.
    Mitchell, J. C.: Allergic contact dermatitis from compositae. Trans. St John's Hosp. derm. Soc. (Lond.)55, 174–183 (1969)Google Scholar
  7. 7.
    Mitchell, J. C., Fritig, B., Singh, B., Towers, H. N.: Allergic contact dermatitis from frullania and compositae. J. invest. Derm.54, 233–239 (1970)Google Scholar
  8. 8.
    Stahl, E.: Dünnschichtchromatographie. Berlin-Heidelberg-New York: Springer 1967Google Scholar
  9. 9.
    Matsueda, S.: Studies on sesquiterpene lactones. II. Chemical constitution of young growth of Artemisia sp. Yakugaku Zasshi90, 1024–1027 (1970)Google Scholar
  10. 10.
    Geissman, T. A., Griffin, T. S.: Sesquiterpene lactones: acid-catalysed color reactions as an aid in structure determination. Phytochem.10, 2475–2485 (1971)Google Scholar
  11. 11.
    Doskotch, R. W., El-Feraly, T. S.: Isolation and characterization of (+)-sesamin andβ-cyclopyrethrosin from pyrethrum flowers. Can. J. Chem.47, 1139–1142 (1969)Google Scholar
  12. 12.
    Romo, J., Romo de Vivar, A., Trevino, R., Joseph-Nathan, P., Diaz, E.: Constituents of artemisia and chrysanthemum species—the structure of chrysartemins A and B. Phytochem.9, 1615–1621 (1970)Google Scholar
  13. 13.
    Osawa, T., Suzuki, A., Tamura, S.: Isolation of chrysartemins A and B as rooting cofactors. Agr. Biol. Chem.35, 1966–1972 (1971)Google Scholar
  14. 14.
    Yoshioka, H., Renold, W., Fischer, N. H., Higo, A., Mabry, T. J.: Sesquiterpene lactones fromAmbrosia confertiflora D.C. Phytochem.9, 823–832 (1970)Google Scholar
  15. 15.
    Doskotch, R. W., Beal, J. L.: The isolation and identification of the numbing principle inChrysanthemum anethifolium. Lloydia33, 393–394 (1970)Google Scholar
  16. 16.
    Knoche, H., Ourisson, G., Perold, G. W., Foussereau, J., Maleville, J.: Allergenic component of a liverwort: a sesquiterpene lactone. Science166, 239–240 (1969)Google Scholar
  17. 17.
    Tsuda, K., Tanabe, T., Iwai, I., Funakoshi, K.: The structure of alantolactone. J. Amer. Chem. Soc.79, 5721–5724 (1957)Google Scholar
  18. 18.
    Marshall, J. A., Cohen, N.: The structure of alantolactone. J. Org. Chem.29, 3727–3729 (1964)Google Scholar
  19. 19.
    Soucek, M., Herout, V., Sorm, F.: On terpenes. CXVIII. Constitution of parthenolide. Coll. Czech. Chem. Comm.26, 803–809 (1961)Google Scholar
  20. 20.
    Govindachari, T. R., Joshi, B. S., Kamat, V. N.: Revised structure of parthenolide. Tetrahedron Lett., 3927–3933 (1964) Heft 52Google Scholar
  21. 21.
    Barton, D. H. R., Mayo, P. de: Sesquiterpenoids. VIII. The constitution of pyrethrosin. J. chem. Soc. 150–158 (1957)Google Scholar
  22. 22.
    Chien, M.-K., Cheng, Z.-X., Tseng, K.-F.: Studies on the constituents of yeyuhua, the flower ofChrysanthemum indicum L. Yao Hsueh Hsueh Pao10, 129–134 (1963)Google Scholar
  23. 23.
    Lee, K. H., Matsueda, S., Geissman, T. A.: Sesquiterpene lactones of artemisia: new guaianolides from fall growth ofA. douglasiana. Phytochem.10, 405–410 (1971)Google Scholar
  24. 24.
    Doskotch, R. W., El-Feraly, T. S.: Antitumor agents. II. Tulipinolide, a new germacranolide sesquiterpene, and costunolide. J. pharm. Sci.58, 877–880 (1969)Google Scholar
  25. 25.
    Kupchan, S. M., Kelsey, J. E., Maruyama, M., Cassady, J. M., Hemingway, J. C., Knox, J. R.: Tumor inhibitors. XLI. Structural elucidation of tumor-inhibitors sesquiterpene lactones fromEupatorium rotundifolium. J. Org. Chem.34, 3876–3883 (1969)Google Scholar
  26. 26.
    Doskotch, R. W., Hufford, C. D., El-Feraly, T. S.: Further studies on the sesquiterpene lactones tulipinolide and epitulipinolide fromLiriodendron tulipifera L. J. Org. Chem.37, 2740–2744 (1972)Google Scholar
  27. 27.
    Govindachari, T. R., Joshi, B. S., Kamat, V. N.: Structure of parthenolide. Tetrahedron21, 1509–1519 (1965)Google Scholar
  28. 28.
    Herout, V.: Sesquiterpenische Lactone — ein neues taxonomisches Merkmal der Compositae. Planta med. (Suppl.) 1966, pp. 97–106Google Scholar
  29. 29.
    Geissman, T. A.: The biogenesis of sesquiterpene lactones of the compositae. Recent Advanc. Phytochem.6, 65–95 (1973)Google Scholar
  30. 30.
    Matsueda, S.: Studies on sesquiterpenelactones. VI. Guaiane type sesquiterpenelactone formation from germacranolide by chemical procedure. Sci. Rep. Hirosaki Uni.18, 8–14 (1971)Google Scholar
  31. 31.
    Leipold, H.: Dermatitis der Hände und des Gesichts infolge Überempfindlichkeit gegen Chrysanthemen und Kamillen. Zbl. Haut- u. Geschl.-Kr.57, 248 (1938)Google Scholar
  32. 32.
    Mitchell, J. C., Geissman, T. A., Dupuis, G., Towers, G. H. N.: Allergic contact dermatitis caused by Artemisia and Chrysanthemum species. J. invest. Derm.56, 98–101 (1971)Google Scholar
  33. 33.
    Johnson, C. K.: ORTEP, OR NL-3794 Revised Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1965Google Scholar
  34. 34.
    Hausen, B. M., Schulz, K. H., Jarchow, O., Klaska, K. H., Schmalle, H.: A first allergenic sesquiterpene lactone fromChrysanthemum indicum L.: Arteglasin-A. Naturwissenschaften62, 585 (1975)Google Scholar
  35. 35.
    Osawa, T., Suzuki, A., Tamura, S., Ohashi, Y., Sasada, Y.: Structure of chlorochrymorin, a novel sesquiterpene lactone fromChrysanthemum morifolium. Tetrahedron Lett., 5135–5138 (1973) Heft 51Google Scholar
  36. 36.
    Samek, Z., Holub, M., Grabarczyk, H., Drozdz, B., Herout, V.: On terpenes. CCXXIX. Structure of sesquiterpene lactones fromTanacetum vulgare L. Coll. Czech. Chem. Comm.38, 1971–1976 (1973)Google Scholar

Copyright information

© Springer-Verlag 1976

Authors and Affiliations

  • B. M. Hausen
    • 1
  • K. H. Schulz
    • 1
  1. 1.Department of Dermatology, Division of AllergologyUniversity HospitalHamburgGermany

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