Chronic actinic dermatitis to sesquiterpene lactones: [2+2] photoreaction toward thymidine of (+) and (-) α-Methylene-Hexahydrobenzofuranone with a cis Ring Junction

Photochemistry and Photobiology

Volumn 86, Issue 3, 2010, Pages 545-552

  Fuchs, Sébastien ^a   Berl, Valérie ^a   Lepoittevin, Jean Pierre ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLENE BUTYROLACTONE; ALPHA-METHYLENE GAMMA-BUTYROLACTONE; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; LACTONE; SESQUITERPENE; THYMIDINE;

ARTICLE; CHEMICALLY INDUCED DISORDER; CHEMISTRY; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOSENSITIVITY DISORDER; RADIATION EXPOSURE; SKIN ALLERGY; ULTRAVIOLET RADIATION; ANALOGS AND DERIVATIVES; CHEMICALLY INDUCED; DERMATITIS, ALLERGIC CONTACT; PHOTOSENSITIVITY DISORDERS; RADIATION RESPONSE;

4-BUTYROLACTONE; DERMATITIS, ALLERGIC CONTACT; HUMANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; PHOTOSENSITIVITY DISORDERS; SESQUITERPENES; THYMIDINE; ULTRAVIOLET RAYS;

EID: 77951808914     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2009.00691.x     Document Type: Article

References (29)

1. Mitchell, J. C. G. Dupuis (1971) Allergic contact dermatitis from sesquiterpenoids of the Compositae family of plants. Br. J. Dermatol. 84, 139 150.
2. Paulsen, E. (1992) Compositae dermatitis: A survey. Contact Derm. 26, 76 86.
3. Dirsch, V. M., H. Stuppner, E. P. Ellmerer-Müller A. M. Vollmar (2000) Structural requirements of sesquiterpene lactones to inhibit LPS-induced nitric oxide synthesis in RAW 264.7 macrophages. Bioorg. Med. Chem. 8, 2747 2753.
4. Rüngeler, P., V. Castro, G. Mora, N. Gören, W. Vichnewski, H. L. Pahl, I. Merfort T. J. Schmidt (1999) Inhibition of transcription factor NF-kB by sesquiterpene lactones: A proposed molecular mechanism of action. Bioorg. Med. Chem. 7, 2343 2352. (Pubitemid 30122736)
5. Kupchan, S. M., M. A. Eakin A. M. Thomas (1971) Tumor inhibitors. 69. Structure-cytotoxicity relationships among the sesquiterpene lactones. J. Med. Chem. 14, 1147 1152.
6. Huang, P.-R., Y.-M. Yeh T.-C. V. Wang (2005) Potent inhibition of human telomerase by helenalin. Cancer Lett. 227, 169 174.
7. 13C NMR. Bioorg. Med. Chem. 1, 389 397.
8. Murphy, G. M., I. R. White J. L. M. Hawk (1990) Allergic airborne contact dermatitis to Compositae with photosensitivity-chronic actinic dermatitis in evolution. Photodermatol. Photoimmunol. Photomed. 7, 38 39. (Pubitemid 20307481)
9. Ross, J. S., H. Du Peloux Menagé, J. L. M. Hawk I. R. White (1993) Sesquiterpene lactone contact sensitivity: Clinical patterns of Compositae dermatitis and relationship to chronic actinic dermatitis. Contact Derm. 29, 84 87. (Pubitemid 23226506)
10. Du Peloux Menagé, H., J. L. Hawk I. R. White (1998) Sesquiterpene lactone mix contact sensitivity and its relationship to chronic actinic dermatitis: A follow-up study. Contact Derm. 39, 119 122.
11. Du Peloux Menagé, H., G. I. Harrison, C. S. Plotten, A. R. Young J. L. M. Hawk (1995) The action spectrum for induction of chronic actinic dermatitis is similar to that for sunburn inflammation. Photochem. Photobiol. 62, 976 979.
12. Gimenez-Arnau, E., S. Mabic J.-P. Lepoittevin (1995) Synthesis and photocyclisation of α-methylene-γ-butyrolactone-thymine heterodimers. Chem. Res. Toxicol. 8, 22 26.
13. Berl, V. J.-P. Lepoittevin (1999) Evidence for [2+2] photoreaction of α-metyhene-γ-butyrolactones with thymine: An explanation for chronic actinic dermatitis to sequiterpene lactones? Photochem. Photobiol. 69, 653 657. (Pubitemid 129548823)
14. Patel, B. B., T. G. Waddell R. M. Pagni (2001) Explaining photodermatosis: Cyclopentenone vs. α-methylene-γ-lactone natural products. Fitoterapia 72, 511 515.
15. Benezra, C., J.-L. Stampf, P. Barbier G. Ducombs (1985) Enantiospecificity in allergic contact dermatitis. A review and new results in Frullania-sensitive patients. Contact Derm. 13, 110 114. (Pubitemid 15016258)
16. Talaga, P., M. Schaeffer, H. Mattes, C. Benezra J.-L. Stampf (1989) Synthesis of Boc-Cys-Ala-Ome and its stereoselective addition to α-methylene-γ-butyrolactones. Tetrahedron 45, 5029 5038. (Pubitemid 19220692)
17. Fuchs, S., V. Berl J.-P. Lepoittevin (2007) A highly stereoselective divergent synthesis of bicyclic models of photoreactive sesquiterpene lactones. Eur. J. Org. Chem. 1145 1152.
18. Kilfoil, V. L. Salter (1988) Kinetics of thymine dimerization. J. Chem. Soc., Chem. Commun. 732 734.
19. Ravanat, J.-L., T. Douki J. Cadet (2001) Direct and indirect effects of UV radiation on DNA and its components. J. Photochem. Photobiol. B, Biol. 63, 88 102. (Pubitemid 33040727)
20. Musajo, L., F. Bordin, G. Caporale, S. Marciani G. Rigatti (1967) Photoreaction at 3655 Å between pyrimidine bases and skin-photosensitizing furocoumarins. Photochem. Photobiol. 6, 711 719.
21. Amaud, R., A. Deflandre, G. Lang J. Lemaire (1981) Proprié tés photosensibilisatrices des furocoumarines. IV - Etude photochimique des furocoumarines méthoxylées en solution aqueuse. J. Chim. Phys. 78, 597 605.
22. Wood, P. D. R. W. Redmond (1996) Triplet state interactions between nucleic acid bases in solution at room temperature: Intermolecular energy and electron transfer. J. Am. Chem. Soc. 118, 4256 4263.
23. Selig, P. T. Bach (2006) Photochemistry of 4-(2′-aminoethyl) quinolones: Enantioselective synthesis of tetracyclic tetrahydro-1aH- pyrido[4′,3′:2,3]-cyclobuta[1,2-c] quinoline-2,11(3H,8H)-diones by intra- and intermolecular [2+2]-photocycloaddition reactions in solution. J. Org. Chem. 71, 5662 5673. (Pubitemid 44117013)
24. Bach, T. (1998) Stereoselective intermolecular [2+2]-photocycloaddition reactions and their application in synthesis. Synthesis 683 703. (Pubitemid 28215983)
25. Schuster, D. I., G. Lem N. A. Kaprinidis (1993) New insights into an old mechanism: [2+2] photocycloaddition of enones to alkenes. Chem. Rev. 93, 3 22.
26. Anselmino, C., L. Voituriez J. Cadet (1993) Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine. Chem. Res. Toxicol. 6, 858 865. (Pubitemid 23351210)
27. Farrow, S. J., C. R. Jones, D. L. Severance, R. M. Deibel, W. M. Baird H. A. Morrison (1990) Urocanic acid photobiology. Identification and characterization of the major photoadducts formed between urocanic acid and thymidine. J. Org. Chem. 55, 275 282.
28. Fisher G. H. Johns (1976) Pyrimidine photodimers. In Photochemistry and Photobiology of Nucleic Acids (Edited by S. Y. Wang pp. 225 294. Academic Press
29. Bertrand, S., N. Hoffmann J.-P. Pete (1998) Photochemical [2+2] cycloaddition of cyclic enones to (5R)-5-menthyloxy-2[5H]-furanone. Tetrahedron 54, 4873 4888. (Pubitemid 28179499)