Chronic Actinic Dermatitis to Sesquiterpene Lactones: [2+2] Photoreaction Toward Thymidine of (+) and (−) α-Methylene-Hexahydrobenzofuranone with a cis Ring Junction
(+) and (−) α‐methylene‐hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six [2...
Saved in:
| Published in: | Photochemistry and photobiology Vol. 86; no. 3; pp. 545 - 552 |
|---|---|
| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Oxford, UK
Blackwell Publishing Ltd
01-05-2010
|
| Subjects: | |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Abstract | (+) and (−) α‐methylene‐hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six [2+2] photoadducts were isolated for each enantiomer and fully characterized by a combination of NMR experiments. A common syn regioselectivity and exo stereoselectivity were observed for photoadducts. This high photoreactivity of α‐methylene‐γ‐butyrolactone ring toward thymidine could be an explanation of the progressive evolution of allergic contact dermatitis toward chronic actinic dermatitis. |
|---|---|
| AbstractList | (+) and (-) alpha-methylene-hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six [2+2] photoadducts were isolated for each enantiomer and fully characterized by a combination of NMR experiments. A common syn regioselectivity and exo stereoselectivity were observed for photoadducts. This high photoreactivity of alpha-methylene-gamma-butyrolactone ring toward thymidine could be an explanation of the progressive evolution of allergic contact dermatitis toward chronic actinic dermatitis. (+) and (−) α‐methylene‐hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six [2+2] photoadducts were isolated for each enantiomer and fully characterized by a combination of NMR experiments. A common syn regioselectivity and exo stereoselectivity were observed for photoadducts. This high photoreactivity of α‐methylene‐γ‐butyrolactone ring toward thymidine could be an explanation of the progressive evolution of allergic contact dermatitis toward chronic actinic dermatitis. (+) and (−) α‐methylene‐hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six [2+2] photoadducts were isolated for each enantiomer and fully characterized by a combination of NMR experiments. A common syn regioselectivity and exo stereoselectivity were observed for photoadducts. This high photoreactivity of α‐methylene‐γ‐butyrolactone ring toward thymidine could be an explanation of the progressive evolution of allergic contact dermatitis toward chronic actinic dermatitis. |
| Author | Fuchs, Sébastien Berl, Valérie Lepoittevin, Jean-Pierre |
| Author_xml | – sequence: 1 givenname: Sébastien surname: Fuchs fullname: Fuchs, Sébastien organization: Laboratoire de Dermatochimie, Institut de Chimie, CNRS et Université de Strasbourg, Strasbourg, France – sequence: 2 givenname: Valérie surname: Berl fullname: Berl, Valérie email: vberl@unistra.fr organization: E-mail: vberl@unistra.fr – sequence: 3 givenname: Jean-Pierre surname: Lepoittevin fullname: Lepoittevin, Jean-Pierre organization: Laboratoire de Dermatochimie, Institut de Chimie, CNRS et Université de Strasbourg, Strasbourg, France |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/20113426$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkUGO0zAUhi00iOkUroC8Y0ajFDtx4wSxGXVgAhSooIgFQpbrvBCXJu7YjtpyAtacgi0X4RCcBGc6dI03z3r-___56TtBR61pASFMyYiG83g5onxMI0pyPooJyUeEpDkdbe-gweHhCA0ISWiUpePxMTpxbkkIZTmn99BxTChNWJwO0M9JbU2rFb5QXvf1EmwjvfbaYW_we3DXnfZg19ACnkrlw0fcE_wpPo8_41ltvLEQutq0eG420pZ4Xu8aXeogNxU-PT_Dsi3x6Z_vP87w71_Ra_D1bhXCogK2st6V1iyg_Waqzsp-SbzRvsYSqzD_nW6_4JddexN_H92t5MrBg9s6RB-eP5tPimj69urF5GIaKUbC5hVVCqiiUgHJeElSwrjkSRonakHiLF8wYBUjLE0llxJomY5ZFudQsayKs1glQ_Ron7u25roD50WjnYLVSrZgOid4kiSM01CGKNsrlTXOWajE2upG2p2gRPSYxFL0NERPQ_SYxA0msQ3Wh7dDukUD5cH4j0sQPN0LNnoFu_8OFrNiFi7BHu3t2nnYHuzSfhUpT_hYfHxzJYrLV9OMzQuRJ38B5Va0bA |
| CitedBy_id | crossref_primary_10_1111_jdv_16068 crossref_primary_10_3109_10408444_2013_813905 crossref_primary_10_1111_1346_8138_14818 crossref_primary_10_1039_c2pp25186h crossref_primary_10_1039_D0QO00093K crossref_primary_10_1021_acs_chemrev_5b00723 crossref_primary_10_1097_DER_0000000000000383 |
| Cites_doi | 10.1111/j.1600-0536.1985.tb02514.x 10.1016/S0968-0896(00)82146-X 10.1111/j.1751-1097.1995.tb02396.x 10.1021/tx00036a016 10.1016/S0968-0896(00)00202-9 10.1111/j.1600-0536.1998.tb05859.x 10.1016/B978-0-12-734601-4.50011-2 10.1111/j.1751-1097.1999.tb03341.x 10.1021/tx00043a002 10.1002/ejoc.200600611 10.1051/jcp/1981780597 10.1016/j.canlet.2004.11.045 10.1055/s-1998-2054 10.1021/jm00294a001 10.1016/S0040-4020(98)00171-9 10.1021/ja954340 10.1111/j.1600-0536.1993.tb03488.x 10.1111/j.1365-2133.1971.tb06857.x 10.1016/S1011-1344(01)00206-8 10.1016/S0367-326X(01)00257-X 10.1111/j.1751-1097.1967.tb08736.x 10.1016/S0968-0896(99)00195-9 10.1021/jo00288a046 10.1016/S0040-4020(01)81082-6 10.1021/cr00017a001 10.1111/j.1600-0536.1992.tb00888.x 10.1039/c39880000732 10.1021/jo0606608 |
| ContentType | Journal Article |
| Copyright | 2010 The Authors. Journal Compilation. The American Society of Photobiology |
| Copyright_xml | – notice: 2010 The Authors. Journal Compilation. The American Society of Photobiology |
| DBID | BSCLL CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 |
| DOI | 10.1111/j.1751-1097.2009.00691.x |
| DatabaseName | Istex Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef MEDLINE - Academic |
| DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef MEDLINE - Academic |
| DatabaseTitleList | MEDLINE CrossRef MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: ECM name: MEDLINE url: https://search.ebscohost.com/login.aspx?direct=true&db=cmedm&site=ehost-live sourceTypes: Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Medicine Chemistry Biology |
| EISSN | 1751-1097 |
| EndPage | 552 |
| ExternalDocumentID | 10_1111_j_1751_1097_2009_00691_x 20113426 PHP691 ark_67375_WNG_HDKL84TH_9 |
| Genre | article Research Support, Non-U.S. Gov't Journal Article |
| GroupedDBID | --- -JH -~X .3N .GA .GJ .Y3 05W 0R~ 10A 123 1OB 1OC 29O 31~ 33P 3O- 3SF 3V. 4.4 41~ 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5HH 5LA 5RE 5VS 66C 702 7PT 7RV 7X2 7X7 8-0 8-1 8-3 8-4 8-5 88A 88E 88I 8AF 8AO 8FE 8FH 8FI 8FJ 8FW 8R4 8R5 8UM 8WZ 930 A03 A6W AAESR AAEVG AAHHS AANLZ AAONW AAPSS AASGY AAXRX AAZKR ABCQN ABCUV ABDPE ABEFU ABEML ABUWG ACAHQ ACBWZ ACCFJ ACCZN ACGFO ACGFS ACGOD ACNCT ACPOU ACPRK ACSCC ACXBN ACXQS ADBBV ADEOM ADHSS ADIZJ ADKYN ADMGS ADOZA ADZMN AEEZP AEIGN AEIMD AENEX AEPYG AEQDE AEUQT AEUYR AFBPY AFFIJ AFFPM AFGKR AFKRA AFNWH AFPWT AFRAH AFZJQ AHBTC AHEFC AHMBA AIAGR AITYG AIURR AIWBW AJBDE AJXKR AKPMI ALAGY ALIPV ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ASPBG ATCPS ATUGU AUFTA AVWKF AZBYB AZFZN AZQEC AZVAB BAFTC BBNVY BDRZF BENPR BFHJK BHBCM BHPHI BKEYQ BLYAC BMNLL BNHUX BPHCQ BROTX BRXPI BSCLL BVXVI BY8 C1A CAG CCPQU COF CS3 D-E D-F DC7 DCZOG DPXWK DR2 DRFUL DRSTM DU5 DWQXO E3Z EBS ECGQY EJD ESX EX3 F00 F01 F04 F5P FEDTE FYUFA FZ0 G-S G.N GNUQQ GODZA H.T H.X H13 HCIFZ HF~ HGLYW HMCUK HVGLF HZ~ H~9 IH2 IX1 J0M K48 LATKE LC2 LC3 LEEKS LH4 LITHE LK8 LOXES LP6 LP7 LUTES LW6 LYRES M0K M0L M1P M2P M2Q M7P MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NAPCQ NDZJH NF~ O66 O9- OIG P2P P2W P2X P4D PALCI PQ0 PQQKQ PROAC PSQYO Q.N Q11 Q2X Q5J QB0 R.K RBO RIG RIWAO RJQFR ROL RWL RX1 S0X SAMSI SJN SUPJJ TAE UB1 UKHRP W8V W99 WBKPD WH7 WIH WIK WNSPC WOHZO WOW WQJ WRC WSB WXSBR WYISQ XG1 XOL YNT ZGI ZXP ZZTAW ~02 ~IA ~KM ~WT G8K CGR CUY CVF ECM EIF NPM AAMNL AAYXX CITATION 7X8 |
| ID | FETCH-LOGICAL-c4051-f1cce1c1ace087d06047a73623cb0289b4e4f40466a7aae1d654829ef48f282c3 |
| IEDL.DBID | 33P |
| ISSN | 0031-8655 |
| IngestDate | Fri Oct 25 02:48:25 EDT 2024 Thu Nov 21 23:02:15 EST 2024 Sat Sep 28 08:37:30 EDT 2024 Sat Aug 24 00:56:48 EDT 2024 Wed Oct 30 09:52:18 EDT 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 3 |
| Language | English |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c4051-f1cce1c1ace087d06047a73623cb0289b4e4f40466a7aae1d654829ef48f282c3 |
| Notes | ark:/67375/WNG-HDKL84TH-9 istex:550B75D73BF1474CB7E6CC9B309CCEEA49742CD9 ArticleID:PHP691 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 20113426 |
| PQID | 733347173 |
| PQPubID | 23479 |
| PageCount | 8 |
| ParticipantIDs | proquest_miscellaneous_733347173 crossref_primary_10_1111_j_1751_1097_2009_00691_x pubmed_primary_20113426 wiley_primary_10_1111_j_1751_1097_2009_00691_x_PHP691 istex_primary_ark_67375_WNG_HDKL84TH_9 |
| PublicationCentury | 2000 |
| PublicationDate | 2010-05 May/June 2010 2010 May-Jun 2010-05-00 20100501 |
| PublicationDateYYYYMMDD | 2010-05-01 |
| PublicationDate_xml | – month: 05 year: 2010 text: 2010-05 |
| PublicationDecade | 2010 |
| PublicationPlace | Oxford, UK |
| PublicationPlace_xml | – name: Oxford, UK – name: United States |
| PublicationTitle | Photochemistry and photobiology |
| PublicationTitleAlternate | Photochem Photobiol |
| PublicationYear | 2010 |
| Publisher | Blackwell Publishing Ltd |
| Publisher_xml | – name: Blackwell Publishing Ltd |
| References | Ross, J. S., H. Du Peloux Menagé, J. L. M. Hawk and I. R. White (1993) Sesquiterpene lactone contact sensitivity: Clinical patterns of Compositae dermatitis and relationship to chronic actinic dermatitis. Contact Derm. 29, 84-87. Huang, P.-R., Y.-M. Yeh and T.-C. V. Wang (2005) Potent inhibition of human telomerase by helenalin. Cancer Lett. 227, 169-174. Anselmino, C., L. Voituriez and 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. Patel, B. B., T. G. Waddell and R. M. Pagni (2001) Explaining photodermatosis: Cyclopentenone vs. α-methylene-γ-lactone natural products. Fitoterapia 72, 511-515. Franot, C., C. Benezra and J.-P. Lepoittevin (1993) Synthesis and interaction studies of 13C labeled lactone derivatives with a model protein using 13C NMR. Bioorg. Med. Chem. 1, 389-397. Rüngeler, P., V. Castro, G. Mora, N. Gören, W. Vichnewski, H. L. Pahl, I. Merfort and T. J. Schmidt (1999) Inhibition of transcription factor NF-κB by sesquiterpene lactones: A proposed molecular mechanism of action. Bioorg. Med. Chem. 7, 2343-2352. Du Peloux Menagé, H., G. I. Harrison, C. S. Plotten, A. R. Young and 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. Gimenez-Arnau, E., S. Mabic and J.-P. Lepoittevin (1995) Synthesis and photocyclisation of α-methylene-γ-butyrolactone-thymine heterodimers. Chem. Res. Toxicol. 8, 22-26. Musajo, L., F. Bordin, G. Caporale, S. Marciani and G. Rigatti (1967) Photoreaction at 3655 Å between pyrimidine bases and skin-photosensitizing furocoumarins. Photochem. Photobiol. 6, 711-719. Schuster, D. I., G. Lem and N. A. Kaprinidis (1993) New insights into an old mechanism: [2+2] photocycloaddition of enones to alkenes. Chem. Rev. 93, 3-22. Murphy, G. M., I. R. White and J. L. M. Hawk (1990) Allergic airborne contact dermatitis to Compositae with photosensitivity-chronic actinic dermatitis in evolution. Photodermatol. Photoimmunol. Photomed. 7, 38-39. Dirsch, V. M., H. Stuppner, E. P. Ellmerer-Müller and 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. Selig, P. and 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. Paulsen, E. (1992) Compositae dermatitis: A survey. Contact Derm. 26, 76-86. Kilfoil, V. and L. Salter (1988) Kinetics of thymine dimerization. J. Chem. Soc., Chem. Commun. 732-734. Wood, P. D. and 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. Mitchell, J. C. and G. Dupuis (1971) Allergic contact dermatitis from sesquiterpenoids of the Compositae family of plants. Br. J. Dermatol. 84, 139-150. Benezra, C., J.-L. Stampf, P. Barbier and G. Ducombs (1985) Enantiospecificity in allergic contact dermatitis. A review and new results in Frullania-sensitive patients. Contact Derm. 13, 110-114. Du Peloux Menagé, H., J. L. Hawk and 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. Berl, V. and 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. Farrow, S. J., C. R. Jones, D. L. Severance, R. M. Deibel, W. M. Baird and 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. Bertrand, S., N. Hoffmann and J.-P. Pete (1998) Photochemical [2+2] cycloaddition of cyclic enones to (5R)-5-menthyloxy-2[5H]-furanone. Tetrahedron 54, 4873-4888. Talaga, P., M. Schaeffer, H. Mattes, C. Benezra and J.-L. Stampf (1989) Synthesis of Boc-Cys-Ala-Ome and its stereoselective addition to α-methylene-γ-butyrolactones. Tetrahedron 45, 5029-5038. Bach, T. (1998) Stereoselective intermolecular [2+2]-photocycloaddition reactions and their application in synthesis. Synthesis 683-703. Amaud, R., A. Deflandre, G. Lang and J. Lemaire (1981) Propriétés photosensibilisatrices des furocoumarines. IV-Etude photochimique des furocoumarines méthoxylées en solution aqueuse. J. Chim. Phys. 78, 597-605. Fuchs, S., V. Berl and J.-P. Lepoittevin (2007) A highly stereoselective divergent synthesis of bicyclic models of photoreactive sesquiterpene lactones. Eur. J. Org. Chem. 1145-1152. Ravanat, J.-L., T. Douki and J. Cadet (2001) Direct and indirect effects of UV radiation on DNA and its components. J. Photochem. Photobiol. B, Biol. 63, 88-102. Kupchan, S. M., M. A. Eakin and A. M. Thomas (1971) Tumor inhibitors. 69. Structure-cytotoxicity relationships among the sesquiterpene lactones. J. Med. Chem. 14, 1147-1152. 2006; 71 2001; 72 1990; 55 1993; 29 1989; 45 1971; 84 2000; 8 1999; 69 1998 1976 2007 1999; 7 1993; 1 2001; 63 1995; 8 1993; 6 1967; 6 1995; 62 1998; 39 1993; 93 1971; 14 2005; 227 1992; 26 1998; 54 1990; 7 1996; 118 1985; 13 1981; 78 1988 e_1_2_6_30_2 e_1_2_6_18_2 e_1_2_6_19_2 e_1_2_6_12_2 e_1_2_6_13_2 e_1_2_6_10_2 e_1_2_6_11_2 e_1_2_6_16_2 e_1_2_6_17_2 e_1_2_6_14_2 e_1_2_6_15_2 e_1_2_6_20_2 Murphy G. M. (e_1_2_6_9_2) 1990; 7 e_1_2_6_8_2 e_1_2_6_7_2 e_1_2_6_29_2 e_1_2_6_4_2 e_1_2_6_3_2 e_1_2_6_6_2 e_1_2_6_5_2 e_1_2_6_24_2 e_1_2_6_23_2 e_1_2_6_2_2 e_1_2_6_22_2 e_1_2_6_21_2 e_1_2_6_28_2 e_1_2_6_27_2 e_1_2_6_26_2 e_1_2_6_25_2 |
| References_xml | – volume: 45 start-page: 5029 year: 1989 end-page: 5038 article-title: Synthesis of Boc‐Cys‐Ala‐Ome and its stereoselective addition to α‐methylene‐γ‐butyrolactones publication-title: Tetrahedron – volume: 1 start-page: 389 year: 1993 end-page: 397 article-title: Synthesis and interaction studies of C labeled lactone derivatives with a model protein using C NMR publication-title: Bioorg. Med. Chem. – volume: 7 start-page: 38 year: 1990 end-page: 39 article-title: Allergic airborne contact dermatitis to Compositae with photosensitivity‐chronic actinic dermatitis in evolution publication-title: Photodermatol. Photoimmunol. Photomed. – volume: 7 start-page: 2343 year: 1999 end-page: 2352 article-title: Inhibition of transcription factor NF‐κB by sesquiterpene lactones: A proposed molecular mechanism of action publication-title: Bioorg. Med. Chem. – volume: 14 start-page: 1147 year: 1971 end-page: 1152 article-title: Tumor inhibitors. 69. Structure‐cytotoxicity relationships among the sesquiterpene lactones publication-title: J. Med. Chem. – volume: 6 start-page: 858 year: 1993 end-page: 865 article-title: Characterization of the and diastereoisomers of 5‐methoxypsoralen pyrone‐side monocycloadducts to thymidine publication-title: Chem. Res. Toxicol. – volume: 26 start-page: 76 year: 1992 end-page: 86 article-title: Compositae dermatitis: A survey publication-title: Contact Derm. – volume: 8 start-page: 22 year: 1995 end-page: 26 article-title: Synthesis and photocyclisation of α‐methylene‐γ‐butyrolactone‐thymine heterodimers publication-title: Chem. Res. Toxicol. – start-page: 1145 year: 2007 end-page: 1152 article-title: A highly stereoselective divergent synthesis of bicyclic models of photoreactive sesquiterpene lactones publication-title: Eur. J. Org. Chem. – volume: 29 start-page: 84 year: 1993 end-page: 87 article-title: Sesquiterpene lactone contact sensitivity: Clinical patterns of Compositae dermatitis and relationship to chronic actinic dermatitis publication-title: Contact Derm. – volume: 54 start-page: 4873 year: 1998 end-page: 4888 article-title: Photochemical [2+2] cycloaddition of cyclic enones to (5R)‐5‐menthyloxy‐2[5H]‐furanone publication-title: Tetrahedron – volume: 71 start-page: 5662 year: 2006 end-page: 5673 article-title: Photochemistry of 4‐(2′‐aminoethyl)quinolones: Enantioselective synthesis of tetracyclic tetrahydro‐1a ‐pyrido[4′,3′:2,3]‐cyclobuta[1,2‐ ] quinoline‐2,11(3 ,8 )‐diones by intra‐ and intermolecular [2+2]‐photocycloaddition reactions in solution publication-title: J. Org. Chem. – volume: 62 start-page: 976 year: 1995 end-page: 979 article-title: The action spectrum for induction of chronic actinic dermatitis is similar to that for sunburn inflammation publication-title: Photochem. Photobiol. – volume: 72 start-page: 511 year: 2001 end-page: 515 article-title: Explaining photodermatosis: Cyclopentenone vs. α‐methylene‐γ‐lactone natural products publication-title: Fitoterapia – volume: 93 start-page: 3 year: 1993 end-page: 22 article-title: New insights into an old mechanism: [2+2] photocycloaddition of enones to alkenes publication-title: Chem. Rev. – volume: 8 start-page: 2747 year: 2000 end-page: 2753 article-title: Structural requirements of sesquiterpene lactones to inhibit LPS‐induced nitric oxide synthesis in RAW 264.7 macrophages publication-title: Bioorg. Med. Chem. – volume: 63 start-page: 88 year: 2001 end-page: 102 article-title: Direct and indirect effects of UV radiation on DNA and its components publication-title: J. Photochem. Photobiol. B, Biol. – volume: 39 start-page: 119 year: 1998 end-page: 122 article-title: Sesquiterpene lactone mix contact sensitivity and its relationship to chronic actinic dermatitis: A follow‐up study publication-title: Contact Derm. – volume: 6 start-page: 711 year: 1967 end-page: 719 article-title: Photoreaction at 3655 Å between pyrimidine bases and skin‐photosensitizing furocoumarins publication-title: Photochem. Photobiol. – start-page: 225 year: 1976 end-page: 294 – volume: 84 start-page: 139 year: 1971 end-page: 150 article-title: Allergic contact dermatitis from sesquiterpenoids of the Compositae family of plants publication-title: Br. J. Dermatol. – start-page: 732 year: 1988 end-page: 734 article-title: Kinetics of thymine dimerization publication-title: J. Chem. Soc., Chem. Commun. – volume: 227 start-page: 169 year: 2005 end-page: 174 article-title: Potent inhibition of human telomerase by helenalin publication-title: Cancer Lett. – volume: 69 start-page: 653 year: 1999 end-page: 657 article-title: Evidence for [2+2] photoreaction of α‐metyhene‐γ‐butyrolactones with thymine: An explanation for chronic actinic dermatitis to sequiterpene lactones? publication-title: Photochem. Photobiol. – volume: 13 start-page: 110 year: 1985 end-page: 114 article-title: Enantiospecificity in allergic contact dermatitis. A review and new results in Frullania‐sensitive patients publication-title: Contact Derm. – start-page: 683 year: 1998 end-page: 703 article-title: Stereoselective intermolecular [2+2]‐photocycloaddition reactions and their application in synthesis publication-title: Synthesis – volume: 78 start-page: 597 year: 1981 end-page: 605 article-title: Propriétés photosensibilisatrices des furocoumarines. IV—Etude photochimique des furocoumarines méthoxylées en solution aqueuse publication-title: J. Chim. Phys. – volume: 118 start-page: 4256 year: 1996 end-page: 4263 article-title: Triplet state interactions between nucleic acid bases in solution at room temperature: Intermolecular energy and electron transfer publication-title: J. Am. Chem. Soc. – volume: 55 start-page: 275 year: 1990 end-page: 282 article-title: Urocanic acid photobiology. Identification and characterization of the major photoadducts formed between urocanic acid and thymidine publication-title: J. Org. Chem. – ident: e_1_2_6_16_2 doi: 10.1111/j.1600-0536.1985.tb02514.x – ident: e_1_2_6_8_2 doi: 10.1016/S0968-0896(00)82146-X – ident: e_1_2_6_12_2 doi: 10.1111/j.1751-1097.1995.tb02396.x – ident: e_1_2_6_27_2 doi: 10.1021/tx00036a016 – ident: e_1_2_6_4_2 doi: 10.1016/S0968-0896(00)00202-9 – ident: e_1_2_6_11_2 doi: 10.1111/j.1600-0536.1998.tb05859.x – ident: e_1_2_6_29_2 doi: 10.1016/B978-0-12-734601-4.50011-2 – ident: e_1_2_6_14_2 doi: 10.1111/j.1751-1097.1999.tb03341.x – ident: e_1_2_6_13_2 doi: 10.1021/tx00043a002 – ident: e_1_2_6_18_2 doi: 10.1002/ejoc.200600611 – ident: e_1_2_6_22_2 doi: 10.1051/jcp/1981780597 – ident: e_1_2_6_7_2 doi: 10.1016/j.canlet.2004.11.045 – ident: e_1_2_6_25_2 doi: 10.1055/s-1998-2054 – ident: e_1_2_6_6_2 doi: 10.1021/jm00294a001 – ident: e_1_2_6_30_2 doi: 10.1016/S0040-4020(98)00171-9 – ident: e_1_2_6_23_2 doi: 10.1021/ja954340 – ident: e_1_2_6_10_2 doi: 10.1111/j.1600-0536.1993.tb03488.x – ident: e_1_2_6_2_2 doi: 10.1111/j.1365-2133.1971.tb06857.x – ident: e_1_2_6_20_2 doi: 10.1016/S1011-1344(01)00206-8 – ident: e_1_2_6_15_2 doi: 10.1016/S0367-326X(01)00257-X – ident: e_1_2_6_21_2 doi: 10.1111/j.1751-1097.1967.tb08736.x – ident: e_1_2_6_5_2 doi: 10.1016/S0968-0896(99)00195-9 – ident: e_1_2_6_28_2 doi: 10.1021/jo00288a046 – volume: 7 start-page: 38 year: 1990 ident: e_1_2_6_9_2 article-title: Allergic airborne contact dermatitis to Compositae with photosensitivity‐chronic actinic dermatitis in evolution publication-title: Photodermatol. Photoimmunol. Photomed. contributor: fullname: Murphy G. M. – ident: e_1_2_6_17_2 doi: 10.1016/S0040-4020(01)81082-6 – ident: e_1_2_6_26_2 doi: 10.1021/cr00017a001 – ident: e_1_2_6_3_2 doi: 10.1111/j.1600-0536.1992.tb00888.x – ident: e_1_2_6_19_2 doi: 10.1039/c39880000732 – ident: e_1_2_6_24_2 doi: 10.1021/jo0606608 |
| SSID | ssj0014971 |
| Score | 2.0237129 |
| Snippet | (+) and (−) α‐methylene‐hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to... (+) and (-) alpha-methylene-hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to... (+) and (−) α‐methylene‐hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to... |
| SourceID | proquest crossref pubmed wiley istex |
| SourceType | Aggregation Database Index Database Publisher |
| StartPage | 545 |
| SubjectTerms | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemistry Dermatitis, Allergic Contact - etiology Humans Lactones - chemistry Magnetic Resonance Spectroscopy Photosensitivity Disorders - chemically induced Photosensitivity Disorders - etiology Sesquiterpenes - chemistry Sesquiterpenes - radiation effects Thymidine - chemistry Ultraviolet Rays - adverse effects |
| Title | Chronic Actinic Dermatitis to Sesquiterpene Lactones: [2+2] Photoreaction Toward Thymidine of (+) and (−) α-Methylene-Hexahydrobenzofuranone with a cis Ring Junction |
| URI | https://api.istex.fr/ark:/67375/WNG-HDKL84TH-9/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1111%2Fj.1751-1097.2009.00691.x https://www.ncbi.nlm.nih.gov/pubmed/20113426 https://search.proquest.com/docview/733347173 |
| Volume | 86 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1ba9RAFB604uXFy3pbb5wHkZYSySSTnYlvpdsaalsWu6IgMszOTNgibmrTwK5PPvoo_g5f_CP-iP4Sz0k2iyt9EPEpgZDJ5dy-M-fG2OMUNZ5JLMp35OJARCYMVO5NoIRFPBz6hNfZhNmB3H-j-lvUJmenrYVp-kMsNtxIMmp9TQJuRuWykMuE0rFS2bad7KX8KeFJdBrqao54sAgoiFQ2w_NiHlAt5h9JPWcttGSpLtBPn54FQ5dRbW2Wtq_9zw-6zq7OwSlsNNx0g53zkw672IyrnHXY5c12OlyHXdqbB-Vvsu_zBruwgbqTjn3f4ODDEk4KOPDlx4oKnY9QrcIuzfdB9foM3kbr0TsYjAv0-n1TXgHDOokXhuPZh0M0qh6KHFbX18BMHKyefvm2Bj9_nH7-uueRvdBcejzP_NSMZ46qmiafirxC24vrA-0vgwGL7_ASrTPsoP2mR9xir7a3hptZMB8CEVjEkjzIubWeW26sD5V01OtHGolmN7YjipKOhBe5QC-_Z6Qxnrse-mBR6nOhcnQnbXybrdBz7zIwDp1ho5xSDq9KlwobRj6xTo5SExnVZbwluD5qen3o33wkJE4Tryfi6Jo4etplT2rOWNxgjt9TrpxM9Ov95zrrv9hVYpjptMugZR2NpKKwjJn4oiq1jONYUDJEl91pWGqxGKGzGDFUlyU15_z1a-lBNsCTe_943312pc2SCPkDtnJyXPmH7Hzpqke1WP0CeUMhZQ |
| link.rule.ids | 315,782,786,1408,27933,27934,46064,46488 |
| linkProvider | Wiley-Blackwell |
| linkToHtml | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1Jb9NAFB5BKygXlrCZdQ4ItaqMPPY4M-ZWNS2GLIqoEUgIjSYzY6VCxKWppYQTR46I38GFP8KP6C_hPTuOCOoBIU62ZHm8vO178zZCHiWg8XRsQL5DG_k81IEvc6d9yQ3g4cDFrMomTA_E4I3s7GGbnG5TC1P3h1huuKFkVPoaBRw3pFelXMSYj5WIpu9kO2FPAFCu8zbwJdZzRMNlSIEnoh6fFzEfqzH_SOs5a6UVW7WOv312FhBdxbWVYdq_8l8_6Sq5vMCndKdmqGvknJu0yIV6YuW8RTZ2mwFxLXKxv4jLXyffFz126Q6oTzx2XA2FD6f0pKAHbvqxxFrnI9CstIcjfkDDPqVvw-3wHR2OC3D8XV1hQbMqj5dm4_mHQ7CrjhY53dzeonpi6ebpl29b9OeP089f-w44DCymg_PUzfR4brGwafKpyEswv7A-xS1mqqmBd3gJBpq-ABOOj7hBXu3vZbupv5gD4RuAk8zPmTGOGaaNC6Sw2O5HaAGWNzIjDJSOuOM5B0e_rYXWjtk2uGFh4nIuc_AoTXSTrOFzbxOqLfjDWlopLVwVNuEmCF1srBglOtTSI6yhuDqq232o39wkIE4dskfiqIo4auaRxxVrLG_Qx-8xXU7E6vXgmUo73Z7kWaoSj9CGdxSQCiMzeuKKcqpEFEUc8yE8cqvmqeViCNAigFEeiSvW-evXUsN0CCd3_vG-h2Qjzfo91Xs-6N4ll5qkiYDdI2snx6W7T85PbfmgkrFfuqkljQ |
| linkToPdf | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV3LbtNAFB1BKwobHoGCec4CoVaVK49nnLHZVU2DadPIokFFQmg0mRkrFSIOTSMlrFiyRHwHG36Ej-iXcK8dRwR1gRArW7I8ftzXuXNfhDxNQOPpyIB8h5b7ItSBH-dO-7EwgIcDF7EymzA9kt03cWsP2-Ts17UwVX-IxYYbSkapr1HARzZfFnIZYTpWIuu2k82EbQOeXBWAyrGPPufZIqIgEllNz-PMx2LMP7J6LlppyVSt4l-fXoRDl2FtaZfaN_7nF90k1-folO5U7HSLXHLDBrlSzaucNcjV3Xo8XIOsHc6j8rfJ93mHXboDyhOPLVcB4ZMxPSvokRt_nGCl8wj0Ku3ggB_Qr8_p23ArfEezQQFuv6vqK2ivzOKlvcHswwlYVUeLnG5sbVI9tHTj_Mu3Tfrzx_nnr4cO-AvspYPz1E31YGaxrGn4qcgnYHxhfYobzFRTA-_wCswz3QcDjo-4Q16393q7qT-fAuEbAJPMz5kxjhmmjQtiabHZj9QS7C43fQyT9oUTuQA3v6ml1o7ZJjhhYeJyEefgTxq-TlbwufcI1Ra8YR3bOLZwVdpEmCB0kbGyn-hQxx5hNcHVqGr2oX5zkoA4VcAeiaNK4qipR56VnLG4QZ--x2Q5Ganj7guVtg46seilKvEIrVlHAakwLqOHrpiMleScC8yG8MjdiqUWiyE84wCiPBKVnPPXr6WyNIOT-_943xOylrXaqvOye_CAXKszJgL2kKycnU7cI3J5bCePSwn7Bf60JDM |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Chronic+Actinic+Dermatitis+to+Sesquiterpene+Lactones%3A+%5B2%2B2%5D+Photoreaction+Toward+Thymidine+of+%28%2B%29+and+%28%E2%88%92%29+%CE%B1%E2%80%90Methylene%E2%80%90Hexahydrobenzofuranone+with+a+cis+Ring+Junction&rft.jtitle=Photochemistry+and+photobiology&rft.au=Fuchs%2C+S%C3%A9bastien&rft.au=Berl%2C+Val%C3%A9rie&rft.au=Lepoittevin%2C+Jean%E2%80%90Pierre&rft.date=2010-05-01&rft.pub=Blackwell+Publishing+Ltd&rft.issn=0031-8655&rft.eissn=1751-1097&rft.volume=86&rft.issue=3&rft.spage=545&rft.epage=552&rft_id=info:doi/10.1111%2Fj.1751-1097.2009.00691.x&rft.externalDBID=10.1111%252Fj.1751-1097.2009.00691.x&rft.externalDocID=PHP691 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0031-8655&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0031-8655&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0031-8655&client=summon |