3,3′-dihydroxyisorenieratene, a natural carotenoid with superior antioxidant and photoprotective properties

Angewandte Chemie - International Edition

Volumn 48, Issue 2, 2009, Pages 400-403

  Martin, Hans Dieter ^a   Kock, Sebastian ^a   Scherrers, Roger ^a   Lutter, Kaya ^a   Wagener, Tanja ^a   Hundsdörfer, Claas ^a   Frixel, Susanne ^a   Schaper, Klaus ^a   Ernst, Hansgeorg ^b   Schrader, Wolfgang ^a,c   Görner, Helmut ^b,d   Stahl, Wilhelm ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b BASF SE   (Germany)

^c MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^d MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

Carotenoids; Photooxidation; Photoprotection; Quinones; Singlet oxygen

Indexed keywords

OXYGEN; PHENOLS;

ANTI-OXIDANTS; CAROTENOIDS; END GROUPS; MODEL SYSTEMS; OXIDATION PRODUCTS; PHOTOPROTECTION; QUINONES; SINGLET OXYGEN;

PHOTOOXIDATION;

3,3' DIHYDROXYISORENIERATENE; 3,3'-DIHYDROXYISORENIERATENE; ANTIOXIDANT; CAROTENOID; FREE RADICAL; HEME OXYGENASE 1; LIPOSOME; OXYGEN; PHOSPHOLIPID; PYRIMIDINE DIMER; RADIOPROTECTIVE AGENT; UNCLASSIFIED DRUG; XANTHOPHYLL;

ARTICLE; BIOSYNTHESIS; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; FIBROBLAST; HUMAN; METABOLISM; OXIDATION REDUCTION REACTION; OXYGEN CONSUMPTION; RADIATION EXPOSURE; SKIN; STEREOISOMERISM; SYNTHESIS; ULTRAVIOLET RADIATION;

ANTIOXIDANTS; CAROTENOIDS; CELLS, CULTURED; FIBROBLASTS; FREE RADICALS; HEME OXYGENASE-1; HUMANS; LIPOSOMES; LUTEIN; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXYGEN; OXYGEN CONSUMPTION; PHOSPHOLIPIDS; PYRIMIDINE DIMERS; RADIATION-PROTECTIVE AGENTS; SKIN; STEREOISOMERISM; ULTRAVIOLET RAYS;

EID: 58249122130     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803668     Document Type: Article

References (25)

1. a) F. Arcamone, B. Camerino, E. Cotta, G. Franceschi, A. Grein, S. Penco, C. Spalla, Experientia 1969, 25, 241-242;
2. b) W. Kohl, H. Achenbach, H. Reichenbach, Phytochemistry 1983, 22, 207-210;
3. c) L. Dufosse, M. C. de Echanove, Food Res. Int. 2005, 38, 967-973;
4. d) F. Guyomarćh, A. Binet, L. Dufosse, J. Ind. Microbiol. Biotechnol. 2000, 24, 64-70;
5. e) L. Dufosse, Food Technol. Biotechnol. 2006, 44, 313-321.
6. a) D. Baltschun, S. Beutner, K. Briviba, H. D. Martin, J. Paust, M. Peters, S. Röver, H. Sies, W. Stahl, A. Steigel, F. Stenhorst, Liebigs Ann. 1997, 1887-1893;
7. b) H. D. Martin, C. Jäger, C. Ruck, M. Schmidt, R. Walsh, J. Paust, J. Prakt. Chem. 1999, 341, 302-308;
8. c) H. D. Martin, C. Ruck, M. Schmidt, S. Sell, S. Beutner, B. Mayer, R. Walsh, Pure Appl. Chem. 1999, 71, 2253-2262;
9. d) S. Beutner, B. Bloedorn, S. Frixel, I. Hernández-Blanco, T. Hoffmann, H. D. Martin, B. Mayer, P. Noack, C. Ruck, M. Schmidt, I. Schülke, S. Sell, H. Ernst, S. Haremza, G. Seybold, H. Sies, W. Stahl, R. Walsh, J. Sci. Food Agric. 2001, 81, 559-568.
10. G. Nybraaten, S. Liaaen-Jensen, Acta Chem. Scand. 1971, 25, 370-372.
11. J. Terao, Lipids 1989, 24, 659-661.
12. The concept of induction period, inhibition times, and chain-breaking antioxidants is described in G. W. Burton, D. O. Foster, B. Perly, T. F. Slater, I. C. P. Smith, K. U. Ingold, Philos. Trans. R. Soc. London Ser. B 1985, 311, 565-578.
13. a) G. W. Burton, K. U. Ingold, Science 1984, 224, 569-573;
14. b) G. W. Burton, J. Nutr. 1989, 119, 109-111.
15. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, C. Rice-Evans, Free Radical Biol. Med. 1999, 26, 1231-1237.
16. S. Hünig, H. Balli, H. Conrad, A. Schott, Justus Liebigs Ann. Chem. 1964, 676, 36-51.
17. a) P. F. Conn, W. Schalch, T. G. Truscott, J. Photochem. Photobiol. B 1991, 11, 41-47;
18. b) P. di Mascio, S. Raiser, H. Sies, Arch. Biochem. Biophys. 1989, 274, 532-538;
19. c) R. Schmidt, J. Phys. Chem. A 2004, 108, 5509-5513;
20. d) C. Schweitzer, R. Schmidt, Chem. Rev. 2003, 103, 1685-1757.
21. a) C. R. Lambert, H. S. Black, T. G. Truscott, Free Radical Biol. Med. 1996, 21, 395-400;
22. b) C. Tournaire, S. Croux, M. T. Maurette, I. Beck, M. Hocquaux, A. M. Braun, E. Oliveros, J. Photochem. Photobiol. B 1993, 19, 205-215;
23. c) V. Avila, S. G. Bertolotti, S. Criado, N. Pappano, N. Debattista, N. A. Garcia, Int. J. Food Sci. Technol. 2001, 36, 25-33;
24. d) S. Beutner, B. Bloedorn, T. Hoffmann, H. D. Martin, Methods Enzymol. 2000, 319, 226-241.
25. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, M. R. Boyd, J. Natl. Cancer Inst. 1990, 82, 1107-1112.