{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,16]],"date-time":"2026-04-16T17:12:40Z","timestamp":1776359560446,"version":"3.51.2"},"reference-count":41,"publisher":"Walter de Gruyter GmbH","issue":"9","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2009,8,19]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Anthocyanins, the major red, purple, and blue pigments of plants, absorb visible as well as UV radiation and are effective antioxidants and scavengers of active oxygen species. In plant leaves, one of the functional roles proposed for anthocyanins is protection of the photosynthetic apparatus from the effects of excess incident visible or UV-B radiation and photooxidative stress. In essence, a photoprotective role requires that the excited singlet states of both complexed and uncomplexed anthocyanins deactivate back to the ground state so quickly that intersystem crossing, photoreaction, and diffusion-controlled quenching processes cannot compete. Studies of the photochemical properties of synthetic analogs of anthocyanins and of several naturally occurring anthocyanins show that this is indeed the case, uncomplexed anthocyanins decaying back to the ground state via fast (subnanosecond) excited-state proton transfer (ESPT) and anthocyanin-copigment complexes by fast (subpicosecond) charge-transfer-mediated internal conversion.<\/jats:p>","DOI":"10.1351\/pac-con-08-09-28","type":"journal-article","created":{"date-parts":[[2009,8,19]],"date-time":"2009-08-19T20:24:05Z","timestamp":1250713445000},"page":"1687-1694","source":"Crossref","is-referenced-by-count":87,"title":["Photochemistry of anthocyanins and their biological role in plant tissues"],"prefix":"10.1515","volume":"81","author":[{"given":"Frank H.","family":"Quina","sequence":"first","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidade de S\u00e3o Paulo, CP 26790, S\u00e3o Paulo 05513-970, Brazil"}]},{"suffix":"Jr.","given":"Paulo F.","family":"Moreira","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidade de S\u00e3o Paulo, CP 26790, S\u00e3o Paulo 05513-970, Brazil"}]},{"given":"Carolina","family":"Vautier-Giongo","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias Exatas e da Terra, Universidade Federal de S\u00e3o Paulo, Diadema, SP, Brazil"}]},{"given":"Daniel","family":"Rettori","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias Exatas e da Terra, Universidade Federal de S\u00e3o Paulo, Diadema, SP, Brazil"}]},{"given":"Rita F.","family":"Rodrigues","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Technical University of Lisbon, Portugal"}]},{"given":"Adilson A.","family":"Freitas","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Technical University of Lisbon, Portugal"}]},{"given":"Palmira F.","family":"Silva","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Technical University of Lisbon, Portugal"}]},{"given":"Ant\u00f3nio L.","family":"Ma\u00e7anita","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Technical University of Lisbon, Portugal"}]}],"member":"374","published-online":{"date-parts":[[2009,8,19]]},"reference":[{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_001","doi-asserted-by":"crossref","unstructured":"doi:10.1016\/S0308-8146(96)00222-1, P. Bridle, C. F. Timberlake. Food Chem. 58, 103 (1997).","DOI":"10.1016\/S0308-8146(96)00222-1"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_002","unstructured":"R. Brouillard, P. Figueiredo, M. Elhabiri, O. Dangles. In Phytochemistry of Fruit and Vegetables, F. A. Tomas-Barberan, R. J. Robins (Eds.), pp. 2949, Clarendon Press, Oxford (1997)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_003","doi-asserted-by":"crossref","unstructured":"doi:10.1039\/b311404j, (a) C. A. Williams, R. J. Grayer. Nat. Prod. Rep. 21, 539 (2004);","DOI":"10.1039\/b311404j"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_004","doi-asserted-by":"crossref","unstructured":"doi:10.1039\/b718040n, (b) N. C. Veitch, R. J. Grayer. Nat. Prod. Rep. 25, 555 (2008).","DOI":"10.1039\/b718040n"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_005","unstructured":"O. M. Andersen, M. Jordheim. In Flavenoids, Chemistry, Biochemistry and Applications, O. M. Andersen, K. R. Markham (Eds.), pp. 471551, CRC Press, Boca Raton (2006)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_006","doi-asserted-by":"crossref","unstructured":"doi:10.1034\/j.1399-3054.2002.1160310.x, K. L. Hale, H. A. Tufan, I. J. Pickering, G. N. George, N. Terry, M. Pilon, E. A. H. Pilon-Smits. Physiol. Plant. 116, 351 (2002).","DOI":"10.1034\/j.1399-3054.2002.1160310.x"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_007","doi-asserted-by":"crossref","unstructured":"doi:10.1016\/j.phytochem.2005.04.002, K. Takeda, A. Osakabe, S. Saito, D. Furuyama, A. Tomita, Y. Kojima, M. Yamadera, M. Sakuta. Phytochemistry 66, 1607 (2005).","DOI":"10.1016\/j.phytochem.2005.04.002"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_008","doi-asserted-by":"crossref","unstructured":"doi:10.1016\/j.phytochem.2006.03.013, K. Yoshida, S. D. Kitahara, D. Ito, T. Kondo. Phytochemistry 67, 992 (2006).","DOI":"10.1016\/j.phytochem.2006.03.013"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_009","doi-asserted-by":"crossref","unstructured":"K. Takeda. Proc. Jpn. Acad., Ser. B 82, 142 (2006).","DOI":"10.2183\/pjab.82.142"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_010","unstructured":"M. Wheldale. The Anthocyanin Pigments of Plants, Cambridge University Press, Cambridge (1916)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_011","unstructured":"K. S. Gould, D. W. Lee. Anthocyanins in Leaves (Adv. Bot. Res., 37), Academic Press, New York (2002)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_012","doi-asserted-by":"crossref","unstructured":"doi:10.1046\/j.1469-8137.2002.00482.x, W. J. Steyn, S. J. E. Wand, D. M. Holcroft, G. Jacobs. New Phytol. 155, 349 (2002).","DOI":"10.1046\/j.1469-8137.2002.00482.x"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_013","unstructured":"doi:10.1155\/S1110724304406147, K. S. Gould. J. Biomed. Biotechnol. 2004, 314 (2004)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_014","unstructured":"A. A. Lima, E. M. Sussuchi, W. F. Giovani. Croat. Chem. Acta 80, 29 (2007)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_015","doi-asserted-by":"crossref","unstructured":"doi:10.1046\/j.1365-3040.2002.00905.x, K. S. Gould, J. McKelvie, K. R. Markham. Plant Cell Environ. 25, 1261 (2002).","DOI":"10.1046\/j.1365-3040.2002.00905.x"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_016","doi-asserted-by":"crossref","unstructured":"doi:10.1104\/pp.103.027631, W. A. Hoch, E. L. Singsaas, B. H. McCown. Plant Physiol. 133, 1296 (2003).","DOI":"10.1104\/pp.103.027631"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_017","doi-asserted-by":"crossref","unstructured":"doi:10.1104\/pp.105.066845, J. Keskitalo, G. Bergquist, P. Gardestrom, S. Jansson. Plant Physiol. 139, 1635 (2005).","DOI":"10.1104\/pp.105.066845"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_018","doi-asserted-by":"crossref","unstructured":"doi:10.1104\/pp.010063, T. S. Feild, D. W. Lee, N. M. Holbrook. Plant Physiol. 127, 566 (2001).","DOI":"10.1104\/pp.010063"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_019","doi-asserted-by":"crossref","unstructured":"doi:10.1663\/0006-8101(2003)069[0149:TEOFA]2.0.CO;2, D. C. Close, C. L. Beadle. Bot. Rev. 69, 149 (2003).","DOI":"10.1663\/0006-8101(2003)069[0149:TEOFA]2.0.CO;2"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_020","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/jp014081c, J. C. Lima, C. Vautier-Giongo, E. Melo, A. Lopes, F. H. Quina, A. L. Macanita. J. Phys. Chem. A 106, 5851 (2002).","DOI":"10.1021\/jp014081c"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_021","doi-asserted-by":"crossref","unstructured":"A. A. Freitas, K. Shimizu, L. G. Dias, F. H. Quina. J. Braz. Chem. Soc. 18, 1537 (2007).","DOI":"10.1590\/S0103-50532007000800014"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_022","doi-asserted-by":"crossref","unstructured":"doi:10.1016\/S0009-2614(98)01199-3, J. C. Lima, I. Abreu, M. H. Santos, R. Brouillard, A. L. Macanita. Chem. Phys. Lett. 298, 189 (1998).","DOI":"10.1016\/S0009-2614(98)01199-3"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_023","doi-asserted-by":"crossref","unstructured":"M. Maestri, F. Pina, A. Roque, P. Passaniti. J. Photochem. Photobiol., A 137, 21 (2000).","DOI":"10.1016\/S1010-6030(00)00349-X"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_024","unstructured":"F. H. Quina, A. A. Freitas, A. Macanita, P. F. Silva, J. C. Lima. Spectrum 19, 18 (2006)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_025","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/jp054038f, L. Paulo, A. A. Freitas, P. F. Silva, K. Shimizu, F. H. Quina, A. L. Macanita. J. Phys. Chem. A 110, 2089 (2006).","DOI":"10.1021\/jp054038f"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_026","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/la0608314, A. A. Freitas, L. Paulo, A. L. Macanita, F. H. Quina. Langmuir 22, 7986 (2006).","DOI":"10.1021\/la0608314"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_027","doi-asserted-by":"crossref","unstructured":"doi:10.1002\/ejoc.200400318, A. C. Fernandes, C. C. Romao, C. P. Rosa, V. P. Vieira, A. Lopes, P. F. Silva, A. L. Macanita. Eur. J. Org. Chem. 23, 4877 (2004).","DOI":"10.1002\/ejoc.200400318"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_028","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/jp0265900, L. Giestas, C. Yihwa, J. C. Lima, C. Vautier-Giongo, A. Lopes, F. H. Quina, A. L. Macanita. J. Phys. Chem. A 107, 3263 (2003).","DOI":"10.1021\/jp0265900"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_029","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/la0522911, R. Rodrigues, C. Vautier-Giongo, P. F. Silva, A. C. Fernandes, R. Cruz, A. L. Macanita, F. H. Quina. Langmuir 22, 933 (2006).","DOI":"10.1021\/la0522911"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_030","unstructured":"A. A. Freitas, F. H. Quina, A. C. Fernandes, A. L. Macanita. Submitted for publication."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_031","unstructured":"P. F. Silva, J. C. Lima, F. H. Quina, A. L. Macanita. J. Phys. Chem. A 107, 3263 (2004)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_032","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/jp0140421, A. L. Macanita, P. F. Moreira Jr., J. C. Lima, F. H. Quina, C. Yihwa, C. Vautier-Giongo. J. Phys. Chem. A 106, 1248 (2002).","DOI":"10.1021\/jp0140421"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_033","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/jp027260i, P. F. Moreira Jr., L. Giestas, C. Yihwa, C. Vautier-Giongo, F. H. Quina, A. L. Macanita, J. C. Lima. J. Phys. Chem. A 107, 4203 (2003).","DOI":"10.1021\/jp027260i"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_034","doi-asserted-by":"crossref","unstructured":"doi:10.1093\/pcp\/pcg033, K. Yoshida, Y. Toyama-Kato, K. Kameda, T. Kondo. Plant Cell Physiol. 44, 262 (2003).","DOI":"10.1093\/pcp\/pcg033"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_035","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/jp972197w, N. J. Cherepy, G. P. Smestad, M. Gratzel, J. Z. Zhang. J. Phys. Chem. B 101, 9342 (1997).","DOI":"10.1021\/jp972197w"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_036","unstructured":"A. A. Lima, E. M. Sussuchi, W. F. Giovani. Croat. Chem. Acta 80, 29 (2007)."},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_037","doi-asserted-by":"crossref","unstructured":"doi:10.1016\/j.phytochem.2008.03.015, M. Mori, T. Kondo, K. Yoshida. Phytochemistry 69, 3151 (2008).","DOI":"10.1016\/j.phytochem.2008.03.015"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_038","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/jp052106s, P. F. Silva, J. C. Lima, A. A. Freitas, K. Shimizu, F. H. Quina, A. L. Macanita. J. Phys. Chem. A 109, 7329 (2005).","DOI":"10.1021\/jp052106s"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_039","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/jf035507i, M. J. Rein, M. Heinonen. J. Agric. Food Chem. 52, 3106 (2004).","DOI":"10.1021\/jf035507i"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_040","doi-asserted-by":"crossref","unstructured":"doi:10.1002\/chem.200801207, R. Rodrigues, P. F. Silva, K. Shimizu, A. A. Freitas, S. Kovalenko, N. Ernsting, F. H. Quina, A. Macanita. Chem.Eur. J. 15, 1397 (2009)","DOI":"10.1002\/chem.200801207"},{"key":"2022030519121882800_j_PAC-CON-08-09-28_ref_041","doi-asserted-by":"crossref","unstructured":"doi:10.1021\/cr00028a009, M. A. Miranda, H. Garcia. Chem. Rev. 94, 1063 (1994).","DOI":"10.1021\/cr00028a009"}],"container-title":["Pure and Applied Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.degruyter.com\/view\/journals\/pac\/81\/9\/article-p1687.xml","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1351\/PAC-CON-08-09-28\/xml","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1351\/PAC-CON-08-09-28\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,3,5]],"date-time":"2022-03-05T19:18:15Z","timestamp":1646507895000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1351\/PAC-CON-08-09-28\/html"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,8,19]]},"references-count":41,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2009,8,10]]},"published-print":{"date-parts":[[2009,8,10]]}},"alternative-id":["10.1351\/PAC-CON-08-09-28"],"URL":"https:\/\/doi.org\/10.1351\/pac-con-08-09-28","relation":{},"ISSN":["1365-3075","0033-4545"],"issn-type":[{"value":"1365-3075","type":"electronic"},{"value":"0033-4545","type":"print"}],"subject":[],"published":{"date-parts":[[2009,8,19]]}}}