Abstract
The free radical scavenging activity of protocatechuic acid has been studied in aqueous and lipid solutions, using the density functional theory. It was found to be a moderately good protector in non-polar environments (lipid), while in aqueous solution it is predicted to be an excellent peroxyl radical scavenger. In such media, the pH has an important role in the free radical scavenging activity of protocatechuic acid. At physiological pH, after the first peroxyl radical is scavenged, and in the presence of a good electron-donor species, such as the superoxide radical anion, the latter is consumed and protocatechuic acid is regenerated. This means that, under such conditions, it has the ability of scavenging several radical equivalents, two per cycle. An equivalent cyclic process can be assumed as possible also for other scavengers with the catechol moiety. If this assumption is confirmed, the role of compounds with a catechol moiety as free radical scavengers might be even more important that what has been assumed so far.
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Cabrini L, Barzanti V, Cipollone M, Fiorentini D, Grossi G, Tolomelli B, Zambonin L, Landi L (2001) J Agric Food Chem 49:6026–6032
Madrera RR, Lobo AP, Valles BS (2006) J Agric Food Chem 54:120–124
Slimestad R, Fossen T, Vagen IM (2007) J Agric Food Chem 55:10067–10080
Ma YQ, Ye XQ, Fang ZX, Chen JC, Xu GH, Liu DH (2008) J Agric Food Chem 56:5682–5690
Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (2008) J Agric Food Chem 56:4631–4636
Lin C-Y, Huang C-S, Huang C-Y, Yin M-C (2009) J Agric Food Chem 57:6661–6667
Vari R, D’Archivio M, Filesi C, Carotenuto S, Scazzocchio B, Santangelo C, Giovannini C, Masella R (2011) J Nutr Biochem 22:409–417
Vitaglione P, Donnarumma G, Napolitano A, Galvano F, Gallo A, Scalfi L, Fogliano V (2007) J Nutr 137:2043–2048
Chao CY, Yin MC (2009) Foodborne Pathog Dis 6:201–206
Stagos D, Kazantzoglou G, Theofanidou D, Kakalopoulou G, Magiatis P, Mitaku S, Kouretas D (2006) Mutat Res 609:165–175
Kwon YI, Vattem DA, Shetty K (2006) Asia Pac J Clin Nutr 15:107–118
Yen GC, Hsieh CL (2000) J Agric Food Chem 48:3431–3436
Liu CL, Wang JM, Chu CY, Cheng MT, Tseng TH (2002) Food Chem Toxicol 40:635–641
Shi GF, An LJ, Jiang B, Guan S, Bao YM (2006) Neurosci Lett 403:206–210
Hyogo A, Kobayashi T, del Saz EG, Seguchi H (2010) Int J Morphol 28:911–920
Zhang X, Shi G-F, Liu X-Z, An L-J, Guan S (2011) Cell Biochem Funct 29:342–347
Boyd NF, McGuire V (1991) Free Radic Biol Med 10:185–190
Nelson RL (1992) Free Radic Biol Med 12:161–168
Knekt P, Reunanen A, Takkunen H, Aromaa A, Heliovaara M, Hakuunen T (1994) Int J Cancer 56:379–382
Willcox JK, Ash SL, Catignani GL (2004) Crit Rev Food Sci Nutr 44:275–295
Riemersma RA, Wood DA, Macintyre CCA, Elton RA, Gey KF, Oliver MF (1991) Lancet 337:1–5
Salonen JT, Nyyssoner K, Korpela H, Tuomilehto J, Seppanen R, Salonen R (1992) Circulation 86:803–811
Street DA, Comstock G, Salkeld R, Klag M (1994) Circulation 90:1154–1161
Stephens NG, Parsons A, Schofield PM, Kelly F, Cheesman K, Mitchinson MJ, Brown MJ (1996) Lancet 347:781–786
Panasenko OM, Nova TV, Azizova OA, Vladimirov YA (1991) Free Radic Biol Med 10:137–148
Steinberg D (1991) Circulation 84:1421–1425
Janero DR (1991) Free Radic Biol Med 11:129–144
Hodis HN, Mack WJ, LaBree L, Cashin-Hemphill L, Sevanian A, Johnson R, Azen S (1995) J Am Med Assoc 273:1849–1854
Braekke K, Harsem NK, Staff AC (2006) Pediatr Res 60:560–564
Biri A, Bozkurt N, Turp A, Kavutcu M, Himmetoglu O, Durak I (2007) Gynecol Obstet Invest 64:187–192
Hracsko Z, Orvos H, Novak Z, Pal A, Varga IS (2008) Redox Rep 13:11–16
Christen Y (2000) Am J Clin Nutr 71:621S–629S
Halliwell B (2001) Drugs Aging 8:685–716
Butterfield DA (2002) Free Radic Res 36:1307–1313
Hatzipanayioti D, Karaliota A, Kamariotaki M, Aletras V, Petropouleas P (2006) Chem Phys 325:341–350
Kawabata J, Okamoto Y, Kodama A, Makimoto T, Kasai T (2002) J Agric Food Chem 50:5468–5471
Saito S, Okamoto Y, Kawabata J (2003) Biosci Biotechnol Biochem 67:1578–1579
Saito S, Kawabata J (2005) Tetrahedron 61:8101–8108
Saito S, Kawabata J (2006) Helv Chim Acta 89:1395–1407
Saito S, Gao H, Kawabata J (2006) Helv Chim Acta 89:821–831
Zhao Y, Schultz NE, Truhlar DG (2006) J Chem Theory Comput 2:364–382
Marenich AV, Cramer CJ, Truhlar DG (2009) J Phys Chem B 113:6378–6396
Velez E, Quijano J, Notario R, Pabón E, Murillo J, Leal J, Zapata E, Alarcon G (2009) J Phys Org Chem 22:971–977
Galano A, Alvarez-Idaboy JR (2009) Org Lett 11:5114–5117
Black G, Simmie JM (2010) J Comput Chem 31:1236–1248
Furuncuoglu T, Ugur I, Degirmenci I, Aviyente V (2010) Macromolecules 43:1823–1835
Zhao Y, Truhlar DG (2008) J Phys Chem A 112:1095–1099
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision A. 02. Gaussian, Wallingford
Okuno Y (1997) Chem Eur J 3:210–218
Benson SW (1960) The foundations of chemical kinetics, chap XV. McGraw-Hill, New York, pp 504–508
Eyring H (1935) J Chem Phys 3:107–115
Evans MG, Polanyi M (1935) Trans Faraday Soc 31:875–894
Truhlar DG, Hase WL, Hynes JT (1983) J Phys Chem 87:2664–2682
Truhlar DG, Kuppermann A (1971) J Am Chem Soc 93:1840–1851
Marcus RA (1964) Annu Rev Phys Chem 15:155–196
Marcus RA (1993) Rev Mod Phys 65:599–610
Marcus RA (1997) Pure Appl Chem 69:13–30
Collins FC, Kimball GE (1949) J Colloid Sci 4:425–437
Smoluchowski M (1917) Z Phys Chem 92:129–168
Truhlar DG (1985) J Chem Ed 62:104–106
Einstein A (1905) Ann Phys (Leipzig) 17:549–560
Stokes GG (1903) Mathematical and physical papers, vol 3. Cambridge University Press, Cambridge, p 55
Young D (2001) Computational chemistry: a practical guide for applying techniques to real world problems. Wiley, New York, pp 227–228
Allodi MA, Kirschner KN, Shields GC (2008) J Phys Chem A 112:7064–7071
Erdemgil FZ, Sanli S, Sanli N, Ozkan G, Barbosa J, Guiteras J, Beltran JL (2007) Talanta 72:489–496
Belcastro M, Marino T, Russo N, Toscano M (2006) Theor Chem Acc 115:361–369
Leopoldini M, Russo N, Chiodo S, Toscano M (2006) J Agric Food Chem 54:6343–6351
Leopoldini M, Rondinelli F, Russo N, Toscano M (2010) J Agric Food Chem 58:8862–8871
Leopoldini M, Russo N, Toscano M (2011) Food Chem 125:288–306
Perez-Gonzalez A, Galano A (2011) J Phys Chem B 115:1306–1314
Chiodo SG, Leopoldini M, Russo N, Toscano M (2010) Phys Chem Chem Phys 12:7662–7670
Galano A (2011) Theor Chem Acc 130:51–60
León-Carmona JR, Galano A (2011) J Phys Chem B 115:4538–4546
Terpinc P, Abramovic H (2010) Food Chem 121:366–371
Sies H (1997) Exp Physiol 82:291–295
Valko M, Rhodes CJ, Moncola J, Izakovic M, Mazur M (2006) Chem Biol Interact 160:1–40
Itagaki S, Kurokawa T, Nakata C, Saito Y, Oikawa S, Kobayashi M, Hirano T, Iseki K (2009) Food Chem 114:466–471
Masuda T, Yamada K, Maekawa T, Takeda Y, Yamaguchi H (2006) Food Sci Technol Res 12:173–177
Masuda T, Yamada K, Maekawa T, Takeda Y, Yamaguchi H (2006) J Agric Food Chem 54:6069–6074
De Grey AND (2002) J DNA Cell Biol 21:251–257
Rose RC, Bode AM (1993) FASEB J 7:1135–1142
Galano A, Tan DX, Reiter RJ (2011) J Pineal Res 51:1–16
Hatzipanayioti D, Petropouleas P (2010) Spectrochim Acta A 75:997–1007
Bielski BH (1978) J Photochem Photobiol 28:645–649
Galano A, Francisco-Márque M (2009) J Phys Chem B 113:11338–11345
Martínez A, Vargas R, Galano A (2010) Theor Chem Acc 127:595–603
Iuga C, Alvarez-Idaboy JR, Vivier-Bunge A (2011) J Phys Chem B 115:12234–12246
Galano A, Francisco-Márquez M, Alvarez-Idaboy JR (2011) J Phys Chem B 115:8590–8596
Galano A, Alvarez-Idaboy JR, Francisco-Marquez M, Medina ME (2012) Theor Chem Acc 131:1173
Galano A, Alvarez-Idaboy JR, Francisco-Marquez M (2011) J Phys Chem B 115:13101–13109
Galano A, Francisco-Marquez M, Alvarez-Idaboy JR (2011) Phys Chem Chem Phys 13:11199–11205
Martínez A, Galano A, Vargas R (2011) J Phys Chem B 115:12591–12598
Galano A (2011) Phys Chem Chem Phys 13:7147–7157
Galano A, Francisco-Márquez M (2009) J Phys Chem B 113:16077–16081
Galano A, Alvarez-Idaboy JR (2011) RSC Adv 1:1763–1771
Laitinen HA, Harris WE (1975) Chemical analysis: an advanced text and reference, chap 11, 2nd edn. McGraw-Hill, New York, pp 189–216
Rojas A, Gonzalez I (1986) Anal Chim Acta 187:279–285
Rojas-Hernández A, Ramírez MT (1991) Anal Chim Acta 246:435–442
Harvey D (2000) Modern analytical chemistry, chap 9. McGraw-Hill, New York, pp 273–367
Evans G, Uri N (1949) Trans Faraday Soc 45:224–230
Acknowledgments
The authors thank Laboratorio de Visualización y Cómputo Paralelo at UAM—Iztapalapa for the access to its computer facilities and project SEP-CONACyT 167491. Adriana Pérez-González acknowledges CONACyT for Doctoral fellowship.
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Galano, A., Pérez-González, A. On the free radical scavenging mechanism of protocatechuic acid, regeneration of the catechol group in aqueous solution. Theor Chem Acc 131, 1265 (2012). https://doi.org/10.1007/s00214-012-1265-0
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DOI: https://doi.org/10.1007/s00214-012-1265-0