DFT study of free radical scavenging activity of erodiol

[1] Bartmess, J. E. (1994). Thermodynamics of the electron and the proton. The Journal of Physical Chemistry, 98, 6420–6424. DOI: 10.1021/j100076a029. http://dx.doi.org/10.1021/j100076a02910.1021/j100076a029Suche in Google Scholar

[2] Bors, W., Heller, W., Michel, C., & Saran, M. (1990). Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods in Enzymology, 186, 343–355. DOI: 10.1016/0076-6879(90)86128-i. http://dx.doi.org/10.1016/0076-6879(90)86128-I10.1016/0076-6879(90)86128-ISuche in Google Scholar

[3] Cai, Y. Z., Sun, M., Xing, J., Luo, Q., & Corke, H. (2006). Structure-radical scavenging activity relationship of phenolic compounds from traditional Chinese medical plants. Life Sciences, 78, 2872–2888. DOI: 10.1016/j.lfs.2005.11.004. http://dx.doi.org/10.1016/j.lfs.2005.11.00410.1016/j.lfs.2005.11.004Suche in Google Scholar

[4] Cao, G. H., Sofic, E., & Prior, R. L. (1997). Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships. Free Radical Biology and Medicine, 22, 749–760. DOI: 10.1016/s0891-5849(96)00351-6. http://dx.doi.org/10.1016/S0891-5849(96)00351-610.1016/S0891-5849(96)00351-6Suche in Google Scholar

[5] de Heer, M. I., Korth, H. G., & Mulder, P. (1999). Poly methoxy phenols in solution: O-H bond dissociation enthalpies, structures, and hydrogen bonding. The Journal of Organic Chemistry, 64, 6969–6975. DOI: 10.1021/jo9901485. http://dx.doi.org/10.1021/jo990148510.1021/jo9901485Suche in Google Scholar

[6] Fecka, I., & Cisowski, W. (2005). Tannins and flavonoids from the Erodium cicutarium herb. Zeitschrift für Naturforschung Section B, 60, 555–560. 10.1515/znb-2005-0513Suche in Google Scholar

[7] Foti, M. C., Daquino, C., & Geraci, C. (2004). Electron-transfer reaction of cinnamic acids and their methyl esters with the DPPH. radical in alcoholic solutions. The Journal of Organic Chemistry, 69, 2309–2314. DOI: 10.1021/jo035758q. http://dx.doi.org/10.1021/jo035758q10.1021/jo035758qSuche in Google Scholar PubMed

[8] Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery, J. A., Stratmann, R. E., Burant, J. C., Dapprich, S., Millam, J. M., Daniels, A. D., Kudin, K. N., Strain, M. C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q., Morokuma, K., Malick, A. D., Rabuck, K. D., Raghavachari, K., Foresman, J. B., Cioslowski, J., Ortiz, J. V., Baboul, A. G., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J. L., Gonzalez, C., Head-Gordon, M., Replogle, E. S., & Pople, J. A. (2009). Gaussian 09, Revision A1 [computer software]. Wallingford, CT, USA: Gaussian. Suche in Google Scholar

[9] Glendening, E. D., Badenhoop, J, K., Reed, A. E., Carpenter, J. E., Bohmann, J. A., Morales, C. M., & Weinhold, F. (2001). NBO 5.0. [computer software]. Madison, WI, USA: Theoretical Chemistry Institute, University of Wisconsin. Suche in Google Scholar

[10] Hertog, M. G. L., & Hollman, P. C. H. (1996). Potential health effects of the dietary flavonol quercetin. European Journal of Clinical Nutrition, 50, 63–71. Suche in Google Scholar

[11] Hillenbrand, M., Zapp, J., & Becker, H. (2004). Depsides from the petals of Papaver rhoeas. Planta Medica, 70, 380–382. DOI: 10.1055/s-2004-818956. http://dx.doi.org/10.1055/s-2004-81895610.1055/s-2004-818956Suche in Google Scholar PubMed

[12] Huynh, M. H. V., & Meyer, T. J. (2007). Proton-coupled electron transfer. Chemical Reviews, 107, 5004–5064. DOI: 10.1021/cr0500030. http://dx.doi.org/10.1021/cr050003010.1021/cr0500030Suche in Google Scholar PubMed PubMed Central

[13] Klein, E., & Lukeš, V. (2006). DFT/B3LYP study of the substituent effect on the reaction enthalpies of the individual steps of single electron transfer-proton transfer and sequential proton loss electron transfer mechanisms of phenols antioxidant action. The Journal of Physical Chemistry A, 110, 12312–12320. DOI: 10.1021/jp063468i. http://dx.doi.org/10.1021/jp063468i10.1021/jp063468iSuche in Google Scholar PubMed

[14] Klein, E., Lukeš, V., & Iličin, M. (2007). DFT/B3LYP study of tocopherols and chromans antioxidant action energetics. Chemical Physics, 336, 51–57. DOI: 10.1016/j.chemphys.2007.05.007. http://dx.doi.org/10.1016/j.chemphys.2007.05.00710.1016/j.chemphys.2007.05.007Suche in Google Scholar

[15] Kumar, S., & Müller, K. (1999). Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth. Journal of Natural Products, 62, 821–823. DOI: 10.1021/np980378z. http://dx.doi.org/10.1021/np980378z10.1021/np980378zSuche in Google Scholar

[16] Kumar, S., & Müller, K. (2000). Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid. European Journal of Medicinal Chemistry, 35, 405–411. DOI: 10.1016/s0223-5234(00)00132-x. http://dx.doi.org/10.1016/S0223-5234(00)00132-X10.1016/S0223-5234(00)00132-XSuche in Google Scholar

[17] Leopoldini, M., Marino, T., Russo, N., & Toscano, M. (2004a). Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent. Theoretical Chemistry Accounts, 111, 210–216. DOI: 10.1007/s00214-003-0544-1. http://dx.doi.org/10.1007/s00214-003-0544-110.1007/s00214-003-0544-1Suche in Google Scholar

[18] Leopoldini, M., Pitarch, I. P., Russo, N., & Toscano, M. (2004b). Structure, conformation, and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study. The Journal of Physical Chemistry A, 108, 92–96. DOI: 10.1021/jp035901j. http://dx.doi.org/10.1021/jp035901j10.1021/jp035901jSuche in Google Scholar

[19] Leopoldini, M., Marino, T., Russo, N., & Toscano, M. (2004c). Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism. The Journal of Physical Chemistry A, 108, 4916–4922. DOI: 10.1021/jp037247d. http://dx.doi.org/10.1021/jp037247d10.1021/jp037247dSuche in Google Scholar

[20] Litwinienko, G., & Ingold, K. U. (2007). Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Accounts of Chemical Research, 40, 222–230. DOI: 10.1021/ar0682029. http://dx.doi.org/10.1021/ar068202910.1021/ar0682029Suche in Google Scholar PubMed

[21] Lv, P. C., Xiao, Z. P., Fang, R. Q., Li, H. Q., Zhu, H. L., & Liu, C. H. (2009). Synthesis, characterization, and structure-activity relationship analysis of novel depsides as potential antibacterials. European Journal of Medicinal Chemistry, 44, 1779–1787. DOI: 10.1016/j.ejmech.2008.04.019. http://dx.doi.org/10.1016/j.ejmech.2008.04.01910.1016/j.ejmech.2008.04.019Suche in Google Scholar PubMed

[22] Mandado, M., Graña, A. M., & Mosquera, R. A. (2004). AIM charge density study of simple natural phenolic antioxidants. Chemical Physics Letters, 400, 169–174. DOI: 10.1016/j.cplett.2004.10.097. http://dx.doi.org/10.1016/j.cplett.2004.10.09710.1016/j.cplett.2004.10.097Suche in Google Scholar

[23] Marenich, A. V., Cramer, C. J., & Truhlar, D. G. (2009). Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. The Journal of Physical Chemistry B, 113, 6378–6396. DOI: 10.1021/jp810292n. http://dx.doi.org/10.1021/jp810292n10.1021/jp810292nSuche in Google Scholar PubMed

[24] Marković, Z., Mentus, S. V., & Marković, J. M. D. (2009). Electrochemical and density functional theory study on the reactivity of fisetin and its radicals: Implications on in vitro antioxidant activity. The Journal of Physical Chemistry A, 113, 14170–14179. DOI: 10.1021/jp907071v. http://dx.doi.org/10.1021/jp907071v10.1021/jp907071vSuche in Google Scholar PubMed

[25] Marković, Z. S., & Manojlović, N. T. (2010). Analytical characterization of lichexanthone in lichen: HPLC, UV spectroscopic, and DFT analysis of lichexanthone extracted from Laurera benguelensis (Mull. Arg.) Zahlbr. Monatshefte für Chemie, 141, 945–952. DOI: 10.1007/s00706-010-0349-6. http://dx.doi.org/10.1007/s00706-010-0349-610.1007/s00706-010-0349-6Suche in Google Scholar

[26] Marković, Z., Milenković, D., Đorović, J., Marković, J. M. D., Stepanić, V., Lučić, B., & Amić, D. (2012a). PM6 and DFT study of free radical scavenging activity of morin. Food Chemistry, 134, 1754–1760. DOI: 10.1016/j.foodchem.2012.03.124. http://dx.doi.org/10.1016/j.foodchem.2012.03.12410.1016/j.foodchem.2012.03.124Suche in Google Scholar PubMed

[27] Marković, Z., Milenković, D., Đorović, J., Marković, J. M. D., Stepanić, V., Lučić, B., & Amić, D. (2012b). Free radical scavenging activity of morin 2′-O − phenoxide anion. Food Chemistry, 135, 2070–2077. DOI: 10.1016/j.foodchem.2012.05.119. http://dx.doi.org/10.1016/j.foodchem.2012.05.11910.1016/j.foodchem.2012.05.119Suche in Google Scholar PubMed

[28] McLean, A. D., & Chandler, G. S. (1980). Contracted Gaussianbasis sets for molecular calculations. 1. Second row atoms, Z = 11–18. Journal of Chemical Physics, 72, 5639–5648. DOI: 10.1063/1.438980. http://dx.doi.org/10.1063/1.43898010.1063/1.438980Suche in Google Scholar

[29] McQuarrie, D. A. (2000). Statistical mechanics. Sausalito, CA, USA: University Science Books. Suche in Google Scholar

[30] Merrick, J. P., Moran, D., & Radom, L. (2007). An evaluation of harmonic vibrational frequency scale factors. The Journal of Physical Chemistry A, 111, 11683–11700. DOI: 10.1021/jp073974n. http://dx.doi.org/10.1021/jp073974n10.1021/jp073974nSuche in Google Scholar PubMed

[31] Meyer, T. J., Huynh, M. H. V., & Thorp, H. H. (2007). The possible role of proton-coupled electron transfer (PCET) in water oxidation by photosystem II. Angewandte Chemie International Edition, 46, 5284–5304. DOI: 10.1002/anie.200600917. http://dx.doi.org/10.1002/anie.20060091710.1002/anie.200600917Suche in Google Scholar PubMed

[32] Moa, M. J. G., Mandado, M., & Mosquera, R. A. (2006). QTAIM charge density study of natural cinnamic acids. Chemical Physics Letters, 424, 17–22. DOI: 10.1016/j.cplett.2006.04.034. http://dx.doi.org/10.1016/j.cplett.2006.04.03410.1016/j.cplett.2006.04.034Suche in Google Scholar

[33] Musialik, M., & Litwinienko, G. (2005). Scavenging of DPPH. radicals by vitamin E is accelerated by its partial ionization: The role of sequential proton loss electron transfer. Organic Letters, 7, 4951–4954. DOI: 10.1021/ol051962j. http://dx.doi.org/10.1021/ol051962j10.1021/ol051962jSuche in Google Scholar PubMed

[34] Neamati, N., Hong, H. X., Mazumder, A., Wang, S. M., Sunder, S., Nicklaus, M. C., Milne, G. W. A., Proksa, B., & Pommier, Y. (1997). Depsides and depsidones as inhibitors of HIV-1 integrase: Discovery of novel inhibitors through 3D database searching. Journal of Medicinal Chemistry, 40, 942–951. DOI: 10.1021/jm960759e. http://dx.doi.org/10.1021/jm960759e10.1021/jm960759eSuche in Google Scholar PubMed

[35] Nielsen, J., Nielsen, P. H., & Frisvad, J. C. (1999). Fungal depside, guisinol, from a marine derived strain of Emericella unguis. Phytochemistry, 50, 263–265. DOI: 10.1016/s0031-9422(98)00517-2. http://dx.doi.org/10.1016/S0031-9422(98)00517-210.1016/S0031-9422(98)00517-2Suche in Google Scholar

[36] Ono, M., Masuoka, C., Koto, M., Tateishi, M., Komatsu, H., Kobayashi, H., Igoshi, K., Ito, Y., Okawa, M., & Nohara, T. (2002). Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (Vaccinium ashei). Chemical and Pharmaceutical Bulletin, 50, 1416–1417. DOI: 10.1248/cpb.50.1416. http://dx.doi.org/10.1248/cpb.50.141610.1248/cpb.50.1416Suche in Google Scholar

[37] Proksa, B., Adamcová, J., Šturdová, M., & Fuska, J. (1994). Metabolites of Pseudevernia furfuracea (L.) Zopf. and their inhibition potential of proteolytic enzymes. Pharmazie, 49, 282–283. Suche in Google Scholar

[38] Raghavachari, K., Binkley, J. S., Seeger, R., & Pople, J. A. (1980). Self-consistent molecular orbital methods. XX. Basis set for correlated wave-functions. Journal of Chemical Physics, 72, 650–654. DOI: 10.1063/1.438955. http://dx.doi.org/10.1063/1.43895510.1063/1.438955Suche in Google Scholar

[39] Reynertson, K. A., Wallace, A. M., Adachi, S., Gil, R. R., Yang, H., Basile, M. J., D’Armiento, J., Weinstein, I. B., & Kennelly, E. J. (2006). Bioactive depsides and anthocyanins from Jaboticaba (Myrciaria cauliflora). Journal of Natural Products, 69, 1228–1230. DOI: 10.1021/np0600999. http://dx.doi.org/10.1021/np060099910.1021/np0600999Suche in Google Scholar

[40] Rice-Evans, C. A., & Miller, N. J. (1996). Antioxidant activities of flavonoids as bioactive components of food. Biochemical Society Transactions, 24, 790–795. DOI: 10.1042/bst0240790. 10.1042/bst0240790Suche in Google Scholar

[41] Rice-Evans, C. A., Miller, N. J., & Paganga, G. (1996). Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biology and Medicine, 20, 933–956. DOI: 10.1016/0891-5849(95)02227-9. http://dx.doi.org/10.1016/0891-5849(95)02227-910.1016/0891-5849(95)02227-9Suche in Google Scholar

[42] Rimarčík, J., Lukeš, V., Klein, E., & Ilčin, M. (2010). Study of the solvent effect on the enthalpies of homolytic and heterolytic N-H bond cleavage in p-phenylenediamine and tetracyano-p-phenylenediamine. Journal of Molecular Structure: THEOCHEM, 952, 25–30. DOI: 10.1016/j.theochem.2010.04.002. http://dx.doi.org/10.1016/j.theochem.2010.04.00210.1016/j.theochem.2010.04.002Suche in Google Scholar

[43] Trouillas, P., Marsal, P., Siri, D., Lazzaroni, R., & Duroux, J. L. (2006). A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: The specificity of the 3-OH site. Food Chemistry, 97, 679–688. DOI: 10.1016/j.foodchem.2005.05.042. http://dx.doi.org/10.1016/j.foodchem.2005.05.04210.1016/j.foodchem.2005.05.042Suche in Google Scholar

[44] Wayner, D. D. M., Lusztyk, E., & Ingold, K. U. (1996). Application of photoacoustic calorimetry to the measurement of the O-H bond strength in vitamin E (α- and δ-tocopherol) and related phenolic antioxidants. The Journal of Organic Chemistry, 61, 6430–6433. DOI: 10.1021/jo952167u. http://dx.doi.org/10.1021/jo952167u10.1021/jo952167uSuche in Google Scholar PubMed

[45] Weinhold, F., & Landis, C. R. (2005). Valency and bonding: A natural bond orbital donor-acceptor perspective. New York, NY, USA: Cambridge Academic Press. http://dx.doi.org/10.1017/CBO978051161456910.1017/CBO9780511614569Suche in Google Scholar

[46] Wright, J. S., Johnson, E. R., & DiLabio, G. A. (2001). Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants. Journal of the American Chemical Society, 123, 1173–1183. DOI: 10.1021/ja002455u. http://dx.doi.org/10.1021/ja002455u10.1021/ja002455uSuche in Google Scholar PubMed

[47] Yamamoto, Y., Miura, Y., Kinoshita, Y., Higuchi, M., Yamada, Y., Murakami, A., Ohigashi, H., & Koshimizu, K. (1995). Screening of tissue cultures and thalli of lichens and some of their active constituents for inhibition of tumor promoter-induced Epstein-Barr virus activation. Chemical and Pharmaceutical Bulletin, 43, 1388–1390. DOI: 10.1248/cpb.43.1388. http://dx.doi.org/10.1248/cpb.43.138810.1248/cpb.43.1388Suche in Google Scholar PubMed

[48] Zhao, Y., Schultz, N. E., & Truhlar, D. G. (2006). Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. Journal of Chemical Theory and Computation, 2, 364–382. DOI: 10.1021/ct0502763. http://dx.doi.org/10.1021/ct050276310.1021/ct0502763Suche in Google Scholar PubMed