Einzeltreffer — DigiBib

Vitamin C or ascorbic acid is an indispensable micronutrient for human health found principally on citrus species such as lemon and orange fruits and vegetables. It was involved in the production of proteins such as collagen. Its biochemical mechanism is related to its antioxidant capacity; however, its function at the cellular level is still unclear. Several theoretical studies about antioxidant and redox mechanisms for ascorbic acid were suggested; however, no derivative was proposed. Thereby, an electronic study of antioxidant capacity for ascorbic acid derivatives was performed using theoretical chemistry at the DFT/ B3LYP/6-311 + + (2d,2p) level of theory. Simplified derivatives show that enol hydroxyls are more important than any other functional group. The vicinal enolic hydroxyl on β position is more important for antioxidant capacity of ascorbic than hydroxyl on α position. According to our molecular modifications, the keto-alkene compound showed the best values when compared to ascorbic acid in some molecular characteristics. No lactone derivatives have superior application potential as antioxidant when compared with ascorbic acid. Several structures are possible to be proposed and were related to spin density contributions and the increase of chemical stability. New promising structural derivatives related to ascorbic acid can be developed in the future.

Titel:	Essential features for antioxidant capacity of ascorbic acid (vitamin C).
Autor/in / Beteiligte Person:	Santos, KLB ; Bragança, VAN ; Pacheco, LV ; Ota, SSB ; Aguiar, CPO ; Borges, RS
Zeitschrift:	Journal of molecular modeling, Jg. 28 (2021-12-03), Heft 1, S. 1
Veröffentlichung:	Berlin : Springer, c1996-, 2021
Medientyp:	academicJournal
ISSN:	0948-5023 (electronic)
DOI:	10.1007/s00894-021-04994-9
Schlagwort:	Antioxidants metabolism Ascorbic Acid metabolism Humans Lactones chemistry Lactones metabolism Metabolic Networks and Pathways Molecular Structure Oxidation-Reduction Antioxidants chemistry Antioxidants pharmacology Ascorbic Acid chemistry Ascorbic Acid pharmacology
Sonstiges:	Nachgewiesen in: MEDLINE Sprachen: English Publication Type: Journal Article Language: English [J Mol Model] 2021 Dec 03; Vol. 28 (1), pp. 1. <i>Date of Electronic Publication: </i>2021 Dec 03. MeSH Terms: Antioxidants / chemistry ; Antioxidants / pharmacology ; Ascorbic Acid / chemistry ; Ascorbic Acid / pharmacology ; Antioxidants / metabolism ; Ascorbic Acid / metabolism ; Humans ; Lactones / chemistry ; Lactones / metabolism ; Metabolic Networks and Pathways ; Molecular Structure ; Oxidation-Reduction References: Sorice A, Guerriero E, Capone F, Colonna G, Castello G, Costantini S (2014) Mini Rev Med Chem 14(5):444–452. (PMID: 10.2174/1389557514666140428112602) ; Du J, Cullen JJ, Buettner GR (2012) Biochim Biophys Acta 1826(2):443–457. (PMID: 227280503608474) ; Aditi A, Graham DY (2012) Dig Dis Sci 57(10):2504–2515. (PMID: 10.1007/s10620-012-2203-7) ; Padayatty SJ, Katz A, Wang Y, Eck P, Kwon O, Lee J-H, Chen S, Corpe C, Dutta A, Dutta SK, Levine M (2013) J Am College Nut 22(1):18–35. (PMID: 10.1080/07315724.2003.10719272) ; Berg RW (2015) Appl Spect Rev 50(3):193–239. (PMID: 10.1080/05704928.2014.952431) ; Higgins MR, Izadi A, Kaviani M (2020) Int J Environ Res Public Health 17(22):8452. (PMID: 10.3390/ijerph17228452) ; Baschieri A, Amorati R, Benelli T, Mazzocchetti L, D’Angelo E, Valgimigli L (2019) Antioxidants 8(2):30. (PMID: 10.3390/antiox8020030) ; Bradshaw MP, Barril C, Clark AC, Prenzler PD, Scollary GR (2011) Crit Rev Food Sci Nut 51(6):479–498. (PMID: 10.1080/10408391003690559) ; Gueguen S, Pirollet P, Leroy P, Guilland J-C, Arnaud J, Paille F, Siest G, Visvikis S, Hercberg S, Herbeth B (2003) J Am Coll Nut 22(4):303–310. (PMID: 10.1080/07315724.2003.10719308) ; Rahal A, Kumar A, Singh V, Yadav B, Tiwari R, Chakraborty S, Dhama K (2014) Biomed Res Int 2014:761264. ; Kaźmierczak-Barańska J, Boguszewska K, Adamus-Grabicka A, Karwowski BT (2020) Nutrients 12(5):1501. (PMID: 10.3390/nu12051501) ; Gale CR, Ashurst HE, Powers HJ, Martyn CN (2001) Am J Clin Nutr 74(3):402–408. (PMID: 10.1093/ajcn/74.3.402) ; Kim T-J, Byun J-S, Kwon HS, Kim D-Y (2018) Biochem Biophys Res Commun 497(1):347–353. (PMID: 10.1016/j.bbrc.2018.02.083) ; Shenoy N, Creagan E, Witzig T, Levine M (2018) Cancer Cell 34(5):700–706. (PMID: 10.1016/j.ccell.2018.07.014) ; Moritz B, Schmitz AE, Rodrigues ALS, Dafre AL, Cunha MP (2020) J Nut Biochem 85:108459. (PMID: 10.1016/j.jnutbio.2020.108459) ; Nimse SB, Pal D (2015) RSC Adv 5:27986–28006. (PMID: 10.1039/C4RA13315C) ; Stewart JJP (2004) J Mol Model 10(2):155–164. (PMID: 10.1007/s00894-004-0183-z) ; Theophilou AK (2018) J Chem Phys 149:074104. (PMID: 10.1063/1.5038262) ; Lee C, Yang W, Parr RG (1998) Phys Rev B 37:785–789. (PMID: 10.1103/PhysRevB.37.785) ; Yu JK, Bannwarth C, Hohenstein EG, Martínez TJ (2020) J Chem Theory Comput 16(9):5499–5511. (PMID: 10.1021/acs.jctc.0c00644) ; Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich A, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery-Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2016) Gaussian 09, Revision A.02. ; Lobato CC, Ordoñez ME, Queiroz RL, Santos CBR, Borges RS (2020) Chem Data Collect 28:100464. (PMID: 10.1016/j.cdc.2020.100464) ; Messaadia L, Bekkar Y, Benamira M, Lahmar H (2020) Chem Phys Impact 1:100007. (PMID: 10.1016/j.chphi.2020.100007) ; Queiroz AN, Gomes BAQ, Moraes WM, Borges RS (2009) Eur J Med Chem 44(4):1644–1649. (PMID: 10.1016/j.ejmech.2008.09.023) ; Rajan VK, Muraleedharan K (2017) Food Chem 220:93–99. (PMID: 10.1016/j.foodchem.2016.09.178) ; Leopoldini M, Russo N, Toscano M (2011) Food Chem 125(2):288–306. (PMID: 10.1016/j.foodchem.2010.08.012) ; Borges RS, Castle SL (2015) Bioorg Med Chem Lett 25(21):4808–4811. (PMID: 10.1016/j.bmcl.2015.07.001) ; Ma Y, Feng Y, Diao T, Zeng W, Zuo Y (2020) J Mol Struct 1204:127509. (PMID: 10.1016/j.molstruc.2019.127509) ; Hernandez DA, Rodriguez-Zavala JG, Tenorio FJ (2020) Struct Chem 31(1):359–369. (PMID: 10.1007/s11224-019-01411-z) ; Santos KLB, Queiroz AN, Lobato CC, Vale JKL, Borges RS (2021) J Mol Model 27(2):26. (PMID: 10.1007/s00894-020-04647-3) ; Borges RS, Carneiro AS, Barros TG, Barros CAL, Chaves Neto AMJ, da Silva ABF (2014) J Mol Model 20(12):2541. (PMID: 10.1007/s00894-014-2541-9) ; Demianenko E, Ilchenko M, Grebenyuk A, Lobanov V, Tsendra O (2014) J Mol Model 20(3):2128. (PMID: 10.1007/s00894-014-2128-5) ; Bichara LC, Lanús HE, Nieto CG, Brandán AS (2010) J Phys Chem A 114(14):4997–5004. (PMID: 10.1021/jp912251g) ; Borges RS, Costa FM, Pereira TL, Araújo RL, Almeida ED, da Silva ABF (2018) J Braz Chem Soc 29(3):609–614. ; Diniz JEM, Borges RS, Alves CN (2004) J Mol Struct THEOCHEM 673(1–3):93–97. (PMID: 10.1016/j.theochem.2003.12.002) ; Alves CN, Borges RS, da Silva ABF (2006) Int J Quantum Chem 106(13):2617–2623. (PMID: 10.1002/qua.20992) ; Borges RS, Queiroz AN, Mendes APS, Araújo SC, França LCS, Franco ECS, Leal WG, da Silva ABF (2012) Int J Mol Sci 13(6):7594–7606. (PMID: 10.3390/ijms13067594) ; Liu Y, Liu C, Li J (2020) ACS Omega 5(39):25467–25475. (PMID: 10.1021/acsomega.0c04318) ; das Neves PAPFG, Lobato CC, Ferreira LR, Bragança VAN, Veiga AAS, Ordoñez ME, Barros VA, de Aguiar CPO, Borges RS (2020) J Mol Model 26:318. Contributed Indexing: Keywords: Antioxidant mechanism; Ascorbic acid; DFT; Pharmacophore; Redox capacity Substance Nomenclature: 0 (Antioxidants) ; 0 (Lactones) ; PQ6CK8PD0R (Ascorbic Acid) Entry Date(s): Date Created: 20211204 Date Completed: 20220321 Latest Revision: 20220321 Update Code: 20240513

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Essential features for antioxidant capacity of ascorbic acid (vitamin C).