Study of Flavonoids presente in Pomelo (Citrus máxima) by DSC, UV-VIS, IR, 1H AND 13C NMR AND MS
DOI:
https://doi.org/10.22456/2527-2616.74097Keywords:
Naringin, naringenin, flavonoids, Citrus maximaAbstract
Flavonoids are among the most important plant metabolites. Due to their potential benefits, there is a considerable interest in this natural product. In genus Citrus, some plants have not yet been much exploited in Brazil, as in the case of grapefruit (Citrus maxima), whose main flavonoids are naringin and their aglycone naringenin. The physico-chemical characteristics are important pre-requisites of reference chemical in future studies. In this context, the objective of this study was to determine the characterization of naringin and naringenin by melting point, DSC, UV-VIS, 1H and 13C NMR, IR and MS. Results revealed that, naringin and naringenin after characterization, can be used as a chemical of reference in future studies and contribute to seeking possible technological applications.Downloads
References
Verpoorte, R. Exploration of nature’s chemodiversity: the role of secondary metabolites as leads in drug development. Drug Discover Today. 1998; 3:232-238.
Balunas, M.J., Kinghorn, A.D. Drug discovery from medicinal plants. Life Sciences. 2005; 78:431- 441.
Middleton, E.J.R., Kandaswami, C., Theoharides, C.T. The Effects of Plant Flavonoids on Mammalian Cells: Implications for Inflammation, Heart Disease, and Cancer. Pharmacol. Rev. 2000; 52:673-751.
Sudto, K., Pornpalakul, S., Wanichwecharungruang, S. An efficient method for the large scale isolation of naringin from pomelo (Citrus grandis) peel. Int. J. Food Sci. Technol. 2009; 44:1737-1742.
Sayre, C.L., Gerde, K.D., Yáñez, J.A., Davies, N.M., Yáñez, J.A. Clinical Pharmacokinetics of Flavonoids, in Flavonoid Pharmacokinetics: Methods of Analysis, Preclinical and Clinical Pharmacokinetics, Safety, and Toxicology. 1st Ed, John Wiley & Sons, 2012
Yokozawa, T., Dong, E., Liu, Z.W., Shimizu, M. Antioxidative Activity of Flavones and Flavonols. Phytother. Res. 1997; 11:446-449.
Aherne, A.S., O’Brien, N.M. Dietary Flavonols: Chemistry, Food Content, and Metabolism. Nutrition. 2002; 18:75-81.
Gandhi, R., Pillai, O., Thilagavathi, R., Gopalakrishnan, B., Lal Kaul, C., Panchagnula, R. Characterization of Azithromycin hydrates. Eur. J. Pharm. Sci. 2002; 16:175-184.
Guengerich, F.P., Kim, H.D. In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis. 1990; 11:2275-2279.
Cook, N.C., Samman, S. Flavonoids— Chemistry, metabolism, cardioprotective effects, and dietary sources. J Nutr Biochem. 1996; 7:66-76
Wilcox, L.J., Borradaile, N.M., Huff, M.W. Secretion of hepatocyte apoB is inhibited by the flavonoids, naringenin and hesperetin, via reduced activity and expression of ACAT2 and MTP. Cardiovasc Drug Rev. 1999; 42:725-734.
Badarya, O.A., Abdel-Maksoudb, S., Ahmedd, W.A., Owieda, G.H. Naringenin attenuates cisplatin nephrotoxicity in rats. Life Sciences. 2005; 76:2125- 2135.
Ali, G., Hawa, Z.E.J. Synthesis of Phenolics and Flavonoids in Ginger (Zingiber officinale Roscoe) and Their Effects on Photosynthesis Rate. Asmah R., Int J Mol Sci. 2010; 11:4539-4555.
Liu, Q., Lu, L., Xião M. Cell surface engineering ofa-L-rhamnosidase for naringin hydrolysis. Bioresour Technol, 2012; 123:144-149.
ICH - International Conference on Harmonization. Q2R1- validation of Analytical procedure: Text and Methodology, 2005.
Ko, M.A., Cheigh, C., Chung M. Relationship analysis between flavonoids structure and subcritical water extraction (SWE). Food Chem. 2014; 143:147- 155.
Giron, D. Applications of thermal analysis and coupled techniques in pharmaceutical industry. J. Therm. Anal. Calorim. 2002; 68:335-357.
Armijo, C.J.V., Cristian, J., Costa, I.M., Longhini, R., Petzhold, C.L., Petrovick, P.R. Métodos termo-analíticos e suas aplicações nas ciências farmacêuticas. Caderno de Farmácia. 2004; 20:29-47.
Yu, L. Amorphous pharmaceutical solids: preparation, characterization and stabilization. Adv. Drug Delivery Rev. 2001; 48:27-42.
Lauro, M.R., Simone, F., Sansone, F., Iannelli, P., Aquino, R.P. Preparations and release characteristics of naringin and naringenin gastroresistant microparticles by spray-drying. J. Drug Delivery Sci. Technol. 2007 17:119-124.
Binello, A., Robaldo, B., Barge, A., Cavalli, R., Cravotto, G. Synthesis of Cyclodextrin Based Polymers and Their Use as Debittering Agents. J. Appl. Polym. Sci. 2008; 107:2549-2557.
Semalty, A., Semalty, M., Singh, D., Rawat, M.S.M. Preparation and characterization of phospholipid complexes of naringenin for effective drug delivery. Inclusion Phenom. Mol. Recognit. Chem. 2010; 67:253-260.
Sansone, F., Picerno, P., Mencherini, T., Villecco, F., D’ursi, A.M., Aquino, R.P., Lauro, M.R. Flavonoid microparticles by spray-drying: Influence of enhancers of the dissolution rate on properties and stability. J. Food Eng. 2011; 103:188-196.
Yang, L., Ma, S., Zhou, S., Chen, W., Yuan, M., Yin, Y., Yang, X. Preparation and characterization of inclusion complexes of naringenin with cyclodextrin or its derivative. Carbohydr. Polym. 2013; 98:861-869.
Ford, J.L., Tinmins, P. Pharmaceutical thermal analysis: technique and application. 1st Ed, New York: Willey-Interscience, 1986.
Silverstein, R.M., Webster, F.X., Kiemle, D.J. Identificação Espectrométrica de Compostos Orgânicos. 6th Ed, LTC: Rio de Janeiro, 2000.
Suetsugu, T., Iwai, H., Tanaka, M., Hoshino, M., Quitain, A., Sasaki, M., Goto, M. Extraction of Citrus Flavonoids from Peel of Citrus Junos Using Supercritical Carbon Dioxide with Polar Solvent. Adv. Chem. Eng. Sci. 2013; 1:87-90.
Farajtabar, A., Ghari, F. Spectral analysis of naringenin deprotonation in aqueous ethanol solutions. Chem. Pap. 2013; 67:538-545.
Harborne, J.B., Williams, C.A. Advances in flavonoid research since. Phytochemistry. 2000; 55:481-504.
Pereira, R.M.S., Andrades, N.E.D., Paulino, N., Sawaya, A.C.H.F., Eberlin, M.N., Marcucci, M.C., Favero, G.M., Novak, E.M., Bydlowski, S.P. Synthesis and Characterization of a Metal Complex Containing Naringin and Cu, and its Antioxidant, Antimicrobial, Antiinflammatory and Tumor Cell Cytotoxicity. Molecules. 2007; 12:1352-1366
Lopes, W.A., Fascio, M. Esquema para interpretação de espectros de substancias organicas na região do infravermelho. Quim. Nova. 2004; 27:670- 673.
Ma, X., Chen, R., Zheng, X., Youn, H., Chen, C. Preparation of molecularly imprinted CS membrane for recognizing naringin in aqueous media. Polym. Bull. 2011; 66:853-863.
Pavia, D.L., Lampman, G.M., Kriz, G.S. Introduction to Spectroscopy: a guide for students of organic chemistry. 3rd Ed, South Melbourme: Brooks/Cole, 2011.
Unsalan, O., Erdogdub, Y., Gulluoglub, M.T. FT-Raman and FT-IR spectral and quantum chemical studies on some flavonoid derivatives: Baicalein and Naringenin. J. Raman Spectrosc. 2009; 40:562-570.
Agrawal, P.K. Carbon-13 NMR of Flavonoids. 1st Ed, Amsterdam: Elsevier, 1989.
Moreira, F.P.M., Coutinho, V., Montanher, A.B.P., Caro, M.S.B., Brighente, I.M.C., et al. Flavonoides e triterpenos de Baccharis pseudotenuifolia– Bioatividade sobre Artemia salina. Quim. Nova, 2003.
Moccelini, S.K., Silva, V.C., Ndiaye, E.A., Sousa, P.T., Vieira, P.C. Estudo fitoquímico das cascas das raízes de Zanthoxylum rigidum Humb. & Bonpl. ex Willd (rutaceae). Quim. Nova. 2009 32:131-133.
Tang, D., Zhu, C., Zhong, S., Zhou, M. Extraction of naringin from pomelo peels as dihydrochalcone’s precursor. J. Sep. Sci. 2001; 34:113-117.
Pretsch, E., Buhlmann, P., Affolter, C. Structure determination of organic compounds. 3rd Ed, London: Springer, 2000.
Silva, T.M.S., Carvalho, M.G., Braz-Filho, R. Estudo espectroscópico em elucidação estrutural de flavonoides de Solanum jabrense agraa & nee S. paludosum moric. Quim. Nova. 2009; 32:1119-1128.
Maltese, F., Erkelens, C., Kooy, F., Choi,Y.H., Verpoorte, R. Identification of natural epimeric flavanone glycosides by NMR spectroscopy. Food Chemistry. 2009; 116:575-579.
Queiroz, L.H.K., Queiroz, D.P.K., Dhooghe, L., Ferreira, A.G., Giraudeau, P. Real-time separation of natural products by ultrafast 2D NMR coupled to online HPLC. Analyst. 2012; 137:2357-2361.
Costa, D.A., Silva, D.A., Costa, D.F., Silva, M.F.V., Souza, M.F., Agra, I.A., et al. Flavonóides glicosilados de Herissantia tiubae(K. Schum) Brizicky (Malvaceae) e testes farmacológicos preliminares do canferol 3,7-di-O-α-L-ramnopiranosídeo. Rev. Bras. Farmacogn. 2005; 15:23-29.
Bagno, A., Rastrelli, F., Saielli, G. Prediction of the 1H and 13C NMR Spectra of r-D-Glucose in Water by DFT Methods and MD Simulations. J. Org. Chem. 2007; 72:7373-7381
Fang, T., Wang, T., Ma, Y., Su, W., Bai, Y., Zhao, P. A rapid LC/MS/MS quantitation assay for naringin and its two metabolites in rats plasma. J. Pharm. Biomed. Anal. 2006; 40:454-459.
Ma, Y., Li, P., Chen, D., Fang, T., Li, H. Su, W. LC/MS/MS quantitation assay for pharmacokinetics of naringenin and double peaks phenomenon in rats plasm. Int. J. Pharm. 2006; 307:292-299.
Xiong, X., Jiang, J., Duan, J., Xie, Y., Wang, J., Zhai, S. Development and Validation of a Sensitive Liquid Chromatography–Tandem Mass Spectrometry Method for the Determination of Naringin and Its Metabolite, Naringenin, in Human Plasma J. Chromatogr. Sci. 2013.
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