This is an outdated version published on 08-03-2026. Read the most recent version.

Study of Flavonoids presente in Pomelo (Citrus máxima) by DSC, UV-VIS, IR, 1H AND 13C NMR AND MS

Authors

  • Leticia Malgarim Cordenonsi Programa de Pós-Graduação em Ciências Farmacêuticas (PPGCF) da Universidade Federal do Rio Grande do Sul
    • Rafaela Martins Sponchiado Programa de Pós-Graduação em Ciências Farmacêuticas (PPGCF) da Universidade Federal do Rio Grande do Sul
      • Sarah Chagas Campanharo Programa de Pós-Graduação em Ciências Farmacêuticas (PPGCF) da Universidade Federal do Rio Grande do Sul
        • Cassia Virgina Garcia Programa de Pós-Graduação em Ciências Farmacêuticas (PPGCF) da Universidade Federal do Rio Grande do Sul
          • Renata Platcheck Raffin Programa de Pós Graduação em Nanociências; Centro Universitário Franciscano
            • Elfrides Eva Schermann Schapoval Programa de Pós-Graduação em Ciências Farmacêuticas (PPGCF) da Universidade Federal do Rio Grande do Sul

              DOI:

              https://doi.org/10.22456/2527-2616.74097

              Keywords:

              Naringin, naringenin, flavonoids, Citrus maxima

              Abstract

              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

              Download data is not yet available.

              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. DOI: https://doi.org/10.1016/S1359-6446(97)01167-7

              Balunas, M.J., Kinghorn, A.D. Drug discovery from medicinal plants. Life Sciences. 2005; 78:431- 441. DOI: https://doi.org/10.1016/j.lfs.2005.09.012

              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. DOI: https://doi.org/10.1016/S0031-6997(24)01472-8

              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. DOI: https://doi.org/10.1111/j.1365-2621.2009.01989.x

              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 DOI: https://doi.org/10.1002/9781118468524.ch5

              Yokozawa, T., Dong, E., Liu, Z.W., Shimizu, M. Antioxidative Activity of Flavones and Flavonols. Phytother. Res. 1997; 11:446-449. DOI: https://doi.org/10.1002/(SICI)1099-1573(199709)11:6<446::AID-PTR128>3.3.CO;2-#

              Aherne, A.S., O’Brien, N.M. Dietary Flavonols: Chemistry, Food Content, and Metabolism. Nutrition. 2002; 18:75-81. DOI: https://doi.org/10.1016/S0899-9007(01)00695-5

              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. DOI: https://doi.org/10.1016/S0928-0987(02)00087-8

              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. DOI: https://doi.org/10.1093/carcin/11.12.2275

              Cook, N.C., Samman, S. Flavonoids— Chemistry, metabolism, cardioprotective effects, and dietary sources. J Nutr Biochem. 1996; 7:66-76 DOI: https://doi.org/10.1016/S0955-2863(95)00168-9

              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. DOI: https://doi.org/10.1016/S0022-2275(20)31634-5

              Badarya, O.A., Abdel-Maksoudb, S., Ahmedd, W.A., Owieda, G.H. Naringenin attenuates cisplatin nephrotoxicity in rats. Life Sciences. 2005; 76:2125- 2135. DOI: https://doi.org/10.1016/j.lfs.2004.11.005

              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. DOI: https://doi.org/10.3390/ijms11114539

              Liu, Q., Lu, L., Xião M. Cell surface engineering ofa-L-rhamnosidase for naringin hydrolysis. Bioresour Technol, 2012; 123:144-149. DOI: https://doi.org/10.1016/j.biortech.2012.05.083

              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. DOI: https://doi.org/10.1016/j.foodchem.2013.07.104

              Giron, D. Applications of thermal analysis and coupled techniques in pharmaceutical industry. J. Therm. Anal. Calorim. 2002; 68:335-357. DOI: https://doi.org/10.1023/A:1016015113795

              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. DOI: https://doi.org/10.1016/S0169-409X(01)00098-9

              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. DOI: https://doi.org/10.1016/S1773-2247(07)50018-3

              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. DOI: https://doi.org/10.1002/app.27249

              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. DOI: https://doi.org/10.1007/s10847-009-9705-8

              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. DOI: https://doi.org/10.1016/j.jfoodeng.2010.10.015

              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. DOI: https://doi.org/10.1016/j.carbpol.2013.07.010

              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. DOI: https://doi.org/10.12691/ces-1-4-7

              Farajtabar, A., Ghari, F. Spectral analysis of naringenin deprotonation in aqueous ethanol solutions. Chem. Pap. 2013; 67:538-545. DOI: https://doi.org/10.2478/s11696-013-0309-9

              Harborne, J.B., Williams, C.A. Advances in flavonoid research since. Phytochemistry. 2000; 55:481-504. DOI: https://doi.org/10.1016/S0031-9422(00)00235-1

              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 DOI: https://doi.org/10.3390/12071352

              Lopes, W.A., Fascio, M. Esquema para interpretação de espectros de substancias organicas na região do infravermelho. Quim. Nova. 2004; 27:670- 673. DOI: https://doi.org/10.1590/S0100-40422004000400025

              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. DOI: https://doi.org/10.1007/s00289-011-0453-8

              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. DOI: https://doi.org/10.1002/jrs.2166

              Agrawal, P.K. Carbon-13 NMR of Flavonoids. 1st Ed, Amsterdam: Elsevier, 1989. DOI: https://doi.org/10.1016/B978-0-444-87449-8.50007-9

              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. DOI: https://doi.org/10.1590/S0100-40422003000300004

              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. DOI: https://doi.org/10.1590/S0100-40422009000100025

              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. DOI: https://doi.org/10.1002/jssc.201000475

              Pretsch, E., Buhlmann, P., Affolter, C. Structure determination of organic compounds. 3rd Ed, London: Springer, 2000. DOI: https://doi.org/10.1007/978-3-662-04201-4

              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. DOI: https://doi.org/10.1590/S0100-40422009000500008

              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. DOI: https://doi.org/10.1016/j.foodchem.2009.03.023

              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. DOI: https://doi.org/10.1039/c2an16208c

              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. DOI: https://doi.org/10.1590/S0102-695X2005000100006

              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 DOI: https://doi.org/10.1021/jo071129v

              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. DOI: https://doi.org/10.1016/j.jpba.2005.07.031

              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. DOI: https://doi.org/10.1016/j.ijpharm.2005.10.018

              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. DOI: https://doi.org/10.1093/chromsci/bmt095

              Downloads

              Published

              28-08-2017 — Updated on 08-03-2026

              Versions

              How to Cite

              Cordenonsi, L. M., Sponchiado, R. M., Chagas Campanharo, S., Garcia, C. V., Raffin, R. P., & Schapoval, E. E. S. (2026). Study of Flavonoids presente in Pomelo (Citrus máxima) by DSC, UV-VIS, IR, 1H AND 13C NMR AND MS. Drug Analytical Research, 1(1), 31–37. https://doi.org/10.22456/2527-2616.74097 (Original work published August 28, 2017)

              Issue

              Vol. 1 No. 1 (2017)

              Section

              ORIGINAL ARTICLES

              License

              Copyright (c) 2017 Drug Analytical Research

              Creative Commons License

              This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.

              The Copyright holder of manuscripts published is Drug Analytical Research. Authors who publish with this journal are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.


              Licensing:

              Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License

              Users are allowed to read, download, copy, distribute, print, search, or link to the full texts of the articles, or use them for any other lawful purpose, without asking prior permission from the publisher or the author.

              Crossref
              Scopus
              Google Scholar
              Europe PMC

              Most read articles by the same author(s)