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Synthesis and evaluation of the thermal behavior of flavonoids

Thermal decomposition of flavanone and 6-hydroxyflavanone

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Abstract

Flavonoids in the broad sense of the term are virtually universal plant pigments. Synthesis of flavanone and 6-hydroxyflavanone was carried out and identified by H and C NMR. Details concerning the thermal behavior were evaluated by thermogravimetry under oxygen and nitrogen purge gases. Additionally, the kinetic studies were evaluated from several heating rates (5, 10 and 20 °C min−1) and sample mass of 2 mg in open crucibles. The obtained data were evaluated with the isoconversional method, where the values of activation energy (E a/kJ mol−1) were plotted in function of the conversion degree (α). The results of thermal behavior of the flavanone under a nitrogen purge gas showed that this compound has a homogeneous degradation process while the hydroxyl group in the aromatic ring of 6-hydroxyflavanone there are two mass losses.

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References

  1. Harborne JB, Williams CA. Advances in flavonoid research since 1992. Phytochemistry. 2000;55:481–504.

    Article  CAS  Google Scholar 

  2. Gronquist M, Bezzerides A, Attygalle A, Meinwald J, Eisner M, Eisner T. Attractive and defensive function of the ultraviolet pigments of a flower (Hypericum calycinum). Proc Natl Acad Sci. 2001;98:13745–50.

    Article  CAS  Google Scholar 

  3. Rousseff RL, Martin SF, Yutsey CO. Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in citrus. J Agric Food Chem. 1987;35:1027–30.

    Article  Google Scholar 

  4. Heo HJ, Kim DO, Shin SC, Kim MJ, Kim BG, Shin DH. Effect of antioxidant flavanone, naringenin, from Citrus junoson neuroprotection. J Agric Food Chem. 2004;52:1520–5.

    Article  CAS  Google Scholar 

  5. Jjamen D, Mbafor JT, Fomum ZT, Kamanyi A, Mbanya JC, Recio MC, Giner RM, Máñez S, Rios JL. Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoids B, from Erythrina sigmoidea. Planta Med. 2004;70:104–7.

    Article  Google Scholar 

  6. Smejkal K, Svacinova J, Slapetova T, Schneiderova K, DallAcqua S, Innocenti G, Závalova V, Kollar P, Chudik S, Marek R, Julinek O, Urbanova M, Kartal M, Csollei M, Dolezal K. Cytotoxic activities of several geranyl-substituted flavanones. J Nat Prod. 2010;73:568–72.

    Article  CAS  Google Scholar 

  7. Toumi ML, Merzoug S, Boutefnouchet A, Tahraoui A, Ouali K, Guellati MA. Hesperidin, a natural citrus flavanone, alleviates hyperglycaemic state and attenuates embryopathies in pregnant diabetic mice. J Med Plants Res. 2009;3:862–9.

    CAS  Google Scholar 

  8. Bandgar BP, Gawande SS, Bodade RG, Gawande NM, Khobragade CN. Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidante and antimicrobial agentes. Bioorg Med Chem. 2009;17:8168–73.

    Article  CAS  Google Scholar 

  9. Cao G, Sofic E, Prior RL. Antioxidant and prooxidant behavior of flavonoids: structure-activity relationship. Free Radic Biol Med. 1997;22:749–60.

    Article  CAS  Google Scholar 

  10. Calderone V, Chericone S, Martinelli C, Testai L, Nardi A, Morelli I, Breschi MC, Matinotti E. Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels. Naunyn-Schmiedeberg’s Arch Pharmacol. 2004;370:290–8.

    Article  CAS  Google Scholar 

  11. Szliska E, Kostrzewa-Suslow E, Bronikowska J, Jaworska D, Janeczko T, Czuba ZP, Krol W. Synthetic flavanones augment the anticancer effect of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL). Molecules. 2012;17(10):11693–711.

    Article  Google Scholar 

  12. Kobenik M, Bernabé GA, Ribeiro CA, Capela JMV, Fertonani FL. Decomposition kinetics of iron (III)-diclofenac compound. J Therm Anal Calorim. 2009;97:493–6.

    Article  Google Scholar 

  13. Souza JL, Kobelnik M, Ribeiro CA, Capela JMV. Kinetics study of crystallization of PHB in presence of hydrociacids. J Therm Anal Calorim. 2009;97:525–852.

    Article  Google Scholar 

  14. Kobelnik M, Fontanari GG, Marques MR, Ribeiro CA, Crespi MS. Thermal behavior and chromatographic characterization of oil extracted from the nut of the Butia (Butia capitata). J Therm Anal Calorim. 2016;123:2517–22.

    Article  CAS  Google Scholar 

  15. Marques MR, Fontanari GG, Kobelnik M, Freitas RAMS, Arêas JAG. Effect of cooking on the thermal behavior of the cowpea bean oil (Vigna unguiculata L. Walp). J Therm Anal Calorim. 2015;120:289–96.

    Article  CAS  Google Scholar 

  16. Capela JMV, Capela MV, Ribeiro CA. Nonisothermal kinetic parameters estimated using nonlinear regression. J Math Chem. 2009;45:769.

    Article  CAS  Google Scholar 

  17. Zeraik ML, Ximenes VF, Regasini LO, Dutra LA, Silva DHS, Fonseca LM, Coelho D, Machado SAS, Bolzani VS. 4′-Aminochalcones as novel inhibitors of the chlorinating activity of myeloperoxidase. Curr Med Chem. 2012;19:5405–13.

    Article  CAS  Google Scholar 

  18. Vyazovkin S, Chrissafis K, Di Lorenzo ML, Koga N, Pijolat M, Roduitf B, Sbirrazzuoli N, Suñol JJ. ICTAC Kinetics Committee recommendations for collecting experimental thermal analysis data for kinetic computations. Therm Acta. 2014;590:1–23.

    Article  CAS  Google Scholar 

  19. Ledeti I, Vlase G, Vlase T, Fulias A. Kinetic analysis of solid-state degradation of pure pravastatin versus pharmaceutical formulation. J Therm Anal Calorim. 2015;121:1103–10.

    Article  CAS  Google Scholar 

  20. Zhang S, Wang S, Huang Z, Li Y, Tan Z. A kinetic analysis of thermal decomposition of polyaniline and its composites with rare earth oxides. J Therm Anal Calorim. 2015;119:1853–60.

    Article  CAS  Google Scholar 

  21. Du R, Wu K, Zhang L, She Y, Xu D, Chao C, Qin X, Zhang B. Thermal behavior and kinetic study on the pyrolysis of Shenfu coal by sectioning method. J Therm Anal Calorim. doi:10.1007/s10973-016-5475-x.

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Authors and Affiliations

  1. Departamento de Química Analítica, Instituto de Química, UNESP—Universidade Estadual Paulista, C.P. 355, Araraquara, SP, 14800-900, Brazil

    Leonardo Miziara Barboza Ferreira & Clóvis Augusto Ribeiro

  2. Centro Universitário do Norte Paulista, UNORP, São José do Rio Preto, SP, Brazil

    Marcelo Kobelnik

  3. Departamento de Química Orgânica, Instituto de Química, UNESP—Universidade Estadual Paulista, C.P. 355, Araraquara, SP, 14800-900, Brazil

    Luis Octavio Regasini, Luiz Antonio Dutra & Vanderlan da Silva Bolzani

Authors
  1. Leonardo Miziara Barboza Ferreira
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  2. Marcelo Kobelnik
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  3. Luis Octavio Regasini
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  4. Luiz Antonio Dutra
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  5. Vanderlan da Silva Bolzani
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  6. Clóvis Augusto Ribeiro
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Correspondence to Marcelo Kobelnik.

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Ferreira, L.M.B., Kobelnik, M., Regasini, L.O. et al. Synthesis and evaluation of the thermal behavior of flavonoids. J Therm Anal Calorim 127, 1605–1610 (2017). https://doi.org/10.1007/s10973-016-5896-6

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  • DOI: https://doi.org/10.1007/s10973-016-5896-6

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