The sonochemical effects of ultrasound (US) treatment on 14 flavonoids representing the main flavonoids in citrus fruit were investigated in a standard mixture by stability evaluation of a model system. Degradation products were further tentatively identified by Fourier transform infrared spectroscopy and high-performance liquid chromatography–ultraviolet detection–electrospray ionization tandem mass spectrometry. Thirteen flavonoids (i.e., eriocitrin, narirutin, neohesperidin, quercitrin, eridictyol, didymin, naringenin, luteolin, sinensetin, nobiletin, tangeretin, naringin, and hesperidin) were fairly stable whereas quercetin was degraded significantly by US treatment. The types of solvent and temperature used were important factors that determined the resulting degradation reactions. The degradation rate of quercetin was highest in 80% ethanol aqueous solution and decreased with increasing temperature. Longer US durations caused increases in the extent of quercetin degradation. Liquid height, ultrasonic intensity, pulse length, and duty cycle of US affected degradation rates but did not change the nature of degradation of the flavonoids. Four types of reactions occurred simultaneously for quercetin under US treatment: oxidation, addition, polymerization, and decomposition. Eight degradation products were tentatively identified as dimer, alcohol addition, oxidation, and decomposition products.
References
[1]
Grotewold E (2006) The science of flavonoids. New York: Springer. 1 p.
[2]
Xu GH, Ye XQ, Chen JC, Liu DH (2007) Effect of heat treatment on the phenolic compounds and antioxidant capacity of citrus peel extract. J. Agric. Food Chem 55: 330–335. doi: 10.1021/jf062517l
[3]
Tripoli E, Guardia ML, Giammanco S, Majo DD, Giammanco M (2007) Citrus flavonoids: molecular structure, biological activity and nutritional properties: a review. Food Chem 104: 466–479. doi: 10.1016/j.foodchem.2006.11.054
[4]
Zhou J, Zheng XX, Yang Q, Liang ZY, Li DH, et al. (2013) Optimization of ultrasonic-assisted extraction and radical-scavenging capacity of phenols and flavonoids from Clerodendrum cyrtophyllum Turcz Leaves. PloS one 8: e68392. doi: 10.1371/journal.pone.0068392
[5]
Cao DD, Li H, Yi JY, Zhang JJ, Che HL, et al. (2011) Antioxidant properties of the mung bean flavonoids on alleviating heat stress. PloS one 6: e21071. doi: 10.1371/journal.pone.0021071
[6]
Ioannou I, Hafsa I, Hamdi S, Charbonnel C, Ghoul M (2012) Review of the effects of food processing and formulation on flavonol and anthocyanin behaviour. J Food Eng 111: 208–217. doi: 10.1016/j.jfoodeng.2012.02.006
[7]
Buchner N, Krumbein A, Rohn S, Kroh LW (2006) Effect of thermal processing on the flavonols rutin and quercetin. Rapid Commun Mass Sp 20: 3229–3235. doi: 10.1002/rcm.2720
[8]
Vilkhu K, Mawson R, Simons L, Bates D (2008) Applications and opportunities for ultrasound assisted extraction in the food industry–A review. Innov Food Sci Emerg 9: 161–169. doi: 10.1016/j.ifset.2007.04.014
[9]
Sun YJ, Ma GP, Ye XQ, Kakuda Y, Meng RF (2010) Stability of all-trans-β-carotene under ultrasound treatment in a model system: effects of different factors, kinetics and newly formed compounds. Ultrason Sonochem 17: 654–661. doi: 10.1016/j.ultsonch.2009.12.005
[10]
Qiao LP, Ye XQ, Sun YJ, Ying J Q, Shen Y, et al. (2013) Sonochemical effects on free phenolic acids under ultrasound treatment in a model system. Ultrason Sonochem 20: 1017–1025. doi: 10.1016/j.ultsonch.2012.12.007
[11]
Iida Y, Tuziuti T, Yasui K, Towata A, Kozuka T (2008) Control of viscosity in starch and polysaccharide solutions with ultrasound after gelatinization. Innov Food Sci Emerg 9: 140–146. doi: 10.1016/j.ifset.2007.03.029
[12]
Paniwnyk L, Beaufoy E, Lorimer JP, Mason TJ (2001) The extraction of rutin from flower buds of Sophora japonica. Ultrason Sonochem 8: 299–301. doi: 10.1016/s1350-4177(00)00075-4
[13]
Robak J, Kisiel W, Wolbi? M (1991) Ultrasound-induced oxidation of flavonoids. Polish journal of pharmacology and pharmacy 43: 145–152.
[14]
Biesaga M, Pyrzynska K (2013) Stability of bioactive polyphenols from honey during different extraction methods. Food Chem 136: 46–54. doi: 10.1016/j.foodchem.2012.07.095
[15]
Biesaga M (2011) Influence of extraction methods on stability of flavonoids. J Chromatogr A 1218: 2505–2512. doi: 10.1016/j.chroma.2011.02.059
[16]
Kiani H, Sun DW, Zhang ZH (2012) The effect of ultrasound irradiation on the convective heat transfer rate during immersion cooling of a stationary sphere. Ultrason Sonochem 19: 1238–1245. doi: 10.1016/j.ultsonch.2012.04.009
[17]
Zhang YM, Zhou ZQ, Sun YJ, Shen Y, Zhong LZ, et al. (2012) Simultaneous determination of 18 flavonoids in citrus fruits by high-performance liquid chromatography. Scientia Agricultura Sinica 45: 3558–3565 (In Chinese)..
[18]
Ma YQ, Ye XQ, Hao YB, Xu GN, Xu GH, et al. (2008) Ultrasound - assisted extraction of hesperidin from penggan (Citrus reticulata) peel. Ultrason Sonochem 15: 227–232. doi: 10.1016/j.ultsonch.2007.03.006
[19]
Ma YQ, Ye XQ, Fang ZX, Chen JC, Xu GH, et al. (2008) Phenolic compounds and antioxidant activity of extracts from ultrasonic treatment of satsuma mandarin (Citrus unshiu Marc.) peel. J Agr Food Chem 56: 5682–5690. doi: 10.1021/jf072474o
[20]
Khan MK, Abert-Vian M, Fabiano-Tixier AS, Dangles O, Chemat F (2010) Ultrasound - assisted extraction of polyphenols (flavanone glycosides) from orange (Citrus sinensis L.) peel. Food Chem 119: 851–858. doi: 10.1016/j.foodchem.2009.08.046
[21]
Londo?o-Londo?o J, Lima VR, Lara O, Gil A, Pasa TBC, et al. (2010) Clean recovery of antioxidant flavonoids from citrus peel: optimizing an aqueous ultrasound-assisted extraction method. Food Chem 119: 81–87. doi: 10.1016/j.foodchem.2009.05.075
[22]
Elhamirad AH, Zamanipoor MH (2012) Thermal stability of some flavonoids and phenolic acids in sheep tallow olein. Eur J Lipid Sci Tech 114: 602–606. doi: 10.1002/ejlt.201100240
Hemwimol S, Pavasant P, Shotipruk A (2006) Ultrasound-assisted extraction of anthraquinones from roots of Morinda citrifolia. Ultrason Sonochem 13: 543–548. doi: 10.1016/j.ultsonch.2005.09.009
[25]
Sun YJ, Qiao LP, Ye XQ, Liu DH, Zhang XZ, et al. (2013) The sonodegradation of caffeic acid under ultrasound treatment: relation to stability. Molecules 18: 561–573. doi: 10.3390/molecules18010561
[26]
Romdhane M, Gourdon C, Casamatta G (1995) Local investigation of some ultrasonic devices by means of a thermal sensor. Ultrasonics 33: 221–227. doi: 10.1016/0041-624x(94)00023-i
[27]
Entezari MH, Nazary SH, Khodaparast MHH (2004) The direct effect of ultrasound on the extraction of date syrup and its micro-organisms. Ultrason Sonochem 11: 379–384.
[28]
Raso J, Manas P, Pagan R, Sala FJ (1999) Influence of different factors on the output power transferred into medium by ultrasound. Ultrason Sonochem 5: 157–162. doi: 10.1016/s1350-4177(98)00042-x
[29]
Kanthale PM, Gogate PR, Pandit AB, Wilhelm AM (2003) Mapping of an ultrasonic horn: link primary and secondary effects of ultrasound. Ultrason Sonochem 10: 331–335. doi: 10.1016/s1350-4177(03)00104-4
[30]
Gutiérrez M, Henglein A (1990) Chemical action of pulsed ultrasound: Observation of an unprecedented intensity effect. J Phys Chem 94: 3625–3628. doi: 10.1021/j100372a048
[31]
Sun YJ, Ye XQ (2013) Enhancement or reduction of sonochemical activity of pulsed ultrasound compared to continuous ultrasound at 20 kHz? Molecules 18: 4858–4867. doi: 10.3390/molecules18054858
[32]
Luque-García JL, Luque de Castro MD (2004) Ultrasound-assisted soxhlet extraction: an expeditive approach for solid sample treatment: application to the extraction of total fat from oleaginous seeds. J Chromatogr A 1034: 237–242. doi: 10.1016/j.chroma.2004.02.020
[33]
Mendoza-Wilson AM, Glossman-Mitnik D (2004) CHIH-DFT determination of the molecular structure, infrared and ultraviolet spectra of the flavonoid quercetin. J Mol Struc-Theochem 681: 71–76. doi: 10.1016/j.theochem.2004.04.054
[34]
Krishnamachari V, Levine LH, Pare PW (2002) Flavonoid oxidation by the radical generator AIBN: a unified mechanism for quercetin radical scavenging. J Agr Food Chem 50: 4357–4363. doi: 10.1021/jf020045e
[35]
Maini S, Hodgson H L, Krol E S (2012) The UVA and aqueous stability of flavonoids is dependent on B-ring substitution. J Agr Food Chem 60: 6966–6976. doi: 10.1021/jf3016128
[36]
Zhou A, Sadik OA (2008) Comparative analysis of quercetin oxidation by electrochemical, enzymatic, autoxidation, and freer adical generation techniques: a mechanistic study. J Agric Food Chem 56: 12081–12091. doi: 10.1021/jf802413v
[37]
Fahlman BM, Krol ES (2009) UVA and UVB radiation-induced oxidation products of quercetin. J Photoch Photobio B 97: 123–131. doi: 10.1016/j.jphotobiol.2009.08.009
[38]
Ramos FA, Takaishi Y, Shirotori M, Kawaguchi Y, Tsuchiya K, et al. (2006) Antibacterial and antioxidant activities of quercetin oxidation products from yellow onion (Allium cepa) skin. J Agric Food Chem 54: 3551–3557. doi: 10.1021/jf060251c
[39]
Gül?en A, Makris DP, Kefalas P (2007) Biomimetic oxidation of quercetin: isolation of a naturally occurring quercetin heterodimer and evaluation of its in vitro antioxidant properties. Food Res Int 40: 7–14. doi: 10.1016/j.foodres.2006.07.009
[40]
Cherviakovsky EM, Bolibrukh DA, Baranovsky AV, Vlasova TM, Kurchenko VP, et al. (2006) Oxidative modification of quercetin by hemeproteins. Biochem Bioph Res Co 342: 459–464. doi: 10.1016/j.bbrc.2006.12.105