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Structures and biological activities of proanthocyanidins obtained from chinese quince by optimized subcritical water-ethanol extraction

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Abstract

Subcritical water-ethanol extraction (SWE) was performed to extract proanthocyanidins (PAs) from Chinese quince fruits. The extraction parameters (temperature, time, liquid-solid ratio) were optimized using response surface methodology (RSM), based on single-factor experiments. The optimal SWE conditions were: temperature, 135 °C; time, 31 min; liquid-solid ratio, 32 mL/g. The maximum PAs obtained were 22.36 ± 0.35 mg PB2/g DW, which matched predicted values. In the analysis of PAs, 7 compounds were identified: catechin, epicatechin, epicatechin gallate, epigallocatechin-3-gallate, and proanthocyanidins dimers, trimers and tetramers. Structurally, these PAs contained substantial procyanidin (PC) but little prodelphinidin (PD). The findings revealed that SWE yielded more total PA than the conventional method extraction (CME). Furthermore, compared with CME PAs, PAs obtained by SWE showed higher radical scavenging capacities (IC50: 139.32 µg/mL for DPPH; IC50: 113.11 µg/mL for ABTS) and stronger α-amylase inhibition (IC50: 88.29 µg/mL). These results indicate that SWE is an efficient method for the separation of PAs from Chinese quince. Chinese quince PAs represent a potentially valuable resource for use in functional foods and nutraceuticals.

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References

  1. X.C. Cheng, X.R. Guo, Z. Qin, H.M. Liu, J.R. He, X.D. Wang, Sequential aqueous acetone fractionation and characterization of Brauns native lignin separated from chinese quince fruit. Int. J. Biol. Macromol. 201, 67–74 (2022)

    Article  CAS  PubMed  Google Scholar 

  2. L.H. Zhang, H.D. Xu, S.f. Li, Effects of micronization on properties of Chaenomeles sinensis (Thouin) Koehne fruit powder. Innov. Food Sci. Emerg. Technol. 10(4), 633–637 (2009)

    Article  CAS  Google Scholar 

  3. J. Miao, C. Zhao, X. Liu, X. Chen, X. Mao, H. Huang, T. Wang, W. Gao, Chemical Composition and Bioactivities of Two Common Chaenomeles Fruits in China: Chaenomeles speciosa and Chaenomeles sinensis. J. Food Sci. 81(8), H2049-H2058 (2016)

  4. Z. Qin, H.M. Liu, X.C. Cheng, X.D. Wang, Effect of drying pretreatment methods on structure and properties of pectins extracted from chinese quince fruit. Int. J. Biol. Macromol. 137, 801–808 (2019)

    Article  CAS  PubMed  Google Scholar 

  5. Y. Hamauzu, H. Yasui, T. Inno, C. Kume, M. Omanyuda, P. Profile, Antioxidant property, and anti-influenza ViralActivity of chinese quince (Pseudocydonia sinensis Schneid.), Quince (Cydonia oblonga Mill.), and Apple (Malus domestica Mill.) Fruits. J. Agric. Food Chem. 53, 928–934 (2005)

    Article  CAS  PubMed  Google Scholar 

  6. M. Pinent, M. Blay, M.C. Bladé, M.J. Salvadó, L. Arola, A. Ardévol, Grape seed-derived procyanidins have an antihyperglycemic effect in streptozotocin-induced diabetic rats and insulinomimetic activity in insulin-sensitive cell lines. Endocrinology. 145(11), 4985–4990 (2004)

    Article  CAS  PubMed  Google Scholar 

  7. M. Monagas, M. Urpi-Sarda, F. Sanchez-Patan, R. Llorach, I. Garrido, C. Gomez-Cordoves, C. Andres-Lacueva, B. Bartolome, Insights into the metabolism and microbial biotransformation of dietary flavan-3-ols and the bioactivity of their metabolites. Food Funct. 1(3), 233–253 (2010)

    Article  CAS  PubMed  Google Scholar 

  8. H. Cao, B.H. Chen, B.S. Inbaraj, L. Chen, G. Alvarez-Rivera, A. Cifuentes, N. Zhang, D.J. Yang, J. Simal-Gandara, M. Wang, J. Xiao, Preventive potential and mechanism of dietary polyphenols on the formation of heterocyclic aromatic amines. Food Front. 1(2), 134–151 (2020)

    Article  Google Scholar 

  9. P.M. Aron, J.A. Kennedy, Flavan-3-ols: nature, occurrence and biological activity. Mol. Nutr. Food Res. 52(1), 79–104 (2008)

    Article  CAS  PubMed  Google Scholar 

  10. D. Ballesteros-Vivas, G. Alvarez-Rivera, E. Ibánez, F. Parada- Alfonso, A. Cifuentes, Integrated strategy for the extraction and profiling of bioactive metabolites from Passiflora mollissima seeds combining pressurized-liquid extraction and gas/liquid chromatography–high resolution mass spectrometry. J. Chromatogr. A 1595, 144–157 (2019)

    Article  CAS  PubMed  Google Scholar 

  11. K. Ou, L. Gu, Absorption and metabolism of proanthocyanidins. J. Funct. Foods 7, 43–53 (2014)

    Article  CAS  Google Scholar 

  12. S.T. Wang, W.L. Zhuo, Y.Q. Dan, Z. Qin, C.X. Zhang, J. Xi, H.M. Liu, Y.X. Ma, X.D. Wang, Inhibitory effects of chinese quince fruit proanthocyanidins with different polymerisation degrees on the formation of heterocyclic aromatic amines in chemical model systems. Int. J. Food Sci. Technol. 57(1), 330–341 (2021)

    Article  Google Scholar 

  13. T. Esatbeyoglu, B. Jaschok-Kentner, V. Wray, P. Winterhalter, Structure elucidation of procyanidin oligomers by low-temperature 1H NMR spectroscopy. J. Agric. Food Chem. 59(1), 62–69 (2011)

    Article  CAS  PubMed  Google Scholar 

  14. L. Montero, M. Herrero, M. Prodanov, E. Ibáñez, A. Cifuentes, Characterization of grape seed procyanidins by comprehensive two-dimensional hydrophilic interaction × reversed phase liquid chromatography coupled to diode array detection and tandem mass spectrometry. Anal. Bioanal Chem. 405(13), 4627–4638 (2012)

    Article  PubMed  Google Scholar 

  15. F. Dahmoune, B. Nayak, K. Moussi, H. Remini, K. Madani, Optimization of microwave-assisted extraction of polyphenols from Myrtus communis L. leaves. Food Chem. 166, 585–595 (2015)

    Article  CAS  PubMed  Google Scholar 

  16. N.R. Putra, D.N. Rizkiyah, A.H.A. Aziz, S. Machmudah, J. Jumakir, W. Waluyo, M.A.C. Yunus, Procyanidin and proanthocyanidin extraction from Arachis hypogaea skins by using supercritical carbon dioxide: optimization and modeling. J. Food Process. Preserv 45(9), e15689 (2021)

  17. J.K. Monrad, L.R. Howard, J.W. King, K. Srinivas, A. Mauromoustakos, Subcritical solvent extraction of procyanidins from dried red grape pomace. J. Agric. Food Chem. 58(7), 4014–4021 (2010)

    Article  CAS  PubMed  Google Scholar 

  18. S. Ibrahim, R. Santos, S. Bowra, Optimization of subcritical water mediated extraction of apple pomace polyphenolics and their antioxidant activity. J. Chromatogr. Sep. Technol. 9(5), 1000410 (2018)

    Article  Google Scholar 

  19. M. Herrero, A. Cifuentes, E. Ibañez, Sub- and supercritical fluid extraction of functional ingredients from different natural sources: plants, food-by-products, algae and microalgae a review. Food Chem. 98(1), 136–148 (2006)

    Article  CAS  Google Scholar 

  20. R. Bodoira, Y. Rossi, M. Montenegro, D. Maestri, A. Velez, Extraction of antioxidant polyphenolic compounds from peanut skin using water-ethanol at high pressure and temperature conditions. J. Supercrit Fluids 128, 57–65 (2017)

    Article  CAS  Google Scholar 

  21. Z. Yan, H. Zhang, C.S. Dzah, J. Zhang, C. Diao, H. Ma, Y. Duan, Subcritical water extraction, identification, antioxidant and antiproliferative activity of polyphenols from lotus seedpod. Sep. Purif. Technol. 236, 116217 (2020)

    Article  CAS  Google Scholar 

  22. X. Luo, J. Cui, H. Zhang, Y. Duan, Subcritical water extraction of polyphenolic compounds from sorghum (Sorghum bicolor L.) bran and their biological activities. Food Chem. 262, 14–20 (2018)

    Article  CAS  PubMed  Google Scholar 

  23. H. Teng, I.H. Jo, T.H. Choi, Optimization of Ultrasonic-assisted extraction of Phenolic Compounds from Chinese Quince (Chaenomeles sinensis) by response surface methodology. J. Korean Soc. App BI 53(5), 618–625 (2010)

    Article  CAS  Google Scholar 

  24. P.J. Magalhães, J.S. Vieira, L.M. Goncalves, J.G. Pacheco, L.F. Guido, A.A. Barros, Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: characterization by high-performance liquid chromatography–diode array detection–electrospray tandem mass spectrometry. J. Chromatogr. A 1217(19), 3258–3268 (2010)

    Article  PubMed  Google Scholar 

  25. K.M. Kalili, D. Cabooter, G. Desmet, A.D. Villiers, Kinetic optimisation of the reversed phase liquid chromatographic separation of proanthocyanidins on sub-2µm and superficially porous phases. J. Chromatogr. A 1236, 63–76 (2012)

    Article  CAS  PubMed  Google Scholar 

  26. S.F. Xu, B. Zou, J. Yang, P. Yao, C.M. Li, Characterization of a highly polymeric proanthocyanidin fraction from persimmon pulp with strong chinese cobra PLA2 inhibition effects. Fitoterapia 83, 153–160 (2012)

    Article  CAS  PubMed  Google Scholar 

  27. Y. Jiang, H. Zhang, X. Qi, G. Wu, Structural characterization and antioxidant activity of condensed tannins fractionated from sorghum grain. J. Cereal Sci. 92, 102918 (2020)

    Article  CAS  Google Scholar 

  28. C. Fu, D. Yang, W.Y.E. Peh, S. Lai, X. Feng, H. Yang, Structure and antioxidant activities of Proanthocyanidins from Elephant Apple (Dillenia indica Linn). J. Food Sci. 80(10), 2191–2199 (2015)

    Article  Google Scholar 

  29. J. Bao, Y. Cai, M. Sun, G. Wang, H. Corke, Anthocyanins, flavonols, and free radical scavenging activityof chinese bayberry (Myrica rubra) extracts and their color properties and stability. J. Agric. Food Chem. 53, 2327–2332 (2005)

    Article  CAS  PubMed  Google Scholar 

  30. Q. Zhu, S. Zhang, M. Wang, J. Chen, Z.P. Zheng, Inhibitory effects of selected dietary flavonoids on the formation of total heterocyclic amines and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in roast beef patties and in chemical models. Food Funct. 7(2), 1057–1066 (2016)

    Article  CAS  PubMed  Google Scholar 

  31. C. Fu, X. Yang, S. Lai, C. Liu, S. Huang, H. Yang, Structure, antioxidant and α-amylase inhibitory activities of longan pericarp proanthocyanidins. J. Funct. Foods 14, 23–32 (2015)

    Article  CAS  Google Scholar 

  32. Y. Gong, X. Zhang, L. He, Q. Yan, F. Yuan, Y. Gao, Optimization of subcritical water extraction parameters of antioxidant polyphenols from sea buckthorn (Hippophae rhamnoides L.) seed residue. J. Food Sci. Technol. 52(3), 1534–1542 (2015)

    Article  CAS  PubMed  Google Scholar 

  33. F. Ioannone, C.D.,D. Mattia, M.D. Gregorio, M. Sergi, M. Serafini, G. Sacchetti, Flavanols, proanthocyanidins and antioxidant activity changes during cocoa (Theobroma cacao L.) roasting as affected by temperature and time of processing. Food Chem. 174, 256–262 (2015)

    Article  CAS  PubMed  Google Scholar 

  34. B. Zhang, R. Yang, C.Z. Liu, Microwave-assisted extraction of chlorogenic acid from flower buds of Lonicera japonica Thunb. Sep. Purif. Technol. 62(2), 480–483 (2008)

    Article  CAS  Google Scholar 

  35. R. Zhang, D. Su, F. Hou, L. Liu, F. Huang, L. Dong, Y. Deng, Y. Zhang, Z. Wei, M. Zhang, Optimized ultra-high-pressure-assisted extraction of procyanidins from lychee pericarp improves the antioxidant activity of extracts. Biosci. Biotechnol. Biochem. 81(8), 1576–1585 (2017)

    Article  CAS  PubMed  Google Scholar 

  36. L.O. Tedeschi, Assessment of the adequacy of mathematical models. Agric. Syst. 89, 225–247 (2006)

    Article  Google Scholar 

  37. G. Peng, J. Gan, R. Dong, Y. Chen, J. Xie, Z. Huang, Y. Gu, D. Huang, Q. Yu, Combined microwave and enzymatic treatment improve the release of insoluble bound phenolic compounds from the grapefruit peel insoluble dietary fiber. LWT 149, 111905 (2021)

    Article  CAS  Google Scholar 

  38. L. Montero, M. Herrero, E. Ibánez, A. Cifuentes, Profiling of phenolic compounds from different apple varieties using comprehensive two-dimensional liquid chromatography. J. Chromatogr. A 1313, 275–283 (2013)

    Article  CAS  PubMed  Google Scholar 

  39. C.I. Cheigh, E.Y. Chung, M.S. Chung, Enhanced extraction of flavanones hesperidin and narirutin from Citrus unshiu peel using subcritical water. J. Food Eng. 110(3), 472–477 (2012)

    Article  CAS  Google Scholar 

  40. Y. Yazaki, W.E. Hillis, Polyphenolic Extractives of Pinus radiata Bark. Holzforschung 31(1), 20–25 (1977)

    Article  CAS  Google Scholar 

  41. C.S. Ku, S.P. Mun, Characterization of proanthocyanidin in hot water extract isolated from Pinus radiata bark. Wood Sci. Technol. 41(3), 235–247 (2006)

    Article  Google Scholar 

  42. A. Cvetanović, J. Švarc-Gajić. Z. Zeković, U. Gašić, Ž Gašić, G. Zengin, P. Mašković, M.F. Mahomoodally, S. Durović, Subcritical water extraction as a cutting edge technology for the extraction of bioactive compounds from chamomile: influence of pressure on chemical composition and bioactivity of extracts. Food Chem. 266, 389–396 (2018)

    Article  PubMed  Google Scholar 

  43. Q. Li, C. Liu, T. Li, D.J. McClements, Y. Fu, J. Liu, Comparison of phytochemical profiles and antiproliferative activities of different proanthocyanidins fractions from Choerospondias axillaris fruit peels. Food Res. Int. 113, 298–308 (2018)

    Article  CAS  PubMed  Google Scholar 

  44. H.C. Zhou, Y.M. Lin, S.D. Wei, N.F. Tam, Structural diversity and antioxidant activity of condensed tannins fractionated from mangosteen pericarp. Food Chem. 129(4), 1710–1720 (2011)

    Article  CAS  Google Scholar 

  45. T.T. Lv, Z. Qin, S.T. Wang, H.M. Liu, Y.X. Ma, Y.Z. Zheng, X.D. Wang, Effect of proanthocyanidin-rich extracts from chinese quince (Chaenomeles sinensis) fruit on the physical and oxidative stability of sunflower oil‐in‐water emulsions. Int. J. Food Sci. Technol. 56(11), 5547–5559 (2021)

    Article  CAS  Google Scholar 

  46. R. Arimboor, C. Arumughan, Effect of polymerization on antioxidant and xanthine oxidase inhibitory potential of sea buckthorn (H. rhamnoides) proanthocyanidins. J. Food Sci. 77(10), 1036–1041 (2012)

    Article  Google Scholar 

  47. M. Iftikhar, H. Zhang, A. Iftikhar, A. Raza, N. Begum, A. Tahamina, H. Syed, M. Khan, J. Wang, Study on optimization of ultrasonic assisted extraction of phenolic compounds from rye bran. LWT 134, 110243 (2020)

    Article  CAS  Google Scholar 

  48. K. Tadera, Y. Minami, K. Takamatsu, T. Matsuoka, Inhibition of α-glucosidase and α-amylase by flavonoids. J. Nutr. Sci. Vitaminol 53, 149–153 (2006)

    Article  Google Scholar 

  49. H. Rasouli, S.M. Hosseini-Ghazvini, H. Adibi, R. Khodarahmi, Differential alpha-amylase/alpha-glucosidase inhibitory activities of plant-derived phenolic compounds: a virtual screening perspective for the treatment of obesity and diabetes. Food Funct. 8(5), 1942–1954 (2017)

    Article  CAS  PubMed  Google Scholar 

  50. Q. Li, J. Chen, T. Li, C. Liu, Y. Zhai, J. McClements, J. Liu, Separation and characterization of polyphenolics from underutilized by products of fruit production (Choerospondias axillaris peels): inhibitory activity of proanthocyanidins against glycolysis enzymes. Food Funct. 6(12), 3693–3701 (2015)

    Article  CAS  PubMed  Google Scholar 

  51. S. Ersan, ÖG.ç Üstündağ, R. Carle, R.M. Schweiggert, Subcritical water extraction of phenolic and antioxidant constituents from pistachio (Pistacia vera L.) hulls. Food Chem. 253, 46–54 (2018)

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

This work was funded by the Doctor Foundation of Henan University of Technology (No: 2021BS051) and China Agriculture Research System of MOF and MARA (CARS14-1-29).

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Wang, ST., Dan, YQ., Zhang, CX. et al. Structures and biological activities of proanthocyanidins obtained from chinese quince by optimized subcritical water-ethanol extraction. Food Measure 17, 1703–1713 (2023). https://doi.org/10.1007/s11694-022-01739-x

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