Simultaneous Determination of Flavanone Glycosides in the Fruit of Citrus paradisi and C. grandis by HPLC-PDA

  • Piao, Xiang-Lan (Institute of Chinese Minority Traditional Medicine, Minzu University of China) ;
  • Wu, Qian (Institute of Chinese Minority Traditional Medicine, Minzu University of China) ;
  • Han, Saem (Department of Integrative Plant Science, Chung-Ang University) ;
  • Kim, Hyun-Young (Department of Food Science, Gyeongnam National University of Science and Technology) ;
  • Lee, Sang-Hyun (Department of Integrative Plant Science, Chung-Ang University)
  • Received : 2011.09.02
  • Accepted : 2011.12.10
  • Published : 2011.12.30

Abstract

An HPLC (high-performance liquid chromatography)-PDA (photodiode array) detection method was established for the determination of naringin, hesperidin and neohesperidin in the fruit of Citrus paradisi and C. grandis. The flavonoids were separated in less than 20 min using an YMC RP 18 column with isocratic elution using acetonitrile and water (23 : 77, v/v) at a flow rate of 1 ml/min, and a PDA detector. The levels of naringin, hesperidin and neohesperidin were 1345.92, 950.62, and 2078.82 ${\mu}g/g$, respectively, in the peel, and 102.43, 59.13, and 86.68 ${\mu}g/g$, respectively, in the flesh of C. paradisi. In C. grandis, the levels of naringin, hesperidin and neohesperidin were 3530.56, 80.00, and 5.26 ${\mu}g/g$, respectively, in the peel, and 59.59, 7.43, and 38.41 ${\mu}g/g$, respectively, in the flesh. The total content was highest in the peel, reaching 0.44% and 0.36% in C. paradisi and C. grandis, respectively, while the flesh contained only 0.025% and 0.011%, respectively. Therefore, the peels of C. paradisi and C. grandis are necessary for the processing and utilization of flavonoids.

Keywords

References

  1. Benavente-Garcia, O. and Castillo, J., Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity. J. Agric. Food Chem. 56, 6185-6205 (2008). https://doi.org/10.1021/jf8006568
  2. Berkarda, B., Koyuncu, H., Soybir, G., and Baykut, F., Inhibitory effect of hesperidin on tumour initiation and promotion in mouse skin. Res. Exp. Med. 198, 93-99 (1998). https://doi.org/10.1007/s004330050093
  3. Cho, E.J., Piao, X., Piao, L., Piao, H., Park, M.K., Kim, B.K., and Park, J.H., Chemical constituents of the fruit of Citrus junos. Nat. Prod. Sci . 6, 179-182 (2000).
  4. Gerber, M., Boutron-Ruault, M.C., Hercberg, S., Riboli, E., Scalbert, A., and Siess, M.H., Food and cancer: State of the art about the protective effect of fruits and vegetables. Bull. Cancer 89, 293-312 (2002).
  5. Han, S., Kim, H.M., Lee, J.M., Mok, S.Y., and Lee, S., Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong. J. Agric. Food Chem. 58, 9488-9491 (2010). https://doi.org/10.1021/jf102730b
  6. Havsteen, B., Flavonoids, a class of natural products of high pharmacological potency. Biochem. Pharmacol. 32, 1141-1148 (1983). https://doi.org/10.1016/0006-2952(83)90262-9
  7. Inoue, T. and Jackson, E.K., Strong antiproliferative effects of baicalein in cultured rat hepatic stellate cells. Eur. J. Pharmacol. 378, 129-135 (1999). https://doi.org/10.1016/S0014-2999(99)00418-5
  8. Kobayashi, S. and Tanabe, S., Evaluation of the anti-allergic activity of Citrus unshiu using rat basophilic leukemia RBL-2H3 cells as well as basophils of patients with seasonal allergic rhinitis to pollen. Int. J. Mol. Med. 17, 511-515 (2006).
  9. Middleton, E., Jr. Kandaswami, C., and Theoharides, T.C., The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 52, 673-751 (2000).
  10. Miller, E.G., Peacock, J.J., Bourland, T.C., Taylor, S.E., Wright, J.M., Patil, B.S., and Miller, E.G., Inhibition of oral carcinogenesis by citrus flavonoids. Nut. Cancer 60, 69-74 (2008).
  11. Nafisi, S., Hashemi, M., Rajabi, M., and Tajmir-Riahi, H.A., DNA adducts with antioxidant flavonoids: morin, apigenin, and naringin. DNA Cell Biol. 27, 433-442 (2008). https://doi.org/10.1089/dna.2008.0735
  12. Nugroho, A., Park, M.G., Jin, S.E., Choi, J.S., and Park, H.J., Quantitative analysis of flavanone glycosides and peroxynitrite scavenging effect of the five Oriental medicinal drugs (Aurantii nobilis Pericarpium, Citrii unshiu Pericarpium, Citrii unshiu Semen, Aurantii Fructus, Poncirii Fructus). Kor. J. Pharmacogn. 40, 370-375 (2009).
  13. Packer, L., Rimbach, G., and Virgili, F., Antioxidant activity and biologic properties of a procyanidin-rich extract from pine (Pinus maritima) bark, pycnogenol. Free Rad. Biol. Med. 27, 704-724 (1999). https://doi.org/10.1016/S0891-5849(99)00090-8
  14. Patel, A.V., Rojas-Vera, J., and Dacke, C.G., Therapeutic constituents and actions of Rubus species. Curr. Med. Chem. 11, 1501-1512 (2004). https://doi.org/10.2174/0929867043365143
  15. Ren, Y.J., Zhang, H.L., and Li, J.Y., Study on the chemical components and pharmacological action of Citrus paradisi cv. Changshan Huyou. J. Anhui Agric. Sci. 37, 9976-9977 (2009).
  16. Rhyu, M.R., Kim, E.Y., Bae, I.Y, and Park, Y.K., Contents of naringin, hesperidin, and neohesperidin in premature Korean Citrus fruits. Korean J. Food Sci. Technol. 34, 132-135 (2002).
  17. Song, H., Shi, W.J., Meng, X.Y., and He, L., Research progress in anticancer function of dietary fiber. Cereals and Oils 5, 46-48 (2006).
  18. Wang, C., Pan, Y., Fan, G., Chai, Y., and Wu, Y., Application of an efficient strategy based on MAE, HPLC-DAD-MS/MS and HSCCC for the rapid extraction, identification, separation and purification of flavonoids from Fructus Aurantii Immaturus. Biomed. Chromatogr. 24, 235-244 (2010). https://doi.org/10.1002/bmc.1278
  19. Wang, L.G., Jiang, L.Y., Huang, G.H., and Zhang, X.Q., Extraction and application of dietary fiber from Pomelo peel. J. Anhui Agric. Sci. 36, 10492-10494 (2008).
  20. Woo, K.L., Kim, J.I., Kim, M.C., and Chang, D.K., Determination of flavonoid and limonoid compounds in citron (Citrus junos Sieb. et Tanaka) seeds by HPLC and HPLC/MS. J. Korean Soc. Food Sci. Nutr. 35, 353-358 (2006). https://doi.org/10.3746/jkfn.2006.35.3.353
  21. Xu, G.H., Ye, X.Q., Xu, G.N., Hu, Y.X., and Liu, D.H., Effect of microwave treatment on the phenolic acids and flavanone glycosides contents and antioxidant capacity in Huyou peels. J. Chinese Inst. Food Sci. Technol. 7, 69-74 (2007).
  22. Yoo, K.M., Hwang, I.K., Park, J.H., and Moon, B., Major phytochemical composition of 3 native Korean Citrus varieties and bioactive activity on V79-4 cells induced by oxidative stress. J. Food Sci. 74, C462-C468 (2009). https://doi.org/10.1111/j.1750-3841.2009.01229.x
  23. Zhang, T.P., Peng, S.L., Wang, Z.F., and Chen, B.C., Introduction to the study and protection of Pomelo germplasm. Ecol. Sci. 20, 8-13 (2001).
  24. Zhao, X.M., Ye, X.Q., and Xi, Y.F., Study on the extraction of flavonoids and antioxidation in Huyou peels. J. Fruit Sci. 20, 261-265 (2003a).
  25. Zhao, X.M., Ye, X.Q., Zhu, D.Y., and Jiang, S.H., Preliminary study on volatile oil chemical composition and antibacterial activity of peel of Citrus paradise. China J. Chinese Mat. Med. 28, 1087-1089 (2003b).
  26. Zheng, S.H., Preparation and application of Hu You Pi Ba Cough Syrup. J. Jiangxi College of Trad. Chinese Med. 10, 128 (1998).