Journal List > Korean J Nutr > v.42(3) > 1043759

Korean J Nutr. 2009 Apr;42(3):278-290. Korean.
Published online April 30, 2009.  https://doi.org/10.4163/kjn.2009.42.3.278
© 2009 The Korean Nutrition Society
Composition of Flavonoids and Antioxidative Activity from Juice of Jeju Native Citrus Fruits during Maturation
Yong Dug Kim,1 Weon Jun Ko,1 Kyung Soo Koh,1 You Jin Jeon,2 and Soo Hyun Kim3
1Research and Development Center, Jeju Special Self-Governing Province Development Corp., Jeju 690-961, Korea.
2Faculty of Marine Biomedical Science, Jeju National University, Jeju 690-756, Korea.
3Department of Food Bioengineering, Jeju National University, Jeju 690-756, Korea.

To whom correspondence should be addressed. (Email: kshyun@cheju.ac.kr )
Received March 24, 2009; Revised April 09, 2009; Accepted April 13, 2009.

Abstract

This study aims to evaluate the changes of flavonoid contents and antioxidants activity of Jeju native citrus fruits juice according to the harvest date. Flavonoids such as quercatagetin, narirutin, hesperidin and neohesperidin were contained most plentifully in the juice of Jigak (Citrus aur- antium) by 573.73 mg/100 mL, Sadoogam (C. pseudogulgul) by 393.99 mg/100 mL, Soyooja by 29.63 mg/100 mL and Jigak (C. aurantium) by 201.23 mg/100 mL in the late August, respectively. The highest contents of nob-iletin, sinensetin and tangeretin among polymethoxyflavones were found in the juice of Hongkyool (C. tachibana) by 7.39 mg/100 mL, 2.24 mg/100 mL, 0.63 mg/100 mL in the late August, respectively. 3,5,6,7,8,3',4'-Heptamet-hoxyflavone recorded the highest amount in Punkyool (C. tangerina) by 0.27 mg/100 mL in the late August, but the other polymethoxyflavones including 3',4',7,8-tetramethoxyflavone, 3',4'-dimethoxyflavone, 4'-methoxyflavone, 5,6,7,3',4',5'-hexamethoxyflavone, scutellarein tetramethylether were observed only trace amount in all the citrus fruits. Flavonoid contents in the citrus fruit juices were the highest during early maturation and decreased rapidly while ripening. Total polyphenol contents were the highest in the late August and decreased with ripening. However from the late December, the contents were increased again. Antioxidant activities of the fruits were evaluated as electron donating ability and were the lowest in the late September and increased with the fruit ripening. These results suggest that quercetagetin among all the flavonoids was most plentiful in Jigak and Dangyooja (C. grandis), so that the fruits could be used for industrial material of flavonoids and antioxidant agents.

Keywords: citrus; flavonoid; nobiletin; tangeretin; antioxidative activity

Figures


Fig. 1
HPLC chromatogram of standard flavonoids. Retention time (min): narirutin, 13.5; quercetagetin, 16.3; hesperidin, 17.9; neohes-peridin, 20.0; sinensetin, 30.7; 3',4',7,8-tetramethoxyflavone, 32.4; 3',4'-dimethoxy- flavone, 38.9; 5,6,7,3',4',5'-hexamethoxyflavone, 41.3; nobiletin, 46.2; scutellarein tetramethylether, 48.2; 3,5,6,7,8,3',4'-heptamethoxyflavone, 56.1; 4'-methoxyflav-one, 59.1; tangeretin, 68.0. Detector wavelength: 280 nm.
Click for larger image


Fig. 2
Changes of total polyphenolic contents from Jeju native citrus juice according to harvest date. The data represent the mean±SD of three determi- nation.
Click for larger image

Tables


Table 1
Sampling place and time of citrus fruits
Click for larger image


Table 2
Operation conditions of HPLC for flavonoids analysis
Click for larger image


Table 3
Changes of flavonoid contents of Jeju native citrus juice according to harvest date (unit: mg/100 mL)
Click for larger image

Notes

This work was supported by Education program for environment favorable agriculture & subtropical bio-industry.

References
1. Jeju Special self-Governing Province. Annual report of statistics 2006. 2007.
2. Rhyu MR, Kim EY, Bae IY, Park YK. Contents of naringin, hesperidin and neohesperidin in premature Korean citrus fruits. Korean J Food Sci Technol 2002;34(1):132–135.
3. Eun JB, Jung YM, Woo GJ. Identification and determination of dietary fibers and flavonoids in pulp and peel of Korean tangerine (Citrus aurantium var.). Korean J Food Sci Technol 1996;28(2):371–377.
4. Song EY, Choi YH, Kang KH, Koh JS. Free sugar, organic acid, hesperidin, naringin and inorganic elements changes of Cheju citrus fruits according to harvest date. Korean J Food Sci Technol 1998;30(2):306–312.
5. Lee CH, Kang YJ. HPLC analysis of some flavonoids in citrus fruits. Korean J Postharvest Sci Technol 1997;4(2):181–187.
6. Veldhuis MK, Swift LJ, Scott WC. Fully-methoxylated flavones in florida orange juices. J Agric Food Chem 1970;18(4):590–592.
7. Ting SV, Rouseff RL, Dougherty MH, Attaway JA. Determination of some methoxylated flavones in citrus juices by high performance liquid chromatography [HPLC]. J Food Sci 1979;44(1):69–71.
8. Del Rio JA, Arcas MC, Benavente O, Sabater F, Ortuno A. Changes of polymethoxylated flavone levels during development of Citrus aurantium (cv. Sevillano) fruits. Planta Med 1998;64:575–576.
9. Ortuño AM, Arcas MC, Benavente-Garcia O, Del Río JA. Evolution of polymethoxyflavones during development of tangelo Nova fruits. Food Chem 1999;66(2):217–220.
10. Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M. Quantitation of flavonoid constituents in Citrus fruits. J Agric Food Chem 1999;47(9):3565–3571.
11. Kawaii S, Tomono Y, Katase E, Ogawa K, Nonomura-Nakano M, Nesumi H, Yoshida T, Sugiura M, Yano M. Quantitative study of fruit flavonoids in Citrus hybrids of King (C. nobilis) and Mukaku Kishu (C. kinokuni). J Agric Food Chem 2001;49(8):3982–3986.
12. Kim YC, Koh KS, Koh JS. Changes of flavonoids in the peel of Jeju native citrus fruits during maturation. Food Sci Biotechnol 2001;10(5):483–487.
13. Baik SO, Bock JY, Chun HJ, Jeong SI, Han WS, Kim IK. Quantitative distribution and analysis of methoxylated flavonoids in citruses and Korean chung-pi. Anal Sci Technol 2001;14(4):331–339.
14. Nogata Y, Sakamoto K, Shiratsuchi H, Ishii T, Yano M, Ohta H. Flavonoid composition of fruit tissues of citrus species. Biosci Biotechnol Biochem 2006;70(1):178–192.
15. Jeong WS, Park SW, Chung SK. The antioxidative activity of Korean Citrus unshiu peels. Foods Biotechnol 1997;6(4):292–296.
16. Kim HJ, Bae KH, Eun JB, Kim MK. Effects of hesperidin extracted from tangerine peel on Cd and lipid metabolism, and antioxidative capacity in rats. Korean J Nutr 1999;32(2):137–149.
17. Anagnostopoulou MA, Kefalas P, Papageorgiou VP, Assimopoulou AN, Boskou D. Radical scavenging activity of various extracts and fractions of sweet orange peel (Citrus sinensis). Food Chem 2006;94(1):19–25.
18. Mokbel MS, Hashinaga F. Evaluation of the antioxidant activity of extracts from buntan (Citrus grandis Osbeck) fruit tissues. Food Chem 2006;94(4):529–534.
19. Kurowska EM, Borradaile NM, Spence JD, Carroll KK. Hypocholesterolemic effects of dietary citrus juice in rabbits. Nutr Res 2000;20(1):121–129.
20. Kim BK, Cha JY, Cho YS. Effects of citrus flavonoid, hesperidin and naringin on lipid metabolism in HepG2 cells. Korean J Life Sci 1999;9(4):382–388.
21. Lio M, Uyeda M, Iwanami T, Nakagawa Y. Flavonoid as a possible preventive of dental carries. Agric Biol Chem 1984;48(8):2143–2145.
22. Han SS, You IJ. Studies on antimicrobial activities and safety of natural naringin in Korea. Kor J Mycol 1988;16(1):1–8.
23. Son HS, Kim HS, Kwon TB, Ju JS. Isolation, purification and hypotensive effect of bioflavonoids in Citrus sinensis. J Korean Soc Food Sci Nutr 1992;21(2):136–142.
24. Hertog MGL, Hollman PCH, Katan MB. Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J Agric Food Chem 1992;40(12):2379–2383.
25. Middleton E Jr, Kandaswami C. Potential health-promoting properties of citrus flavonoids. Food Technology 1994;48(11):115–119.
26. El-Shafae AM. Bioactive polymethoxyflavones and flavanone glycosides from the peels of Citrus deliciosa. Honghua yao xue za zhi 2002;54:199–206.
27. Hirano T, Abe K, Gotoh M, Oka K. Citrus flavone tangeretin inhibits leukaemic HL-60 cell growth partially through induction of apoptosis with less cytotoxicity on normal lymphocytes. Br J Cancer 1995;72:1380–1388.
28. AOAC. Method 914-915 Association of Official Analytical Chemists. 15th ed. Washington, DC, USA: 1985. Official Method of Analysis.
29. Kang YH, Park YK, Lee GD. The nitrite scavenging and electron donating ability of phenolic compounds. J Korean Food Sci Technol 1996;28(2):232–239.
30. Hertog MG, Feskens EJ, Hollman PC, Katan MB, Kromhout D. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet 1993;342(8878):1007–1011.
31. Li S, Mao W, Cao X, Liang S, Ding Z, Li N. Inhibition of rat lens aldose reductase by quercetagetin and patuletin. Yan Ke Xue Bao 1991;7(1):29–30.
32. Parejo I, Bastida J, Viladomat F, Codina C. Acylated quercetagetin glycosides with antioxidant activity from Tagetes maxima. Phytochemistry 2005;66:2356–2362.
33. Mouly P, Gaydou EM, Auffray A. Simultaneous separation of flavanone glycosides and polymethoxylated flavones in citrus juices using liquid chromatography. J Chromatography A 1998;800(2):171–179.
34. Kang YJ, Yang MH, Ko WJ, Park SR, Lee BG. Studies on the major components and antioxidative properties of whole fruit powder and Juice prepared from premature mandarin orange. Korean J Food Sci Technol 2005;37(5):783–788.
35. Cha JY, Kim SY, Jeong SJ, Cho YS. Effects of hesperetin and naringenin on lipid concentration in orotic acid treated mice. Korean J Life Sci 1999;9(4):389–394.
36. Tanaka T, Makita H, Kawabata K, Mori H, Kakumoto M, Satoh K, Hara A, Sumida T, Tanaka T, Ogawa H. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally ccurring flavonoids, diosmin and hesperidin. Carcinogenesis 1997;18(5):957–965.
37. Ishiwa J, Sato T, Mimaki Y, Sashida Y, Yano M, Ito A. A Citrus flavonoid, nobiletin, suppresses production and gene expression of matrix metalloproteinase 9/gelatinase B in rabbit synovial fibroblasts. J Rheumatol 2000;27(1):20–25.
38. Bracke ME, Bruyneel EA, Vermeulen SJ, Vennekens K, Maeck VN, Mareel MN. Citrus flavonoid effect on tumor invasion and metastasis. Food Technol 1994;48:121–124.
39. An BJ, Bae MJ, Choi HJ, Zhang YB, Sung TS, Choi C. Isolation of polyphenol compounds from the leaves of Korean Persimmon (Diospyrus kaki L. Folium). J Korean Soc Agric Chem Biotechnol 2002;45(4):212–217.
40. Ahmad N, Gupta S, Mukhtar H. Green tea polyphenol epigallocatechin-3-gallate differentially modulates nuclear factor κB in cancer cells versus normal cells. Archives Biochem Biophy 2000;376(2):338–346.
41. Yoo KM, Hwang IK. In vitro effect of yuza (Citrus junos SIEB ex TANAKA) extracts on proliferation of human prostate cancer cells and antioxidant activity. Korean J Food Sci Technol 2004;36(2):339–344.
42. Yoo KM, Kim CE, Kim DI, Huh D, Hwang IK. Antioxidant activity and physicochemical characteristics of tangerine peel tea prepared with Citrus unshiu cultivated in Cheju. Korean J Food Cookery Sci 2005;21(3):354–359.
43. Oh HS, An YS, Na IS, Oh MC, Oh CK, Kim SH. Inhibition of n-nitrosodimethylamine formation of extracts from citrus seeds. Korean J Food Cookery Sci 2003;19(5):640–646.
44. Jung SJ, Lee JH, Song HN, Seong NS, Lee SE, Baek NI. Screening for antioxidant activity of plant medicinal extracts. J Korean Soc Appl Biol Chem 2004;47(1):135–140.
45. Jayaprakasha GK, Patil BS. In vitro evaluation of the antioxidant activities in fruit extracts from citron and blood orange. Food Chemistry 2007;101:410–418.
46. Lim HK, Yoo ES, Moon JY, Jeon YJ, Cho SK. Antioxidant activity of extracts from Dangyuja (Citrus grandis Osbeck) fruits produced in Jeju Island. Food Sci Biotechnol 2006;15(2):312–316.