Plant Foods for Human Nutrition

, Volume 61, Issue 2, pp 55–63 | Cite as

Citrus Flavonoids in Fruit and Traditional Chinese Medicinal Food Ingredients in China

  • Yanhua LuEmail author
  • Chongwei Zhang
  • Peter Bucheli
  • Dongzhi Wei


Flavonoids-enriched tissues of citrus such as peel, immature fruit and flower are consumed as culinary seasonings, tea ingredients in China for centuries. This HPLC quantitative study on the five citrus flavonoids, naringin, hesperidin, neohesperidin, sinensetin and nobiletin on a wide range of Chinese citrus fruits and several Traditional Chinese Medicinal food ingredients in East China, revealed a great diversity in flavonoid composition. Huyou peel (C. paradisi cv. Changshanhuyou) was found to be the best naringin (3.25%) and neohesperidin (2.76%) source; C. aurantium, a major ingredient of several citrus-related TCM, is also a suitable source of naringin and neohesperidin, and a good juice source for flavanone glycosides; the peel of Wenzhoumiju (C. unshiu) is one of the richest local species in hesperidin (up to 6.25%); Zaoju (C. subcompressa) has the highest content of nobiletin (0.59%), a polymethoxylated flavone. LC-ES-MS analysis of Zanthoxylum genus for flavonoids revealed for the first time the presence of significant amounts (0.74%) of hesperidin in the root of Liangmianzhen (Z. nitidum (Roxb.) DC), a relative of Sichuan pepper, which is a spice widely used in China.

Key words:

Citrus Flavonoid Flavanone glycoside Hesperidin HPLC LC-MS Naringin Neohesperidin Nobiletin Polymethoxylated flavone Sinensetin Traditional Chinese Medicine, TCM Zanthoxylum 



We sincerely thank Mr. Wen Falin, Mr. Chen Huashen, Mr. Chen Xiaoyi, Mr. Ge Liang, Mr. Han Zehong and Ms. Pan Xin for their warm help in providing samples and cultivar information.


  1. 1.
    Pizzorno J, Murray M (1999) Textbook of Natural Medicine, (2nd edn.). New York: Churchill Livingstone, p 1393.Google Scholar
  2. 2.
    Garg A, Garg S, Zaneveldand LJD, Singla AK (2001) Chemistry and Pharmacology of the Citrus Bioflavonoid Hesperidin. Phytother Res 15: 655–669.CrossRefGoogle Scholar
  3. 3.
    Galati EM, Monforte MT, Kirjavainen S, Forertieri AM, Tripodo MM (1994) Biological effects of hesperidin, a Citrus flavonoid. Part 1. Anti-inflammatory and analgesic activity. Farmaco 49: 709–712.Google Scholar
  4. 4.
    Tanaka T, Makita H, Ohnishi M, Hirose Y (1994) Chemoprevention of 4-nitroquinoline-1-oxide-induced oral carcinogenesis by dietary curcumin and hesperidin: Comparison with protective effects of beta carotene. Cancer Res 54: 4653–4659.Google Scholar
  5. 5.
    Tanaka T, Makita H, Kawabata K, Mori H, Kakumoto M (1997) Modulation of N-methyl-N-amylnitrosamine induced tumorigenesis by dietary feeding of diosmin and hesperidin, alone and in combination. Carcinogenesis 18: 761–769.CrossRefGoogle Scholar
  6. 6.
    Smith CJ (1964) Non hormonal control of vasomotor flushing in menopausal patients. Chic Med 67: 193–195.Google Scholar
  7. 7.
    Bok SH, Lee SH, Park YB, Bae KH, Son KH, Jeong TS, Choi MS (1999) Plasma and hepatic cholesterol and hepatic activities of 3-hydroxy-3-methyl-glutaryl-CoA reductase and acyl CoA: cholesterol transferase are lower in rats fed citrus peel extract or a mixture of citrus bioflavonoids. J Nutr 129: 1182–1185.Google Scholar
  8. 8.
    Aboobaker VS, Balgi AD, Bhattacharya RK (1994) In vivo effect of dietary factors on the molecular action of aflatoxin B1: role of non-nutrient phenolic compounds on the catalytic activity of liver fraction. In Vivo 8: 1095–1098.Google Scholar
  9. 9.
    Martin MJ, Marhuenda E, Perez-Guerrero C, Franco JM (1994) Antiulcer effect of naringin on gastric lesions induced by ethanol in rats. Pharmacology 49: 144–150.CrossRefGoogle Scholar
  10. 10.
    Gordon PB, Holen I, Seglen PO (1995) Protection by Naringin and Some Other Flavonoids of Hepatocytic Autophagy and Endocytosis against Inhibition by Okadaic Acid. J Biol Chem 270: 5830.CrossRefGoogle Scholar
  11. 11.
    Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A (2003) Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol 65: 2065– 2071.CrossRefGoogle Scholar
  12. 12.
    Bracke ME, Depypere HT, Boterberg T, Van Marck VL (1999) Influence of Tangeretin on Tamoxifen's Therapeutic Benefit in Mammary Cancer. J Nat Cancer Inst 91: 354–359.CrossRefGoogle Scholar
  13. 13.
    Suzuki M, Sasaki K, Yoshizaki F, Oguchi K, Fujisawa M, Cyong JC (2005) Anti-hepatitis C Virus Effect of Citrus Unshiu Peel and Its Active Ingredient Nobiletin. Am J Chinese Med 33: 87–88.CrossRefGoogle Scholar
  14. 14.
    Tanaka S, Sato T, Akimoto N, Yano M, Ito A (2004) Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro. Biochem Pharmacol 68: 433–439.CrossRefGoogle Scholar
  15. 15.
    Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M (1999) Quantitation of Flavonoid Constituents in Citrus Fruits. J Agr Food Chem 47: 3565–3571.CrossRefGoogle Scholar
  16. 16.
    Kawaii S, Tomono Y, Katase E, Ogawa K, Mutsuko N, Nesumi H, Yoshida T, Sugiura M, Yano M (2001) Quantitative Study of Fruit Flavonoids in Citrus Hybrids of King (C. nobilis) and Mukaku Kishu (C. kinokuni). J Agric Food Chem 49: 3982–3986.CrossRefGoogle Scholar
  17. 17.
    Berhow M, Tisserat B, Kanes K, Vandercook C (1996) Survey of Phenolic Compounds Produced in Citrus. U.S. Department of Agriculture, Agricultural Research Service, Technical Bulletin No. 1856: 158.Google Scholar
  18. 18.
    Rouseff RL, Martin SF, Youtsey CO (1987) Quantitative Survey of Narirutin, Naringin, Hesperidin, and Neohesperidin in Citrus. J Agric Food Chem 35: 1027–1030.CrossRefGoogle Scholar
  19. 19.
    Del Rio JA, Fuster MD, Sabater F, Porras I, Garcia-Lidon A, Ortuno A (1997) Selection of citrus varieties highly productive for the neohesperidin dihydrochalcone precursor. Food Chem 59: 433– 437.CrossRefGoogle Scholar
  20. 20.
    Chinese Pharmacopoeia Edition (2005) Beijing China: Chemical Industry Press 1: pp 171–172.Google Scholar
  21. 21.
    Chinese Pharmacopoeia Edition (2005) Beijing China: Chemical Industry Press 1: p 132.Google Scholar
  22. 22.
    Chinese Pharmacopoeia Edition (2005) Beijing China: Chemical Industry Press 1: p 137.Google Scholar
  23. 23.
    Chinese Pharmacopoeia Edition (2005) Beijing China: Chemical Industry Press 1: p 124.Google Scholar
  24. 24.
    Arthur HR, Wui WH, Ma CN (1956) An examination of the Rutaceae of Hong Kong. Part-I. Flavonoid glycosides from Zanthoxylum species and the occurrence of optically active hesperidin. J Chem Soc 1: 632–635.Google Scholar
  25. 25.
    Quang AN, Hanh TV, Sylvie M, Francis T, Vincent D, Thierry SA (2002) New Phenylpropanoid Ester from the Bark of Zanthoxylum scandens Rutaceae. Z Naturforsch 57: 986–989.Google Scholar
  26. 26.
    Binutu OA, Cordell GA (2000) Constituents of Zanthoxylum Sprucei. Pharm Biol 38: 210–213.CrossRefGoogle Scholar
  27. 27.
    Xiong QB, Shi DW (1991) Morphological and histological studies of Chinese traditional drug “hua jiao” (pericarpium zanthoxyli) and its allied drugs. Yao Xue Xue Bao 26: 938–947.Google Scholar
  28. 28.
    Belajov E, Suhaj M (2004) Determination of phenolic constituents in citrus juices: Method of high performance liquid chromatography. Food Chem 86: 339–343.CrossRefGoogle Scholar
  29. 29.
    Xiao R, Chen Z, Li L (1990) Changes of Naringin in Citrus Fruits. Plant Physiol Commun 6: 24–26.Google Scholar
  30. 30.
    Carnat A, Carnat AP, Fraisse D, Lamaison JL (1999) Note technique: Standardisation de la fleur et de la feuille d’oranger amer. Ann Pharm Fr 57: 410–414.Google Scholar
  31. 31.
    Li X, Li L, Xiao H, Liang X (2002) Determination of Hesperidin and Naringin in Fructus Aurantii lmmaturus and Fructus Aurantii by Reversed-Phase High Performance Liquid Chromatography. Chinese J Chromatogr 20: 585–586.Google Scholar
  32. 32.
    US. Food and Drug Administration (2004) “Frozen Concentrated Orange Juice”. US. GPO, Washington, DC: 21, CFR 146.146.Google Scholar

Copyright information

© Springer Science+Business Media, Inc 2006

Authors and Affiliations

  • Yanhua Lu
    • 1
    Email author
  • Chongwei Zhang
    • 1
  • Peter Bucheli
    • 2
  • Dongzhi Wei
    • 1
  1. 1.State Key Laboratory of Bioreactor EngineeringNew World Institute of Biotechnology, East China University of Science and TechnologyShanghai 200237China
  2. 2.Nestlé R&D Center Shanghai Ltd.Shanghai 201819China

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