Polyphenols and Flavonoids: An Overview

Flavonoid Pharmacokinetics: Methods of Analysis, Preclinical and Clinical Pharmacokinetics, Safety, and Toxicology

Volumn , Issue , 2012, Pages 1-69

  Yáñez, Jaime A ^a   Remsberg, Connie M ^b   Takemoto, Jody K ^c   Vega Villa, Karina R ^d   Andrews, Preston K ^e   Sayre, Casey L ^f   Martinez, Stephanie E ^f   Davies, Neal M ^f  

^a ALCON RESEARCH LTD   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF HAWAII   (United States)

^d UNIVERSITY OF OKLAHOMA   (United States)

^e WASHINGTON STATE UNIVERSITY   (United States)

^f UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Antibacterial activity, eriocitrin from peppermint leaves; Hesperidin and Hesperetin; Inflammatory suppression by NF B exerting antiinflammatory; Polyphenols and flavonoids, complex biosynthesis in plants; Selected flavonoids, and pharmacological activities

Indexed keywords

EID: 84887164863     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118468524.ch1     Document Type: Chapter

References (409)

1. Bailey, R. (2003). Nutraceuticals sales to hit $75 billion, Decision News Media SAS.
2. Bailey, R. (2008). Japan: An established market for nutraceuticals. Nutraceuticals World. Accessed February 24, 2009. http://www.nutraceuticalsworld.com/ issues/2008-11/view_features/japan/.
3. Crowther, J. (2008). China's nutraceutical industry: Market potential & regulatory environment. Nutraceuticals World. Accessed February 24, 2009. http://dev2. nutraceuticalsworld.com/issues/2008-11/view_features/china-s-nutraceutic alindustry/.
4. Majszyk, M. (2008). Eastern Europe: The lands of emerging opportunities. Accessed February 24, 2009. http://www.nutraceuticalsworld.com/issues/2008-11/ view_features/eastern-europe/.
5. Mark, D., Abu-Rabia, A. (2008). The Middle East: Exploring the virtues of traditional Arabic Medicine. Nutraceuticals World. Accessed February 24, 2009. http:// www.nutraceuticalsworld.com/issues/2008-11/view_features/the-middle-east /.
6. Puranik, R., Dave, P.K. (2008). India: Now is the time to invest in this market. Nutraceuticals World. Accessed February 24, 2009. http://www.nutraceuticalsworld. com/issues/2008-11/view_features/india/.
7. Washington-Smith, G., Altafer, P. (2008). Latin America: Nutraceutical boom or bust? Nutraceuticals World. Accessed February 24, 2009. http://www. nutraceuticalsworld.com/issues/2008-11/view_features/latin-america/.
8. Zambetti, P. (2008). Spanning the world; Regions around the globe push full steam ahead propelled by the heat of emerging nutraceutical markets. Nutraceuticals World. Accessed February 24, 2009. http://www.nutraceuticalsworld.com/issues/ 2008-11/view_features/spanning-the-world/.
9. Gray, M.J., et al. (2009). Development of liquid chromatography/mass spectrometry methods for the quantitative analysis of herbal medicine in biological fluids: A review. Biomedical Chromatography 24(1):91-103.
10. O rganization, W.H. (2008). Traditonal Medicine. World Health Organization. http://www.who.int/medicines/areas/traditional/en/.
11. Gilbert, J., Henske, P., Aingh, A. (2003). Rebuilding Big Pharma's Business Model. The Business & Medicine Report In Vivo. 21.
12. Sollano, J.A., et al. (2008). The economics of drug discovery and the ultimate valuation of pharmacotherapies in the marketplace. Clinical Pharmacology and Therapeutics 84(2):263-266.
13. DiMasi, J.A., Hansen, R.W., Grabowski, H.G. (2003). The price of innovation: New estimates of drug development costs. Journal of Health Economics 22(2): 151-185.
14. Newman, D.J., Cragg, G.M. (2007). Natural products as sources of new drugs over the last 25 years. Journal of Natural Products 70(3):461-477.
15. Cragg, G.M., Newman, D.J., Snader, K.M. (1997). Natural products in drug discovery and development. Journal of Natural Products 60(1):52-60.
16. Khosla, C., Keasling, J.D. (2003). Metabolic engineering for drug discovery and development. Nature Reviews Drug Discovery 2(12):1019-1025.
17. R askin, I., Ripoll, C. (2004). Can an apple a day keep the doctor away? Current Pharmaceutical Design 10(27):3419-3429.
18. Ferrer, J.L., et al. (2008). Structure and function of enzymes involved in the biosynthesis of phenylpropanoids. Plant Physiology and Biochemistry 46(3): 356-370.
19. Balandrin, M.F., et al. (1985). Natural plant chemicals: Sources of industrial and medicinal materials. Science 228(4704):1154-1160.
20. Stafford, H.A. (1990). Flavonoid Metabolism. Boca Raton, FL: CRC Press, Inc.
21. Beecher, G.R. (2003). Overview of dietary flavonoids: Nomenclature, occurrence and intake. Journal of Nutrition 133(10):3248S-3254S.
22. Bourguad, F., et al. (2001). Production of plant secondary metabolites: A historical perspective. Plant Science 161(5):839.
23. H arborne, J.B., Williams, C.A. (2000). Advances in flavonoid research since 1992. Phytochemistry 55(6):481-504.
24. Naczk, M., Shahidi, F. (2004). Extraction and analysis of phenolic in food. Journal of Chromatography. A 1054:95-111.
25. Cuyckens, F., Claeys, M. (2004). Mass spectrometry in the structural analysis of flavonoids. Journal of Mass Spectrometry 39(1):1-15.
26. Stobiecki, M. (2000). Application of mass spectrometry for identification and structural studies of flavonoid glycosides. Phytochemistry 54(3):237-256.
27. Grundhofer, P., et al. (2001). Biosynthesis and subcellular distribution of hydrolyzable tannins. Phytochemistry 57(6):915-927.
28. L iu, E.H., et al. (2008). Advances of modern chromatographic and electrophoretic methods in separation and analysis of flavonoids. Molecules 13(10):2521-2544.
29. Barros, L., et al. (2009). Phenolic acids determination by HPLC-DAD-ESI/MS in sixteen different Portuguese wild mushrooms species. Food and Chemical Toxicology 47(6):1076-1079.
30. Hollman, P.C.H., van Trijp, J.M.P., Buysman, M.N.C.P. (1996). Fluorescence detection of flavonols in HPLC by postcolumn chelation with aluminum. Analytical Chemistry 68:3511-3515.
31. Scalbert, A., Williamson, G. (2000). Dietary intake and bioavailability of polyphenols. Journal of Nutrition 130(Suppl. 8S):2073S-2085S.
32. Vacek, J., et al. (2008). Current trends in isolation, separation, determination and identification of isoflavones: A review. Journal of Separation Science 31(11): 2054-2067.
33. Cuyckens, F., et al. (2000). Tandem mass spectral strategies for the structural characterization of flavonoid glycosides. Analusis 28(10):888-895.
34. Kodan, A., Kuroda, H., Sakai, F. (2002). A stilbene synthase from Japanese red pine (Pinus densiflora): Implications for phytoalexin accumulation and downregulation of flavonoid biosynthesis. Proceedings of the National Academy of Sciences of the United States of America 99(5):3335-3339.
35. Szent-Györgyi, A. (1936). From Vitamin C to Vitamin P. Current Science 5: 285-286.
36. H aslam, E. (1998). Practical Polyphenolics. From Structure to Molecular Recognition and Physiological Action. Cambridge, UK: Cambridge Universtiy Press.
37. Cook, N.C., Samman, S. (1996). Flavonoids-Chemistry, metabolism, cardioprotective effects, and dietary sources. The Journal of Nutritional Biochemistry 6:66-76.
38. Scalbert, A., Johnson, I.T., Saltmarsh, M. (2005). Polyphenols: Antioxidants and beyond. American Journal of Clinical Nutrition 81(Suppl. 1):215S-217S.
39. Fremont, L. (2000). Biological effects of resveratrol. Life Sciences 66(8): 663-673.
40. Rimando, A.M., et al. (2002). Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. Journal of Agricultural and Food Chemistry 50(12):3453-3457.
41. Roupe, K., et al. (2006). Pharmacometrics of stilbenes: Segueing towards the clinic. Current Clinical Pharmacology 1(1):81-101.
42. Scalbert, A., et al. (2005). Dietary polyphenols and the prevention of diseases. Critical Reviews in Food Science and Nutrition 45(4):287-306.
43. Moon, Y.J., Wang, X., Morris, M.E. (2006). Dietary flavonoids: Effects on xenobiotic and carcinogen metabolism. Toxicol In Vitro 20(2):187-210.
44. Caristi, C., et al. (2003). Flavonoids detection by HPLC-DAD-MS-MS in lemon juices from Sicilian cultivars. Journal of Agricultural and Food Chemistry 51(12):3528-3534.
45. Kawaii, S., et al. (1999). Quantitation of flavonoid constituents in citrus fruits. Journal of Agricultural and Food Chemistry 47(9):3565-3571.
46. Nielsen, S.E., et al. (2002). Flavonoids in human urine as biomarkers for intake of fruits and vegetables. Cancer Epidemiology, Biomarkers and Prevention 11(5): 459-466.
47. Ameer, B., et al. (1996). Flavanone absorption after naringin, hesperidin, and citrus administration. Clinical Pharmacology and Therapeutics 60(1):34-40.
48. Benavente-Carcia, O., et al. (1997). Uses and properties of citrus flavonoids. Journal of Agricultural and Food Chemistry 45(12):4505-4515.
49. Brevik, A., et al. (2004). Urinary excretion of flavonoids reflects even small changes in the dietary intake of fruits and vegetables. Cancer Epidemiology, Biomarkers and Prevention 13(5):843-849.
50. Caccamese, S., Manna, L., Scivoli, G. (2003). Chiral HPLC separation and CD spectra of the C-2 diastereomers of naringin in grapefruit during maturation. Chirality 15(8):661-667.
51. Erlund, I., et al. (2001). Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice. Journal of Nutrition 131(2):235-241.
52. Gil-Izquierdo, A., et al. (2004). Effect of the rootstock and interstock grafted in lemon tree (Citrus limon (L.) Burm.) on the flavonoid content of lemon juice. Journal of Agricultural and Food Chemistry 52(2):324-331.
53. Middleton, E., Kandaswami, C. (1994). The impact of plant flavonoids in mammalian biology: Implications for immunity, inflammation and cancer. In The Flavonoids: Advances in Research since 1986, Harborne, J., editor. London: Chapman & Hall, pp. 619-652.
54. Miyake, Y., et al. (2006). Difference in plasma metabolite concentration after ingestion of lemon flavonoids and their aglycones in humans. Journal of Nutritional Science and Vitaminology 52(1):54-60.
55. Miyake, Y., et al. (2000). Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats. Journal of Agricultural and Food Chemistry 48(8):3217-3224.
56. Montanari, A., Chen, J., Widmer, W. (1998). Citrus flavonoids: A review of plast biological activity against disease. Discovery of new flavonoids from Dancy tangerine cold pressed oil solids and leaves. In Flavonoids in the Living System (Advances in Experimental Medicine and Biology), Manthey, J., Buslig, B., editors. New York: Plenum, pp. 103-116.
57. Wilcox, L.J., Borradaile, N.M., Huff, M.W. (1999). Antiatherogenic properties of naringenin, a citrus flavonoid. Cardiovascular Drug Reviews 17(2):160-178.
58. Bugianesi, R., et al. (2002). Naringenin from cooked tomato paste is bioavailable in men. Journal of Nutrition 132(11):3349-3352.
59. L e Gall, G., et al. (2003). Characterization and content of flavonoid glycosides in genetically modified tomato (Lycopersicon esculentum) fruits. Journal of Agricultural and Food Chemistry 51(9):2438-2446.
60. Stewart, A.J., et al. (2000). Occurrence of flavonols in tomatoes and tomato-based products. Journal of Agricultural and Food Chemistry 48(7):2663-2669.
61. Daigle, D.J., et al. (1988). Peanut hull flavonoids: Their relationship with peanut maturity. Journal of Agricultural and Food Chemistry 36(6):1179-1181.
62. Krause, M., Galensa, R. (1991). Analysis of enantiomeric flavanones in plant extracts by high-performance liquid chromatography on a cellulose triacetate based chiral stationary phase. Chromatographia 32(1/2):69-72.
63. Manach, C., et al. (2003). Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. European Journal of Clinical Nutrition 57(2):235-242.
64. Proksch, P., et al. (1984). Flavonoids from the external leaf resin of four Hemizonza species (Asteraceae). Phytochemistry 23(3):679-680.
65. Geissman, T.A. (1940). The isolation of eriodictyol and homoeriodictyol. An improved procedure. Journal of the American Chemical Society 62(11): 3258-3259.
66. van den Broucke, C.O., et al. (1982). Three methylated flavones from Thymus vulgaris. Phytochemistry 21(10):2581-2583.
67. Formica, J.V., Regelson, W. (1995). Review of the biology of quercetin and related bioflavonoids. Food and Chemical Toxicology 33(12):1061-1080.
68. Pietta, P.G. (2000). Flavonoids as antioxidants. Journal of Natural Products 63(7):1035-1042.
69. van Acker, F.A., et al. (2000). Flavonoids can replace alpha-tocopherol as an antioxidant. FEBS Letters 473(2):145-148.
70. Miyake, Y., Yamamoto, K., Osawa, T. (1997). Metabolism of antioxidant in lemon fruit (Citrus limon Burm. f.) by human intestinal bacteria. Journal of Agricultural and Food Chemistry 45(10):3738-3742.
71. Bocco, A., et al. (1998). Antioxidant activity and phenolic composition of citrus peel and seed extracts. Journal of Agricultural and Food Chemistry 46(6): 2123-2129.
72. Cao, G., Sofic, E., Prior, R.L. (1997). Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships. Free Radical Biology and Medicine 22(5):749-760.
73. Chen, J., Montanari, A.M., Widmer, W.W. (1997). Two new polymethoxylated flavones, a class of compounds with potential anticancer activity, isolated from cold pressed dancy tangerine peel oil solids. Journal of Agricultural and Food Chemistry 45(2):364-368.
74. Di Carlo, G., et al. (1999). Flavonoids: Old and new aspects of a class of natural therapeutic drugs. Life Sciences 65(4):337-353.
75. Marin, F.R., et al. (2002). Changes in nutraceutical composition of lemon juices according to different industrial extraction systems. Food Chemistry 78(3): 319-324.
76. R ice-Evans, C.A., Miller, N.J., Paganga, G. (1996). Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biology and Medicine 20(7):933-956.
77. R usznyak, S., Szent-Györgyi, A. (1936). Vitamin P: Flavonols as vitamins. Nature 138:27.
78. Bok, S.H., et al. (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. Journal of Nutrition 129(6):1182-1185.
79. Borradaile, N.M., Carroll, K.K., Kurowska, E.M. (1999). Regulation of HepG2 cell apolipoprotein B metabolism by the citrus flavanones hesperetin and naringenin. Lipids 34(6):591-598.
80. Santos, K.F., et al. (1999). Hypolipidaemic effects of naringenin, rutin, nicotinic acid and their associations. Pharmacological Research 40(6):493-496.
81. Shin, Y.W., et al. (1999). Hypocholesterolemic effect of naringin associated with hepatic cholesterol regulating enzyme changes in rats. International Journal for Vitamin and Nutrition Research 69(5):341-347.
82. H ertog, M.G., et al. (1993). Dietary antioxidant flavonoids and risk of coronary heart disease: The Zutphen Elderly Study. Lancet 342(8878):1007-1011.
83. Kaul, T.N., Middleton, E., Jr., Ogra, P.L. (1985). Antiviral effect of flavonoids on human viruses. Journal of Medical Virology 15(1):71-79.
84. Wang, H.K., et al. (1998). Recent advances in the discovery and development of flavonoids and their analogues as antitumor and anti-HIV agents. Advances in Experimental Medicine and Biology 439:191-225.
85. Middleton, E., Jr. (1998). Effect of plant flavonoids on immune and inflammatory cell function. Advances in Experimental Medicine and Biology 439:175-182.
86. Fotsis, T., et al. (1997). Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis. Cancer Research 57(14):2916-2921.
87. Knekt, P., et al. (1997). Dietary flavonoids and the risk of lung cancer and other malignant neoplasms. American Journal of Epidemiology 146(3):223-230.
88. So, F.V., et al. (1996). Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices. Nutrition and Cancer 26(2):167-181.
89. Stefani, E.D., et al. (1999). Dietary antioxidants and lung cancer risk: A casecontrol study in Uruguay. Nutrition and Cancer 34(1):100-110.
90. Yang, M., et al. (1997). Chemopreventive effects of diosmin and hesperidin on N-butyl-N-(4-hydroxybutyl)nitrosamine-induced urinary-bladder carcinogenesis in male ICR mice. International Journal of Cancer 73(5):719-724.
91. Samman, S., Wall, P.M., Cook, N.C. (1999). Flavonoids and coronary heart disease: Dietary perspectives. In Flavonoids in the Living System (Advances in Experimental Medicine and Biology), Manthey, J., Buslig, B., editors. New York: Plenum Press, pp. 469-481.
92. USDA (2003). USDA Database for the Flavonoid Content of Selected Foods. Accessed March 25, 2003 and April 9, 2007. http://www.nal.usda.gov/fnic/ foodcomp/Data/Flav/flav.html.
93. Yáñez, J.A., Andrews, P.K., Davies, N.M. (2007). Methods of analysis and separation of chiral flavonoids. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 848(2):159-181.
94. Krause, M., Galensa, R. (1988). Direct enantiomeric separation of racemic flavanones by high-performance liquid chromatography using cellulose triacetate as a chiral stationary phase. Journal of Chromatography. A 441:417-422.
95. Krause, M., Galensa, R. (1990). Improved chiral stationary phase based on cellulose triacetate supported on non-macroporous silica gel diol for the highperformance liquid chromatographic separation of racemic flavanones and diastereomeric flavanone glycosides. Journal of Chromatography. A 502:287-296.
96. Stafford, H.A. (1990). Biosynthesis of flavanones and 3-hydroxyflavanones (dihydroxyflavonols): The "grid" pattern of basic hydroxylations of the B- and C-rings. In Flavonoid Metabolism. Boca Raton, FL: CRC Press, Inc., pp. 39-44.
97. H emingway, R.W., Foo, L.Y., Porter, L.J. (1982). Linkage isomerism in trimeric acid polymeric 2,3-cis procyanidins. Journal of the Chemical Society Perkin Transactions 1:1209.
98. World Health Organization. (2008). The Top Ten Causes of Death. World Health Organization. http://www.who.int/mediacentre/factsheets/fs310/en/index.html.
99. World Health Organization. (2007). The Top Ten Causes of Death. World Health Organization. http://www.who.int/mediacentre/factsheets/fs310/en/index.html.
100. National Cancer Institute. Cardiopulmonary Syndrome Overview. National Cancer Institute. http://www.cancer.gov/cancertopics/pdq/supportivecare/ cardiopulmonary/Patient/page1.
101. Niessen, W.M.A., Tinke, A.P. (1995). Liquid-chromatography mass-spectrometry- General principles and instrumentation. Journal of Chromatography. A 703(1-2): 37-57.
102. Singleton, V.L., Rossi, J.A., Jr. (1985). Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. American Journal of Enology and Viticulture 16(3):144-158.
103. Folin, O., Denis, W. (1912). On phosphotungstic-phosphomolybdic compounds as color reagents. Journal of Biological Chemistry 12:239-243.
104. Yáñez, J.A., et al. (2005). Stereospecific high-performance liquid chromatographic analysis of hesperetin in biological matrices. Journal of Pharmaceutical and Biomedical Analysis 37(3):591-595.
105. Garg, A., et al. (2001). Chemistry and pharmacology of the citrus bioflavonoid hesperidin. Phytotherapy Research 15(8):655-669.
106. Cvetnic, Z., Vladimir-Knezevic, S. (2004). Antimicrobial activity of grapefruit seed and pulp ethanolic extract. Acta Pharmaceutica 54(3):243-250.
107. Panasiak, W., et al. (1989). Influence of flavonoids on combined experimental infections with EMC virus and Staphylococcus aureus in mice. Acta Microbiologica Polonica 38(2):185-188.
108. Bae, E.A., Han, M.J., Kim, D.H. (1999). In vitro anti-Helicobacter pylori activity of some flavonoids and their metabolites. Planta Medica 65(5):442-443.
109. De Clercq, E. (2006). Potential antivirals and antiviral strategies against SARS coronavirus infections. Expert Review of Anti-infective Therapy 4(2):291-302.
110. Paredes, A., et al. (2003). Anti-Sindbis activity of flavanones hesperetin and naringenin. Biological and Pharmaceutical Bulletin 26(1):108-109.
111. R otelli, A.E., et al. (2003). Comparative study of flavonoids in experimental models of inflammation. Pharmacological Research 48(6):601-606.
112. Sugishita, E., Amagaya, S., Ogihara, Y. (1981). Antiinflammatory testing methods: Comparative evaluation of mice and rats. Journal of Pharmacobio-Dynamics 4(8):565-575.
113. Young, J.M., De Young, L.M. (1989). Cutaneous models of inflammation for the evaluation of topical and systemic pharmacological agents. In Pharmacological Methods in the Control of Inflammation, Spector, J., Back, N., editors. New York: Liss, pp. 215-231.
114. Meier, R., Schuler, W., Desaulles, P. (1950). Zur Frage des Mechanismus der Hemmung des Bindegewebswachstums durch. Cortisone Experientia VI/12(12): 469-471.
115. Mizushima, Y., Tsukada, W., Akimoto, T. (1972). A modification of rat adjuvant arthritis for testing antirheumatic drugs. Journal of Pharmacy and Pharmacology 24(10):781-785.
116. Di Rosa, M., Giroud, J.P., Willoughby, D.A. (1971). Studies on the mediators of the acute inflammatory response induced in rats in different sites by carrageenan and turpentine. Journal of Pathology 104(1):15-29.
117. V inegar, R., Truax, J.F., Selph, J.L. (1976). Quantitative studies of the pathway to acute carrageenan inflammation. Federation Proceedings 35(13):2447-2456.
118. V inegar, R., et al. (1982). Pathway of onset, development, and decay of carrageenan pleurisy in the rat. Federation Proceedings 41(9):2588-2595.
119. Yeh, C.C., et al. (2007). The immunomodulation of endotoxin-induced acute lung injury by hesperidin in vivo and in vitro. Life Sciences 80(20):1821-1831.
120. Cho, J. (2006). Antioxidant and neuroprotective effects of hesperidin and its aglycone hesperetin. Archives of Pharmacal Research 29(8):699-706.
121. Wilmsen, P.K., Spada, D.S., Salvador, M. (2005). Antioxidant activity of the flavonoid hesperidin in chemical and biological systems. Journal of Agricultural and Food Chemistry 53(12):4757-4761.
122. Kim, J.Y., et al. (2004). Hesperetin: A potent antioxidant against peroxynitrite. Free Radical Research 38(7):761-769.
123. Balakrishnan, A., Menon, V.P. (2007). Antioxidant properties of hesperidin in nicotine-induced lung toxicity. Fundamental and Clinical Pharmacology 21(5): 535-546.
124. Balakrishnan, A., Menon, V.P. (2007). Effect of hesperidin on matrix metalloproteinases and antioxidant status during nicotine-induced toxicity. Toxicology 238(2-3):90-98.
125. R apavi, E., et al. (2007). The effect of citrus flavonoids on the redox state of alimentary-induced fatty liver in rats. Natural Product Research 21(3):274-281.
126. R apavi, E., et al. (2006). Effects of citrus flavonoids on redox homeostasis of toxininjured liver in rat. Acta Biologica Hungarica 57(4):415-422.
127. Tirkey, N., et al. (2005). Hesperidin, a citrus bioflavonoid, decreases the oxidative stress produced by carbon tetrachloride in rat liver and kidney. BMC Pharmacology 5(1):2.
128. Zheng, Q., et al. (2002). Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells. Journal of Cancer Research and Clinical Oncology 128(10): 539-546.
129. Park, H.J., et al. (2007). Apoptotic effect of hesperidin through caspase3 activation in human colon cancer cells, SNU-C4. Phytomedicine 15(1-2):147-151.
130. Franke, A.A., et al. (1998). Inhibition of neoplastic transformation and bioavailability of dietary flavonoid agents. Advances in Experimental Medicine and Biology 439:237-248.
131. Choi, E.J. (2007). Hesperetin induced G1-phase cell cycle arrest in human breast cancer MCF-7 cells: Involvement of CDK4 and p21. Nutrition and Cancer 59(1):115-119.
132. Corpet, D.E., Tache, S. (2002). Most effective colon cancer chemopreventive agents in rats: A systematic review of aberrant crypt foci and tumor data, ranked by potency. Nutrition and Cancer 43(1):1-21.
133. Corpet, D.E., Pierre, F. (2003). Point: From animal models to prevention of colon cancer. Systematic review of chemoprevention in min mice and choice of the model system. Cancer Epidemiology, Biomarkers and Prevention 12(5): 391-400.
134. Franke, A.A., et al. (2002). Inhibition of colonic aberrant crypt formation by the dietary flavonoids (+)-catechin and hesperidin. Advances in Experimental Medicine and Biology 505:123-133.
135. Tanaka, T., et al. (2000). Suppression of azoxymethane-induced colon carcinogenesis in male F344 rats by mandarin juices rich in beta-cryptoxanthin and hesperidin. International Journal of Cancer 88(1):146-150.
136. Miyagi, Y., et al. (2000). Inhibition of azoxymethane-induced colon cancer by orange juice. Nutrition and Cancer 36(2):224-229.
137. Berkarda, B., et al. (1998). Inhibitory effect of hesperidin on tumour initiation and promotion in mouse skin. Research in Experimental Medicine 198(2):93-99.
138. Tanaka, T., et al. (1997). Modulation of N-methyl-N-amylnitrosamine-induced rat oesophageal tumourigenesis by dietary feeding of diosmin and hesperidin, both alone and in combination. Carcinogenesis 18(4):761-769.
139. Sakata, K., et al. (2003). Inhibition of inducible isoforms of cyclooxygenase and nitric oxide synthase by flavonoid hesperidin in mouse macrophage cell line. Cancer Letters 199(2):139-145.
140. H irata, A., et al. (2005). Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression. Anticancer Research 25(5):3367-3374.
141. H su, C.L., Yen, G.C. (2006). Induction of cell apoptosis in 3T3-L1 pre-adipocytes by flavonoids is associated with their antioxidant activity. Molecular Nutrition and Food Research 50(11):1072-1079.
142. H su, C.L., Yen, G.C. (2007). Effects of flavonoids and phenolic acids on the inhibition of adipogenesis in 3T3-L1 adipocytes. Journal of Agricultural and Food Chemistry 55(21):8404-8410.
143. Philp, H.A. (2003). Hot flashes-A review of the literature on alternative and complementary treatment approaches. Alternative Medicine Review 8(3): 284-302.
144. Klinge, C.M., et al. (2003). Estrogenic activity in white and red wine extracts. Journal of Agricultural and Food Chemistry 51(7):1850-1857.
145. Smith, C.J. (1964). Non-hormonal control of vaso-motor flushing in menopausal patients. Chicago Medicine 67:193-195.
146. H o, P.C., et al. (2000). Content of CYP3A4 inhibitors, naringin, naringenin and bergapten in grapefruit and grapefruit juice products. Pharmaceutica Acta Helvetiae 74(4):379-385.
147. Exarchou, V., et al. (2003). LC-UV-solid-phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano. Analytical Chemistry 75(22):6288-6294.
148. Minoggio, M., et al. (2003). Polyphenol pattern and antioxidant activity of different tomato lines and cultivars. Annals of Nutrition and Metabolism 47(2):64-69.
149. Sanchez-Rabaneda, F., et al. (2003). Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao). Journal of Mass Spectrometry 38(1):35-42.
150. Wang, H., et al. (1999). Antioxidant polyphenols from tart cherries (Prunus cerasus). Journal of Agricultural and Food Chemistry 47(3):840-844.
151. H ungria, M., Johnston, A.W., Phillips, D.A. (1992). Effects of flavonoids released naturally from bean (Phaseolus vulgaris) on nodD-regulated gene transcription in Rhizobium leguminosarum bv. phaseoli. Molecular Plant-Microbe Interactions 5(3):199-203.
152. El-Gammal, A.A., Mansour, R.M. (1986). Antimicrobial activities of some flavonoid compounds. Zentralblatt fur Mikrobiologie 141(7):561-565.
153. Tereschuk, M.L., et al. (2004). Flavonoids from Argentine Tagetes (Asteraceae) with antimicrobial activity. Methods in Molecular Biology 268:317-330.
154. R amesh, N., et al. (2001). Phytochemical and antimicrobial studies on Drynaria quercifolia. Fitoterapia 72(8):934-936.
155. Koru, O., et al. (2007). In vitro antimicrobial activity of propolis samples from different geographical origins against certain oral pathogens. Anaerobe 13(3-4):140-145.
156. Uzel, A., et al. (2005). Chemical compositions and antimicrobial activities of four different Anatolian propolis samples. Microbiological Research 160(2):189-195.
157. Suzgec, S., et al. (2005). Flavonoids of Helichrysum compactum and their antioxidant and antibacterial activity. Fitoterapia 76(2):269-272.
158. L yu, S.Y., Rhim, J.Y., Park, W.B. (2005). Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro. Archives of Pharmacal Research 28(11):1293-1301.
159. Castrillo, J.L., Vanden Berghe, D., Carrasco, L. (1986). 3-Methylquercetin is a potent and selective inhibitor of poliovirus RNA synthesis. Virology 152(1): 219-227.
160. L otito, S.B., Frei, B. (2006). Dietary flavonoids attenuate tumor necrosis factor alpha-induced adhesion molecule expression in human aortic endothelial cells. Structure-function relationships and activity after first pass metabolism. Journal of Biological Chemistry 281(48):37102-37110.
161. H ougee, S., et al. (2005). Decreased pro-inflammatory cytokine production by LPS-stimulated PBMC upon in vitro incubation with the flavonoids apigenin, luteolin or chrysin, due to selective elimination of monocytes/macrophages. Biochemical Pharmacology 69(2):241-248.
162. O lszanecki, R., et al. (2002). Flavonoids and nitric oxide synthase. Journal of Physiology and Pharmacology 53(4 Pt 1):571-584.
163. Kanno, S., et al. (2006). Inhibitory effect of naringin on lipopolysaccharide (LPS)- induced endotoxin shock in mice and nitric oxide production in RAW 264.7 macrophages. Life Sciences 78(7):673-681.
164. Kawaguchi, K., et al. (2004). Suppression of infection-induced endotoxin shock in mice by a citrus flavanone naringin. Planta Medica 70(1):17-22.
165. R ajadurai, M., Prince, P.S. (2007). Preventive effect of naringin on isoproterenolinduced cardiotoxicity in Wistar rats: An in vivo and in vitro study. Toxicology 232(3):216-225.
166. Yu, J., et al. (2005). Antioxidant activity of citrus limonoids, flavonoids, and coumarins. Journal of Agricultural and Food Chemistry 53(6):2009-2014.
167. Jagetia, G.C., et al. (2004). Influence of naringin on ferric iron induced oxidative damage in vitro. Clinica Chimica Acta 347(1-2):189-197.
168. Gorinstein, S., et al. (2005). Changes in plasma lipid and antioxidant activity in rats as a result of naringin and red grapefruit supplementation. Journal of Agricultural and Food Chemistry 53(8):3223-3228.
169. Kanno, S., et al. (2005). Inhibitory effects of naringenin on tumor growth in human cancer cell lines and sarcoma S-180-implanted mice. Biological and Pharmaceutical Bulletin 28(3):527-530.
170. Frydoonfar, H.R., McGrath, D.R., Spigelman, A.D. (2003). The variable effect on proliferation of a colon cancer cell line by the citrus fruit flavonoid naringenin. Colorectal Disease 5(2):149-152.
171. Kanno, S., et al. (2004). Effects of naringin on cytosine arabinoside (Ara-C)- induced cytotoxicity and apoptosis in P388 cells. Life Sciences 75(3):353-365.
172. van Meeuwen, J.A., et al. (2007). (Anti)estrogenic effects of phytochemicals on human primary mammary fibroblasts, MCF-7 cells and their co-culture. Toxicology and Applied Pharmacology 221(3):372-383.
173. Totta, P., et al. (2004). Mechanisms of naringenin-induced apoptotic cascade in cancer cells: Involvement of estrogen receptor alpha and beta signalling. IUBMB Life 56(8):491-499.
174. H armon, A.W., Patel, Y.M. (2004). Naringenin inhibits glucose uptake in MCF-7 breast cancer cells: A mechanism for impaired cellular proliferation. Breast Cancer Research and Treatment 85(2):103-110.
175. Gopalakrishnan, A., et al. (2006). Modulation of activator protein-1 (AP-1) and MAPK pathway by flavonoids in human prostate cancer PC3 cells. Archives of Pharmacal Research 29(8):633-644.
176. Kanno, S., et al. (2006). Naringenin-induced apoptosis via activation of NF-kappaB and necrosis involving the loss of ATP in human promyeloleukemia HL-60 cells. Toxicology Letters 166(2):131-139.
177. Katula, K.S., McCain, J.A., Radewicz, A.T. (2005). Relative ability of dietary compounds to modulate nuclear factor-kappaB activity as assessed in a cell-based reporter system. Journal of Medicinal Food 8(2):269-274.
178. Schindler, R., Mentlein, R. (2006). Flavonoids and vitamin E reduce the release of the angiogenic peptide vascular endothelial growth factor from human tumor cells. Journal of Nutrition 136(6):1477-1482.
179. V anamala, J., et al. (2006). Suppression of colon carcinogenesis by bioactive compounds in grapefruit. Carcinogenesis 27(6):1257-1265.
180. R aso, G.M., et al. (2001). Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1. Life Sciences 68(8):921-931.
181. R ajadurai, M., Stanely Mainzen Prince, P. (2007). Preventive effect of naringin on cardiac markers, electrocardiographic patterns and lysosomal hydrolases in normal and isoproterenol-induced myocardial infarction in Wistar rats. Toxicology 230(2-3):178-188.
182. Arayne, M.S., Sultana, N., Bibi, Z. (2005). Grape fruit juice-drug interactions. Pakistan Journal of Pharmaceutical Sciences 18(4):45-57.
183. Bailey, D.G., et al. (2000). Grapefruit-felodipine interaction: Effect of unprocessed fruit and probable active ingredients. Clinical Pharmacology and Therapeutics 68(5):468-477.
184. Eagling, V.A., Profit, L., Back, D.J. (1999). Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components. British Journal of Clinical Pharmacology 48(4):543-552.
185. Zhang, H., et al. (2000). Effect of the grapefruit flavonoid naringin on pharmacokinetics of quinine in rats. Drug Metabolism and Drug Interactions 17(1-4): 351-363.
186. Yeum, C.H., Choi, J.S. (2006). Effect of naringin pretreatment on bioavailability of verapamil in rabbits. Archives of Pharmacal Research 29(1):102-107.
187. Kim, H.J., Choi, J.S. (2005). Effects of naringin on the
188. Guo, L.Q., et al. (2000). Role of furanocoumarin derivatives on grapefruit juicemediated inhibition of human CYP3A activity. Drug Metabolism and Disposition: The Biological Fate of Chemicals 28(7):766-771.
189. Guo, L.Q., et al. (2000). Inhibitory effect of natural furanocoumarins on human microsomal cytochrome P450 3A activity. Japanese Journal of Pharmacology 82(2):122-129.
190. Chan, W.K., et al. (1998). Mechanism-based inactivation of human cytochrome P450 3A4 by grapefruit juice and red wine. Life Sciences 62(10):PL135-PL142.
191. R unkel, M., et al. (1997). The character of inhibition of the metabolism of 1,2-benzopyrone (coumarin) by grapefruit juice in human. European Journal of Clinical Pharmacology 53(3-4):265-269.
192. Bailey, D.G., et al. (1993). Effect of grapefruit juice and naringin on nisoldipine pharmacokinetics. Clinical Pharmacology and Therapeutics 54(6):589-594.
193. Bailey, D.G., et al. (1993). Grapefruit juice-felodipine interaction: Mechanism, predictability, and effect of naringin. Clinical Pharmacology and Therapeutics 53(6):637-642.
194. Edwards, D.J., Bernier, S.M. (1996). Naringin and naringenin are not the primary CYP3A inhibitors in grapefruit juice. Life Sciences 59:1025-1030.
195. Guengerich, F.P., Kim, D.H. (1990). In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis 11(12):2275-2279.
196. Miniscalco, A., et al. (1992). Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. Journal of Pharmacology and Experimental Therapeutics 261(3):1195-1199.
197. Edwards, D.J., Bellevue, F.H., 3rd, Woster, P.M. (1996). Identification of 6',7'-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice. Drug Metabolism and Disposition: The Biological Fate of Chemicals 24(12):1287-1290.
198. Schmiedlin-Ren, P., et al. (1997). Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents. Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins. Drug Metabolism and Disposition: The Biological Fate of Chemicals 25(11): 1228-1233.
199. Fukuda, K., Ohta, T., Yamazoe, Y. (1997). Grapefruit component interacting with rat and human P450 CYP3A: Possible involvement of non-flavonoid components in drug interaction. Biological and Pharmaceutical Bulletin 20(5):560-564.
200. Ameer, B., Weintraub, R.A. (1997). Drug interactions with grapefruit juice. Clinical Pharmacokinetics 33(2):103-121.
201. Fuhr, U. (1998). Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance. Drug Safety 18(4):251-272.
202. Bailey, D.G., et al. (1998). Grapefruit juice-drug interactions. British Journal of Clinical Pharmacology 46(2):101-110.
203. L own, K.S., et al. (1997). Grapefruit juice increases felodipine oral availability in humans by decreasing intestinal CYP3A protein expression. Journal of Clinical Investigation 99(10):2545-2553.
204. Soldner, A., et al. (1999). Grapefruit juice activates P-glycoprotein-mediated drug transport. Pharmaceutical Research 16(4):478-485.
205. Grundy, J.S., et al. (1998). Grapefruit juice and orange juice effects on the bioavailability of nifedipine in the rat. Biopharmaceutics and Drug Disposition 19(3): 175-183.
206. H ashimoto, K., et al. (1998). Interaction of citrus juices with pranidipine, a new 1,4-dihydropyridine calcium antagonist, in healthy subjects. European Journal of Clinical Pharmacology 54(9-10):753-760.
207. Jagetia, A., Jagetia, G.C., Jha, S. (2007). Naringin, a grapefruit flavanone, protects V79 cells against the bleomycin-induced genotoxicity and decline in survival. Journal of Applied Toxicology 27(2):122-132.
208. Jagetia, G.C., Venkatesha, V.A. (2006). Treatment of mice with stem bark extract of Aphanamixis polystachya reduces radiation-induced chromosome damage. International Journal of Radiation Biology 82(3):197-209.
209. Sudjaroen, Y., et al. (2005). Isolation and structure elucidation of phenolic antioxidants from tamarind (Tamarindus indica L.) seeds and pericarp. Food and Chemical Toxicology 43(11):1673-1682.
210. Kosar, M., et al. (2004). Screening of free radical scavenging compounds in water extracts of Mentha samples using a postcolumn derivatization method. Journal of Agricultural and Food Chemistry 52(16):5004-5010.
211. Parejo, I., et al. (2004). Bioguided isolation and identification of the nonvolatile antioxidant compounds from fennel (Foeniculum vulgare Mill.) waste. Journal of Agricultural and Food Chemistry 52(7):1890-1897.
212. Dapkevicius, A., et al. (2002). Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves. Journal of Natural Products 65(6): 892-896.
213. H vattum, E. (2002). Determination of phenolic compounds in rose hip (Rosa canina) using liquid chromatography coupled to electrospray ionisation tandem mass spectrometry and diode-array detection. Rapid Communications in Mass Spectrometry 16(7):655-662.
214. McKay, D.L., Blumberg, J.B. (2006). A review of the bioactivity and potential health benefits of peppermint tea (Mentha piperita L.). Phytotherapy Research 20(8):619-633.
215. Ahmed, M.S., et al. (2001). A weakly antimalarial biflavanone from Rhus retinorrhoea. Phytochemistry 58(4):599-602.
216. Zhou, L., et al. (2007). Antibacterial phenolic compounds from the spines of Gleditsia sinensis Lam. Natural Product Research 21(4):283-291.
217. Ismaili, H., et al. (2002). Topical antiinflammatory activity of extracts and compounds from Thymus broussonettii. Journal of Pharmacy and Pharmacology 54(8):1137-1140.
218. Xagorari, A., et al. (2001). Luteolin inhibits an endotoxin-stimulated phosphorylation cascade and proinflammatory cytokine production in macrophages. Journal of Pharmacology and Experimental Therapeutics 296(1):181-187.
219. Miyake, Y., et al. (2007). Isolation of antioxidative phenolic glucosides from lemon juice and their suppressive effect on the expression of blood adhesion molecules. Bioscience, Biotechnology, and Biochemistry 71(8):1911-1919.
220. Sroka, Z., Fecka, I., Cisowski, W. (2005). Antiradical and anti-H2O2 properties of polyphenolic compounds from an aqueous peppermint extract. Zeitschrift fur Naturforschung. Section C. Biosciences 60(11-12):826-832.
221. Miyake, Y., et al. (1998). Protective effects of lemon flavonoids on oxidative stress in diabetic rats. Lipids 33(7):689-695.
222. Narvaez-Mastache, J.M., Novillo, F., Delgado, G. (2007). Antioxidant arylprenylcoumarin, flavan-3-ols and flavonoids from Eysenhardtia subcoriacea. Phytochemistry 69(2):451-456.
223. Edenharder, R., Grunhage, D. (2003). Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102. Mutation Research 540(1):1-18.
224. L ee, E.R., et al. (2007). The anti-apoptotic and anti-oxidant effect of eriodictyol on UV-induced apoptosis in keratinocytes. Biological and Pharmaceutical Bulletin 30(1):32-37.
225. O gata, S., et al. (2000). Apoptosis induced by the flavonoid from lemon fruit (Citrus limon Burm. f.) and its metabolites in HL-60 cells. Bioscience, Biotechnology, and Biochemistry 64(5):1075-1078.
226. H abtemariam, S. (1997). Flavonoids as inhibitors or enhancers of the cytotoxicity of tumor necrosis factor-alpha in L-929 tumor cells. Journal of Natural Products 60(8):775-778.
227. Kawaii, S., et al. (1999). Antiproliferative activity of flavonoids on several cancer cell lines. Bioscience, Biotechnology, and Biochemistry 63(5):896-899.
228. Zhang, X., et al. (2006). Antiinflammatory activity of flavonoids from Populus davidiana. Archives of Pharmacal Research 29(12):1102-1108.
229. Cuendet, M., et al. (2000). A stilbene and dihydrochalcones with radical scavenging activities from Loiseleuria procumbens. Phytochemistry 54(8):871-874.
230. Escarpa, A., Gonzalez, M.C. (1998). High-performance liquid chromatography with diode-array detection for the determination of phenolic compounds in peel and pulp from different apple varieties. Journal of Chromatography. A 823(1-2): 331-337.
231. Mancini, S.D., Edwards, J.M. (1979). Cytotoxic principles from the sap of Kalmia latifolia. Journal of Natural Products 42(5):483-488.
232. Tsao, R., et al. (2003). Polyphenolic profiles in eight apple cultivars using highperformance liquid chromatography (HPLC). Journal of Agricultural and Food Chemistry 51(21):6347-6353.
233. Yao, G.M., et al. (2005). Dihydrochalcones from the leaves of Pieris japonica. Journal of Natural Products 68(3):392-396.
234. An, R.B., et al. (2007). Cytoprotective constituent of Hoveniae lignum on both Hep G2 cells and rat primary hepatocytes. Archives of Pharmacal Research 30(6):674-677.
235. Ehrenkranz, J.R., et al. (2005). Phlorizin: A review. Diabetes/Metabolism Research and Reviews 21(1):31-38.
236. H ilt, P., et al. (2003). Detection of phloridzin in strawberries (Fragaria × ananassa Duch.) by HPLC-PDA-MS/MS and NMR spectroscopy. Journal of Agricultural and Food Chemistry 51(10):2896-2899.
237. Yang, W.M., et al. (2004). Antioxidant activities of three dihydrochalcone glucosides from leaves of Lithocarpus pachyphyllus. Zeitschrift fur Naturforschung. Section C. Biosciences 59(7-8):481-484.
238. Yáñez, J.A., Davies, N.M. (2005). Stereospecific high-performance liquid chromatographic analysis of naringenin in urine. Journal of Pharmaceutical and Biomedical Analysis 39(1-2):164-169.
239. McKay, D.L., Blumberg, J.B. (2007). A review of the bioactivity of South African herbal teas: Rooibos (Aspalathus linearis) and honeybush (Cyclopia intermedia). Phytotherapy Research 21(1):1-16.
240. Marnewick, J.L., Gelderblom, W.C., Joubert, E. (2000). An investigation on the antimutagenic properties of South African herbal teas. Mutation Research 471(1-2):157-166.
241. Ulicna, O., et al. (2003). Hepatoprotective effect of rooibos tea (Aspalathus linearis) on CCl4-induced liver damage in rats. Physiological Research 52(4): 461-466.
242. Kawano, A., et al. (2009). Hypoglycemic effect of aspalathin, a rooibos tea component from Aspalathus linearis, in type 2 diabetic model db/db mice. Phytomedicine 16(5):437-443.
243. van der Merwe, J.D., et al. (2009). In vitro hepatic biotransformation of aspalathin and nothofagin, dihydrochalcones of rooibos (Aspalathus linearis), and assessment of metabolite antioxidant activity. Journal of Agricultural and Food Chemistry 58(4):2214-2220.
244. Snijman, P.W., et al. (2009). Antioxidant activity of the dihydrochalcones aspalathin and nothofagin and their corresponding flavones in relation to other rooibos (Aspalathus linearis) flavonoids, epigallocatechin gallate, and Trolox. Journal of Agricultural and Food Chemistry 57(15):6678-6684.
245. Snijman, P.W., et al. (2007). The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): Some dose-response effects on mutagen activationflavonoid interactions. Mutation Research 631(2):111-123.
246. R ezk, B.M., et al. (2002). The antioxidant activity of phloretin: The disclosure of a new antioxidant pharmacophore in flavonoids. Biochemical and Biophysical Research Communications 295(1):9-13.
247. Nakamura, Y., et al. (2003). Dihydrochalcones: Evaluation as novel radical scavenging antioxidants. Journal of Agricultural and Food Chemistry 51(11): 3309-3312.
248. Nelson, J.A., Falk, R.E. (1993). The efficacy of phloridzin and phloretin on tumor cell growth. Anticancer Research 13(6A):2287-2292.
249. Nelson, J.A., Falk, R.E. (1993). Phloridzin and phloretin inhibition of 2-deoxy- D-glucose uptake by tumor cells in vitro and in vivo. Anticancer Research 13(6A):2293-2299.
250. Kobori, M., et al. (1997). Phloretin-induced apoptosis in B16 melanoma 4A5 cells by inhibition of glucose transmembrane transport. Cancer Letters 119(2): 207-212.
251. Molnar, J., et al. (2010). Reversal of multidrug resistance by natural substances from plants. Current Topics in Medicinal Chemistry 10(17):1757-1768.
252. Nguyen, H., Zhang, S., Morris, M.E. (2003). Effect of flavonoids on MRP1- mediated transport in Panc-1 cells. Journal of Pharmaceutical Sciences 92(2): 250-257.
253. Yang, K.C., et al. (2009). Apple polyphenol phloretin potentiates the anticancer actions of paclitaxel through induction of apoptosis in human hep G2 cells. Molecular Carcinogenesis 48(5):420-431.
254. Wang, J., et al. (2010). Estrogenic and antiestrogenic activities of phloridzin. Biological and Pharmaceutical Bulletin 33(4):592-597.
255. Gould, G.W., Holman, G.D. (1993). The glucose transporter family: Structure, function and tissue-specific expression. Biochemical Journal 295(Pt 2):329-341.
256. Chen, C.H., et al. (2007). Interaction of flavonoids and intestinal facilitated glucose transporters. Planta Medica 73(4):348-354.
257. Boyer, J., Liu, R.H. (2004). Apple phytochemicals and their health benefits. Nutrition Journal 3:5.
258. Kellett, G.L., et al. (2008). Sugar absorption in the intestine: The role of GLUT2. Annual Review of Nutrition 28:35-54.
259. Kellett, G.L., Brot-Laroche, E. (2005). Apical GLUT2: A major pathway of intestinal sugar absorption. Diabetes 54(10):3056-3062.
260. Kwon, O., et al. (2007). Inhibition of the intestinal glucose transporter GLUT2 by flavonoids. FASEB Journal 21(2):366-377.
261. Manzano, S., Williamson, G. (2010). Polyphenols and phenolic acids from strawberry and apple decrease glucose uptake and transport by human intestinal Caco- 2 cells. Molecular Nutrition and Food Research 54(12):1773-1780.
262. Stangl, V., et al. (2005). The flavonoid phloretin suppresses stimulated expression of endothelial adhesion molecules and reduces activation of human platelets. Journal of Nutrition 135(2):172-178.
263. Kobori, M., et al. (1999). Phloretin-induced apoptosis in B16 melanoma 4A5 cells and HL60 human leukemia cells. Bioscience, Biotechnology, and Biochemistry 63(4):719-725.
264. Park, S.Y., et al. (2007). Induction of apoptosis in HT-29 colon cancer cells by phloretin. Journal of Medicinal Food 10(4):581-586.
265. Kim, M.S., et al. (2009). Phloretin induces apoptosis in H-Ras MCF10A human breast tumor cells through the activation of p53 via JNK and p38 mitogenactivated protein kinase signaling. Annals of the New York Academy of Sciences 1171:479-483.
266. Zhang, S., et al. (2010). Interactions between the flavonoid biochanin A and P-glycoprotein substrates in rats: In vitro and in vivo. Journal of Pharmaceutical Sciences 99(1):430-441.
267. Zhang, S., Morris, M.E. (2003). Effects of the flavonoids biochanin A, morin, phloretin, and silymarin on P-glycoprotein-mediated transport. Journal of Pharmacology and Experimental Therapeutics 304(3):1258-1267.
268. Jung, M., et al. (2009). Influence of apple polyphenols on inflammatory gene expression. Molecular Nutrition and Food Research 53(10):1263-1280.
269. L u, X.Y., et al. (2009). Antiinflammatory and immunosuppressive effect of phloretin. Yao Xue Xue Bao 44(5):480-485.
270. Pohl, C., et al. (2006). Cytochrome P450 1A1 expression and activity in Caco-2 cells: Modulation by apple juice extract and certain apple polyphenols. Journal of Agricultural and Food Chemistry 54(26):10262-10268.
271. Mossa, J.S., et al. (1996). Free Flavonoids from Rhus retinorrhoea Steud ex Olive. Pharmaceutical Biology 34(3):198-201.
272. Grael, C.F., et al. (2000). A study of the trypanocidal and analgesic properties from Lychnophora granmongolense (Duarte) Semir & Leitao Filho. Phytotherapy Research 14(3):203-206.
273. L ey, J.P., et al. (2005). Evaluation of bitter masking flavanones from yerba santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae). Journal of Agricultural and Food Chemistry 53(15):6061-6066.
274. L in, J.H., Chiou, Y.N., Lin, Y.L. (2002). Phenolic glycosides from Viscum angulatum. Journal of Natural Products 65(5):638-640.
275. Yin, J., et al. (2008). Inhibitory activity of the ethyl acetate fraction from Viscum coloratum on bone resorption. Planta Medica 74(2):120-125.
276. Zhao, Y., et al. (2007). HPLC determination and pharmacokinetic study of homoeriodictyol-7-O-beta-D-glucopyranoside in rat plasma and tissues. Biological and Pharmaceutical Bulletin 30(4):617-620.
277. Fukunaga, T., et al. (1989). Studies on the constituents of Japanese mistletoe, Viscum album L. var. coloratum OHWI grown on different host trees. Chemical and Pharmaceutical Bulletin 37(5):1300-1303.
278. McCormick, S. (1978). Pigment synthesis in maize aleurone from precursors fed to anthocyanin mutants. Biochemical Genetics 16(7-8):777-785.
279. Ibrahim, A.R., et al. (2003). O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans. Chemical and Pharmaceutical Bulletin 51(2):203-206.
280. Schröder, G., et al. (2004). Flavonoid methylation: A novel 4'-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases. Phytochemistry 65(8): 1085-1094.
281. Matsumoto, H., et al. (2004). Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma. Journal of Agricultural and Food Chemistry 52(21):6653-6659.
282. Booth, A.N., Jones, F.T., De, E.F. (1958). Metabolic fate of hesperidin, eriodictyol, homoeridictyol, and diosmin. Journal of Biological Chemistry 230(2):661-668.
283. Zhao, Y., et al. (2007). Simultaneous determination of homoeriodictyol-7-O-beta- D-glucopyranoside and its metabolite homoeriodictyol in rat tissues and urine by liquid chromatography-mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 44(1):293-300.
284. Doostdar, H., Burke, M.D., Mayer, R.T. (2000). Bioflavonoids: Selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1. Toxicology 144(1-3): 31-38.
285. L iu, Y.L., et al. (1992). Isolation of potential cancer chemopreventive agents from Eriodictyon californicum. Journal of Natural Products 55(3):357-363.
286. L ey, J.P., et al. (2008). Structural analogues of homoeriodictyol as flavor modifiers. Part III: Short chain gingerdione derivatives. Journal of Agricultural and Food Chemistry 56(15):6656-6664.
287. Shimizu, K., et al. (2004). Antioxidative bioavailability of artepillin C in Brazilian propolis. Archives of Biochemistry and Biophysics 424(2):181-188.
288. Simoes, L.M., et al. (2004). Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils. Journal of Ethnopharmacology 94(1):59-65.
289. Tavares, D.C., et al. (2007). Effects of propolis crude hydroalcoholic extract on chromosomal aberrations induced by Doxorubicin in rats. Planta Medica 73(15):1531-1536.
290. de Sousa, J.P., et al. (2007). A reliable quantitative method for the analysis of phenolic compounds in Brazilian propolis by reverse phase high performance liquid chromatography. Journal of Separation Science 30(16):2656-2665.
291. Missima, F., et al. (2007). Effect of Baccharis dracunculifolia D.C. (Asteraceae) extracts and its isolated compounds on macrophage activation. Journal of Pharmacy and Pharmacology 59(3):463-468.
292. Garcez, F.R., et al. (2006). Bioactive flavonoids and triterpenes from Terminalia fagifolia (Combretaceae). Journal of Brazilian Chemical Society 17(7):1223- 1228.
293. Suksamrarn, A., et al. (2004). Antimycobacterial activity and cytotoxicity of flavonoids from the flowers of Chromolaena odorata. Archives of Pharmacal Research 27(5):507-511.
294. Metwally, A.M., Ekejiuba, E.C. (1981). Methoxylated Flavonols and flavanones from Eupatorium odoratum. Planta Medica 42(8):403-405.
295. V anamala, J., et al. (2004). Variation in the content of bioactive flavonoids in different brands of orange and grapefruit juices. Journal of Food Composition and Analysis 19:157-166.
296. Anagnostopoulou, M.A., et al. (2005). Analysis of antioxidant compounds in sweet orange peel by HPLC-diode array detection-electrospray ionization mass spectrometry. Biomedical Chromatography 19(2):138-148.
297. Calabro, M.L., et al. (2004). Study of the extraction procedure by experimental design and validation of a LC method for determination of flavonoids in Citrus bergamia juice. Journal of Pharmaceutical and Biomedical Analysis 35(2): 349-363.
298. R oss, S.A., et al. (2000). Variance of common flavonoids by brand of grapefruit juice. Fitoterapia 71(2):154-161.
299. Cancalon, P.F. (1999). Analytical monitoring of citrus juices by using capillary electrophoresis. Journal of AOAC International 82(1):95-106.
300. Avula, B., et al. (2005). Liquid chromatography of separation and quantitative determination of adrenergic amines and flavonoids from Poncirus trifoliatus Raf. fruits at different stages of growth. Chromatographia 62(7/8):379-383.
301. H an, A.R., et al. (2007). A new flavanone glycoside from the dried immature fruits of Poncirus trifoliata. Chemical and Pharmaceutical Bulletin 55(8):1270-1273.
302. Kim, C.Y., et al. (2007). One step purification of flavanone glycosides from Poncirus trifoliata by centrifugal partition chromatography. Journal of Separation Science 30(16):2693-2697.
303. Kim, D.H., Bae, E.A., Han, M.J. (1999). Anti-Helicobacter pylori activity of the metabolites of poncirin from Poncirus trifoliata by human intestinal bacteria. Biological and Pharmaceutical Bulletin 22(4):422-424.
304. Kim, J.B., et al. (2007). Inhibition of LPS-induced iNOS, COX-2 and cytokines expression by poncirin through the NF-kappaB inactivation in RAW 264.7 macrophage cells. Biological and Pharmaceutical Bulletin 30(12):2345-2351.
305. Park, S.H., Park, E.K., Kim, D.H. (2005). Passive cutaneous anaphylaxis-inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata. Planta Medica 71(1):24-27.
306. H orowitz, R.M., Gentili, B. (1977). Flavonoid constituents of citrus. In Citrus Science and Technology, vol. 1, Nagy, S., Shaw, P.E., Veldhius, M.K., editors. Westport, CT: The Avi Publishing Company, Inc., p. 529.
307. Kim, D.H., et al. (2005). Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed in Escherichia coli. Journal of Biotechnology 119(2):155-162.
308. Shimokoriyama, M. (1956). Interconversion of chalcones and flavanones of a phloroglucinol-type structure. Journal of the American Chemical Society 79: 4199-4202.
309. Silberberg, M., et al. (2006). Flavanone metabolism in healthy and tumor-bearing rats. Biomedicine and Pharmacotherapy 60(9):529-535.
310. L ee, D.S., et al. (2002). Fecal metabolic activities of herbal components to bioactive compounds. Archives of Pharmacal Research 25(2):165-169.
311. Kim, D.H., et al. (1998). Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Archives of Pharmacal Research 21(1):17-23.
312. Sacco, S., Maffei, M. (1997). The effect of isosakuranetin (5,7-dihydroxy 4'-methoxy flavanone) on potassium uptake in wheat root segments. Phytochemistry 46(2): 245-248.
313. Finotti, E., Di Majo, D. (2003). Influence of solvents on the antioxidant property of flavonoids. Die Nahrung 47(3):186-187.
314. Furuya, H., et al. (2005). Some flavonoids and DHEA-S prevent the cis-effect of expanded CTG repeats in a stable PC12 cell transformant. Biochemical Pharmacology 69(3):503-516.
315. L iu, L., Cheng, Y., Zhang, H. (2004). Phytochemical analysis of anti-atherogenic constituents of Xue-Fu-Zhu-Yu-Tang using HPLC-DAD-ESI-MS. Chemical and Pharmaceutical Bulletin 52(11):1295-1301.
316. Kunizane, H., Ueda, H., Yamazaki, M. (1995). Screening of phagocyte activators in plants; enhancement of TNF production by flavonoids. Yakugaku Zasshi. Journal of the Pharmaceutical Society of Japan 115(9):749-755.
317. Teixeira, S., et al. (2005). Structure-property studies on the antioxidant activity of flavonoids present in diet. Free Radical Biology and Medicine 39(8):1099-1108.
318. Slimestad, R., Fossen, T., Vagen, I.M. (2007). Onions: A source of unique dietary flavonoids. Journal of Agricultural and Food Chemistry 55(25):10067-10080.
319. Seidel, V., Bailleul, F., Waterman, P.G. (2000). Novel oligorhamnosides from the stem bark of Cleistopholis glauca. Journal of Natural Products 63(1):6-11.
320. H osoi, S., et al. (2006). Structural studies of zoospore attractants from Trachelospermum jasminoides var. pubescens: Taxifolin 3-O-glycosides. Phytochemical Analysis 17(1):20-24.
321. Kim, N.C., et al. (2003). Complete isolation and characterization of sylbins and isosylbins from milk thistle (Sylbum marianum). Organic and Biomolecular Chemistry 1:1684-1689.
322. Minakhmetov, R.A., et al. (2001). Analysis of flavonoids in Silybum marianum fruit by HPLC. Chemistry of Natural Compounds 37(4):318-321.
323. Kiehlmann, E., Slade, P.W. (2003). Methylation of dihydroquercetin acetates: Synthesis of 5-O-methyldihydroquercetin. Journal of Natural Products 66(12): 1562-1566.
324. Bais, H.P., et al. (2003). Structure-dependent phytotoxicity of catechins and other flavonoids: Flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots. Journal of Agricultural and Food Chemistry 51(4):897-901.
325. Delporte, C., et al. (2005). Analgesic-antiinflammatory properties of Proustia pyrifolia. Journal of Ethnopharmacology 99(1):119-124.
326. L ee, E.H., et al. (2003). Constituents of the stems and fruits of Opuntia ficus-indica var. saboten. Archives of Pharmacal Research 26(12):1018-1023.
327. Mbafor, J.T., et al. (1989). Isolation and characterization of taxifolin 6-C-glucoside from Garcinia epunctata. Journal of Natural Products 52(2):417-419.
328. Exarchou, V., et al. (2006). Hyphenated chromatographic techniques for the rapid screening and identification of antioxidants in methanolic extracts of pharmaceutically used plants. Journal of Chromatography. A 1112(1-2):293-302.
329. Sakushima, A., et al. (2002). Separation and identification of taxifolin 3-O-glucoside isomers from Chamaecyparis obtusa (Cupressaceae). Natural Product Letters 16(6):383-387.
330. Nonaka, G.I., et al. (1987). Tannins and related compounds. LII. Studies on the constituents of the leaves of Thujopsis dolobrata Sieb. et Zucc. Chemical and Pharmaceutical Bulletin 35(3):1105-1108.
331. Dai, S.J., Yu, D.Q. (2005). Studies on the flavonoids in stem of Rhododendron anthopogonoide II. Zhongguo Zhong Yao Za Zhi 30(23):1830-1833.
332. V oirin, B., et al. (1986). Flavonoids from the flowers of Acacia latifolia. Journal of Natural Products 49:943.
333. Pistelli, L., et al. (2000). A new isoflavone from Genista corsica. Journal of Natural Products 63(4):504-506.
334. Prati, S., et al. (2007). Composition and content of seed flavonoids in forage and grain legume crops. Journal of Separation Science 30(4):491-501.
335. H araguchi, H., et al. (1996). Protection against oxidative damage by dihydroflavonols in Engelhardtia chrysolepis. Bioscience, Biotechnology, and Biochemistry 60(6):945-948.
336. Cai, Y., Chen, T., Xu, Q. (2003). Astilbin suppresses collagen-induced arthritis via the dysfunction of lymphocytes. Inflammation Research 52(8):334-340.
337. Chen, L., et al. (2007). Simultaneous quantification of five major bioactive flavonoids in Rhizoma smilacis glabrae by high-performance liquid chromatography. Journal of Pharmaceutical and Biomedical Analysis 43(5):1715-1720.
338. Chen, T., et al. (1999). A new flavanone isolated from Rhizoma smilacis glabrae and the structural requirements of its derivatives for preventing immunological hepatocyte damage. Planta Medica 65(1):56-59.
339. Du, Q., Li, L., Jerz, G. (2005). Purification of astilbin and isoastilbin in the extract of smilax glabra rhizome by high-speed counter-current chromatography. Journal of Chromatography. A 1077(1):98-101.
340. L i, Y.Q., et al. (1996). Studies on the structure of isoastilbin. Yao Xue Xue Bao 31(10):761-763.
341. Fukunaga, T., et al. (1989). Studies on the constituents of Japanese mistletoes from different host trees, and their antimicrobial and hypotensive properties. Chemical and Pharmaceutical Bulletin 37(6):1543-1546.
342. Messanga, B., Sondengam, B., Bodo, B. (2000). Calodendroside A: A taxifolin diglucoside from the stem bark of Ochna calodendron. Canadian Journal of Chemistry 78:487-489.
343. Japón-Luján, R., Luque De Castro, M.D. (2007). Static-dynamic superheated liquid extraction of hydroxytyrosol and other biophenols from alperujo (a semisolid residue of the olive oil industry). Journal of Agricultural and Food Chemistry 55(9):3629-3634.
344. Brignolas, F., et al. (1995). Induced responses in phenolic metabolism in two Norway spruce clones after wounding and inoculations with Ophiostoma polonicum, a bark beetle-associated fungus. Plant Physiology 109(3):821-827.
345. L undgren, L.N., Theander, O. (1988). Cis- and trans-dihydroquercetin glucosides from needles of Pinus sylvestris. Phytochemistry 27(3):829-832.
346. Saleem, A., Kivela, H., Pihlaja, K. (2003). Antioxidant activity of pine bark constituents. Zeitschrift fur Naturforschung. Section C. Biosciences 58(5-6): 351-354.
347. Trebatická, J., et al. (2006). Treatment of ADHD with French maritime pine bark extract, Pycnogenol®. European Child and Adolescent Psychiatry 15:329-335.
348. O hmura, W., et al. (2002). Hydrothermolysis of flavonoids in relation to steaming of Japanese larch wood. Holzforschung 56(5):493-497.
349. Willfor, S.M., et al. (2003). Antioxidant activity of knotwood extractives and phenolic compounds of selected tree species. Journal of Agricultural and Food Chemistry 51(26):7600-7606.
350. Tsydendambaev, P.B., et al. (2007). High-performance liquid chromatographic method for the determination of dihydroquercetin in extracts of medicinal plants. Biomeditsinskaia Khimiia 53(2):212-215.
351. Miyazawa, M., Tamura, N. (2007). Inhibitory compound of tyrosinase activity from the sprout of Polygonum hydropiper L. (Benitade). Biological and Pharmaceutical Bulletin 30(3):595-597.
352. Morimura, K., et al. (2006). 5-O-glucosyldihydroflavones from the leaves of Helicia cochinchinensis. Phytochemistry 67(24):2681-2685.
353. Shao, B., et al. (2007). Simultaneous determination of six major stilbenes and flavonoids in Smilax china by high performance liquid chromatography. Journal of Pharmaceutical and Biomedical Analysis 44:737-742.
354. Yi, Y., et al. (1998). Studies on the chemical constituents of Smilax glabra. Acta Pharmacologica Sinica 33(11):873-875.
355. Meyer, P., et al. (1987). A new petunia flower colour generated by transformation of a mutant with a maize gene. Nature 330(6149):677-678.
356. Wang, Y., et al. (2002). Studies on the chemical constituents from Ampelopsis grossedentata. Zhong Yao Cai 25(4):254-256.
357. Souquet, J.M., et al. (2000). Phenolic composition of grape stems. Journal of Agricultural and Food Chemistry 48(4):1076-1080.
358. Baderschneider, B., Winterhalter, P. (2001). Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity. Journal of Agricultural and Food Chemistry 49(6): 2788-2798.
359. Pozo-Bayon, M.A., et al. (2003). Study of low molecular weight phenolic compounds during the aging of sparkling wines manufactured with red and white grape varieties. Journal of Agricultural and Food Chemistry 51(7):2089-2095.
360. Tiukavkina, N.A., Rulenko, I.A., Kolesnik Iu, A. (1997). Dihydroquercetin-A new antioxidant and biologically active food additive. Voprosy Pitaniia 6:12-15.
361. Towatari, K., et al. (2002). Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on proliferation of mouse hair epithelial cells. Planta Medica 68:995-998.
362. Moriguchi, T., et al. (2002). Flavonol synthase gene expression during citrus fruit development. Physiologia Plantarum 114(2):251-258.
363. Matsuda, M., et al. (2008). Biotransformation of (+)-catechin into taxifolin by a two-step oxidation: Primary stage of (+)-catechin metabolism by a novel (+)-catechin-degrading bacteria, Burkholderia sp. KTC-1, isolated from tropical peat. Biochemical and Biophysical Research Communications 366(2):414-419.
364. Kiehlmann, E., Edmond, P.M.L. (1995). Isomerization of dihydroquercetin. Journal of Natural Products 58(3):450-455.
365. Düweler, K.G., Rohdewald, P. (2000). Urinary metabolites of French maritime pine bark extract in humans. Die Pharmazie 55(5):364-368.
366. Grimm, T., et al. (2006). Single and multiple dose pharmacokinetics of maritime pine bark extract (Pycnogenol) after oral administration to healthy volunteers. BMC Clinical Pharmacology 6:4.
367. Schneider, H., Blaut, M. (2000). Anaerobic degradation of flavonoids by Eubacterium ramulus. Archives of Microbiology 173(1):71-75.
368. Schoefer, L., et al. (2003). Anaerobic degradation of flavonoids by Clostridium orbiscindens. Applied and Environmental Microbiology 69(10):5849-5854.
369. Nielsen, S.E., et al. (1998). In vitro biotransformation of flavonoids by rat liver microsomes. Xenobiotica 28(4):389-401.
370. Svobodova, A., Walterova, D., Psotova, J. (2006). Influence of silymarin and its flavonolignans on H(2)O(2)-induced oxidative stress in human keratinocytes and mouse fibroblasts. Burns 32(8):973-979.
371. V itrac, X., et al. (2002). Direct liquid chromatographic analysis of resveratrol derivates and flavanonols in wines with absorbance and fluorescence detection. Analytica Chimica Acta 458:103-110.
372. Trouillas, P., et al. (2004). A theorical study of the conformational behavior and electronic structure of taxifolin correlated with the free radical-scavenging activity. Food Chemistry 88(4):571-582.
373. Theriault, A., et al. (2000). Modulation of hepatic lipoprotein synthesis and secretion by taxifolin, a plant flavonoid. Journal of Lipid Research 41(12): 1969-1979.
374. Braca, A., et al. (2002). Antioxidant activity of flavonoids from
375. Miyazawa, M., Kinoshita, H., Okuno, Y. (2003). Antimutagenic activity of sakuranetin from Prunus Jamasakura. Journal of Food Science: Food Chemistry and Toxicology 68(1):52-56.
376. R ivero-Cruz, I., et al. (2005). Antimycobacterial agents from selected Mexican medicinal plants. Journal of Pharmacy and Pharmacology 57(9):1117-1126.
377. R akwal, R., et al. (2000). Naringenin 7-O-methyltransferase involved in the biosynthesis of the flavanone phytoalexin sakuranetin from rice (Oryza sativa L.). Plant Science 155(2):213-221.
378. Tuchinda, P., et al. (2002). Antiinflammatory cyclohexenyl chalcone derivatives in Boesenbergia pandurata. Phytochemistry 59(2):169-173.
379. O rjala, J., et al. (1994). Cytotoxic and antibacterial dihydrochalcones from Piper aduncum. Journal of Natural Products 57(1):18-26.
380. Danelutte, A.P., et al. (2003). Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth. Phytochemistry 64(2):555-559.
381. Jung, Y.H., et al. (2005). The rice (Oryza sativa) blast lesion mimic mutant, blm, may confer resistance to blast pathogens by triggering multiple defense-associated signaling pathways. Plant Physiology and Biochemistry 43(4):397-406.
382. Aida, Y., et al. (1996). Synthesis of 7-methoxyapigeninidin and its fungicidal activity against Gloeocercospora sorghi. Bioscience, Biotechnology, and Biochemistry 60(9):1495-1496.
383. Kodama, O., et al. (1992). Sakuranetin, a flavonone phytoalexin from ultravioletirradiated rice leaves. Phytochemistry 31(11):3807-3809.
384. R akwal, R., Hasegawa, M., Kodama, O. (1996). A methyltransferase for synthesis of the flavanone phytoalexin sakuranetin in rice leaves. Biochemical and Biophysical Research Communications 222(3):732-735.
385. Tamogami, S., Rakwal, R., Kodama, O. (1997). Phytoalexin production by amino acid conjugates of jasmonic acid through induction of naringenin-7-Omethyltransferase, a key enzyme on phytoalexin biosynthesis in rice (Oryza sativa L.). FEBS Letters 401(2-3):239-242.
386. Jung, Y.H., et al. (2006). Differential expression of defense/stress-related marker proteins in leaves of a unique rice blast lesion mimic mutant (blm). Journal of Proteome Research 5(10):2586-2598.
387. R ojas, A., et al. (1996). Smooth muscle relaxing compounds from Dodonaea viscosa. Planta Medica 62(2):154-159.
388. Abdel-Sattar, E., et al. (2000). Phenolic compounds from Eucalyptus maculata. Die Pharmazie 55(8):623-624.
389. L ambert, J.D., et al. (2005). Cytotoxic lignans from Larrea tridentata. Phytochemistry 66(7):811-815.
390. Moreira, D.D., Guimaraes, E.F., Kaplan, M.A. (2000). A C-glucosylflavone from leaves of Piper lhotzkyanum. Phytochemistry 55(7):783-786.
391. Jerz, G., Waibel, R., Achenbach, H. (2005). Cyclohexanoid protoflavanones from the stem-bark and roots of Ongokea gore. Phytochemistry 66(14):1698-1706.
392. Ghisalberti, E.L., et al. (1978). Constituents of propolis. Cellular and Molecular Life Sciences 34(2):157-158.
393. Tohno, H., et al. (2010). Evaluation of estrogen receptor beta binding of pruni cortex and its constituents. Yakugaku Zasshi. Journal of the Pharmaceutical Society of Japan 130(7):989-997.
394. Duewell, H. (1978). Chemotaxonomy of hte genus Xanthorrhoea. Biochemical Systematics and Ecology 25(8):717-738.
395. Asahina, Y. (1908). Sakuranetin, a new glycoside from the bark of Prunus pseudocerasus. Archiv der Pharmazie 246:259-272.
396. O bara, N., Hasegawa, M., Kodama, O. (2002). Induced volatiles in elicitor-treated and rice blast fungus-inoculated rice leaves. Bioscience, Biotechnology, and Biochemistry 66(12):2549-2559.
397. Kim, B.G., et al. (2006). Regiospecific flavonoid 7-O-methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli. Journal of Agricultural and Food Chemistry 54(3):823-828.
398. Mori, M., et al. (2007). Isolation and molecular characterization of a spotted leaf 18 mutant by modified activation-tagging in rice. Plant Molecular Biology 63(6):847-860.
399. Nakazato, Y., et al. (2000). Methionine-induced phytoalexin production in rice leaves. Bioscience, Biotechnology, and Biochemistry 64(3):577-583.
400. Tamogami, S., Kodama, O. (2000). Coronatine elicits phytoalexin production in rice leaves (Oryza sativa L.) in the same manner as jasmonic acid. Phytochemistry 54(7):689-694.
401. BCC Research, Market Forecasting. (2003). Nutraceuticals sales to hit $75 billion. Accessed February 24, 2009. http://www.nutraingredients-usa.com/Consumer- Trends/Nutraceuticals-sales-to-hit-75-billion.
402. Werner, R.A., et al. (2004). Biosynthesis of gallic acid in Rhus typhina: Discrimination between alternative pathways from natural oxygen isotope abundance. Phytochemistry 65(20):2809-2813.
403. Niemetz, R., Gross, G.G. (2005). Enzymology of gallotannin and ellagitannin biosynthesis. Phytochemistry 66(17):2001-2011.
404. Faried, A., et al. (2007). Anticancer effects of gallic acid isolated from Indonesian herbal medicine, Phaleria macrocarpa (Scheff.) Boerl, on human cancer cell lines. International Journal of Oncology 30(3):605-613.
405. Gross, G.G. (1983). Partial purification and properties of UDP-glucose: Vanillate 1-O-glucosyl transferase from oak leaves. Phytochemistry 22(10):2179-2182.
406. L ing, S.K., Tanaka, T., Kouno, I. (2002). New cyanogenic and alkyl glycoside constituents from Phyllagathis rotundifolia. Journal of Natural Products 65(2): 131-135.
407. Miyaichi, Y., et al. (2006). Studies on nepalese crude drugs. XXVIII. Chemical constituents of Bhote Khair, the underground parts of Eskemukerjea megacarpum Hara. Chemical and Pharmaceutical Bulletin 54(1):136-138.
408. Niemetz, R., Gross, G.G. (2001). Gallotannin biosynthesis: Beta-glucogallin: Hexagalloyl 3-O-galloyltransferase from Rhus typhina leaves. Phytochemistry 58(5): 657-661.
409. Subeki, S., et al. (2005). Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri. Journal of Natural Products 68(4):537-539.