Advance on the Flavonoid C-glycosides and Health Benefits

Critical Reviews in Food Science and Nutrition

Volumn 56, Issue , 2016, Pages S29-S45

  Xiao, Jianbo ^a,b   Capanoglu, Esra ^c   Jassbi, Amir Reza ^d   Miron, Anca ^e  

^a FUJIAN AGRICULTURE AND FORESTRY UNIVERSITY   (China)

^b University of Macau

^c ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

^d SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^e GRIGORE T POPA UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

Author keywords

absorption; biological benefits; Flavonoid C glycosides; stability

Indexed keywords

ABSORPTION; ANTIOXIDANTS; BIOACTIVITY; CONVERGENCE OF NUMERICAL METHODS; FLAVONOIDS; FREE RADICALS;

ANTI-INFLAMMATORY ACTIVITY; ANTI-OXIDANT ACTIVITIES; ANTI-TUMOR ACTIVITIES; ANTIBACTERIAL AND ANTIFUNGAL ACTIVITY; ANTIVIRAL ACTIVITIES; BIOLOGICAL BENEFITS; C-GLYCOSIDES; HEPATOPROTECTIVE ACTIVITIES;

SUGARS;

ANTIDIABETIC AGENT; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; ANTIPARASITIC AGENT; ANTITHROMBOCYTIC AGENT; ANTIVIRUS AGENT; C-GLYCOSIDE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; FLAVONOID; MONOSACCHARIDE; PLANT EXTRACT; PLANT MEDICINAL PRODUCT;

AGING; DRUG EFFECTS; HEALTHY DIET; HUMAN;

AGING; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; ANTI-INFECTIVE AGENTS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; ANTIPARASITIC AGENTS; ANTIVIRAL AGENTS; FLAVONOIDS; HEALTHY DIET; HUMANS; HYPOGLYCEMIC AGENTS; MONOSACCHARIDES; PHYTOCHEMICALS; PLANT EXTRACTS; PLATELET AGGREGATION INHIBITORS;

EID: 84978148867     PISSN: 10408398     EISSN: 15497852     Source Type: Journal    
DOI: 10.1080/10408398.2015.1067595     Document Type: Article

References (136)

1. Y.An,, C.S.Zhang,, Y.Du,, L.Zhao,, Z.Z.Cheng,, W.J.Zhang,, et al. (2013). Comparative excretion of vitexin-2″-O-rhamnoside in mice after oral and intravenous administration. Afr. J. Pharm. Pharmacol. 7:833–837.
2. D.Angelino,, M.Berhow,, P.Ninfali, and E.H.Jeffery, (2013). Caecal absorption of vitexin-2-O-xyloside and its aglycone apigenin, in the rat. Food Funct. 4:1339–1345.
3. S.Aquila,, R.M.Giner,, M.C.Recio,, E.D.Spegazzini, and J.L.Ríos, (2009). Anti-inflammatory activity of flavonoids from Cayaponia tayuya roots. J. Ethnopharmacol. 121:333–337.
4. E.M.Atta,, A.A.Nassar,, N.M.Hasan, and A.R.Hasan, (2013). New flavonoid glycoside and pharmacological activities of Pteranthus dichotomus forssk. Rec. Nat. Prod. 7:69–79.
5. D.Barreca,, E.Bellocco,, C.Caristi,, U.Leuzzi, and G.Gattuso, (2011a). Distribution of C- and O-glycosyl flavonoids, (3-hydroxy-3-methylglutaryl)glycosyl flavanones and furocoumarins in Citrus aurantium L. juice. Food Chem. 124:576–582.
6. D.Barreca,, E.Bellocco,, C.Caristi,, U.Leuzzi, and G.Gattuso, (2011b). Kumquat (Fortunella japonica Swingle) juice: Flavonoid distribution and antioxidant properties. Food Res. Int. 44(7):2190–2197.
7. D.Barreca,, E.Bellocco,, U.Leuzzi, and G.Gattuso, (2014). First evidence of C- and O-glycosyl flavone in blood orange (Citrus sinensis (L.) Osbeck) juice and their influence on antioxidant properties. Food Chem. 149:244–252.
8. N.Batool,, Y.Bibi,, N.Ilyas, (2014). Current status of Ulmus wallichiana: Himalayan endangered Elm. Pure Appl. Bio. 3:60–65.
9. Z.Benayad,, C.Gomez-Cordoves, and N.E.Es-Safi, (2014). Identification and quantification of flavonoid glycosides from fenugreek (Trigonella foenum-graecum) germinated seeds by LC-DAD-ESI/MS analysis. J. Food Compos. Anal. 35:21–29.
10. M.Biesaga, (2011). Influence of extraction methods on stability of flavonoids. J. Chromatogr. A 1218:2505–2512.
11. J.Brango-Vanegas,, G.M.Costaa,, C.F.Ortmann,, E.P.Schenkel,, F.H.Reginatto,, F.A.Ramos,, et al. (2014). Glycosylflavonoids from Cecropia pachystachya Trécul are quorumsensing inhibitors. Phytomed. 21:670–675.
12. A.Braune, and M.Blaut, (2012). Intestinal bacterium Eubacterium cellulosolvens deglycosylates flavonoid C- and O-glucosides. Appl. Environ. Microbiol. 78:8151–8153.
13. M.Brazier-Hicks,, K.M.Evans,, M.C.Gershater,, H.Puschmann,, P.G.Steel, and R.Edwards, (2009). The C-glycosylation of flavonoids in cereals. J. Biol. Chem. 284:17926–17934.
14. S.Q.Cai,, R.F.Wang,, X.W.Yang,, M.Y.Shang,, C.M.Ma, and Y.Shoyama, (2006). Antiviral flavonoid-type C-glycosides from the flowers of Trollius chinensis. Chem. Biodiver. 3:343–348.
15. T.W.Cao,, C.A.Geng,, F.Q.Jiang,, Y.B.Ma,, K.He,, N.J.Zhou,, et al. (2013). Chemical constituents of Swertia yunnanensis and their anti-hepatitis B virus activity. Fitoterapia. 89:175–182.
16. K.Carte,, B.Carr,, S.DeBrosse,, C.Hemling,, M.E.MacKenzie,, L.Offen,, et al. (1991). Aciculatin, a novel flavone-C-glycoside with DNA binding activity from Chrysopogon aciculatis. Tetrahedron. 47:1815–1822.
17. L.H.Cazarolli,, L.H.Cazarolli,, V.D.Kappel,, D.F.Pereira,, H.H.Moresco,, I.M.C.Brighente,, M.G.Pizzolatti,, et al. (2012). Anti-hyperglycemic action of apigenin-6-C-β-fucopyranoside from Averrhoa carambola. Fitoterapia. 83:1176–1183.
18. C.Cerella,, M.H.Teiten,, F.Radogna,, M.Dicato, and M.Diederich, (2014). From nature to bedside: Pro-survival and cell death mechanisms as therapeutic targets in cancer treatment. Biotechnol. Adv. 32:1111–1122.
19. C.C.Chang,, A.F.Ku,, Y.Y.Tseng,, W.B.Yang,, J.M.Fang, and C.H.Wong, (2010). 6,8-Di-C-glycosyl flavonoids from Dendrobium huoshanense. J. Nat. Prod. 73:229–232.
20. Y.G.Chen,, P.Li,, P.Li,, R.Yan,, X.Q.Zhang,, Y.Wang,, et al. (2013a). α-Glucosidase inhibitory effect and simultaneous quantification of three major flavonoid glycosides in Microctis folium. Molecules 18:4221–4232.
21. Y.H.Chen,, W.J.Zhang,, D.Li,, J.J.Ai,, Y.H.Meng,, X.X.Ying,, et al. (2013b). Hepatic and gastrointestinal first-pass effects of vitexin 4″-O-glucoside in rats. J. Pharm. Pharmacol. 65:1500–1507.
22. J.S.Choi,, M.N.Islam,, M.Y.Ali,, E.J.Kim,, Y.M.Kim, and H.A.Jung, (2014a). Effects of C-glycosylation on anti-diabetic, anti-Alzheimer's disease and anti-inflammatory potential of apigenin. Food Chem. Toxicol. 64:27–33.
23. J.S.Choi,, N.Islam,, Y.Ali,, Y.M.Kim,, H.J.Park,, H.S.Sohn,, et al. (2014b). The effects of C-glycosylation of luteolin on its antioxidant, anti-Alzheimer's disease, anti-diabetic, and anti-inflammatory activities. Arch. Pharm. Res. 37:354–363.
24. C.Y.Choo,, N.Y.Sulong,, F.Man, and T.W.Wong, (2012). Vitexin and isovitexin from the leaves of Ficus deltoidea with in-vivo α-glucosidase inhibition. J. Ethnopharmacol. 142:776–781.
25. F.L.Courts, and G.Williamson, (2009). The C-glycosyl flavonoid, aspalathin, is absorbed, methylated and glucuronidated intact in humans. Mol. Nutr. Food Res. 53:1104–1111.
26. M.da Silva Morrone,, A.M.de Assis,, R.F.da Rocha,, J.Gasparotto,, A.C.Gazola, and G.M.Costa, (2013). Passiflora manicata (Juss.) aqueous leaf extract protects against reactive oxygen species and protein glycation in vitro and ex vivo models. Food Chem. Toxicol. 60:45–51.
27. B.D.Davis, and J.S.Brodbelt, (2004). Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry. J. Am. Soc. Mass. Spectr. 15:1287–1299.
28. H.P.Devkota,, K.Fukusako,, K.Ishiguro, and S.Yahara, (2013). Flavone C-glycosides from Lychnis senno and their antioxidative activity. Nat. Prod. Comm. 8:1413–1414.
29. H.Du,, H.Wang,, J.Yu,, C.Liang,, W.Ye, and P.Li, (2012). Enrichment and purification of total flavonoid C-glycosides from Abrus mollis extracts with macroporous resins. Ind. Eng. Chem. Res. 51(21):7349–7354.
30. T.S.El-Alfy,, H.M.A.El-Gohary,, N.M.Sokkar,, M.Hosny, and D.A.Al-Mahdy, (2011). A new flavonoid C-glycoside from Celtis australis L. and Celtis occidentalis L. leaves and potential antioxidant and cytotoxic activities. Sci. Pharm. 79:963–975.
31. M.Elbandy, and J.R.Rho, (2014). New flavone-di-C-glycosides from the seeds of Egyptian lupin (Lupinus termis). Phytochem. Lett. 9:127–131.
32. S.A.El-Toumy,, E.A.Omara,, S.A.Nada, and J.Bermejo, (2011). Flavone C-glycosides from Montanoa bipinnatifida stems and evaluation of hepatoprotective activity of extract. J. Med. Plant Res. 5:1291–1296.
33. J.B.Fang,, W.Jia,, W.Y.Gao,, Z.Yao,, J.Teng,, A.H.Zhao,, et al. (2007). Antitumor constituents from Alternanthera philoxeroides. J. Asian Nat. Prod. Res. 9:511–515.
34. P.Folador,, L.H.Cazarolli,, A.C.Gazola,, F.H.Reginatto,, E.P.Schenkel, and F.R.M.B.Silva, (2010). Potential insuline secretagogue effects of isovitexin and swertisin isolated from Wilbrandia ebracteata roots in non-diabetic rats. Fitoterapia 81:1180–1187.
35. V.Francisco,, A.Figueirinha,, G.Costa,, J.Liberal,, M.C.Lopes,, C.García-Rodríguez,, et al. (2014). Chemical characterization and anti-inflammatory activity of luteolin glycosides isolated from lemongrass. J. Funct. Foods 10:436–443.
36. T.S.Gechev,, J.Hille,, H.J.Woerdenbag,, M.Benina,, N.Mehterov,, V.Toneva,, et al. (2014). Natural products from resurrection plants: Potential for medical applications. Biotechnol. Adv. 32:1091–1101.
37. M.I.Georgiev, (2014). From plants to pharmacy shelf. Biotechnol. Adv. 32:1051–1052.
38. J.B.Harborne, (Ed.), (1993). The Flavonoids: Advances in Research Since 1986, pp. 57–93, Chapman & Hall, London.
39. J.B.Harborne, and C.A.Williams, (2000). Advances in flavonoid research since 1992. Phytochem. 55:481–504.
40. M.Hattori,, Y.Z.Shu,, A.I.El-Sedawy,, T.Namba,, K.Kobashi, and T.Tomimori, (1988). Metabolism of homoorientin by human intestinal bacteria. J. Nat. Prod. 51:874–878.
41. U.W.Hawas,, G.M.Soliman,, A.L.T.El-Kassem,, A.R.H.Farrag,, K.Mahmoud, and F.León, (2013). A new flavonoid C-glycoside from Solanum elaeagnifolium with hepatoprotective and curative activities against paracetamol-induced liver injury in mice. Z. Naturforsch. 68c:19–28.
42. K.E.Heim,, A.R.Tagliaferro, and D.J.Bobilya, (2002). Flavonoid antioxidants: Chemistry, metabolism and structure-activity relationships. J. Nutr. Biochem. 13:572–584.
43. K.Hoffmann-Bohm,, H.Lotter,, O.Seligmann, and H.Wagner, (1992). Antihepatotoxic C-glycosylflavones from the leaves of Allophyllus edulis var. edulis and gracilis. Planta Med. 58:544–548.
44. Y.J.Hong,, F.A.Tomas-Barberan,, A.A.Kader, and A.E.Mitchell, (2006). The flavonoid glycosides and procyanidin composition of Deglet Noor dates (Phoenix dactylifera). J. Agric. Food Chem. 54:2405–2411.
45. H.B.Hu, and J.Fan, (2008). Structural identification and antibacterial activity of chemical constituents of Acanthopanax brachypus Harms. Chin. Hosp. Pharm J. 28:1344–1347.
46. M.Huang,, J.du Plessis,, J.du Preez,, J.Hamman, and A.Viljoen, (2008). Transport of aspalathin, a rooibos tea flavonoid, across the skin and intestinal epithelium. Phytother. Res. 22:699–704.
47. G.M.Huber,, H.P.V.Rupasinghe, and F.Shahidi, (2009). Inhibition of oxidation of omega-3 polyunsaturated fatty acids and fish oil by quercetin glycosides. Food Chem. 117:290–295.
48. P.G.Hultin, (2005). Bioactive C-glycosides from bacterial secondary metabolism. Curr. Top Med. Chem. 5:1299–1331.
49. W.Jiang,, H.Q.Qu,, D.H.Yuan,, G.D.Yang,, F.An, and S.H.Wang, (2012). Protection of orientin and vitexin from flowers and flower buds of Trollius chinensis on brain injury in aging mice induced by D-galactose. Chin. Trad. Herb. Drug 43:1376–1380.
50. J.S.Jin,, T.Nishihata,, N.Kakiuchi, and M.Hattori, (2008). Biotransformation of C-glucosylisoflavone puerarin to estrogenic (3S)-equol in co- culture of two human intestinal bacteria. Biol. Pharm. Bull. 31:1621–1625.
51. I.H.Jung,, H.E.Lee,, S.J.Park,, Y.J.Ahn,, G.Kwon,, H.Woob,, et al. (2014). Ameliorating effect of spinosin, a C-glycoside flavonoid, on scopolamine-induced memory impairment in mice. Pharmacol. Biochem. Behav. 120:88–94.
52. M.S.Kamel, (2003). Flavone C-glycosides from Lupinus hartwegii. Phytochem. 63:449–452.
53. I.Kim,, Y.W.Chin,, S.W.Lim,, Y.C.Kim, and J.Kim, (2004). Norisoprenoids and hepatoprotective flavone glycosides from the aerial Parts of Beta vulgaris var. Cicla. Arch. Pharm. Res. 27:600–603.
54. B.H.Koeppen, and D.G.Roux, (1966). C-Glycosylflavonoids, The chemistry of aspalathin. Biochem. J. 99:604–609.
55. D.Y.Kong, (2012). Introduction to Natural Products Chemistry. In: R.Xu,, Y.Ye,, W.Zhao,, Eds., Taylor & Francis CRC Press, NY, 2012.
56. S.Kreuz,, E.Joubert,, K.H.Waldmann, and W.Ternes, (2008). Aspalathin, a flavonoid in Aspalathus linearis (rooibos), is absorbed by pig intestine as a C-glycoside. Nutr. Res. 28:690–701.
57. G.Kuhnle,, J.P.Spencer,, H.Schroeter,, B.Shenoy,, E.S.Debnam,, S.K.S.Srai, and U.Hahn, (2000). Epicatechin and catechin are O-methylated and glucuronidated in the small intestine. Biochem. Biophys. Res. Com. 277:507–512.
58. Y.S.Kwon,, S.S.Kim,, S.J.Sohn,, P.J.Kong,, I.Y.Cheong,, C.M.Kim,, et al. (2004). Modulation of suppressive activity of lipopolysaccharide-induced nitric oxide production by glycosidation of flavonoids. Arch. Pharm. Res. 27:751–756.
59. C.Y.Lai,, S.L.Pan,, C.C.Chen, and C.M.Teng, (2011). Aciculatin, a C-glycosidic flavonoid, induces p53-dependent cell cycle arrest and apoptosis in HCT116 colorectal cancer cells. FASEB J. 25:621–627.
60. C.Y.Lai,, A.C.Tsai,, M.C.Chen,, L.H.Chang,, H.L.Sun,, Y.L.Chang,, et al. (2012). Aciculatin induces p53-dependent apoptosis via MDM2 depletion in human cancer cells in vitro and in vivo. PLoS ONE. 7:e42192.
61. W.Lee,, S.K.Ku, and J.S.Bae, (2014). Vascular barrier protective effects of orientin and isoorientin in LPS-induced inflammation in vitro and in vivo. Vascular.Pharmacol. 62:3–14.
62. K.J.Lemmens,, B.van de Wier,, N.Vaes,, M.Ghosh,, M.A.van Zandvoort,, W.J.van der Vijgh, and G.R.Haenen, (2014). The flavonoid 7-mono-O-(β-hydroxyethyl)-rutoside is able to protect endothelial cells by a direct antioxidant effect. Toxicol. in Vitro 28:538–543.
63. C.N.A.Leong,, M.Tako,, I.Hanashiro, and H.Tamaki, (2008). Antioxidant flavonoid glycosides from the leaves of Ficus pumila L. Food Chem. 109:415–420.
64. n and SORI-CID FTICR MS. J. Am. Soc. Mass. Spectrom. 20:1496–1503.
65. S.S.Li,, J.Wu,, L.G.Chen,, H.Du,, Y.J.Xu,, L.J.Wang,, H.J.Zhang,, X.C.Zheng, and L.S.Wang, (2014). Biogenesis of C-glycosyl flavones and profiling of flavonoid glycosides in Lotus (Nelumbo nucifera). PLoS ONE. 9(10):e108860. doi:10.1371/journal.pone.0108860
66. S.-H.Li,, Q.Zhao,, Y.Cheng, and F.Liu, (2013). Antimicrobial activities of vitexin from Alsophila spinutosa. Food Res. Develop. 34(14):4–6.
67. M.J.Liang,, W.Xu,, W.D.Zhang,, C.Zhang,, R.H.Liu,, Y.H.Shen,, et al. (2007). Quantitative LC/MS/MS method and in vivo pharmacokinetic studies of vitexin rhamnoside, a bioactive constituent on cardiovascular system from hawthorn. Biomed. Chromatogr. 21:422–429.
68. L.Z.Lin, and J.M.Harnly, (2007). A Screening method for the identification of glycosylated flavonoids and other phenolic compounds using a standard analytical approach for all plant materials. J. Agric. Food Chem. 55:1084–1096.
69. C.N.Lin,, S.H.Kuo, and M.I.Chung, (1997). A new flavone C-glycoside and antiplatelet and vasorelaxing flavones from Gentiana arisanensis. J. Nat. Prod. 60:851–853.
70. J.Y.Liu,, S.Y.Li,, J.Y.Feng,, Y.Sun,, J.N.Cai,, X.F.Sun,, et al. (2013). Flavone C-glycosides from the flowers of Trollius chinensis and their anticomplementary activity. J. Asian Nat. Prod. Res. 15:325–331.
71. L.Y.Ma,, R.H.Liu,, X.D.Xu,, M.Q.Yu,, Q.Zhang, and H.L.Liu, (2010). The pharmacokinetics of C-glycosyl flavones of Hawthorn leaf flavonoids in rat after single dose oral administration. Phytomed. 17:640–645.
72. J.A.Manthey,, N.Guthrie, and K.Grohmann, (2001). Biological properties of citrus flavonoids pertaining to cancer and inflammation. Curr. Med. Chem. 8:135–153.
73. M.Materska, (2015). Flavone C-glycosides from Capsicum annuum L.: Relationships between antioxidant activity and lipophilicity. Eur. Food Res. Technol. 240:549–557.
74. A.Mora,, M.Paya,, J.L.Rios, and M.J.Alcaraz, (1990). Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of non-enzymic lipid peroxidation. Biochem. Pharmacol. 40:793–797.
75. R.Muharini,, V.Wray,, D.Lai, and P.Proksch, (2014). New flavone C-glycosides from leaves of Sarcotheca griffithii (Hook F) Hallier F. Phytochem. Lett. 9:26–32.
76. K.Nakamura,, T.Nishihata,, J.S.Jin,, C.M.Ma,, K.Komatsu,, M.Iwashima, and M.Hattori, (2011). The C-glucosyl bond of puerarin was cleaved hydrolytically by a human intestinal bacterium strain PUE to yield its aglycone daidzein and an intact glucose. Chem. Pharmaceut. Bull. 59:23–27.
77. A.Obmann,, D.Tsendayush,, T.Thalhammer,, M.Zehl,, T.P.N.Vo,, S.Purevsuren,, et al. (2010). Extracts from the Mongolian traditional medicinal plants Dianthus versicolor Fisch. and Lilium pumilum Delile stimulate bile flow in an isolated perfused rat liver model. J. Ethnopharmacol. 131:555–561.
78. A.Obmann,, I.Werner,, A.Presser,, M.Zehl,, Z.Swoboda,, S.Purevsuren, and S.Glasl, (2011). Flavonoid C-and O-glycosides from the Mongolian medicinal plant Dianthus versicolor Fisch. Carbohyd. Res. 346:1868–1875.
79. G.Odontuya,, J.R.S.Hoult, and P.J.Houghton, (2005). Structure-activity relationship for anti-inflammatory effect of luteolin and its derived glycosides. Phytother. Res. 19:782–786.
80. M.H.Omar,, W.Mullen, and A.Crozier, (2011). Identification of proanthocyanidin dimers and trimers, flavone C-glycosides, and antioxidants in Ficus deltoidea, a Malaysian herbal tea. J. Agric. Food Chem. 59:1363–1369.
81. T.Oualid, and M.S.S.Artur, (2012). Advances in C-glycosylflavonoid research. Curr. Org. Chem. 16:859–896.
82. S.Pacifico,, M.Scognamiglio,, B.D'Abrosca,, S.Piccolella,, N.Tsafantakis,, M.Gallicchio, and A.Fiorentino, (2010). Spectroscopic characterization and antiproliferative activity on HepG2 human hepatoblastoma cells of flavonoid C-glycosides from Petrorhagia velutina. J. Nat. Prod. 73:1973–1978.
83. Y.Z.Pan,, Y.Guan,, Z.F.Wei,, X.Peng,, T.T.Li,, X.L.Qi, and Y.J.Fu, (2014). Flavonoid C-glycosides from pigeon pea leaves as color and anthocyanin stabilizing agent in blueberry juice. Indust. Crops. Prod. 58:142–147.
84. S.H.Park,, J.H.Kim,, D.H.Lee,, J.W.Kang,, H.H.Song,, S.R.Oh,, et al. (2013). Luteolin 8-C-β-fucopyranoside inhibits invasion and suppresses TPA-induced MMP-9 and IL-8 via ERK/AP-1 and ERK/NF-kB signaling in MCF-7 breast cancer cells. Biochimie 95:2082–2090.
85. X.F.Peng,, Z.P.Zheng,, K.W.Cheng,, F.Shan,, G.X.Ren,, F.Chen,, et al. (2008). Inhibitory effect of mung bean extract and its constituents vitexin and isovitexin on the formation of advanced glycation endproducts. Food Chem. 106:475–481.
86. S.Perveen,, A.M.El-Shafae,, A.Al-Taweel,, G.A.Fawzy,, A.Malik,, N.Afza,, M.Latif, and L.Iqbal, (2011). Antioxidant and urease inhibitory C-glycosylflavonoids from Celtis africana. J. Asian Nat. Prod. Res. 13:799–804.
87. A.L.Piccinelli,, M.G.Mesa,, D.M.Armenteros,, M.A.Alfonso,, A.C.Arevalo,, L.Campone,, et al. (2008). HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity. J. Agric. Food Chem. 56:1574–1581.
88. M.Plaza,, T.Pozzo,, J.Liu,, K.Z.G.Ara,, C.Turner, and E.N.Karlsson, (2014). Substituent effects on in vitro antioxidizing properties, stability, and solubility in flavonoids. J. Agric. Food Chem. 62:3321–3333.
89. G.W.Plumb,, K.R.Price, and G.Williamson, (1999). Antioxidant properties of flavonol glycosides from tea. Redox. Rep. 4:13–16.
90. R.Praveena,, K.Sadasivam,, R.Kumaresan,, V.Deepha, and R.Sivakumar, (2013). Experimental and DFT studies on the antioxidant activity of a C-glycoside from Rhynchosia capitata. Spectrochim.Acta A: Mol. Biomol. Spectr. 103:442–452.
91. P.Rawat,, M.Kumar,, K.Sharan,, N.Chattopadhyay, and R.Maurya, (2009). Ulmosides A and B: Flavonoid 6-C-glycosides from Ulmus wallichiana, stimulating osteoblast differentiation assessed by alkaline phosphatase. Bioorg. Med. Chem. Lett. 19:4684–4687.
92. A.R.Rechner,, G.Kuhnle,, P.Bremner,, G.P.Hubbard,, K.P.Moore, and C.A.Rice-Evans, (2002). The metabolic fate of dietary polyphenols in humans. Free Rad. Biol. Med. 33:220–235.
93. M.Schnekenburger,, M.Dicato, and M.Diederich, (2014). Plant-derived epigenetic modulators for cancer treatment and prevention. Biotechnol. Adv. 32:1123–1132.
94. M.Shibano,, K.Kakutani,, M.Taniguchi,, M.Yasuda, and K.Baba, (2008). Antioxidant constituents in the dayflower (Commelina communis L.) and their α-glucosidase-inhibitory activity. J. Nat. Med. 62:349–353.
95. K.-H.Shin,, C.-K.Lee,, W.-S.Woo, and S.-S.Kang, (1978). Sedative action of spinosin. Arch. Pharm. Res. 1:7–11.
96. M.J.Simirgiotis,, G.Schmeda-Hirschmann,, J.Borquez, and E.Kennelly, (2013). The Passiflora tripartita (Banana Passion) fruit: A source of bioactive flavonoid C-glycosides isolated by HSCCC and characterized by HPLC–DAD–ESI/MS/MS. Molecules 18(2):1672–1692.
97. D.Simkhada,, N.P.Kurumbang, H.C.Lee, and J.K.Sohng, (2010). Exploration of glycosylated flavonoids from metabolically engineered E. coli. Biotechnol. Biopro. Eng. 15:754–760.
98. A.Stalmach,, W.Mullen,, M.Pecorari,, M.Serafini, and A.Crozier, (2009). Bioavailability of C-linked dihydrochalcone and flavanone glucosides in humans following ingestion of unfermented and fermented rooibos teas. J. Agric. Food Chem. 57:7104–7111.
99. M.Stobiecki, (2000). Application of mass spectrometry for identification and structural studies of flavonoid glycosides. Phytochem. 54:237–256.
100. D.Tasdemir,, M.Kaiser,, R.Brun,, V.Yardley,, T.J.Schmidt,, F.Tosun,, et al. (2006). Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: In vitro, in vivo, structure-activity relationship, and quantitative structure--activity relationship studies. Antimicrob. Agents. Chemother. 50:1352–1364.
101. A.Ulubelen,, H.Ayyildiz, and T.J.Mabry, (1981). C-Glycosylflavonoids and other compounds from Passiflora cyanea, P. oerstedii and P. menispermifolia. J. Nat. Prod. 44:368–369.
102. N.C.Veitch, and R.J.Grayer, (2011). Flavonoids and their glycosides, including anthocyanins. Nat. Prod. Rep. 28:1626–1695.
103. S.H.Venkatesha,, B.M.Berman, and K.D.Moudgil, (2011). Herbal medicinal products target defined biochemical and molecular mediators of inflammatory autoimmune arthritis. Bioorg. Med. Chem. 19:21–29.
104. S.Wada,, P.He,, I.Hashimoto,, N.Watanabe, and K.Sugiyama, (2000). Glycosidic flavonoids as rat-liver injury preventing compounds from green tea. Biosci. Biotech. Biochem. 64:2262–2265.
105. L.E.Wang,, Y.J.Bai,, X.R.Shi,, X.Y.Cui,, S.Y.Cui,, F.Zhang,, et al. (2008). Spinosin, a C-glycoside flavonoid from semen Zizhiphi Spinozae, potentiated pentobarbital-induced sleep via the serotonergic system. Pharmacol. Biochem. Behav. 90:399–403.
106. Y.Wang,, M.Chen,, J.Zhang,, X.L.Zhang,, X.J.Huang,, X.Wu,, et al. (2012d). Flavone C-glycosides from the leaves of Lophatherum gracile and their in vitro antiviral activity. Planta Med. 78:46–51.
107. L.E.Wang,, X.Y.Cui,, S.Y.Cui,, J.X.Cao,, J.Zhang,, Y.H.Zhang,, et al. (2010). Potentiating effect of spinosin, a C-glycoside flavonoid of Semen Ziziphi spinosae, on pentobarbital-induced sleep may be related to postsynaptic 5-HT1A receptors. Phytomed. 17:404–409.
108. Y.J.Wang,, C.H.Han,, A.J.Leng,, W.J.Zhang,, H.F.Xue,, Y.H.Chen,, et al. (2012a). Pharmacokinetics of vitexin in rats after intravenous and oral administration. Afr. J. Pharm. Pharmacol. 6:2368–2373.
109. Z.B.Wang,, B.Yuan,, X.K.Jia, and F.An, (2012b). Investigations on antioxidation of orientin in mice and vitexin in Trollius chinesis. J. Hebei. Normal. Univ. 28(6):72–75.
110. L.E.Wang,, X.Q.Zhang,, Y.Q.Yin, and Y.H.Zhang, (2012c). Augmentative effect of spinosin on pentobarbitalinduced loss of righting reflex in mice associated with presynaptic 5-HT1A receptor. J. Pharm. Pharmacol. 64:277–282.
111. Y.N.Wang,, Y.L.Zhen,, X.L.Li,, X.Shao, and L.Y.Dong, (2013). Comparative study on absorption of vitexin and rhamnosylvitexin in intestin of rat. Anhui. Med. Pharmaceut. J. 10:1660–1663.
112. P.Wipf,, J.G.Pierce, and N.Zhuang, (2005). Silver (I)-catalyzed addition of zirconocenes to glycal epoxides. A new synthesis of α-C-glycosides. Org. Lett. 7:483–485.
113. X.A.Wu,, F.Qing, and M.Q.Du, (2012). The QSAR study on anti-inflammatory activities of C-glycosyflavones. Lishizhen Med. Mater. Res. 23:632–633.
114. J.B.Xiao, and M.I.Georgiev, (2015). International Symposium on Phytochemicals in Medicine and Food (ISPMF 2015): An introduction. Food Chem. 186:1–5.
115. J.B.Xiao, and P.Högger, (2013). Metabolism of dietary flavonoids in liver microsomes. Curr. Drug. Metab. 14:381–391.
116. J.B.Xiao, and P.Högger, (2014). Advance on the pharmacokinetics of natural bioactive polyphenols. Curr. Drug Metab. 15:1–2.
117. J.B.Xiao, and P.Högger, (2015a). Dietary polyphenols and type 2 diabetes: Current insights and future perspectives. Curr. Med. Chem. 22:23–38.
118. J.B.Xiao, and P.Högger, (2015b). Stability of dietary polyphenols under the cell culture condition: Avoiding erroneous conclusions. J. Agri. Food Chem. 63:1547–1557.
119. J.B.Xiao,, G.Y.Kai,, K.Yamamoto, and X.Q.Chen, (2013). Advance in dietary polyphenols as α-glucosidases inhibitors: A review on structure-activity relationship aspect. Crit. Rev. Food Sci. Nutr. 53:818–836.
120. J.B.Xiao,, T.S.Muzashvili, and M.I.Georgiev, (2014). Advance on biotechnology for glycosylation of high-value flavonoids. Biotechnol. Adv. 32:1145–1156.
121. J.B.Xiao,, X.L.Ni,, G.Y.Kai, and X.Q.Chen, (2015). Advance in dietary polyphenols as aldose reductases inhibitors: Structure-activity relationship aspect. Crit. Rev. Food Sci. Nutr. 55:16–31.
122. Y.A.Xu,, G.R.Fan,, S.Gao, and Z.Y.Hong, (2008). Assessment of intestinal absorption of vitexin-2″-O-rhamnoside in hawthorn leaves flavonoids in rat using In situ and in vitro absorption models. Drug. Develop Indust. Pharm. 34:164–170.
123. J.J.Yin,, J.G.Qu,, W.J.Zhang,, D.R.Lu,, Y.C.Gao,, X.X.Ying,, et al. (2014). Tissue distribution comparison between healthy and fatty liver rats after oral administration of hawthorn leaf extract. Biomed. Chromatogr. 28:637–647.
124. X.X.Ying,, X.M.Lu,, X.H.Sun,, X.Q.Li, and F.M.Li, (2007). Determination of vitexin-2″-O-rhamnoside in rat plasma by ultra-performance liquid chromatography electrospray ionization tandem mass spectrometry and its application to pharmacokinetic study. Talanta 72:1500–1506.
125. L.Yuan,, J.Wang,, H.F.Xiao,, C.X.Xiao,, Y.T.Wang, and X.B.Liu, (2012). Isoorientin induces apoptosis through mitochondrial dysfunction and inhibition of PI3K/Akt signalling pathway in HepG2 cancer cells. Toxicol. Appl. Pharmacol. 265:83–92.
126. L.Yuan,, J.Wang,, H.F.Xiao,, W.Q.Wu,, Y.T.Wang, and X.B.Liu, (2013). MAPK signaling pathways regulate mitochondrial-mediated apoptosis induced by isoorientin in human hepatoblastoma cancer cells. Food Chem. Toxicol. 53:62–68.
127. L.Yuan,, S.P.Wei,, J.Wang, and X.B.Liu, (2014). Isoorientin induces apoptosis and autophagy simultaneously by reactive oxygen species (ROS)-related p53, PI3K/Akt, JNK, and p38 signaling pathways in HepG2 cancer cells. J. Agric. Food Chem. 62:5390–5400.
128. N.Zehrmann,, C.Zidorn, and M.Ganzera, (2010). Analysis of rare flavonoid C-glycosides in Celtis australis L. by micellar electrokinetic chromatography. J. Pharmaceut. Biomed. Anal. 51:1165–1168.
129. Y.Zhang,, X.Y.Chen,, J.Cheng,, C.Jin, and Y.Zhang, (2014). The reduction effect of dietary flavone C- and O-glycosides on the formation of acrylamide and its correlation and prediction with the antioxidant activity of Maillard reaction products. RSC Adv. 4:24147–24150.
130. Y.Q.Zhang,, J.G.Luo,, C.Han,, J.F.Xu, and L.Y.Kong, (2015). Bioassay-guided preparative separation of angiotensin-converting enzyme inhibitory C-flavone glycosides from Desmodium styracifolium by recycling complexation high-speed counter-current chromatography. J. Pharmaceut. Biomed. Anal. 102:276–281.
131. X.W.Zhang,, P.P.Shang,, F.Qin,, Q.Zhou,, B.Y.Gao,, H.Q.Huang,, et al. (2013). Chemical composition and antioxidative and anti-inflammatory properties of ten commercial mung bean samples. LWT – Food Sci. Technol. 54:171–178.
132. Y.Zhang,, X.W.Tie,, B.L.Bao,, X.Q.Wu, and Y.Zhang, (2007). Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats. Br. J. Nutr. 97:484–494.
133. W.J.Zhang,, M.Xu,, C.Q.Yu,, G.F.Zhang, and X.Tang, (2010). Simultaneous determination of vitexin-4″-O-glucoside, vitexin-2″-O-rhamnoside, rutin and vitexin from hawthorn leaves flavonoids in rat plasma by UPLC–ESI-MS/MS. J. Chromatogr. B 878:1837–1844.
134. B.Zhou,, G.Blasko, and G.A.Cordell, (1988). Alternanthin A. C-glycosylated flavonoid from Alternanthera philoxeroides. Phytochem. 27:3633–3636.
135. D.X.Zhu,, F.An, and S.H.Wang, (2012). Effects of orientin from TroHius chinensis on cell growth and apoptosis of EC-109 cells. Chin. Trad Patent. Med. 34:2055–2059.
136. S.M.Zucolotto,, C.Fagundes,, F.H.Reginatto,, F.A.Ramos,, L.Castellanos,, C.Duque, and E.P.Schenkel, (2012). Analysis of C-glycosyl flavonoids from South American Passiflora species by HPLC-DAD and HPLC-MS. Phytochem. Anal. 23:232–239.