1,043
Views
70
CrossRef citations to date
0
Altmetric
Original Articles

The Occurrence, Fate and Biological Activities of C-glycosyl Flavonoids in the Human Diet

&

REFERENCES

  • Abad-Garcia, B., Garmon-Lobato, S., Berrueta, L.A., Gallo, B., and Vicente, F. (2008). New features on the fragmentation and differentiation of C-glycosidic flavone isomers by positive electrospray ionization and triple quadruple mass spectrometry. Rapid Commun Mass Spectrom. 22(12):1834–1842.
  • Abdalla, S., Zarga, M.A., and Sabri, S. (1994). Effects of the flavone luteolin, isolated from Colchicum richii, on guinea-pig isolated smooth muscle and heart and on blood pressure and blood flow. Phytother. Res. 8(5):265–270.
  • Afifi, F.U., Khalil, E., and Abdalla, S. (1999). Effect of isoorientin isolated from Arum palaestinum on uterine smooth muscle of rats and guinea pigs. J. Ethnopharmacol. 65(2):173–177.
  • Akinbala, J.O. (1991). Effect of processing on flavonoids in millet (Pennisetum americanum) flour. Cereal Chem. 68(2):189–183.
  • Arab, L., and Liebeskind, D.S. (2010). Tea, flavonoids and stroke in man and mouse. Arch. Biochem. Biophys. 501(1):31–36.
  • Baldi, A., Rosen, R.T., Fukuda, E.K. and Ho, C.-T. (1995). Identification of nonvolatile components in lemon peel by high-performance liquid chromatography with confirmation by mass spectrometry and diode-array detection. J. Chromatogr. A. 718(1):89–97.
  • Bramati, L., Aquilano, F. and Pietta, P. (2003). Unfermented rooibos tea: Quantitative characterization of flavonoids by HPLC-UV and determination of the total antioxidant activity. J. Agric. Food Chem. 51(5):7472–7474.
  • Bramati, L., Minoggio, M., Gardana, C., Simonetti, P., Mauri, P. and Pietta, P. (2002). Quantitative characterization of flavonoid compounds in Rooibos tea (Aspalathus linearis) by LC-UV/DAD. J. Agric. Food Chem. 50(20):5513–5519.
  • Braune, A. and Blaut, M. (2011). Deglycosylation of puerarin and other aromatic C-glucosides by a newly isolated human intestinal bacterium. Environ. Microbiol. 13(2):482–494.
  • Brazier-Hicks, M., Evans, K.M., Gershater, M.C., Puschmann, H., Steel, P.G. and Edwards, R. (2009). The C-glycosylation of flavonoids in cereals. J. Biol. Chem. 284:17926–17934.
  • Breiter, T., Laue, C., Kressel, G., Gröll, S., Engelhardt, U.H. and Hahn, A. (2011). Bioavailability and antioxidant potential of rooibos flavonoids in humans following the consumption of different rooibos formulations. Food Chem. 128(2):338–347.
  • Caristi, C., Bellocco, E., Gargiulli, C., Toscano, G. and Leuzzi, U. (2006). Flavone-di-C-glycosides in citrus juices from Southern Italy. Food Chem. 95(3):431–437.
  • Cavaliere, C., Foglia, P., Pastorini, E., Samperi, R. and Laganà, A. (2005). Identification and mass spectrometric characterization of glycosylated flavonoids in Triticum durum plants by high-performance liquid chromatography with tandem mass spectrometry. Rapid Commun Mass Spectrom. 19(21):3143–3158.
  • Colombo, R., Yariwake, J.H. and McCullagh, M. (2008). Study of C- and O-glycosylflavones in sugarcane extracts using liquid chromatography—Exact mass measurement mass spectrometry. J. Braz. Chem. Soc. 19(3):483–490.
  • Colombo, R., Yariwake, J.H., Queiroz, E.F., Ndjoko, K. and Hostettmann, K. (2006). On-line identification of further flavone C- and O-glycosides from sugarcane (Saccharum officinarum L. Gramineae) by HPLC-UV-MS. Phytochem. Anal. 17(5):337–343.
  • Courts, F.L. and Williamson, G. (2009). The C-glycosyl flavonoid, aspalathin, is absorbed, methylated and glucuronidated intact in humans. Mol. Nutr. Food Res. 53(9):1104–1111.
  • Day, A.J., Cañada, F.J., Diaz, J.C., Kroon, P.A., McLauchlan, R., Faulds, C.B., Plumb, G.W., Morgan, M.R. and Williamson, G. (2000). Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Lett. 468(2–3):166–170.
  • Day, A.J., DuPont, M.S., Ridley, S., Rhodes, M., Rhodes, M.J. C., Morgan, M.R. A. and Williamson, G. (1998). Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver β-glucosidase activity. FEBS Lett. 436(1):71–75.
  • De Melo, G.O., Muzitano, M.F., Legora-Machado, A., Almeida, T.A., De Oliveira, D.B., Kaiser, C.R., Koatz, V.L. G. and Costa, S.n. S. (2005). C-Glycosylflavones from the aerial parts of Eleusine indica inhibit LPS-induced mouse lung inflammation. Planta Medica. 71(4):362–363.
  • Dhawan, K., Kumar, S. and Sharma, A. (2001). Anti-anxiety studies on extracts of Passiflora incarnata Linneaus. J. Ethnopharmacol. 78(2–3):165–170.
  • Dietrych-Szostak, D. and Oleszek, W. (1999). Effect of processing on the flavonoid content in buckwheat (Fagopyrum esculentum Möench) grain. J. Agric. Food Chem. 47(10):4384–4387.
  • dos Santos, M.D., Chen, G.J., Almeida, M.C., Soares, D.M., de Souza, G.E. P., Lopes, N.P. and Lantz, R.C. (2010). Effects of caffeoylquinic acid derivatives and C-flavonoid from Lychnophora ericoides on in vitro inflammatory mediator production. Nat. Product Comm. 5(5):733–740.
  • Erlund, I. (2004). Review of the flavonoids quercetin, hesperetin and naringenin. Dietary sources, bioactivities, bioavailability and epidemiology. Nutr. Res. 24(10):851–874.
  • Feng, X., Jiang, D., Shan, Y., Dai, T.B., Dong, Y.F. and Cao, W.X. (2008). New flavonoid-C-glycosides from Triticum aestivum. Chem. Nat. Compd. 44(2):171–173.
  • Feng, Y. and McDonald, C.E. (1987). C-Glycosyl flavonoid isolated from wheat bran. Cereal Foods World. 32:652.
  • Feng, Y., McDonald, C.E. and Vick, B.A. (1988). C-Glycosylflavones from hard red spring wheat bran. Cereal Chem. 65:452–456.
  • Ferreres, F., Gil-Izquierdo, A., Andrade, P.B., Valentao, P. and Tomas-Barberan, F.A. (2007). Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography-tandem mass spectrometry. J. Chromatogr. A. 1161(1–2):214–223.
  • Ferreres, F., Krskova, Z., Goncalves, R.F., Valentao, P., Pereira, J.A., Dusek, J., Martin, J. and Andrade, P.B. (2009). Free water-soluble phenolics profiling in barley (Hordeum vulgare L.). J. Agric. Food Chem. 57(6):2405–2409.
  • Folador, P., Cazarolli, L.H., Gazola, A.C., Reginatto, F.H., Schenkel, E.P. and Silva, F.R. M. B. (2010). Potential insulin secretagogue effects of isovitexin and swertisin isolated from Wilbrandia ebracteata roots in non-diabetic rats. Fitoterapia. 81(8):1180–1187.
  • Franz, G. and Grun, M. (1983). Chemistry, occurrence and biosynthesis of C-glycosyl compounds in plants. Planta Medica. 47(3):131–140.
  • Gallardo, C., Jiménez, L. and García-Conesa, M.T. (2006). Hydroxycinnamic acid composition and in vitro antioxidant activity of selected grain fractions. Food Chem. 99(3):455–463.
  • Garg, A., Garg, S., Zaneveld, L.J. D. and Singla, A.K. (2001). Chemistry and pharmacology of the citrus bioflavonoid hesperidin. Phytother. Res. 15(8):655–669.
  • Gil-Izquierdo, A., Gil, M.I., Ferreres, F. and Tomas-Barberan, F.A. (2001). In vitro availability of flavonoids and other phenolics in orange juice. J. Agric. Food Chem. 49(2):1035–1041.
  • Gil-Izquierdo, A., Riquelme, M.a. T., Porras, I. and Ferreres, F. (2003). Effect of the rootstock and interstock grafted in lemon tree (Citrus limon (L.) Burm.) on the flavonoid content of lemon juice. J. Agric. Food Chem. 52(2):324–331.
  • Gil, M.I., Ferreres, F. and Tomas-Barberan, F.A. (1998). Effect of modified atmosphere packaging on the flavonoids and vitamin C content of minimally processed Swiss chard (Beta vulgaris subspecies cycla). J. Agric. Food Chem. 46(5):2007–2012.
  • González-Molina, E., Domínguez-Perles, R., Moreno, D.A. and García-Viguera, C. (2010). Natural bioactive compounds of Citrus limon for food and health. J. Pharmaceut. Biomed. Anal. 51(10):327–345.
  • Gorzalczany, S., Marrassini, C., Miño, J., Acevedo, C. and Ferraro, G. (2011). Antinociceptive activity of ethanolic extract and isolated compounds of Urtica circularis. J. Ethnopharmacol. 134(3):733–738.
  • Harborne, J.B. (1965). Plant polyphenols-XIV.: Characterization of flavonoid glycosides by acidic and enzymic hydrolyses. Phytochemistry. 4(1):107–120.
  • Hasslauer, I., Oehme, A., Locher, S., Valotis, A., van't Slot, G., Humpf, H.-U. and Schreier, P. (2010). Flavan-3-ol C-glycosides – Preparation and model experiments mimicking their human intestinal transit. Mol. Nutr. Food Res. 54(11):1546–1555.
  • Hatano, T., Miyatake, H., Natsume, M., Osakabe, N., Takizawa, T., Ito, H. and Yoshida, T. (2002). Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects. Phytochemistry. 59(7):749–758.
  • Hays, W.S., Jenison, S.A., Yamada, T., Pastuszyn, A. and Glew, R.H. (1996). Primary structure of the cytosolic β-glucosidase of guinea pig liver. Biochem. J. 319(3):829–837.
  • Hegnauer, R. and Gpayer-Barkmeijer, R.J. (1993). Relevance of seed polysaccharides and flavonoids for the classification of the leguminosae: A chemotaxonomic approach. Phytochemistry. 34(3):3–16.
  • Hirvonen, T., Virtamo, J., Korhonen, P., Albanes, D. and Pietinen, P. (2000). Intake of flavonoids, carotenoids, vitamins C and E, and risk of stroke in male smokers. Stroke. 31(10):2301–2306.
  • Hoffmann-Bohm, K., Lotter, H., Seligmann, O. and Wagner, H. (1992). Antihepatotoxic C-glycosylflavones from the leaves of Allophyllus edulis var. edulis and gracilis. Planta Medica. 58(6):544–548.
  • Hollman, P.C. H., Bijsman, M.N. C. P., van Gameren, Y., Cnossen, E.P. J., de Vries, J.H. M. and Katan, M.B. (1999). The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free Radical Res. 31(6):569–573.
  • Hollman, P.C. H., Cassidy, A., Comte, B., Heinonen, M., Richelle, M., Richling, E., Serafini, M., Scalbert, A., Sies, H. and Vidry, S.p. (2011). The biological relevance of direct antioxidant effects of polyphenols for cardiovascular health in humans is not established. J. Nutr. 141(5):989S–1009S.
  • Hollman, P.C. H. and Katan, M.B. (1997). Absorption, metabolism and health effects of dietary flavonoids in man. Biomed. Pharmacother. 51(8):305–310.
  • Hultin, P.G. (2005). Bioactive C-glycosides from bacterial secondary metabolism. Curr. Topics Med. Chem. 5(14):1299–1331.
  • Jin, J.-S., Nishihata, T., Kakiuchi, N. and Hattori, M. (2008). Biotransformation of C-glucosylisoflavone puerarin to estrogenic (3S)-equol in co-culture of two human intestinal bacteria. Biol. Pharm. Bull. 31(8):1621–1625.
  • Joubert, E. (1996). HPLC quantification of the dihydrochalcones, aspalathin and nothofagin in rooibos tea (Aspalathus linearis) as affected by processing. Food Chem. 55(4):403–411.
  • Joubert, E. and deVilliers, O.T. (1997). Effect of fermentation and drying conditions on the quality of rooibos tea. Int. J. Food Sci. Technol. 32(2):127–134.
  • Joubert, E., Richards, E.S., Merwe, J.D., De Beer, D., Manley, M. and Gelderblom, W.C. (2008). Effect of species variation and processing on phenolic composition and in vitro antioxidant activity of aqueous extracts of Cyclopia spp. (honeybush tea). J. Agric. Food Chem. 56(3):954–963.
  • Kawano, A., Nakamura, H., Hata, S., Minakawa, M., Miura, Y. and Yagasaki, K. (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.
  • Kazuno, S., Yanagida, M., Shindo, N. and Murayama, K. (2005). Mass spectrometric identification and quantification of glycosyl flavonoids, including dihydrochalcones with neutral loss scan mode. Anal. Biochem. 347(2):182–192.
  • King, H.G. C. (1962). Phenolic compounds of commercial wheat germ. J. Food Sci. 27(5):446–454.
  • Koeppen, B.H. and Roux, D.G. (1965). C-Glycosylflavonoids—Chemistry of orientin and iso-orientin. Biochem. J. 97(2):444–448.
  • Koeppen, B.H. and Roux, D.G. (1966). C-Glycosylflavonoids. The chemistry of aspalathin. Biochem. J. 99(3):604–609.
  • Krafczyk, N. and Glomb, M.A. (2008). Characterization of phenolic compounds in rooibos tea. J. Agric. Food Chem. 56(9):3368–3376.
  • Krafczyk, N., Kotke, M., Lehnert, N. and Glomb, M. (2008). Phenolic composition of rhubarb. European Food Res. Technol. 228(2):187–196.
  • Kreuz, S., Joubert, E., Waldmann, K.-H. and Ternes, W. (2008). Aspalathin, a flavonoid in Aspalathus linearis (rooibos), is absorbed by pig intestine as a C-glycoside. Nutr. Res. 28(10):690–701.
  • Lairson, L.L., Henrissat, B., Davies, G.J. and Withers, S.G. (2008). Glycosyltransferases: Structures, functions, and mechanisms. Ann. Rev. Biochem. 77:521–555.
  • Ma, Z., Wu, Q., Lee, D.Y. W., Tracy, M. and Lukas, S.E. (2005). Determination of puerarin in human plasma by high performance liquid chromatography. J. Chromatogr. B. 823(2):108–114.
  • Manach, C., Scalbert, A., Morand, C., Rãmãsy, C. and Jimãnez, L. (2004). Polyphenols: Food sources and bioavailability. Am. J. Clin. Nutr. 79(5):727–747.
  • Manley, M., Joubert, E. and Botha, M. (2006). Quantification of the major phenolic compounds, soluble solid content and total antioxidant activity of green rooibos (Aspalathus linearis) by means of near infrared spectroscopy. J. Near Infrared Spec. 14(4):213–222.
  • Manthey, J.A. (2000). Biological properties of flavonoids pertaining to inflammation. Microcirculation. 7(6):S29–S34.
  • Marais, C., van Rensburg, W.J., Ferreira, D. and Steenkamp, J.A. (2000). (S)- and (R)-eriodictyol-6-C-beta-D-glucopyranoside, novel keys to the fermentation of rooibos (Aspalathus linearis). Phytochemistry. 55(1):43–49.
  • Marotti, M. and Piccaglia, R. (2002). Characterization of flavonoids in different cultivars of onion (Allium cepa L.). J. Food Sci. 67(3):1229–1232.
  • Mink, P.J., Scrafford, C.G., Barraj, L.M., Harnack, L., Hong, C.P., Nettleton, J.A. and Jacobs, D.R. , Jr. (2007). Flavonoid intake and cardiovascular disease mortality: A prospective study in postmenopausal women. Am. J. Clin. Nutr. 85(3):895–909.
  • Miyake, Y., Yamamoto, K., Morimitsu, Y. and Osawa, T. (1997). Isolation of C-glucosylflavone from lemon peel and antioxidative activity of flavonoid compounds in lemon fruit. J. Agric. Food Chem. 45(3):4619–4623.
  • Mladenka, P., Zatloukalová, L., Filipský, T. and Hrdina, R. (2010). Cardiovascular effects of flavonoids are not caused only by direct antioxidant activity. Free Radical Biol. Med. 49(6):963–975.
  • Mullen, W., Boitier, A., Stewart, A.J. and Crozier, A. (2004). Flavonoid metabolites in human plasma and urine after the consumption of red onions: Analysis by liquid chromatography with photodiode array and full scan tandem mass spectrometric detection. J. Chromatogr. A. 1058(1–2):163–168.
  • Nicolle, E., Souard, F., Faure, P. and Boumendjel, A. (2011). Flavonoids as promising lead compounds in type 2 diabetes mellitus: Molecules of interest and structure-activity relationship. Curr. Med. Chem. 18(17):2661–2672.
  • Orhan, D.D., Aslan, M., Aktay, G.k., Ergun, E., Yesilada, E. and Ergun, F. (2003). Evaluation of hepatoprotective effect of Gentiana olivieri herbs on subacute administration and isolation of active principle. Life Sci. 72(20):2273–2283.
  • Pengilly, M., Joubert, E., van Zyl, W.H., Botha, A. and Bloom, M. (2008). Enhancement of rooibos (Aspalathus linearis) aqueous extract and antioxidant yield with fungal enzymes. J. Agric. Food Chem. 56(11):4047–4053.
  • Quílez, A., Berenguer, B., Gilardoni, G., Souccar, C., de Mendonça, S., Oliveira, L.F. S., Martín-Calero, M.J. and Vidari, G. (2010). Anti-secretory, anti-inflammatory and anti-Helicobacter pylori activities of several fractions isolated from Piper carpunya Ruiz & Pav. J. Ethnopharmacol. 128(3):583–589.
  • Rabe, C., Steenkamp, J.A., Joubert, E., Burger, J.F. W. and Ferreira, D. (1994). Phenolic metabolites from rooibos tea (Aspalathus-linearis). Phytochemistry. 35(6):1559–1565.
  • Ragone, M.I., Sella, M., Conforti, P., Volonté, M.G. and Consolini, A.E. (2007). The spasmolytic effect of Aloysia citriodora, Palau (South American cedrón) is partially due to its vitexin but not isovitexin on rat duodenums. J. Ethnopharmacol. 113(2):258–266.
  • Ramarathnam, N., Osawa, T., Namiki, M. and Kawakishi, S. (1989). Chemical studies on novel rice hull antioxidants. 2. Identification of isovitexin, a C-glycosyl flavonoid. J. Agric. Food Chem. 37(2):316–319.
  • Ren, F., Jing, Q., Shen, Y., Ma, H. and Cui, J. (2006). Quantitative determination of puerarin in dog plasma by HPLC and study on the relative bioavailability of sustained release tablets. J. Pharm. Biomed. Anal. 41(2):549–553.
  • Saito, K. (1990). Enzyme-catalyzed cleavage of the C-glycosidic linakage to the aromatic ring-A of a 3′,4′,5′7-tetrahydroxyflavone 8-C-glycoside. Biochim. Biophys. Acta. 1035(3):340–347.
  • Sanugul, K., Akao, T., Li, Y., Kakiuchi, N., Nakamura, N. and Hattori, M. (2005). Isolation of a human intestinal bacterium that transforms mangiferin to norathyriol and inducibility of the enzyme that cleaves a C-glucosyl bond. Biol. Pharm. Bull. 28(9):1672–1678.
  • Scalbert, A. and Williamson, G. (2000). Dietary intake and bioavailability of polyphenols. J. Nutr. 130(8S):2073S–2085S.
  • Schmandke, H. (2005). Antioxidants in rooibos tea: Dihydrochalcones and flavonoids. Ernahrungs-Umschau. 52(1):18–23.
  • Schuit, F.C., Huypens, P., Heimberg, H. and Pipeleers, D.G. (2001). Glucose sensing in pancreatic β-cells. Diabetes. 50(1):1–11.
  • Schulz, H., Joubert, E. and Schutze, W. (2003). Quantification of quality parameters for reliable evaluation of green rooibos (Aspalathus linearis). European Food Res. Technol. 216(6):539–543.
  • Sena, L.M., Zucolotto, S.M., Reginatto, F.H., Schenkel, E.P. and De Lima, T.C. M. (2009). Neuropharmacological activity of the pericarp of Passiflora edulis flavicarpa degener: Putative involvement of C-glycosylflavonoids. Exp. Biol. Med. 234(8):967–975.
  • Shen, J., Meng, Z., Su, H., Xing, D., Ding, Y. and Du, L. (2007). Different kinetics of puerarin in plasma of normal and depressed rats after oral administration of Chinese medicine TZ18. Tsinghua Sci. Technol. 12(4):394–399.
  • Shie, J.J., Chen, C.A., Lin, C.C., Ku, A.F., Cheng, T.J. R., Fang, J.M. and Wong, C.H. (2010). Regioselective synthesis of di-C-glycosylflavones possessing anti-inflammation activities. Organic Biomol. Chem. 8(19):4451–4462.
  • Singh, R., Akhtar, N. and Haqqi, T.M. (2011). Green tea polyphenol epigallocatechin-3-gallate: Inflammation and arthritis. Life Sci. 86(26):907–918.
  • Slimestad, R., Fossen, T. and Verheul, M.J. (2008). The flavonoids of tomatoes. J. Agric. Food Chem. 56(7):2436–2441.
  • Snijman, P.W., Swanevelder, S., Joubert, E., Green, I.R. and Gelderblom, W.C. A. (2007). The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): Some dose-response effects on mutagen activation-flavonoid interactions. Mutat. Res.-Gen. Toxicol. Environ. Mutagenesis. 631(2):111–123.
  • Stalmach, A., Mullen, W., Pecorari, M., Serafini, M. and Crozier, A. (2009). Bioavailability of C-linked dihydrochalcone and flavanone glucosides in humans following ingestion of unfermented and fermented rooibos teas. J. Agric. Food Chem. 57(15):7104–7111.
  • Standley, L., Winterton, P., Marnewick, J.L., Gelderblom, W.C., Joubert, E. and Britz, T.J. (2001). Influence of processing stages on antimutagenic and antioxidant potentials of rooibos tea. J. Agric. Food Chem. 49(1):114–117.
  • Stark, T. and Hofmann, T. (2006). Application of a molecular sensory science approach to alkalized cocoa (Theobroma cacao): Structure determination and sensory activity of nonenzymatically C-glycosylated flavan-3-ols. J. Agric. Food Chem. 54(25):9510–9521.
  • Stark, T., Keller, D., Wenker, K., Hillmann, H. and Hofmann, T. (2007). Nonenzymatic C-glycosylation of flavan-3-ols by oligo- and polysaccharides. J. Agric. Food Chem. 55(23):9685–9697.
  • Steinmetz, K.A. and Potter, J.D. (1996). Vegetables, fruit, and cancer prevention: A review. J. Am. Dietetic Assoc. 96(10):1027–1039.
  • Stevens, J.F. and Page, J.E. (2004). Xanthohumol and related prenylflavonoids from hops and beer: To your good health! Phytochemistry. 65(10):1317–1330.
  • Tomás-Barberán, F.A. and Clifford, M.N. (2000). Flavanones, chalcones and dihydrochalcones – nature, occurrence and dietary burden. J. Sci. Food Agr. 80(7):1073–1080.
  • vonGadow, A., Joubert, E. and Hansmann, C.F. (1997). Effect of extraction time and additional heating on the antioxidant activity of rooibos tea (Aspalathus linearis) extracts. J. Agric. Food Chem. 45(4):1370–1374.
  • Wagner, H., Obermeier, G., Chari, V.M. and Galle, K. (1980). Flavonoid-C-glycosides from Triticum aestivum L. J. Nat. Products. 43(5):583–587.
  • Walgren, R.A., Lin, J.-T., Kinne, R.K.-H. and Walle, T. (2000). Cellular uptake of dietary flavonoid quercetin β-glucoside by sodium-dependent glucose transporter SGLT1. J. Pharm. Exp. Ther. 294(3):837–843.
  • Wallace, J.W. and Alston, R.E. (1966). C-Glycosylation of flavonoids. Plant Cell Physiol. 7(4):699–700.
  • Walle, T., Browning, A.M., Steed, L.L., Reed, S.G. and Walle, U.K. (2005). Flavonoid glucosides are hydrolyzed and thus activated in the oral cavity in humans. J. Nutr. 135(1):48–52.
  • Watanabe, M. (1998). Catechins as antioxidants from buckwheat (Fagopyrum esculentum Möench) groats. J. Agric. Food Chem. 46(3):839–845.
  • Yun, J.H., Tomas-Barberan, F.A., Kader, A.A. and Mitchell, A.E. (2006). The flavonoid glycosides and procyanidin composition of deglet noor dates (Phoenix dactylifera). J. Agric. Food Chem. 54(6):2405–2411.
  • Zhang, Y., Tie, X., Bao, B., Wu, X. and Zhang, Y. (2007). Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats. Br. J. Nutr. 97(3):484–494.
  • Zucolotto, S.M., Goulart, S., Montanher, A.B., Reginatto, F.v. H., Schenkel, E.P. and Frãde, T.n. S. (2009). Bioassay-guided isolation of anti-inflammatory C-glucosylflavones from Passiflora edulis. Planta Medica. 75:1221–1226.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.