Isolation and free-radical-scavenging properties of cyanidin 3-O-glycosides from the fruits of Ribes biebersteinii Berl.

Delazar, Abbas; Khodaie, Laleh; Afshar, Jalil; Nahar, Lutfun; Sarker, Satyajit

doi:10.2478/v10007-010-0007-x

Abstract

The reversed-phase preparative high performance liquid chromatographic purification of the methanol extract of the fruits of Ribes biebersteinii Berl. (Grossulariaceae) afforded five cyanidin glycosides, 3-O-sambubiosyl-5-O-glucosyl cyanidin (1), cyanidin 3-O-sambubioside (2), cyanidin 3-O-glucoside (3), cyanidin 3-O-(2^G-xylosyl)-rutinoside (4) and cyanidin 3-O-rutinoside (5). They showed considerable free-radical-scavenging properties in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay with the RC₅₀ values of 9.29 × 10^-6, 9.33 × 10^-6, 8.31 × 10^-6, 8.96 × 10^-6 and 9.55 × 10^-6 mol L^-1, respectively. The structures of these compounds were elucidated by various chemical hydrolyses and spectroscopic means. The total anthocyanin content was 1.9 g per 100 g dried fruits on cyanidin 3-glucoside basis.

References

N. Saint-Cricq de Gaulejac, Y. Glories and N. Vivas, Free radical scavenging effect of anthocyanins in red wines, Food Res. Int. 32 (1999) 327-333; DOI: 10.1016/S0963-9969(99)00093-9.10.1016/S0963-9969(99)00093-9
Search in Google Scholar
A.R. Clapham, T.G. Tutin and E.F. Warburg, Flora of the British Isles, Cambridge University Press, Cambridge, 1962, pp. 110-123, 459-460, 786-787.
Search in Google Scholar
A. Scharrer and M. Ober, Anthocyanosides in the treatment of retinopathies, Klin. Monatsbl. Augen. 178 (1981) 386-389; DOI: 10.1055/s-2008-1057228.10.1055/s-2008-1057228
Search in Google Scholar
W.E. Glassgen, R. Hofmann, M. Emmerling, G.D. Neumann and H.U. Seitz, Structure elucidation of saccharides in anthocyanins and flavonols by means of methylation analysis and gas-chromatography, J. Chromatogr. 598 (1992) 81-87; DOI: 10.1016/0021-9673(92)85117-C.10.1016/0021-9673(92)85117-C
Search in Google Scholar
L. Longo, A. Scardino, G. Vasapollo and F. Blando, Anthocyanins from Eugenia myrtifolia Sims, Innov. Food Emerging Technol. 8 (2007) 329-332; DOI: 10.1016/j.ifset.2007.03.023.10.1016/j.ifset.2007.03.023
Search in Google Scholar
P. Markakis, Anthocyanins as Food Colors, Academic Press, 1982, pp. 190.10.1016/B978-0-12-472550-8.50013-5
Search in Google Scholar
G.E. Pantelidis, M. Vasilakakis, G.A. Manganaris and G.R. Diamantidis, Antioxidant capacity, phenol, anthocyanin and ascorbic acid contents in raspberries, blackberries, red currants, gooseberries and Cornelian cherries, Food Chem. 102 (2007) 777-783; DOI: 10.1016/j.foodchem.2006.06.021.10.1016/j.foodchem.2006.06.021
Search in Google Scholar
Q. Du, J. Zheng and Y. Xu, Composition of anthocyanins in mulberry and their antioxidant activity, J. Food Composition Anal. 21 (2008) 390-395; DOI: 10.1016/j.jfca.2008.02.007.10.1016/j.jfca.2008.02.007
Search in Google Scholar
J.B. Harborne, Phytochemical Methods, Chapman and Hall, London 1988, pp. 46-55, 61-68.
Search in Google Scholar
J.B. Harborne, Comparative Biochemistry of the Flavonoids, Academic Press, New York 1967, pp. 1-36.
Search in Google Scholar
D. Strack and V. Wray, Methods in Plant Biochemistry (Ed. J.B. Harborne), Academic Press, London 1989, Vol. 1, pp. 325-356.10.1016/B978-0-12-461011-8.50015-9
Search in Google Scholar
J.B. Harborne, Spectral methods of characterizing anthocyanins, Biochem. J. 70 (1958) 22-28.10.1042/bj0700022
Search in Google Scholar
N. Saito, C.F. Timberlake, O.G. Tucknott and I.A.S. Lewis, Fast atom bombardment mass-spectroscopy of the anthocyanins violanin and platconin, Photochem. 22 (1983) 1007-1009; DOI: 10.1016/0031-9422(83)85043-2.10.1016/0031-9422(83)85043-2
Search in Google Scholar
D. Strack and V. Wray, The Anthocyanin, in Flavonoids Advances in Research Since 1986 (Ed. J.B. Harborne), Chapman and Hall, London 1994, pp. 1-22.
Search in Google Scholar
D. Strack, V. Wray, W. Metzger and W. Grosse, Two anthocyanins acylated with gallic acid from the leaves of Victoria amazonica, Phytochem. 31 (1992) 989-991; DOI: 10.1016/0031-9422(92) 80054-I.
Search in Google Scholar
F. Tatsuzawa, N. Saito, K. Shinoda, A. Shigihara and T. Honda, Acylated cyanidin 3-sambubio-side-5-glucosides in three garden plants of the Cruciferae, Phytochem. 67 (2006) 1287-1295; DOI: 10.1016/j.phytochem.2006.05.001.10.1016/j.phytochem.2006.05.001
Search in Google Scholar
N. Saito, F. Tatsuzawa, E. Suenaga, K. Toki, K. Shinoda, A. Shigihara and T. Honda, Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae), Phytochem. 69 (2008) 3139-3150; DOI: 10.1016/j.phytochem.2008.04.010.10.1016/j.phytochem.2008.04.010
Search in Google Scholar
F. Tatsuzawa, Y. Mikanagi, N. Saito, K. Shinoda, A. Shigihara and T. Honda, Cyanidin glycosides in flowers of genus Corydalis (Fumariaceae), Biochem. Syst. Ecol. 33 (2005) 789-798; DOI: 10.1016/j.bse.2004.12.021.10.1016/j.bse.2004.12.021
Search in Google Scholar
N. Saito, F. Tatsuzawa, A. Nishiyama, M. Yokoi, A. Shigihara and T. Honda, Acylated cyaniding 3-sambubioside-5-glucosides in Matthiola incana, Phytochem. 38 (1995) 1027-1032; DOI: 10.1016/0031-9422(94)00659-H.10.1016/0031-9422(94)00659-H
Search in Google Scholar
K. Takeda, D. Fischer and H. Grisebach, Anthocyanin composition of Sinapis alba, light induction of enzymes and biosynthesis, Phytochem. 27 (1988) 1351-1353; DOI: 10.1016/0031-9422(88) 80192-4.
Search in Google Scholar
J-P. Goiffon, P.P. Mouly and E.M. Gaydou, Anthocyanic pigment determination in red fruit juices, concentrated juices and syrups using liquid chromatography, Anal. Chim. Acta 382 (1999) 39-50; DOI: 10.1016/S0003-2670(98)00756-9.10.1016/S0003-2670(98)00756-9
Search in Google Scholar
A. Castañeda-Ovando, M.D. Pacheco-Hernández, M.E. Páez-Hernández, J.A. Rodríguez and C.A. Galán-Vidal, Chemical studies of anthocyanins: A review, Food Chem. 113 (2009) 859-871; DOI: 10.1016/j.foodchem.2008.09.001.10.1016/j.foodchem.2008.09.001
Search in Google Scholar
C.A. Williams, J.B. Harborne and N.L. Demenezis, The utility of leaf flavonoids as taxonomic markers in the subfamily and generic classification of the Velloziaceae, Biochem. Syst. Ecol. 19 (1991) 483-495; DOI: 10.1016/0305-1978(91)90069-C.10.1016/0305-1978(91)90069-C
Search in Google Scholar
B.E. Vanwyk and P.J.D. Winter, Chemotaxonomic value of anthocyanins in Podalyria and Virgilia (tribe Podalyrieae, Fabaceae), Biochem. Syst. Ecol. 22 (1994) 813-818; DOI: 10.1016/0305- 1978 (94)90085-X.
Search in Google Scholar
Y. Kumarasamy, M. Byres, P.J. Cox, A. Delazar, M. Jaspars, L. Nahar, M. Shoeb and S.D. Sarker, Isolation, structure elucidation and biological activity of flavone C-glycosides from the seeds of Alliaria petiolata, Chem. Nat. Compds. 40 (2004) 122-128; DOI: 10.1023/B:CONC.0000033926.72396.41.10.1023/B:CONC.0000033926.72396.41
Search in Google Scholar

Isolation and free-radical-scavenging properties of cyanidin 3-O-glycosides from the fruits of Ribes biebersteinii Berl.

Abstract

Paradigm

My account