Quercus ilex L.: A rich source of polyacylated flavonoid glucosides

Food Chemistry

Volumn 123, Issue 1, 2010, Pages 131-142

  Karioti, Anastasia ^a   Bilia, Anna Rita ^a   Skaltsa, Helen ^b  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

2D NMR; Acylated flavonol glucosides; Fagaceae; HPLC DAD MS; Oak leaves; Quercus ilex

Indexed keywords

FLAVONOID; GLUCOSIDE; KAEMPFEROL; METHANOL; PLANT EXTRACT; QUERCUS ILEX EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; MASS SPECTROMETRY; NONHUMAN; OAK; PLANT LEAF; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; QUERCUS ILEX;

FAGACEAE; QUERCUS ILEX;

EID: 77952669392     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2010.04.020     Document Type: Article

References (40)

1. Andrenšek S., Simonovska B., Vovka I., Fyhrquist P., Vuorela H., and Vuorela P. Antimicrobial and antioxidative enrichment of oak (Quercus robur) bark by rotation planar extraction using ExtraChrom. International Journal of Food Microbiology 92 (2004) 181-187
2. Berahou A., Auhmani A., Fdil N., Benharref A., Jana M., and Gadhi C.A. Antibacterial activity of Quercus ilex bark's extracts. Journal of Ethnopharmacology 112 (2007) 426-429
3. Bilia A.R., Bergonzi M.C., Lazari D., and Vincieri F.F. Characterization of commercial kava-kava herbal drug and herbal drug preparations by means of nuclear magnetic resonance spectroscopy. Journal of Agricultural and Food Chemistry 50 (2002) 5016-5025
4. Bilia A.R., Bergonzi M.C., Mazzi G., and Vincieri F.F. Analysis of plant complex matrices by use of nuclear magnetic resonance spectroscopy: St. John's wort extract. Journal of Agricultural and Food Chemistry 49 (2001) 2115-2124
5. Cantos E., Espín J.C., López-Bote C., De la Hoz L., Ordóñez J.A., and Tomás-Barberán F. Phenolic compounds and fatty acids from acorns (Quercus sp.), the main dietary constituent of free-ranged Iberian pigs. Journal of Agricultural and Food Chemistry 51 (2003) 6248-6255
6. Crublet M.-L., Long C., Sevenet T., Hadi H.A., and Lavaud C. Acylated flavonol glycosides from leaves of Planchonia grandis. Phytochemistry 64 (2003) 589-594
7. Espín J.C., García-Conesa M.T., and Tomás-Barberán F.A. Nutraceuticals: Facts and fiction. Phytochemistry 68 (2007) 2986-3008
8. Fontana N., and Romussi G. Triterpenoids, steroids, and flavonoids from Quercus virginiana. Part 22. Contents of Fagaceae (Cupuliferae). Pharmazie 52 (1997) 331-332
9. Frangipane M.T., De Santis D., and Ceccarelli A. Influence of oak woods of different geographical origins on quality of wines aged in barriques and using oak chips. Food Chemistry 103 (2007) 46-54
10. Gerothanassis I.P., Exarchou V., Lagouri V., Troganis A., Tsimidou M., and Boskou D. Methodology for identification of phenolic acids in complex phenolic mixtures by high-resolution two-dimensional nuclear magnetic resonance. Application to methanolic extracts of two oregano species. Journal of Agricultural and Food Chemistry 46 (1998) 4185-4192
11. Harbaum B., Hubbermann E.M., Zhu Z., and Schwarz K. Free and bound phenolic compounds in leaves of pak choi (Brassica campestris L. ssp. chinensis var. communis) and Chinese leaf mustard (Brassica juncea Coss). Food Chemistry 110 (2008) 838-846
12. Harborne J.B., and Whilliams C.A. Flavone and flavonol glycosides. In: Harborne J.B., Mabry T.J., and Mabry H. (Eds). The flavonoids (1975), Chapman & Hall, London 376-441
13. Higuchi R., and Donnelly D.M.X. Acylated flavonol glycosides of Pinus contorta needles. Phytochemistry 17 (1978) 787-791
14. Ito N., Fukushima S., Hagiwara A., Shibata M., and Ogiso T. Carcinogenicity of butylated hydroxyanisole in F344 rats. Journal of the National Cancer Institute 70 (1983) 343-347
15. Ito H., Yamagushi K., Kim T.H., Khennouf S., Gharzouli K., and Yoshida T. Dimeric and trimeric hydrolysable tannins from Quercus coccifera and Quercus suber. Journal of Natural Products 65 (2002) 339-345
16. Lee S.S., Lin H.C., and Chen C.K. Acylated flavonol monorhamnosides, α-glucidase inhibitors, from Machilus philippinensis. Phytochemistry 66 (2008) 2347-2353
17. Lin L.Z., Chen P., and Harnly J.M. New phenolic components and chromatographic profiles of green and fermented teas. Journal of Agricultural and Food Chemistry 56 (2008) 8130-8140
18. Mellou F., Lazari D., Skaltsa H., Tselepis A.D., Kolisis F.N., and Stamatis H. Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity. Journal of Biotechnology 116 (2005) 295-304
19. O'Connell J.E., and Fox P.F. Effect of extracts of oak (Quercus petraea) bark, oak leaves, aloe vera (Curacao aloe), coconut shell and wine on the colloidal stability of milk and concentrated milk. Food Chemistry 66 (1999) 93-96
20. Ovaskainen M.L., Törrönen R., Koponen J.M., Sinkko H., Hellströ J., Reinivuo H., et al. Dietary intake and major food sources of polyphenols in Finnish adults. The Journal of Nutrition 138 (2008) 562-566
21. Parejo I., Bastida J., Viladomat F., and Codina C. Acylated quercetagetin glycosides with antioxidant activity from Tagetes maxima. Phytochemistry 66 (2005) 2356-2362
22. Rakíc S., Povrenović D., Tešević V., Simić M., and Maletić R. Oak acorn, polyphenols and antioxidant activity in functional food. Journal of Food Engineering 74 (2006) 416-423
23. Romussi G., Barbieri G., and Caviglioli G. Components of Fagaceae 20. Triterpene saponins, and flavonoids from Quercus imbricaria. Part 22. Pharmazie 49 (1994) 703-704
24. Romussi G., Ciarallo G., and Parodi. Composition of the Cupuliferae. Part 11. Glycosides from Quercus cerris L. Pharmazie 43 (1988) 294-295
25. Romussi G., Parodi B., and Caviglioli G. Flavonoid glycosides from Quercus pubescens Willd., Quercus cerris L. and Quercus ilex L. 14. Contents of Cupuliferae. Pharmazie 46 (1991) 679
26. Romussi G., Parodi B., and Caviglioli G. Flavonoid glycosides from Quercus canariensis Willd. 15. Contents of Cupuliferae. Pharmazie 47 (1992) 877
27. Romussi G., Parodi B., and Sancassan F. Ein ungewöhnlicher diester des Astragalins mit cis- und trans-p-cumarsaüre aus Quercus ilex L. Archiv der Pharmazie 1867 (1984) 1868
28. Romussi S., and Sancassan F. Astragalin 6"-gallate from Quercus ilex L. Archiv der Pharmazie 316 (1983) 648-649
29. Schwarz O. Fagaceae. In: Tutin T.G., Burges N.A., Chater A.O., Edmonso J.R., Heywood V.H., Moore D.M., et al. (Eds). Flora Europaea. 2nd Ed. Vol. 1 (1991), Cambridge University Press 74
30. Simirgiotis M.J., Theoduloz C., Caligari P.D.S., and Schmeda-Hirschmann G. Comparison of phenolic composition and antioxidant properties of two native Chilean and one domestic strawberry genotypes. Food Chemistry 113 (2009) 377-385
31. Soliman F.M., Shehata A.H., Khaleel A.E., and Ezzat S.M. An acylated kaempferol glycoside from flowers of Foeniculum vulgare and F. Dulce. Molecules 7 (2002) 245-251
32. Steinmetz K.A., and Potter J.D. Vegetables, fruit and cancer prevention: A review. Journal of the American Dietetic Association 96 (1996) 1027-1039
33. Susanti D., Sirat H.M., Ahmad F., Ali R.M., Aimi N., and Kitajima M. Antioxidant and cytotoxic flavonoids from the flowers of Melastoma malabathricum L. Food Chemistry 103 (2007) 710-716
34. Tsukamoto S., Tomise K., Aburatani M., Onuki H., Hirorta H., Ishiharajima E., et al. Isolation of cytochrome P450 inhibitors from strawberry fruit, Fragaria ananassa. Journal of Natural Products 67 (2004) 1839-1841
35. Vivas N., Nonier M.F., Vivas de Gaulejac N., and Pianet de Boissel I. Occurence and partial characterization of polymeric ellagitannins in Quercus petraea Liebl., and Q. robur L. wood. Comptes Rendus - Chimie 7 (2004) 945-954
36. Walch N.B., Kühn T., Moskau D., and Zerbe O. Strategies and tools for structure determination of natural products using modern methods of NMR spectroscopy. Chemistry and Biodiversity 2 (2005) 147-177
37. Williams C.A., and Harborne J.B. Flavone and flavonol glycosides. In: Harborne J.B. (Ed). The flavonoids, advances in research since 1986 (1994), Chapman & Hall, London 337
38. Yamashita N., Etoh H., Sakata K., Yagi A., Ina H., and Ina K. An acylated kaempferol glucoside isolated from Quercus dentata as a repellent against the blue mussel Mytilus edulis. Agricultural and Biological Chemistry 53 (1989) 1383-1385
39. 2. Chemical and Pharmaceutical Bulletin 55 (2007) 1308-1315
40. Zhou Y.J., Xu S.X., Che Q.M., and Sun Q.S. Flavonoids from the leaves of Quercus dentata. Indian Journal of Chemistry B 40 (2001) 394-398