Antioxidant and free radical-scavenging properties of three flavonoids isolated from the leaves of Rhamnus alaternus L. (Rhamnaceae) : A structure-activity relationship study

Food Chemistry

Volumn 116, Issue 1, 2009, Pages 258-264

  Ammar, Rebai Ben ^a   Bhouri, Wissem ^a   Sghaier, Mohamed Ben ^a   Boubaker, Jihed ^a   Skandrani, Ines ^a   Neffati, Aicha ^a   Bouhlel, Ines ^a   Kilani, Soumaya ^a   Mariotte, Anne Marie ^b   Chekir Ghedira, Leila ^a   Dijoux Franca, Marie Geneviève ^c   Ghedira, Kamel ^a  

^a UNIVERSITY OF MONASTIR   (Tunisia)

^b UFR de Pharmacie   (France)

^c University of Lyon   (France)

Author keywords

DPPH radical dot ; Flavonoids; Lipid peroxidation; Rhamnus alaternus L.; Superoxide anions; Xanthine oxidase

Indexed keywords

ANTIOXIDANT; APIGENIN; FLAVONOID; FREE RADICAL; HYDROGEN PEROXIDE; KAEMPFEROL; KAEMPFEROL 3 O ISORHAMNINOSIDE; LIPID; PLANT EXTRACT; QUERCETIN; RHAMNETIN 3 O ISORHAMNINOSIDE; RHAMNOCITRIN 3 O SORHAMNINOSIDE; RHAMNUS ALATERNUS EXTRACT; SCAVENGER; SUPEROXIDE; UNCLASSIFIED DRUG; XANTHINE OXIDASE;

ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN K 562; CONTROLLED STUDY; CORRELATIONAL STUDY; ENZYME ACTIVITY; ENZYME INHIBITION; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HUMAN; HUMAN CELL; IC 50; ISOLATION PROCEDURE; LIPID PEROXIDATION; MASS SPECTROMETRY; PLANT LEAF; PROTON NUCLEAR MAGNETIC RESONANCE; RHAMNACEAE; RHAMNUS ALATERNUS; STRUCTURE ACTIVITY RELATION;

RHAMNACEAE; RHAMNUS ALATERNUS;

EID: 64449083125     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2009.02.043     Document Type: Article

References (53)

1. Abegaz B.M., and Peter M.G. Emodin and emodinanthrone rhamnoside acetates from fruits of Rhamnus prinoides. Phytochemistry 39 (1995) 1411-1414
2. Al-Azzawie H.F., and Mohamed-Saiel S.A. Hypoglycemic and antioxidant effect of oleuropein in alloxan-diabetic rabbits. Life Science 78 (2006) 1371-1377
3. Alemayu G., Abegaz B., Snatzke G., and Duddeck H. Bianthrones from Senna longiracemosa. Phytochemistry 32 (1993) 1273-1277
4. Ames S.N., Shigrenaga M.K., and Hagen T.M. Oxidant, antioxidant and degenerative disease of aging. Proceedings of the National Academy of Sciences of the United States of America 90 (1993) 7915-7922
5. Bandyopadhyay M., Chakraborty R., and Raychaudhuri U. A process for preparing a natural antioxidant enriched dairy product (Sandesh). LWT-Food Science and Technology 40 (2007) 842-851
6. 1-, nifuroxazide-, and sodium azide-induced mutagenicity by extracts from Rhamnus alaternus L. Chemico-Biological Interactions 174 (2008) 1-10
7. 2 and pre-treated with (Tunisian) Rhamnus alaternus extracts: Combination with polyphenolic compounds and classic in vitro assays. Chemico-Biological Interactions 168 (2007) 171-183
8. Ben Ammar R., Kilani S., Abdelwahed A., Hayder N., Mahmoud A., Chibani J., et al. In vitro mutagenicity, antimutagenicity and free radical scavenging activities of Rhamnus alaternus L. (Rhamnaceae) extracts. Pakistan Journal of Biological Sciences 8 (2005) 439-445
9. Ben Ammar R., Kilani S., Bouhlel I., Ezzi L., Skandrani I., Boubaker J., et al. Antiproliferative, antioxidant and antimutagenic activities of flavonoids-enriched extracts from (Tunisian) Rhamnus alaternus L. combination with the phytochemical composition. Drug and Chemical Toxicology 31 (2008) 61-80
10. Ben Ammar R., Kilani S., Bouhlel I., Skandrani I., Naffeti A., Boubaker J., et al. Antibacterial and cytotoxic activities of extracts from (Tunisian) Rhamnus alaternus (Rhamnaceae). Annals of Microbiology 57 (2007) 453-460
11. Bondent V., Brand-Williams W., and Bereset C. Kinetic and mechanism of antioxidant activity using the DPPH free radical methods. Lebensmittel Wissenschaft and Technologie 30 (1997) 609-615
12. Bors W., Michel C., and Stettmaier K. Structure-activity relationships governing antioxidant capacities of plant polyphenols. Methods in Enzymology 335 (2001) 166-180
13. Boukef K. Rhamnus alaternus. Essaydali 81 (2001) 34-35
14. Burda S., and Oleszek W. Antioxidant and antiradical activities of flavonoids. Journal of Agricultural and Food Chemistry 49 (2001) 2774-2779
15. Cai Y.-Z., Sun M., Xing J., Luo Q., and Corke H. Structure-radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants. Life Sciences 78 (2006) 2872-2888
16. Cheel Ch.J., Theoduloz C., Rodriguez J.A., Caligari P.D.S., and Schmeda-Hirschmann G. Free radical scavenging activity and phenolic content in achenes and thalamus from Fragaria chiloensis ssp. chiloensis, F. vesca and F. xananassa cv. Food Chemistry 102 (2007) 36-44
17. Chevolleau S., Debal A., and Ucciani E. Détermination de l'activité antioxydante d'extraits végétaux. Revue Française des Corps Gras 39 (1992) 3-8
18. Cimanga K., De Bruyne T., Hu J.P., Cos P., Apers S., Pieters L., et al. Constituents from Morinda morindoides leaves as inhibitors of xanthine oxidase and scavengers of superoxide anions. Pharmacy and Pharmacology Communications 5 (1991) 419-424
19. Coskun M., Satake T., Hori K., and Tanker M. Anthraquinone glycosides from Rhamnus libanoticus. Phytochemistry 29 (1990) 2018-2020
20. Cotelle N., Bernier J., Catteau J., Pommery J., Wallet J., and Gaydou E.M. Antioxidant properties of hydroxy-flavones. Free Radical Biology and Medicine 20 (1996) 35-43
21. Da Silva S.L., Da Silva A., Honorio K.M., Marangoni S., Toyama M.H., and Da Silva A.B.F. The influence of electronic, steric and hydrophobic properties of flavonoid compounds in the inhibition of the xanthine oxidase. Journal of Molecular Structure (Theochem) 684 (2004) 1-7
22. Frum Y., Viljoen A.M., and Van Heerden F.R. Verbascoside and luteolin-5-O-β-d-glucoside isolated from Halleria lucida L. exhibit antagonistic anti-oxidant properties in vitro. South African Journal of Botany 73 (2007) 583-587
23. Janero D.R. Malondialdehyde and thiobarbituric acid reactivity as diagnostic indices of lipid peroxidation and peroxidative tissue injury. Free Radical Biology and Medicine 9 (1990) 515-540
24. Kahkonen M.P., Hopia A.I., Vuorela H.J., Rauha J.-P., Pihlaja K., Kujala T.S., et al. Antioxidant activity of plant extracts containing phenolic compounds. Journal of Agricultural and Food Chemistry 47 (1999) 3954-3962
25. Kunzelmann C., Toti F., Freyssinet J.M., and Meyer D. Interference of activated factor VII in apoptosis of erythroleukemic K562 cells. Comptes Rendues Biologies 325 (2002) 1111-1118
26. Lee S.E., Shin H.T., Hwang H.J., and Kim H.J. Antioxidant activity of extracts from Alpinia katsumadar seed. Phytotherapy Research 17 (2003) 1041-1047
27. Lin C., Chen C., Chen C., Liang Y., and Lin J. Molecular modeling of flavonoids that inhibits xanthine oxidase. Biochemical and Biophysical Research Communications 294 (2002) 167-172
28. Lin C.-N., Chung M.-I., Can K.-H., and Lu Ch.-M. Flavonol and anthraquinone glycosides from Rhamnus formosana. Phytochmistry 30 (1991) 3103-3106
29. Lin C.-N., and Wei B.-L. Flavonol and naphthalene glycosides from Rhamnus nakaharai. Journal of Natural Products 57 (1994) 294-297
30. {radical dot} scavenging by ascorbic acid. Food Chemistry 107 (2008) 40-43
31. Lu Y., Sun Y., Foo L.Y., McNabb W.C., and Molan A.L. Phenolic glycosides of forage legume Onobrychis viciifolia. Phytochemistry 55 (2000) 67-75
32. Mai L.P., Guéritte F., Dumontet V., Tri M.V., Hill B., Thoison O., et al. Cytotoxicity of Rhamnosylanthraquinones and Rhamnosylanthrones from Rhamnus nepalensis. Journal of Natural Products 64 (2001) 1162-1168
33. Marzouk M.S., El-Toumy S.A.A., Merfort I., and Nawwar M.A.M. Polyphenolic metabolites of Rhamnus disperma. Phytochemistry 52 (1999) 943-946
34. Middleton E.J., Kandaswami C., and Theoharides T.C. The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacological Reviews 52 (2000) 673-751
35. Montoro P., Braca A., Pizza C., and De Tommasi N. Structure-antioxidant activity relationships of flavonoids isolated from different plant species. Food Chemistry 92 (2005) 349-355
36. Moskovitz J., Yim K.A., and Choke P.B. Free radicals and disease. Archives of Biochemistry and Biophysics 397 (2002) 354-359
37. Natella F., Nardini M., Di Felice M., and Saccini C. Benzoic and cinnamic acid derivatives as antioxidants: Structure-activity relation. Journal of Agricultural and Food Chemistry 47 (1999) 1453-1459
38. Nenandis N., Wang L.F., Tsimidou M.Z., and Zhang H.Y. Radical scavenging potential of phenolic compounds encountered in O. europaea products as indicated by calculation of bond dissociation enthalpy and ionization potential values. Journal of Agricultural and Food Chemistry 26 (2005) 295-299
39. Ohkawa A., Ohishi N., and Yagi K. Assay for lipid peroxide in animal tissues by thiobarbituric acid reaction. Analytical Biochemistry 95 (1979) 351-358
40. Özipek M., Calis I., Ertant M., and Rüedi P. Rhamnetin 3-p-Coumaroylrhamninoside from Rhamnus petiolaris. Phytochemistry 37 (1994) 249-253
41. Pezzuto J.M., and Park E.J. Autoxidation and antioxidants. In: Swarbrick J., and Boylan J.C. (Eds). Encyclopedia of pharmaceutical technology (2002), Marcel Dekker, New York 97-113
42. Ponce A.M., Blanco S.E., Molina A.S., Garcia-Domenech R., and Galvez J. Study of the action of flavonoids on xanthine-oxidase by molecular topology. Journal of Chemical Information and Computer Sciences 40 (2000) 1039-1045
43. Pong K. Oxidative stress in neurodegenerative diseases: Therapeutic implications for superoxide dismutase mimetics. Expert Opinion in Biological Therapy 3 (2003) 127-139
44. Pottier-Alapetite G. Flore de la Tunisie (1978), imprimerie officielle de la République Tunisienne, Tunis pp. 492-496
45. Ross J.A., and Kasum C.M. Dietary flavonoids: Bioavailability, metabolic effects and safety. Annual Review of Nutrition 22 (2002) 19-34
46. Russo A., Cardile V., Lombardo L., Vanella L., Vanella A., and Garbarino J.A. Antioxidant and antiproliferative action of methanolic extract of Geum Quellyon sweet roots in human tumor cell lines. Journal of Ethnopharmacology 100 (2005) 323-332
47. Satake T., Hori K., Kamiya K., Saiki Y., Fujimoto Y., Kimura Y., et al. Studies on the constituents of Turkish Plants. I. Flavonol Triglycosides from the fruit of Rhamnus thymifolius. Chemical and Pharmaceutical Bulletin 41 (1993) 1743-1745
48. Seyoum A., Asres K., and El-Fiky F.K. Structure-radical scavenging activity relationships of flavonoids. Phytochemistry 67 (2006) 2058-2070
49. 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
50. Wei B.L., Lin C.-N., and Won S.-J. Nakahalene and cytotoxic principles of formosan Rhamnus species. Journal of Natural Products 55 (1992) 967-969
51. Werns S.W., and Lucchesi R. Free radicals and ischemic tissue injury. Trends in Pharmacological Sciences 11 (1990) 161-166
52. Williams R.J., Spencer J.P., and Rice-Evans C. Flavonoids: Antioxidants or signalling molecules?. Free Radical Biology and Medicine 36 (2004) 838-849
53. Wu S.-J., and Ng L.-T. Antioxidant and free radical scavenging activities of wild bitter melon (Momordica charantia Linn. var. abbreviata Ser.) in Taiwan. LWT-Food Science and Technology 41 (2007) 323-330