Biological activities of flavonoids from Nitraria retusa (Forssk.) Asch. and their acylated derivatives

Food Chemistry

Volumn 124, Issue 2, 2011, Pages 486-494

  Hadj Salem, Jamila ^a   Chevalot, Isabelle ^a   Harscoat Schiavo, Christelle ^a   Paris, Cédric ^b   Fick, Michel ^a   Humeau, Catherine ^b  

^a UNIVERSITÉ DE LORRAINE   (France)

^b UNIVERSITÉ DE LORRAINE   (France)

Author keywords

Antioxidant activity; Antiproliferative activity; Enzymatic acylation; Flavonoid esters; Nitraria retusa flavonoids

Indexed keywords

ANTIOXIDANT ACTIVITIES; ANTIPROLIFERATIVE ACTIVITY; ENZYMATIC ACYLATION; FLAVONOID ESTERS; NITRARIA RETUSA FLAVONOIDS;

ACYLATION; ESTERIFICATION; ESTERS; FATTY ACIDS; METHANOL; PHENOLS;

FLAVONOIDS;

ANTIOXIDANT; BUTYRIC ACID ETHYL ESTER; CHLOROFORM; FLAVONOID; ISOQUERCITRIN; ISORHAMNETIN; ISORHAMNETIN 3 GLUCOSIDE; ISORHAMNETIN 3 O RUTINOSIDE; ISORHAMNETIN 3 ROBINOBIOSIDE; LAURIC ACID; NITRARIA RETUSA EXTRACT; PHENOL DERIVATIVE; PLANT EXTRACT; QUERCETIN; RUTOSIDE; SCAVENGER; UNCLASSIFIED DRUG; XANTHINE OXIDASE;

ACYLATION; ANTIOXIDANT ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CELL STRAIN CACO 2; DRUG ACTIVITY; DRUG MECHANISM; HUMAN; HUMAN CELL; NITRARIA RETUSA; PLANT LEAF; SHRUB;

NITRARIA RETUSA;

EID: 77955774729     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2010.06.059     Document Type: Article

References (38)

1. Ardhaoui M., Falcimaigne A., Ognier S., Engasser J.M., Moussou P., Pauly G., et al. Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoïdes. Journal of Biotechnology 2004, 110(3):265-271.
2. Atoui A.K., Mansouri A., Boskou G., Kefalas P. Tea and herbal infusions: Their antioxidant activity and phenolic profile. Food Chemistry 2005, 89(1):27-36.
3. Böhm H., Boeing H., Hempel J., Raab B., Kroke A. Flavonols, flavones and anthocyanins as native antioxidants of food and their possible role in the prevention of chronic diseases. European Journal of Nutrition 1998, 37(2):147-163.
4. Bravo L. Polyphenols: Chemistry, dietary sources, metabolism, and nutritional significance. Nutrition Reviews 1998, 56(11):317-333.
5. Chebil L., Anthoni J., Humeau C., Gerardin C., Engasser J.M., Ghoul M. Enzymatic acylation of flavonoids: Effect of the nature of the substrate, origin of lipase, and operating conditions on conversion yield and regioselectivity. Journal of Agricultural and Food Chemistry 2007, 55(23):9496-9502.
6. Chebil L., Humeau C., Falcimaigne A., Engasser J.M., Ghoul M. Enzymatic acylation of flavonoïdes. Process Biochemistry 2006, 41(11):2237-2251.
7. Chiang Y.M., Chuang D.Y., Wang S.Y., Kuo Y.H., Tsai P.W., Shyur L.F. Metabolite profiling and chemopreventive bioactivity of plant extracts from Bidens pilosa. Journal of Ethnopharmacology 2004, 95(2-3):409-419.
8. Cos P., Ying L., Calomme M., Hu J.P., Cimanga K., Van Poel B., et al. Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. Journal of Natural Products 1998, 61(1):71-76.
9. Csokay B., Prajda N., Weber G., Olah E. Molecular mechanisms in the antiproliferative action of quercetin. Life Sciences 1997, 60(24):2157-2163.
10. Do Y.K., Kim J.M., Chang S.M., Hwang J.H., Kim W.S. Enhancement of polyphenol bio-activities by enzyme reaction. Journal of Molecular Catalysis B: Enzymatic 2009, 56(2-3):173-178.
11. Gülçin I. Antioxidant properties of resveratrol: A structure-activity insight. Innovative Food Science and Emerging Technologies 2010, 11(1):210-218.
12. Hadj Salem J., Humeau C., Chevalot I., Harscoat-Schiavo C., Vanderesse R., Blanchard F., et al. Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters. Process Biochemistry 2010, 45:382-389.
13. Halim A.F., Saad H.E., Hashish N.E. Flavonol glycosides from Nitraria retusa. Phytochemistry 1995, 40(1):349-351.
14. Hsu H.F., Houng J.Y., Chang C.L., Wu C.C., Chang F.R., Wu Y.C. Antioxidant activity, cytotoxicity, and DNA information of Glossogyne tenuifolia. Journal of Agricultural and Food Chemistry 2005, 53(15):6117-6125.
15. Jagadeeshwar Rao R., Tiwari A.K., Kumar U.S., Reddy S.V., Ali A.Z., Rao J.M. Novel 3-O-acyl mesquitol analogues as free-radical scavengers and enzyme inhibitors: Synthesis, biological evaluation and structure-activity relationship. Bioorganic and Medicinal Chemistry Letters 2003, 13(16):2777-2780.
16. Kim M.Y., Kim Y.C., Chung S.K. Identification and in vitro biological activities of flavonols in garlic leaf and shoot: Inhibition of soybean lipoxygenase and hyaluronidase activities and scavenging of free radicals. Journal of the Science of Food and Agriculture 2005, 85(4):633-640.
17. Kuo S.M. Antiproliferative potency of structurally distinct dietary flavonoids on human colon cancer cells. Cancer Letters 1996, 110(1-2):41-48.
18. Li J., Chase H.A. Use of expanded bed adsorption to purify flavonoids from Ginkgo biloba L. Journal of Chromatography A 2009, 1216:8759-8770.
19. Liu X., Dong M., Chen X., Jiang M., Lv X., Yan G. Antioxidant activity and phenolics of an endophytic Xylaria sp. from Ginkgo biloba. Food Chemistry 2007, 105:548-554.
20. Loa J., Chow P., Zhang K. Studies of structure-activity relationship on plant polyphenol-induced suppression of human liver cancer cells. Cancer Chemotherapy and Pharmacology 2009, 63(6):1007-1016.
21. Martin S., Andriambeloson E., Takeda K., Andriantsitohaina R. Red wine polyphenols increase calcium in bovine aortic endothelial cells: A basis to elucidate signalling pathways leading to nitric oxide production. British Journal of Pharmacology 2002, 135(6):1579-1587.
22. Matkowski A., Piotrowska M. Antioxidant and free radical scavenging activities of some medicinal plants from the Lamiaceae. Fitoterapia 2006, 77(5):346-353.
23. Mellou F., Lazari D., Skaltsa H., Tselepis A.D., Kolisis F.N., Stamatis H. Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity. Journal of Biotechnology 2005, 116(3):295-304.
24. Mellou F., Loutrari H., Stamatis H., Roussos C., Kolisis F.N. Enzymatic esterification of flavonoids with unsaturated fatty acids: Effect of the novel esters on vascular endothelial growth factor release from K562 cells. Process Biochemistry 2006, 41(9):2029-2034.
25. Mosman T. Rapid calorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods 1983, 65:55-63.
26. Nagao A., Seki M., Kobayashi H. Inhibition of xanthine oxidase by flavonoids. Bioscience, Biotechnology and Biochemistry 1999, 63(10):1787-1790.
27. Ordoñez A.A.L., Gomez J.D., Vattuone M.A., Isla M.I. Antioxidant activities of Sechium edule (Jacq.) Swartz extracts. Food Chemistry 2006, 97(3):452-458.
28. Pierini R., Gee J.M., Belshaw N.J., Johnson I.T. Flavonoids and intestinal cancers. British Journal of Nutrition 2008, 99(E-Suppl. 1):ES53-ES59.
29. Plochmann K., Korte G., Koutsilieri E., Richling E., Riederer P., Rethwilm A., et al. Structure-activity relationships of flavonoid-induced cytotoxicity on human leukemia cells. Archives of Biochemistry and Biophysics 2007, 460(1):1-9.
30. Pottier-Alapetite G. Flore de la Tunisie. Angiospermes-dicotylédones Apétales-Dialypetales 1979, 291-293.
31. Regasini L.O., Vellosa J.C.R., Silva D.H.S., Furlan M., de Oliveira O.M.M., Khalil N.M., et al. Phytochemistry 2008, 69(8):1739-1744.
32. Schmidt S., Zietz M., Schreiner M., Rohn S., Kroh L.W., Krumbein A. Genotypic and climatic influences on the concentration and composition of flavonoids in kale (Brassica oleracea var. sabellica). Food Chemistry 2010, 119(4):1293-1299.
33. Shahidi F., Wanasundara U.N., Amarowicz R. Natural antioxidants from low-pungency mustard flour. Food Research International 1994, 27(5):489-493.
34. Shaltout K.H., Sheded M.G., El-Kady H.F., Al-Sodany Y.M. Phytosociology and size structure of Nitraria retusa along the Egyptian Red Sea coast. Journal of Arid Environments 2003, 53(3):331-345.
35. Takahashi N., Tamagawa K., Kubo Y., Fukui T., Wakabayashi H., Honda T. Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation. Bioorganic and Medicinal Chemistry 2003, 11(15):3255-3260.
36. Teng B.S., Lu Y.H., Wang Z.T., Tao X.Y., Wei D.Z. In vitro anti-tumor activity of isorhamnetin isolated from Hippophae rhamnoides L. against BEL-7402 cells. Pharmacological Research 2006, 54(3):186-194.
37. Yu S.F., Chen T.M., Chen Y.H. Apoptosis and necrosis are involved in the toxicity of Sauropus androgynus in an in vitro study. Journal of the Formosan Medical Association 2007, 106(7):537-547.
38. Zielińska M., Gulden M., Seibert H. Effects of quercetin and quercetin-3-O-glycosides on oxidative damage in rat C6 glioma cells. Environmental Toxicology and Pharmacology 2003, 13(1):47-53.