Purification and characterization of flavonoids from the leaves of Zanthoxylum bungeanum and correlation between their structure and antioxidant activity

PLoS ONE

Volumn 9, Issue 8, 2014, Pages

  Zhang, Yujuan ^a   Wang, Dongmei ^a   Yang, Lina ^a   Zhou, Dan ^a   Zhang, Jingfang ^a  

^a NORTHWEST A F UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); FLAVONOID; HYDROXYL GROUP; HYPERIN; ISOQUERCITRIN; ISOQUERCITRIN 3 O ALPHA LEVO RHAMNOSIDE; KAEMPFEROL 3 GALACTOSIDE; KAEMPFEROL 3 RHAMNOSIDE; OIL; PEROXIDE; QUERCETIN; QUERCITRIN; RUTOSIDE; UNCLASSIFIED DRUG; VITEXIN; WATER; 2,2'-AZINO-DI-(3-ETHYLBENZOTHIAZOLINE)-6-SULFONIC ACID; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTIOXIDANT; BENZOTHIAZOLE DERIVATIVE; BIPHENYL DERIVATIVE; PICRIC ACID; SULFONIC ACID DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CORRELATION ANALYSIS; DRUG DETERMINATION; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; EMULSION; ESCHERICHIA COLI; FLUORESCENCE RECOVERY AFTER PHOTOBLEACHING; GENUS; IN VITRO STUDY; IN VIVO STUDY; LIPID PEROXIDATION; NONHUMAN; PLANT LEAF; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; ZANTHOXYLUM; ZANTHOXYLUM BUNGEANUM; CHEMISTRY; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; METABOLISM;

ANTIOXIDANTS; BENZOTHIAZOLES; BIPHENYL COMPOUNDS; ESCHERICHIA COLI; FLAVONOIDS; LIPID PEROXIDATION; PICRATES; PLANT LEAVES; SULFONIC ACIDS; ZANTHOXYLUM;

EID: 84926477874     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0105725     Document Type: Article

References (56)

1. Wang S, Xie JC, Yang W, Sun BG (2011) Preparative separation and purification of alkylamides from Zanthoxylum bungeanum Maxim by high-speed counter-current chromatography. J Liq Chromatogr R T 34: 2640-2652.
2. Yang X (2008) Aroma constituents and alkylamides of red and green huajiao (Zanthoxylum bungeanum and Zanthoxylum schinifolium). J Agric Food Chem 56: 1689-1696.
3. Lim TK (2012) Zanthoxylum simulans. Edible medicinal and non-medicinal plants: Springer, 904-911.
4. Chang ZQ, Liu F, Wang SL, Zhao TZ, Wang MT (1981) Studies on the chemical constituents of Zanthoxylum simulans Hance. Acta Pharm Sinica 16: 394-396.
5. Duke JA, Ayensu ES (1985) Medicinal plants of China. Reference Publications, Inc, Algonac, 705.
6. Yeung HC (1985) Handbook of Chinese herbs and formulas. Institute of Chinese Medicine, Los Angeles.
7. Bauer R, Xiao PG (2011) Pericarpium Zanthoxyli Huajiao. Chromatographic fingerprint analysis of herbal medicines: Springer 191-202.
8. Mizutani K, Fukunaga Y, Tanaka O, Takasugi N, Saruwatari YI, et al. (1988) Amides from Huajiao, pericarps of Zanthoxylum bungeanum Maxim. Chem Pharm Bull 36: 2362-2365.
9. Xiong Q, Dawen S, Mizuno M (1995) Flavonol glucosides in pericarps of Zanthoxylum bungeanum. Phytochem 39: 723-725.
10. Tirillini B, Stoppini AM (1994) Volatile constituents of the fruit secretory glands of Zanthoxylum bungeanum Maxim. J Essent Oil Res 6: 249-252.
11. Li Y, Zeng J, Liu L, Jin X (2001) GC-MS analysis of supercritical carbon dioxide extraction products from pericarp of Zanthoxylum bungeanum. Journal of Chinese medicinal materials 24: 572-573.
12. Xiong Q, Dawen S, Yamamoto H, Mizuno M (1997) Alkylamides from pericarps of Zanthoxylum bungeanum. Phytochem 46: 1123-1126. (Pubitemid 27500650)
13. Ren L, Xie F (1981) Alkaloids from the root of Zanthoxylum bungeanum Maxim. Acta Pharm Sinica 16: 672-677.
14. Huang XL, Kakiuchi N, Che QM, Huang SL, Sheng L, et al. (1993) Effects of extracts of Zanthoxylum fruit and their constituents on spontaneous beating rate of myocardial cell sheets in culture. Phytother Res 7: 41-48. (Pubitemid 23044565)
15. Deng ZY, Sun BY, Kang KG, Dong YG (2005) Analysis of the main nutritional labeling in the tender bud of Zanthoxylum bungeanum. Journal of Northwest Forestry University 20: 179-180.
16. Xu HD, Fan JH (2010) Macroporous adsorption resin purification of total flavonoids from the crude extract of Zanthoxylum bungeanum leaves and their reducing power and free radical scavenging activity. Food Sci 31: 111-115.
17. Yang LC, Li R, Tan J, Jiang ZT (2013) Polyphenolics composition of the leaves of Zanthoxylum bungeanum Maxim. grown in Hebei, China, and their radical scavenging activities. J Agric Food Chem 61: 1772-1778.
18. Oshima R, Yamauchi Y, Kumanotani J (1982) Resolution of the enantiomers of aldoses by liquid chromatography of diastereoisomeric 1-(N-acetyl-[α]- methyl-benzylamino)- 1- deoxyalditol acetates. Carbohydr Res 2: 169-176.
19. Yen GC, Chen HY (1995) Antioxidant activity of various tea extracts in relation to their antimutagenicity. J Agric Food Chem 43: 27-32.
20. Wang DM, Zhang YJ, Wang SS, Li DW (2013) Antioxidant and antifungal activities of extracts and fractions from Anemone taipaiensis, China. Allelopathy J 32: 67-68.
21. Rice-Evans CA, Miller NJ, Paganga G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Bio Med 20: 933- 956.
22. Tachakittirungrod S, Okonogi S, Chowwanapoonpohn S (2007) Study on antioxidant activity of certain plants in Thailand: Mechanism of antioxidant action of guava leaf extract. Food Chem 103: 381-388. (Pubitemid 46241693)
23. Sandra G (2012) Helichrysum monizii Lowe: Phenolic composition and antioxidant potential. Phytochem Anal 23: 72-83.
24. Benzie IFF, Strain J (1996) The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": the FRAP assay. Anal Biochem 239: 70-76.
25. Dorman HJD, Deans SG, Noble RC, Surai P (1995) Evaluation in vitro of plant essential oils as natural antioxidants. J Essent Oil Res 7: 645-651.
26. Miguel G, Simões M, Figueiredo AC, Barroso JG, Pedro LG, et al. (2004) Composition and antioxidant activities of the essential oils of Thymus caespititius, Thymus camphoratus and Thymus mastichina. Food Chem 86: 183-188.
27. Dhar P, Bajpai PK. Tayade AB, Chaurasia OP, Srivastava RB, et al. (2013) Chemical composition and antioxidant capacities of phytococktail extracts from trans-Himalayan cold desert. BMC Complem Altern Med 13: 259.
28. Smirnova GV, Samoylova ZY, Muzyka NG, Oktyabrsky ON (2009) Influence of polyphenols on Escherichia coli resistance to peroxide stress. Free Radical Bio Med 46: 759-768.
29. Smirnova GV, Vysochina GI, Muzyka NG, Samoylova ZY, Kukushkina TA, et al. (2010) Evaluation of antioxidant properties of medical plants using microbial test systems. World J Microbiol Biotechnol 26: 2269-2276.
30. Azimova SS, Vinogradova VI (2013) Physicochemical and Pharmacological Properties of Flavonoids. Natural compounds-flavonoids, Springer Science+ Business Media New York.
31. Kimura YM, Kubo T, Tani S, Arichi S, Okuda H (1981) Study on Scutellaria radix IV. Effects on lipid peroxidation in rat liver. Chem Pharm Bull 29: 2610- 2617.
32. Ma XF, Tian WX, Wu LH, Cao XL, Ito Y (2005) Isolation of quercetin-3-O- l-rhamnoside from Acer truncatum Bunge by high-speed counter-current chromatography. J Chromatogr A 1070: 211-214.
33. Jung HA, Islam MD, Kwon YS, Jin SE, Son YK, et al. (2011) Extraction and identification of three major aldose reductase inhibitors from Artemisia montana. Food ChemToxicol 49: 376-384.
34. Ibrahim LF, Kawashty SA, El-Hagrassy AM, Nassar MI, Mabry TJ (2002) An acylated kaempferol glycoside from flowers of Foeniculum vulgare and F. Dulce. Molecules 7: 245-251.
35. Rodríguez P, González-Mujica F, Bermúdez J, Hasegawa M (2010) Inhibition of glucose intestinal absorption by kaempferol 3-O-α-L-rhamnoside purified from Bauhinia megalandra leaves. Fitoterapia 81: 1220-1223.
36. Nassar MI, Aboutabl EA, Makled YA, El-Khrisy EA, Osman AF (2010) Secondary metabolites and pharmacology of Foeniculum vulgare Mill. Subsp. Piperitum. Revista latinoamericana de química 38: 103-112.
37. Zhou X, Peng JY, Fan GY, Wu YT (2005) Isolation and purification of flavonoid glycosides from Trollius ledebouri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase. J Chromatogr A 1092: 216-221. (Pubitemid 41393930)
38. Li H, Cao DD, Yi JY, Cao JK, Jiang WB (2012) Identification of the flavonoids in mungbean (Phaseolus radiatus L.) soup and their antioxidant activities. Food Chem 135: 2942-2946.
39. Lee KW, Kim YJ, Kim DO, Lee HJ, Lee CY (2003) Major phenolics in apple and their contribution to the total antioxidant capacity. J Agric Food Chem 51: 6516-6520.
40. Rice-Evans CA, Miller NJ, Pagangu G (1997) Antioxidant properties of phenolic compounds. Trends Plant Sci 2: 152-159. (Pubitemid 27158898)
41. Matsuda H, Morikawa T, Toguchida I, Yoshikawa M (2002) Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull 50: 788-795. (Pubitemid 41694896)
42. Dubeau S, Samson G, Tajmir-Riahi HA (2010) Dual effect of milk on the antioxidant capacity of green, Darjeeling and English breakfast teas. Food Chem 122: 539-545.
43. Bourassa P, Côté R, Hutchandani S, Samson G, Tajmir-Riahi H (2013) The effect of milk alpha-casein on the antioxidant activity of tea polyphenols. J Photoch Photobio B 128: 43-49.
44. Decker EA, Warner K, Richards MP, Shahidi F (2005) Measuring antioxidant effectiveness in food. J Agric Food Chem 53: 4303-4310. (Pubitemid 40936798)
45. De Freitas N, Mateus S (2001) Structural features of procyanidin interactions with salivary proteins. J Agric Food Chem 4: 940-945.
46. Aherne SA, O'Brien NM (2000) Mechanism of protection by the flavonoids, quercetin and rutin, against tert-butylhydroperoxide- and menadione-induced DNA single strand breaks in Caco-2 cells. Free Radic Biol Med 29: 507-514.
47. Wätjen W, Michels G, Steffan B, Niering P, Chovolou Y, et al. (2005) Low concentrations of flavonoids are protective in rat H4IIE cells whereas high concentrations cause DNA damage and apoptosis. J Nutr 135: 525-531. (Pubitemid 40365213)
48. Melidou M, Riganakos K, Galaris D (2005) Protection against nuclear DNA damage offered by flavonoids in cells exposed to hydrogen peroxide: The role of iron chelation. Free Radic Biol Med 39: 1591-1600. (Pubitemid 41642590)
49. Ferrali M, Signorini C, Caciotti B, Sugherini L, Ciccoli L, et al. (1997) Protection against peroxide damage of erythrocyte membrane by the flavonoids quercetin and its relation to iron chelating activity. FEBS Lett 416: 123-129. (Pubitemid 27462770)
50. Williams RJ, Spencer JP, Rice-Evans C (2004) Flavonoids: antioxidants or signaling molecules? Free Radic Biol Med 36: 838-849.
51. Harwood M, Danielewska-Nikiel B, Borzelleca J, Flamm G, Williams G, et al. (2007) A critical review of the data related to the safety of quercetin and lack of evidence of in vivo toxicity, including lack of genotoxic/carcinogenic properties. Food Chem Toxicol 45: 2179-2205. (Pubitemid 47451573)
52. Galvez J, Crespo ME, Jimenez J, Suárez A, Zarzuelo A (1993) Antidiarrhoeic activity of quercitrin in mice and rats. J Pharm Pharmacol 45: 157-159. (Pubitemid 23081900)
53. Nijveldt RJ, van Nood E, van Hoorn DEC, Boelens PG, van Norren K, et al. (2001) Flavonoids: a review of probable mechanisms of action and potential applications. Am J Clin Nutr 74: 418-425. (Pubitemid 32880250)
54. Costantino L, Rastelli G, Cignarella G, Vianello P, Barlocco D (1997) New aldose reductase inhibitors as potential agents for the prevention of long-term diabetic complications. Exp Opin Ther Patents 7: 843-858.
55. Rastelli G, Antolini L, Benvenuti S, Constantino L (2000) Structural bases for the inhibition of aldose reductase by phenolic compounds. Bioorg Med Chem 8: 1151-1158. (Pubitemid 30336409)
56. Urzumtzev A, Tete-Favier F, Mitscier A, Barbanton J, Barth P, et al. (1997) A 'specificity' pocket inferred from the crystal structures of the complexes of aldose reductase with the pharmaceutically important inhibitors tolrestat and sorbinil. Structure 5: 601-612. (Pubitemid 27236260)