ABTS+ scavenging potency of selected flavonols from Hypericum perforatum L. by HPLC-ESI/MS QQQ: Reaction observation, adduct characterization and scavenging activity determination

Food Research International

Volumn 58, Issue , 2014, Pages 47-58

  Liu, Yan Ru ^a,b   Li, Wei Guang ^a   Chen, Li Fang ^a,c   Xiao, Bing Kun ^a   Yang, Jian Yun ^a   Yang, Liu ^a   Zhang, Cheng Gang ^a   Huang, Rong Qing ^a   Dong, Jun Xing ^a,b  

^a BEIJING INSTITUTE OF RADIATION MEDICINE   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^c JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

ABTS+ scavenging; HPLC ESI MS QQQ; Hypericum perforatum L; Hyperoside; Quercetin; Quercitrin; Rutin

Indexed keywords

EID: 84893820972     PISSN: 09639969     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodres.2014.01.051     Document Type: Article

References (67)

1. Abdali K., Khajehei M., Tabatabaee H.R. Effect of St John's wort on severity, frequency, and duration of hot flashes in premenopausal, perimenopausal and postmenopausal women: a randomized, double-blind, placebo-controlled study. Menopause 2010, 17(2):326-331.
2. Agati G., Azzarello E., Pollastri S., Tattini M. Flavonoids as antioxidants in plants: Location and functional significance. Plant Science 2012, 196:67-76.
3. Akerstrom B., Maghzal G.J., Winterbourn C.C., Kettle A.J. The lipocalin alpha1-microglobulin has radical scavenging activity. Journal of Biological Chemistry 2007, 282(43):31493-31503.
4. Arts M.J.T.J., Haenen G.R.M.M., Wilms L.C., Beetstra S.A.J.N., Heijnen C.G.M., Voss H.-P., Bast A. Interactions between flavonoids and proteins: Effect on the total antioxidant capacity. Journal of Agricultural and Food Chemistry 2002, 50(5):1184-1187.
5. Barnes J.S., Foss F.W., Schug K.A. Thermally accelerated oxidative degradation of quercetin using continuous flow kinetic electrospray-ion trap-time of flight mass spectrometry. Journal of the American Society for Mass Spectrometry 2013, 24(10):1513-1522.
6. Biskup I., Golonka I., Gamian A., Sroka Z. Antioxidant activity of selected phenols estimated by ABTS and FRAP methods. Postepy Higieny I Medycyny Doswiadczalnej 2013, 67:958-963.
7. Boulanouar B., Abdelaziz G., Aazza S., Gago C., Miguel M.G. Antioxidant activities of eight Algerian plant extracts and two essential oils. Industrial Crops and Products 2013, 46:85-96.
8. Brunetti C., Di Ferdinando M., Fini A., Pollastri S., Tattini M. Flavonoids as antioxidants and developmental regulators: Relative significance in plants and humans. International Journal of Molecular Sciences 2013, 14(2):3540-3555.
9. Cao J., Xia X., Chen X., Xiao J., Wang Q. Characterization of flavonoids from Dryopteris erythrosora and evaluation of their antioxidant, anticancer and acetylcholinesterase inhibition activities. Food and Chemical Toxicology 2013, 51:242-250.
10. Childs R.E., Bardsley W.G. The steady-state kinetics of peroxidase with 2,2'-azino-di-(3-ethyl-benzthiazoline-6-sulphonic acid) as chromogen. The Biochemical Journal 1975, 145(1):93-103.
11. Corsinovi L., Biasi F., Poli G., Leonarduzzi G., Isaia G. Dietary lipids and their oxidized products in Alzheimer's disease. Molecular Nutrition & Food Research 2011, 55:S161-S172.
12. Cuyckens F., Claeys M. Mass spectrometry in the structural analysis of flavonoids. Journal of Mass Spectrometry 2004, 39(1):1-15.
13. Dante G., Facchinetti F. Herbal treatments for alleviating premenstrual symptoms: A systematic review. Journal of Psychosomatic Obstetrics and Gynaecology 2011, 32(1):42-51.
14. de Rijke E., Out P., Niessen W.M., Ariese F., Gooijer C., Brinkman U.A. Analytical separation and detection methods for flavonoids. Journal of Chromatography A 2006, 1112(1-2):31-63.
15. deHoffmann E. Tandem mass spectrometry: A primer. Journal of Mass Spectrometry 1996, 31(2):129-137.
16. Delazar A., Delnavazi M.R., Yassa N., Parkhideh S., Delazar N., Nahar L., Sarker S.D. Essential oil composition and isolation of free-radical-scavenging phenolic glycosides from the aerial parts of Ajuga chamaepitys growing in Iran. Revista Brasileira De Farmacognosia-Brazilian Journal of Pharmacognosy 2012, 22(2):299-305.
17. Duan K., Yuan Z., Guo W., Meng Y., Cui Y., Kong D., Zhang L., Wang N. LC-MS/MS determination and pharmacokinetic study of five flavone components after solvent extraction/acid hydrolysis in rat plasma after oral administration of Verbena officinalis L. extract. Journal of Ethnopharmacology 2011, 135(2):201-208.
18. Eden J.A. Phytoestrogens for menopausal symptoms: A review. Maturitas 2012, 72(2):157-159.
19. Fearon I.M., Faux S.P. Oxidative stress and cardiovascular disease: Novel tools give (free) radical insight. Journal of Molecular and Cellular Cardiology 2009, 47(3):372-381.
20. Guedes A.C., Amaro H.M., Giao M.S., Malcata F.X. Optimization of ABTS radical cation assay specifically for determination of antioxidant capacity of intracellular extracts of microalgae and cyanobacteria. Food Chemistry 2013, 138(1):638-643.
21. Gulcin I. Antioxidant activity of food constituents: An overview. Archives of Toxicology 2012, 86(3):345-391.
22. Gulcin I., Topal F., Cakmakci R., Bilsel M., Goren A.C., Erdogan U. Pomological features, nutritional quality, polyphenol content analysis, and antioxidant properties of domesticated and 3 wild ecotype forms of raspberries (Rubus idaeus L.). Journal of Food Science 2011, 76(4):C585-C593.
23. Hernandez I., Alegre L., Van Breusegem F., Munne-Bosch S. How relevant are flavonoids as antioxidants in plants?. Trends in Plant Science 2009, 14(3):125-132.
24. Ho C.S., Lam C.W., Chan M.H., Cheung R.C., Law L.K., Lit L.C., Ng K.F., Suen M.W., Tai H.L. Electrospray ionisation mass spectrometry: Principles and clinical applications. Clinical Biochemistry Reviews 2003, 24(1):3-12.
25. Holcapek M., Jirasko R., Lisa M. Recent developments in liquid chromatography-mass spectrometry and related techniques. Journal of Chromatography A 2012, 1259:3-15.
26. Ignat I., Volf I., Popa V.I. A critical review of methods for characterisation of polyphenolic compounds in fruits and vegetables. Food Chemistry 2011, 126(4):1821-1835.
27. Jarussophon S., Acoca S., Gao J.M., Deprez C., Kiyota T., Draghici C., Purisima E., Konishi Y. Automated molecular formula determination by tandem mass spectrometry (MS/MS). Analyst 2009, 134(4):690-700.
28. Jiang X.Y., Chen X.Q., Wei Y. Free radical scavenging activity and flavonoids contents of polygonum orientale leaf, stem and seed extracts. Latin American Journal of Pharmacy 2009, 28(2):284-287.
29. Khoddami A., Wilkes M.A., Roberts T.H. Techniques for analysis of plant phenolic compounds. Molecules 2013, 18(2):2328-2375.
30. Konishi Y., Kiyota T., Draghici C., Gao J.M., Yeboah F., Acoca S., Jarussophon S., Purisima E. Molecular formula analysis by an MS/MS/MS technique to expedite dereplication of natural products. Analytical Chemistry 2007, 79(3):1187-1197.
31. Kweon M.H., Kwak J.H., Ra K.S., Sung H.C., Yang H.C. Structural characterization of a flavonoid compound scavenging superoxide anion radical isolated from Capsella bursa-pastoris. Journal of Biochemistry and Molecular Biology 1996, 29(5):423-428.
32. Lai C.Y., Yang J.Y., Rayalam S., Della-Fera M.A., Ambati S., Lewis R.D., Hamrick M.W., Hartzell D.L., Baile C.A. Preventing bone loss and weight gain with combinations of vitamin D and phytochemicals. Journal of Medicinal Food 2011, 14(11):1352-1362.
33. Li W., Zhang Y., Liu Y., Yue F., Lu Y., Qiu H., Gao D., Gao Y., Wu Y., Wang Z., Huang R., Zhang C. In vitro kinetic evaluation of the free radical scavenging ability of propofol. Anesthesiology 2012, 116(6):1258-1266.
34. Liu Y.R., Jiang Y.L., Huang R.Q., Yang J.Y., Xiao B.K., Dong J.X. Hypericum perforatum L. preparations for menopause: A meta-analysis of efficacy and safety. Climacteric 2013, 16:1-11. http://informahealthcare.com/doi/abs/10.3109/13697137.2013.861814.
35. Low Dog T. Menopause: A review of botanical dietary supplements. The American Journal of Medicine 2005, 118(Suppl. 12B):98-108.
36. Ma Y.L., Li Q.M., Van den Heuvel H., Claeys M. Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry. Rapid Communications in Mass Spectrometry 1997, 11(12):1357-1364.
37. Ma Y.L., Vedernikova I., Van den Heuvel H., Claeys M. Internal glucose residue loss in protonated O-diglycosyl flavonoids upon low-energy collision-induced dissociation. Journal of the American Society for Mass Spectrometry 2000, 11(2):136-144.
38. March R.E., Miao X.S. A fragmentation study of kaempferol using electrospray quadrupole time-of-flight mass spectrometry at high mass resolution. International Journal of Mass Spectrometry 2004, 231(2-3):157-167.
39. Miller N.J., Rice-Evans C., Davies M.J., Gopinathan V., Milner A. A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates. Clinical Science (London) 1993, 84(4):407-412.
40. Naczk M., Shahidi F. Extraction and analysis of phenolics in food. Journal of Chromatography A 2004, 1054(1-2):95-111.
41. Niederlander H.A.G., van Beek T.A., Bartasiute A., Koieva I.I. Antioxidant activity assays on-line with liquid chromatography. Journal of Chromatography A 2008, 1210(2):121-134.
42. Orcic D.Z., Mimica-Dukic N.M., Franciskovic M.M., Petrovic S.S., Jovin E.D. Antioxidant activity relationship of phenolic compounds in Hypericum perforatum L. Chemistry Central Journal 2011, 5:34.
43. Osman A.M., Wong K.K., Fernyhough A. ABTS radical-driven oxidation of polyphenols: isolation and structural elucidation of covalent adducts. Biochemical and Biophysical Research Communications 2006, 346(1):321-329.
44. Osman A.M., Wong K.K.Y., Fernyhough A. ABTS radical-driven oxidation of polyphenols: Isolation and structural elucidation of covalent adducts. Biochemical and Biophysical Research Communications 2006, 346(1):321-329.
45. Osman A.M., Wong K.K.Y., Hill S.J., Fernyhough A. Isolation and the characterization of the degradation products of the mediator ABTS-derived radicals formed upon reaction with polyphenols. Biochemical and Biophysical Research Communications 2006, 340(2):597-603.
46. Pansini F., Mollica G., Bergamini C.M. Management of the menopausal disturbances and oxidative stress. Current Pharmaceutical Design 2005, 11(16):2063-2073.
47. Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine 1999, 26(9-10):1231-1237.
48. Resende F.A., de Oliveira A.P.S., de Camargo M.S., Vilegas W., Varanda E.A. Evaluation of estrogenic potential of flavonoids using a recombinant yeast strain and MCF7/BUS cell proliferation assay. PLoS One 2013, 8(10).
49. Riccioni G. Carotenoids and cardiovascular disease. Current Atherosclerosis Reports 2009, 11(6):434-439.
50. RiceEvans C.A., Miller N.J. Antioxidant activities of flavonoids as bioactive components of food. Biochemical Society Transactions 1996, 24(3):790-795.
51. Sarris J., Panossian A., Schweitzer I., Stough C., Scholey A. Herbal medicine for depression, anxiety and insomnia: A review of psychopharmacology and clinical evidence. European Neuropsychopharmacology 2011, 21(12):841-860.
52. Tesch B.J. Herbs commonly used by women: An evidence-based review (reprinted from Cln Jnl Womens Health, vol 1, pg 89-102, 2001). Dm Disease-a-Month 2002, 48(10):671-696.
53. Thornton M.J. Estrogens and aging skin. Dermato-Endocrinology 2013, 5(2):264-270.
54. Mabry Tom J., Markham K.R., Thomas M.B. The systematic identification of flavonoids 1970, Springer Berlin Heidelberg, NewYork.
55. Tsimogiannis D., Samiotaki M., Panayotou G., Oreopoulou V. Characterization of flavonoid subgroups and hydroxy substitution by HPLC-MS/MS. Molecules 2007, 12(3):593-606.
56. van Die M.D., Bone K.M., Burger H.G., Reece J.E., Teede H.J. Effects of a combination of Hypericum perforatum and Vitex agnus-castus on PMS-like symptoms in late-perimenopausal women: Findings from a subpopulation analysis. Journal of Alternative and Complementary Medicine 2009, 15(9):1045-1048.
57. Vukics V., Guttman A. Structural characterization of flavonoid glycosides by multi-stage mass spectrometry. Mass Spectrometry Reviews 2010, 29(1):1-16.
58. Weston L.A., Mathesius U. Flavonoids: Their structure, biosynthesis and role in the rhizosphere, including allelopathy. Journal of Chemical Ecology 2013, 39(2):283-297.
59. Wiacek M., Jegal B.S., Hagner W., Hagner-Derengowska M., Zubrzycki I.Z. Age- and menopause-related differences in physiological factors of health quality in women aged 35-60. Archives of Gerontology and Geriatrics 2012, 54(2):385-390.
60. Williams R.J., Spencer J.P.E., Rice-Evans C. Flavonoids: Antioxidants or signalling molecules?. Free Radical Biology and Medicine 2004, 36(7):838-849.
61. Wu H., Guo J., Chen S., Liu X., Zhou Y., Zhang X., Xu X. Recent developments in qualitative and quantitative analysis of phytochemical constituents and their metabolites using liquid chromatography-mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 2013, 72:267-291.
62. Wu H.F., Guo J., Chen S.L., Liu X., Zhou Y., Zhang X.P., Xu X.D. Recent developments in qualitative and quantitative analysis of phytochemical constituents and their metabolites using liquid chromatography-mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 2013, 72:267-291.
63. Yamaguchi M. beta-Cryptoxanthin and bone metabolism: The preventive role in osteoporosis. Journal of Health Science 2008, 54(4):356-369.
64. Yamaguchi M. Role of carotenoid beta-cryptoxanthin in bone homeostasis. Journal of Biomedical Science 2012, 19.
65. Yang W.Z., Ye M., Qiao X., Wang Q., Bo T., Guo D.A. Collision-induced dissociation of 40 flavonoid aglycones and differentiation of the common flavonoid subtypes using electrospray ionization ion-trap tandem mass spectrometry and quadrupole time-of-flight mass spectrometry. European Journal of Mass Spectrometry (Chichester, England) 2012, 18(6):493-503.
66. Yanikkerem E., Koltan S.O., Tamay A.G., Dikayak S. Relationship between women's attitude towards menopause and quality of life. Climacteric 2012, 15(6):552-562.
67. Zheleva-Dimitrova D., Nedialkov P., Kitanov G. Radical scavenging and antioxidant activities of methanolic extracts from Hypericum species growing in Bulgaria. Pharmacognosy Magazine 2010, 6(22):74-78.