Influence of side chain structure changes on antioxidant potency of the [6]-gingerol related compounds

Food Chemistry

Volumn 165, Issue , 2014, Pages 191-197

  Lu, Dong Liang ^a   Li, Xiu Zhuang ^a   Dai, Fang ^a   Kang, Yan Fei ^a   Li, Yan ^a   Ma, Meng Meng ^a   Ren, Xiao Rong ^a   Du, Gao Wei ^a   Jin, Xiao Ling ^a   Zhou, Bo ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Antioxidant; DNA damage; Gingerol; Lipid peroxidation; Shogaol

Indexed keywords

DNA; LIPIDS; TOXICITY;

ANTI-OXIDANT ACTIVITIES; DNA DAMAGES; ELECTRON-DONATING ABILITY; GINGEROL; LIPID PEROXIDATION; RELATED COMPOUNDS; SHOGAOL; SIDE CHAIN STRUCTURE;

ANTIOXIDANTS;

(12) DEHYDROSHOGAOL; (12) GINGEROL; (12) SHOGAOL; (6) DEHYDROGINGEROL; (6) DEHYDROSHOGAOL; (6) GINGEROL; 4 (4' HYDROXY 3' METHOXYPHENYL) 3 BUTEN 2 ONE; ANTIOXIDANT; GINGEROL; PLANT MEDICINAL PRODUCT; SHOGAOL; UNCLASSIFIED DRUG; CATECHOL DERIVATIVE; FATTY ALCOHOL; PLANT EXTRACT;

AGAR GEL ELECTROPHORESIS; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA DAMAGE; DNA STRAND BREAKAGE; DRUG STRUCTURE; DRUG SYNTHESIS; ERYTHROCYTE; GINGER; HEMOLYSIS; HUMAN; HUMAN CELL; LIPID PEROXIDATION; NUCLEAR MAGNETIC RESONANCE; OXIDATIVE STRESS; CHEMISTRY;

ANTIOXIDANTS; CATECHOLS; DNA DAMAGE; FATTY ALCOHOLS; LIPID PEROXIDATION; PLANT EXTRACTS;

EID: 84902353133     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2014.05.077     Document Type: Article

References (39)

1. M.S. Baliga, R. Haniadka, M.M. Pereira, J.J. D'souza, P.L. Pallaty, and H.P. Bhat et al. Update on the chemopreventive effects of ginger and its phytochemicals Critical Reviews in Food Science and Nutrition 51 2011 499 523
2. I.F.F. Benzie, and J. Strain The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": The FRAP assay Analytical Biochemistry 239 1996 70 76
3. X.-Y. Cao, J. Yang, F. Dai, D.-J. Ding, Y.-F. Kang, and F. Wang et al. Extraordinary radical-scavengers: 4-Mercaptostilbenes Chemistry - A European Journal 18 2012 5898 5905
4. N.S.C. de Gaulejac, C. Provost, and N. Vivas Comparative study of polyphenol scavenging activities assessed by different methods Journal of Agricultural and Food Chemistry 47 1999 425 431 (Pubitemid 29185203)
5. M.I. de Heer, P. Mulder, H.G. Korth, K.U. Ingold, and J. Lusztyk Hydrogen atom abstraction kinetics from intramolecularly hydrogen bonded ubiquinol-10 and other (poly)methoxy phenols Journal of the American Chemical Society 122 2000 2355 2360 (Pubitemid 30164648)
6. S. Dugasani, M.R. Pichika, V.D. Nadarajah, M.K. Balijepalli, S. Tandra, and J.N. Korlakunta Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]-gingerol, [10]-gingerol and [6]-shogaol Journal of Ethnopharmacology 127 2010 515 520
7. H. Esterbauer, and P. Ramos Chemistry and pathophysiology of oxidation of LDL Reviews of Physiology, Biochemistry and Pharmacology 127 1996 31 64
8. S.A. Fleming, C.W. Dyer, and J. Eggington A convenient one-step gingerol synthesis Synthetic Communications 29 1999 1933 1939 (Pubitemid 29193873)
9. F.-F. Gan, A.A. Nagle, X. Ang, O.H. Ho, S.-H. Tan, and H. Yang et al. Shogaols at proapoptotic concentrations induce G2/M arrest and aberrant mitotic cell death associated with tubulin aggregation Apoptosis 16 2011 856 867
10. S.R. Gundala, R. Mukkavilli, C. Yang, P. Yadav, V. Tandon, and S. Vangala et al. Enterohepatic recirculation of bioactive ginger phytochemicals is associated with enhanced tumor growth-inhibitory activity of ginger extract Carcinogenesis 2014 10.1093/carcin/bgu011
11. B.L. Halvorsen, M.H. Carlsen, K.M. Phillips, S.K. Bøhn, K. Holte, and D.R. Jacobs et al. Content of redox-active compounds (ie, antioxidants) in foods consumed in the United States The American Journal of Clinical Nutrition 84 2006 95 135 (Pubitemid 44699176)
12. S.P. Hussain, L.J. Hofseth, and C.C. Harris Radical causes of cancer Nature Reviews Cancer 3 2003 276 285 (Pubitemid 37328863)
13. K. Ishiguro, T. Ando, O. Watanabe, and H. Goto Specific reaction of α,β-unsaturated carbonyl compounds such as 6-shogaol with sulfhydryl groups in tubulin leading to microtubule damage FEBS Letters 582 2008 3531 3536
14. S.D. Jolad, R.C. Lantz, G.J. Chen, R.B. Bates, and B.N. Timmermann Commercially processed dry ginger (Zingiber officinale): Composition and effects on LPS-stimulated PGE2 production Phytochemistry 66 2005 1614 1635 (Pubitemid 40950555)
15. A. Kahlenberg, and D. Dolansky Structural requirements of d-glucose for its binding to iaolated human erythrocyte membranes Canadian Journal of Biochemistry 50 1972 638 643
16. H. Kikuzaki, and N. Nakatani Antioxidant effects of some ginger constituents Journal of Food Science 6 1993 1407 1410
17. Y. Li, F. Dai, X.-L. Jin, M.-M. Ma, Y.-H. Wang, and X.-R. Ren et al. An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains Food Chemistry 158 2014 41 47
18. F. Li, V. Nitteranon, X. Tang, J. Liang, G. Zhang, and K.L. Parkin et al. In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]- gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin Food Chemistry 135 2012 332 337
19. Y. Masuda, H. Kikuzaki, M. Hisamoto, and N. Nakatani Antioxidant properties of gingerol related compounds from ginger BioFactors 21 2004 293 296 (Pubitemid 40921871)
20. E. Niki Assessment of antioxidant capacity in vitro and in vivo Free Radical Biology & Medicine 49 2010 503 515
21. E. Niki, E. Komuro, M. Takahashi, S. Uranoz, E. Itos, and K. Terao Oxidative hemolysis of erythrocytes and its inhibition by free radical scavengers The Journal of Biological Chemistry 263 1988 19809 19814 (Pubitemid 19016466)
22. E. Niki, and N. Noguchi Dynamics of antioxidant action of vitamin E Accounts of Chemical Research 37 2004 45 51
23. M.-H. Pan, M.-C. Hsieh, P.-C. Hsu, S.-Y. Ho, C.-S. Lai, and H. Wu et al. 6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages Molecular Nutrition & Food Research 52 2008 1467 1477
24. M.-H. Pan, M.-C. Hsieh, J.-M. Kuo, C.-S. Lai, H. Wu, and S. Sang et al. 6-Shogaol induces apoptosis in human colorectal carcinoma cells via ROS production, caspase activation, and GADD 153 expression Molecular Nutrition & Food Research 52 2008 527 537
25. F. Peng, Q. Tao, X. Wu, H. Dou, S. Spencer, and C. Mang et al. Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger Fitoterapia 83 2012 568 585
26. Y.-P. Qian, Y.-J. Shang, Q.-F. Teng, J. Chang, G.-J. Fan, and X. Wei et al. Hydroxychalcones as potent antioxidants: Structure-activity relationship analysis and mechanism considerations Food Chemistry 126 2011 241 248
27. M.S. Ramachandra, and G.V. Subbaraju Synthesis and bioactivity of novel caffeic acid esters from Zuccagnia punctata Journal of Asian Natural Products Research 8 2006 683 688 (Pubitemid 44915749)
28. S. Reuter, S.C. Gupta, M.M. Chaturvedi, and B.B. Aggarwal Oxidative stress, inflammation, and cancer: How are they linked? Free Radical Biology & Medicine 49 2010 1603 1616
29. S. Sang, J. Hong, H. Wu, J. Liu, C.S. Yang, and M.-H. Pan et al. Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols Journal of Agricultural and Food Chemistry 57 2009 10645 10650
30. Y.-J. Shang, X.-L. Jin, X.-L. Shang, J.-J. Tang, G.-Y. Liu, and F. Dai et al. Antioxidant capacity of curcumin-directed analogues: Structure-activity relationship and influence of microenvironment Food Chemistry 119 2010 1435 1442
31. Y.-J. Shang, Y.-P. Qian, X.-D. Liu, F. Dai, X.-L. Shang, and W.-Q. Jia et al. Radical-scavenging activity and mechanism of resveratrol-oriented analogues: Influence of the solvent, radical, and substitution The Journal of Organic Chemistry 74 2009 5025 5031
32. Y. Shukla, and M. Singh Cancer preventive properties of ginger: A brief review Food and Chemical Toxicology 45 2007 683 690 (Pubitemid 46452881)
33. J.-J. Tang, G.-J. Fan, F. Dai, D.-J. Ding, Q. Wang, and D.-L. Lu et al. Finding more active antioxidants and cancer chemoprevention agents by elongating the conjugated links of resveratrol Free Radical Biology & Medicine 50 2011 1447 1457
34. C.-J. Weng, C.-P. Chou, C.-T. Ho, and G.-C. Yen Molecular mechanism inhibiting human hepatocarcinoma cell invasion by 6-shogaol and 6-gingerol Molecular Nutrition & Food Research 56 2012 1304 1314
35. C.-J. Weng, C.-F. Wu, H.-W. Huang, C.-T. Ho, and G.-C. Yen Anti-invasion effects of 6-shogaol and 6-gingerol, two active components in ginger, on human hepatocarcinoma cells Molecular Nutrition & Food Research 54 2010 1618 1627
36. L.L. Wu, C.C. Chiou, P.Y. Chang, and J.T. Wu Urinary 8-OHdG: A marker of oxidative stress to DNA and a risk factor for cancer, atherosclerosis and diabetics Clinica Chimica Acta 339 2004 1 9 (Pubitemid 37542453)
37. H. Wu, M.-C. Hsieh, C.-Y. Lo, C.B. Liu, S. Sang, and C.-T. Ho et al. 6-Shogaol is more effective than 6-gingerol and curcumin in inhibiting 12-O-tetradecanoylphorbol 13-acetate-induced tumor promotion in mice Molecular Nutrition & Food Research 54 2010 1296 1306
38. H.-Y. Yeh, C.-H. Chuang, H.-C. Chen, C.-J. Wan, T.-L. Chen, and L.-Y. Lin Bioactive components analysis of two various gingers (Zingiber officinale Roscoe) and antioxidant effect of ginger extracts LWT - Food Science and Technology 55 2014 329 334
39. B. Zhou, Q. Miao, L. Yang, and Z.-L. Liu Antioxidative effects of flavonols and their glycosides against the free-radical-induced peroxidation of linoleic acid in solution and in micelles Chemistry - A European Journal 11 2005 680 691 (Pubitemid 40143066)