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Protective action on human LDL against oxidation and glycation by four organosulfur compounds derived from garlic

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Lipids

Abstract

Human LDL were used to study the protective action of four organosulfur compounds (diallyl sulfide, DAS; diallyl disulfide, DADS; S-ethylcysteine, SEC; N-acetylcysteine, NAC) derived from garlic against oxidation and glycation. The four organosulfur compounds significantly inhibited superoxide production by xanthine-xanthine oxidase (P<0.05) and showed marked copper-chelating capability. DAS and DADS exhibited greater antioxidant activities against copper- and amphotericin B-induced LDL oxidation (P<0.05) than SEC and NAC. However, SEC and NAC were more effective in sparing LDL α-tocopherol (P<0.05). When oxidation was minimized, SEC was the most powerful agent against LDL glycation (P<0.05); however, DADS was superior to other agents in suppressing both oxidation and glycation when LDL oxidation occurred simultaneously with glycation. These results suggest that the four organosulfur compounds derived from garlic are potent agents for protecting LDL against oxidation and glycation, and that they may benefit patients with diabetes mellitus or cardiovascular diseases by preventing complications.

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Abbreviations

AmB:

amphotericin B

CD:

conjugated diene

DADS:

diallyl disulfide

DAS:

diallyl sulfide

MDA:

malondialdehyde

NAC:

N-acetylcysteine

SEC:

S-ethylcysteine

TBA:

thiobarbituric acid

References

  1. Lyons, T.J. (1993) Glycation and Oxidation: A Role in the Pathogenesis of Atherosclerosis, Am. J. Cardiol. 71, 26B-31B.

    Article  PubMed  CAS  Google Scholar 

  2. Hunt, J.V., and Wolff, S.P. (1991) Oxidative Glycation and Free Radical Production, a Causal Mechanism of Diabetic Complications, Free Rad. Res. Commun. 12, 115–123.

    Article  Google Scholar 

  3. Li, D., Devaraj, S., Fuller, C., Bucala, R., and Jialal, I. (1996) Effect of α-Tocopherol on LDL Oxidation and Glycation: In vitro and in vivo Studies, J. Lipid Res. 37, 1978–1986.

    PubMed  CAS  Google Scholar 

  4. Picard, S. (1995) Lipoprotein Glyco-oxidation, Diabete Metab. 21, 89–94.

    PubMed  CAS  Google Scholar 

  5. Albertini, R., Moratti, R., and De Luca, G. (2002) Oxidation of Low-Density Lipoprotein in Atherosclerosis from Basic Biochemistry to Clinical Studies, Curr. Mol. Med. 2, 579–592.

    Article  PubMed  CAS  Google Scholar 

  6. Hunt, J.V., Bottoms, M.A., Clare, K., Skamarauskas, J.T., and Mitchinson, M.J. (1994) Glucose Oxidation and Low Density Lipoprotein-Induced Macrophage Ceroid Accumulation: Possible Implications for Diabetic Atherosclerosis, Biochem. J. 300, 243–249.

    PubMed  CAS  Google Scholar 

  7. Dwivedi, C., Abu-Ghazaleh, A., and Guenther, J. (1996) Effects of Diallyl Sulfide and Diallyl Disulfide on Cisplatin-Induced Changes in Glutathione and Glutathione-S-transferase Activity, Anti-Cancer Drugs 7, 792–794.

    Article  PubMed  CAS  Google Scholar 

  8. Wu, C.C., Sheen, L.Y., Chen, H.W., Tsai, S.J., and Lii, C.K. (2001) Effects of Organosulfur Compounds from Garlic Oil on the Antioxidation System in Rat Liver and Red Blood Cells, Food Chem. Toxicol. 39, 563–569.

    Article  PubMed  CAS  Google Scholar 

  9. O'Gara, E.A., Hill, D.J., and Maslin, D.J. (2000) Activities of Garlic Oil, Garlic Powder and Their Diallyl Constituents Against Helicobacter pylori, Appl. Environ. Microbiol. 66, 2269–2273.

    Article  PubMed  Google Scholar 

  10. Tsao, S.M., and Yin, M.C. (2001) In vitro Activity of Garlic Oil and Four Diallyl Sulphides Against Antibiotic-Resistant Pseudomonas aeruginosa and Klebsiella pneumoniae, J. Antimicrob. Chemother. 47, 665–670.

    Article  PubMed  CAS  Google Scholar 

  11. Yin, M.C., Huang, S.W., and Chan, K.C. (2002) Non-enzymatic Antioxidant Activity of Four Organosulfur Compounds Derived from Garlic, J. Agric. Food. Chem. 50, 6143–6147.

    Article  PubMed  CAS  Google Scholar 

  12. Tsao, S.M., and Yin, M.C. (2001) In-vitro Antimicrobial Activity of Four Diallyl Sulphides Occurring Naturally in Garlic and Chinese Leek Oils, J. Med. Microbiol. 50, 646–649.

    PubMed  CAS  Google Scholar 

  13. Barwicz, J., Dumont, I., Ouellet, C., and Gruda, I. (1998) Amphotericin B Toxicity as Related to the Formation of Oxidatively Modified Low Density Lipoproteins, Biospectroscopy 4, 135–144.

    Article  PubMed  CAS  Google Scholar 

  14. Wasan, K.M., Kennedy, A.L., Cassidy, S.M., Ramaswamy, M., Holtorf, L., Chou, J.W., and Pritchard, P.H. (1998). Pharmacokinetics, Distribution in Serum Lipoproteins and Tissues and Renal Toxicities of Amphotericin B and Amphotericin B Lipid Complex in a Hypercholesterolemic Rabbit Model: Single-Dose-Studies, Antimicrob. Agents Chemother. 42, 3146–3152.

    PubMed  CAS  Google Scholar 

  15. Barwicz, J., Gruda, I., and Tancrede, P. (2000) A Kinetic Study of the Oxidation Effects of Amphotericin B on Human Low Density Lipoproteins, FEBS Lett. 465, 83–86.

    Article  PubMed  CAS  Google Scholar 

  16. Nourooz-Zadeh, J., Tajaddini-Sarmadi, J., Ling, K.L., and Wolff, S.P. (1996) Low-Density Lipoprotein Is the Major Carrier of Lipid Hydroperoxides in Plasma, Biochem. J. 313, 781–786.

    PubMed  CAS  Google Scholar 

  17. Lowry, O.H., Rosebrough, N.J., Farr, A.L., and Randall, R.J. (1951) Protein Measurement with Folin Phenol Reagent, J. Biol. Chem. 193, 265–275.

    PubMed  CAS  Google Scholar 

  18. Palozza, P., and Krinsky, N.I. (1992) Effects of β-Carotene and α-Tocopherol on Radical Initiated Peroxidation of Microsomes, Free Radic. Biol. Med. 13, 127–136.

    Article  PubMed  CAS  Google Scholar 

  19. Dillon, S.A., Burmi, R.S., Lowe, G.M., Billington, D., and Rahman, K. (2003) Antioxidant Properties of Aged Garlic Extract: An in vitro Study Incorporating Human Low Density Lipoprotein, Life Sci. 72, 1583–1594.

    Article  PubMed  CAS  Google Scholar 

  20. Lawson, L.D., Wang, Z.J., and Hughes, B.G. (1991) Identification and HPLC Quantification of the Sulfides and Dialk(en)yl Thiosulfides in Commercial Garlic Products, Planta Med. 57, 363–370.

    PubMed  CAS  Google Scholar 

  21. Jain, S.K., and Palmer, M. (1997) The Effect of Oxygen Radical Metabolites and Vitamin E on Glycosylation of Proteins, Free Radic. Biol. Med. 22, 593–596.

    Article  PubMed  CAS  Google Scholar 

  22. Esterbauer, H., Striegl, G., Puhl, H., and Rotheneder, M. (1989) Continuous Monitoring of in vitro Oxidation of Human Low Density Lipoprotein, Free Radic. Res. Commun. 6, 67–75.

    PubMed  CAS  Google Scholar 

  23. Duell, P.B., Oram, J.F., and Biermann, E.L. (1990) Nonenzymatic Glycation of HDL Resulting in Inhibition of High-Affinity Binding to Cultured Human Fibroblasts, Diabetes 39, 1257–1263.

    PubMed  CAS  Google Scholar 

  24. SAS, SAS/STAT User's Guide, version 6, Statistical Analysis System Institute, Cary, NC, 1990.

    Google Scholar 

  25. Lau, B.H.S. (2001) Suppression of LDL Oxidation by Garlic, J. Nutr. 131, 985s-988s.

    PubMed  CAS  Google Scholar 

  26. Phelps, S., and Harris, W.S. (1993) Garlic Supplementation and Lipoprotein Oxidation Susceptibility, Lipids 28, 475–477.

    PubMed  CAS  Google Scholar 

  27. Lynch, S.M., and Frei, B. (1993) Mechanisms of Copper- and Iron Dependent Oxidative Modification of Human Low Density Lipoprotein, J. Lipid Res. 34, 1745–1753.

    PubMed  CAS  Google Scholar 

  28. Swain, J., and Gutteridge, J.M. (1995) Prooxidant Iron and Copper, with Ferroxidase and Xanthine Oxidase Activities in Human Atherosclerotic Material, FEBS Letters 368, 513–515.

    Article  PubMed  CAS  Google Scholar 

  29. Avato, P., Tursil, E., Vitali, C., Miccolis, V., and Candido, V. (2000) Allylsulfide Constituents of Garlic Volatile Oil as Antimicrobial Agents, Phytomedicine 7, 239–243.

    PubMed  CAS  Google Scholar 

  30. Moro, E., Alessandrini, P., Zambon, C., Pianetti, S., Pais, M., Cazzolato, G., and Bon, G.B. (1999) Is Glycation of Low Density Lipoproteins in Patients with Type 2 Diabetes Mellitus a LDL Pre-oxidative Condition? Diabet. Med. 16, 663–669.

    Article  PubMed  CAS  Google Scholar 

  31. Menzel, E.J., Sobal, G., and Staudinger, A. (1997) The Role of Oxidative Stress in the Long-Term Glycation of LDL, Biofactors 6, 111–124.

    PubMed  CAS  Google Scholar 

  32. Nakayama, M., Izumi, G., Nemoto, Y., Shibata, K., Hasegawa, T., Numata, M., Wang, K., Kawaguchi, Y., and Hosoya, T. (1999) Suppression of Nɛ-(Carboxymethyl)lysine Generation by the Antioxidant N-Acetyl Cysteine, Perit. Dial. Int. 19, 207–210.

    PubMed  CAS  Google Scholar 

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Correspondence to Mei-chin Yin.

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Ou, Cc., Tsao, Sm., Lin, Mc. et al. Protective action on human LDL against oxidation and glycation by four organosulfur compounds derived from garlic. Lipids 38, 219–224 (2003). https://doi.org/10.1007/s11745-003-1054-4

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  • DOI: https://doi.org/10.1007/s11745-003-1054-4

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