Characterization of antioxidant activity of sulfur compounds in black garlic

Wei-dong Wang; Yue-E Sun; Hong-wei Chen

doi:10.14715/cmb/2018.64.12.15

Issue

Vol. 64 No. 12: Issue 12

Issue Published : October 2, 2018

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Characterization of antioxidant activity of sulfur compounds in black garlic

https://doi.org/10.14715/cmb/2018.64.12.15

Wei-dong Wang

College of Food Engineering, Xuzhou University of Technology, 2 Lishui Road, XuZhou 221111, Jiangsu Province, China

Yue-E Sun

College of Food Engineering, Xuzhou University of Technology, 2 Lishui Road, XuZhou 221111, Jiangsu Province, China

Hong-wei Chen

College of Food Engineering, Xuzhou University of Technology, 2 Lishui Road, XuZhou 221111, Jiangsu Province, China

Corresponding Author(s) : Yue-E Sun

yueesun@163.com

Cellular and Molecular Biology, Vol. 64 No. 12: Issue 12
Article Published : September 30, 2018

Abstract

Different types of sulfur compounds, namely S-allyl-L-cysteine (SAC), S-allyl-L-cysteine sulfoxide (ACSO) and a synthetic Î³-L-glutamyl-S-allyl-L-cysteine (GSAC) were extracted from black garlic and their inhibition to the advanced glycation end-products (AGEs) were investigated. Upon addition of inhibitor, the amount of produced fructosamine was determined by UV visible spectroscopy. The change of pentosidine and fluorescent AGEs during reaction was detected by fluorescence method and the change of carboxymethyl lysine (CML) was detected by high performance liquid chromatography. It was found that the inhibitory effects of SAC and ACSO are stronger to the early and mid non-fluorescent products in glycosylation reaction, and GSAC has an obvious inhibitory effect on the later reaction products. All these three inhibitors can effectively inhibit advanced glycation reaction. Although their effects on glycation products are different due to different chemical structures, they have similar inhibitory effects on fluorescent products.

Keywords

S-allyl-L-cysteine S-allyl-L-cysteine sulfoxide Î³-L-glutamyl-S-allyl-L-cysteine antioxidant activity Black garlic.

Wang, W.- dong, Sun, Y.-E., & Chen, H.- wei. (2018). Characterization of antioxidant activity of sulfur compounds in black garlic. Cellular and Molecular Biology, 64(12), 76–80. https://doi.org/10.14715/cmb/2018.64.12.15

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References

Block E. The chemistry of garlic and onions. Sci Am 1985; 252:114-9.
Reuter HD, Koch HP, Lawson LD. Therapeutic effects of garlic and its preparations. In: Garlic: The Science and Therapeutic Application of Black garlic L and Related Species. Koch HP. and Lawson LD. (eds), London, UK: Williams & Wilkins, 1996, pp. 13-162.
Lawson LD, Gardner CD. Composition, stability, and bioavailability of garlic products used in a clinical trial. J Agr Food Chem 2005; 53:6254-61.
Amagase H, Petesch BL, Matsuura H, Kasuga S, Itakura Y. Intake of garlic and its bioactive components. J Nutr 2001; 131:955-62.
Kosuge, Y., Koen, Y., Ishige, K., Minami, K., Urasawa, H., Saito, H., et al. S-allyl-l-cysteine selectively protects cultured rat hippocampal neurons from amyloid beta-protein- and tunicamycin-induced neuronal death. Neuroscience 2003; 122: 885-95.
Ray, B., Chauhan, N. B., Lahiri, D. K. The "aged garlic extract:" (age) and one of its active ingredients s-allyl-l-cysteine (sac) as potential preventive and therapeutic agents for alzheimer's disease (ad). Int Med J 2012; 42: 274-80.
Yoshihisa, I., Yasuhiro, K., Taeko, S., Kayo, H., Natsue, I., Naoya, O., et al. Protective effect of s-allyl-l-cysteine, a garlic compound, on amyloid beta-protein-induced cell death in nerve growth factor-differentiated pc12 cells. Neurosci Res 2003; 46:119-25.
Panjehpour M, Alaie SH. N-acetylcysteine prevents cadmium-induced apoptosis in human breast cancer mda-mb468 cell line. Cell Mol Bio 2014; 60:33-8.
Borek C. Antioxidant health effects of aged garlic extract. J Nutr 2001; 131:1010-5.
Ide N, Lau BHS. Aged garlic extract attenuates intracellular oxidative stress. Phytomedicine 1999; 6:125-31.
Morihara N, Sumioka I, Moriguchi T, Uda N, Kyo E. Aged garlic extract enhances production of nitric oxide. Life Sci 2002; 71:509-17.
Kodera Y, Suzuki A, Imada O, Kasuga S, Sumioka I, Kanezawa A, et al. Physical, chemical, and biological properties of S-allylcysteine, an amino acid derived from garlic. J Agr Food Chem 2002; 50:622-32.
Nagae S, Ushijima M, Hatono S, Imai J, Kasuga S, Matsuura H, et al. Pharmacokinetics of the garlic compound S-allylcysteine. Planta Med 1994; 60:214-7.
Flora SJS, Pande M, Kannan GM, Mehta A. Lead induced oxidative stress and its recovery following co-administration of melatonin or n-acetylcysteine during chelation with succimer in male rats. Cell Mol Bio 2004; 50:543-51.
Numagami Y, Ohnishi ST. S-allylcysteine inhibits free radical production, lipid peroxidation and neuronal damage in rat brain ischemia. J Nutr 2001; 131:1100-5.
Yamasaki T, Li L, Lau BHS. Garlic compounds protect vascular endothelial cells from hydrogen peroxide-induced oxidant injury. Phytother Res 1994; 8:408-12.
Ide N, Lau BHS. Garlic compounds protect vascular endothelial cells from oxidized low density lipoprotein-induced injury. J Pharm Pharmacol. 1997; 49:908-11.
Medina-Campos ON, Barrera D, Segoviano-Murillo S, Rocha D, Maldonado PD, Mendoza-Patiño N, et al. S-allylcysteine scavenges singlet oxygen and hypochlorous acid and protects LLC-PK1 cells of potassium dichromate-induced toxicity. Food Chem Toxicol 2007; 45:2030-9.
Chung LY. The antioxidant properties of garlic compounds: alyl cysteine, alliin, allicin, and allyl disulfide. J Med Food. 2006; 9:205-13.
Maldonado PD, Alvarez-Idaboy JR, Aguilar-González A, Lira-Rocha A, Jung-Cook H, Medina-Campos ON, et al. Role of allyl group in the hydroxyl and peroxyl radical scavenging activity of s-allylcysteine. J Phys Chem B. 2011; 115:13408-17.
Maldonado PD, Barrera D, Medina-Campos ON, Hernández-Pando R, Ibarra-Rubio ME, Pedraza-Chaverrí J. Aged garlic extract attenuates gentamicin induced renal damage and oxidative stress in rats. Life Sci 2003; 73:2543-56.
Wei Z, Lau BHS. Garlic inhibits free radical generation and augments antioxidant enzyme activity in vascular endothelial cells. Nutr Res 1998; 18:61-70.
Ide N, Lau BHS, Ryu K, Matsuura H, Itakura Y. Antioxidant effects of fructosyl arginine, a maillard reaction product in aged garlic extract. J Nutr Biochem 1999; 10:372-6.
Ide N, Matsuura H, Itakura Y. Scavenging effect of aged garlic extract and its constituents on active oxygen species. Phytother Res 1996; 10:340-1.
Kim JM, Lee JC, Chang N, Chun HS, Kim WK. S-Allyl-l-cysteine attenuates cerebral ischemic injury by scavenging peroxynitrite and inhibiting the activity of extracellular signal-regulated kinase. Free Radical Res 2006; 40:827-35.

References

Block E. The chemistry of garlic and onions. Sci Am 1985; 252:114-9.

Reuter HD, Koch HP, Lawson LD. Therapeutic effects of garlic and its preparations. In: Garlic: The Science and Therapeutic Application of Black garlic L and Related Species. Koch HP. and Lawson LD. (eds), London, UK: Williams & Wilkins, 1996, pp. 13-162.

Lawson LD, Gardner CD. Composition, stability, and bioavailability of garlic products used in a clinical trial. J Agr Food Chem 2005; 53:6254-61.

Amagase H, Petesch BL, Matsuura H, Kasuga S, Itakura Y. Intake of garlic and its bioactive components. J Nutr 2001; 131:955-62.

Kosuge, Y., Koen, Y., Ishige, K., Minami, K., Urasawa, H., Saito, H., et al. S-allyl-l-cysteine selectively protects cultured rat hippocampal neurons from amyloid beta-protein- and tunicamycin-induced neuronal death. Neuroscience 2003; 122: 885-95.

Ray, B., Chauhan, N. B., Lahiri, D. K. The "aged garlic extract:" (age) and one of its active ingredients s-allyl-l-cysteine (sac) as potential preventive and therapeutic agents for alzheimer's disease (ad). Int Med J 2012; 42: 274-80.

Yoshihisa, I., Yasuhiro, K., Taeko, S., Kayo, H., Natsue, I., Naoya, O., et al. Protective effect of s-allyl-l-cysteine, a garlic compound, on amyloid beta-protein-induced cell death in nerve growth factor-differentiated pc12 cells. Neurosci Res 2003; 46:119-25.

Panjehpour M, Alaie SH. N-acetylcysteine prevents cadmium-induced apoptosis in human breast cancer mda-mb468 cell line. Cell Mol Bio 2014; 60:33-8.

Borek C. Antioxidant health effects of aged garlic extract. J Nutr 2001; 131:1010-5.

Ide N, Lau BHS. Aged garlic extract attenuates intracellular oxidative stress. Phytomedicine 1999; 6:125-31.

Morihara N, Sumioka I, Moriguchi T, Uda N, Kyo E. Aged garlic extract enhances production of nitric oxide. Life Sci 2002; 71:509-17.

Kodera Y, Suzuki A, Imada O, Kasuga S, Sumioka I, Kanezawa A, et al. Physical, chemical, and biological properties of S-allylcysteine, an amino acid derived from garlic. J Agr Food Chem 2002; 50:622-32.

Nagae S, Ushijima M, Hatono S, Imai J, Kasuga S, Matsuura H, et al. Pharmacokinetics of the garlic compound S-allylcysteine. Planta Med 1994; 60:214-7.

Flora SJS, Pande M, Kannan GM, Mehta A. Lead induced oxidative stress and its recovery following co-administration of melatonin or n-acetylcysteine during chelation with succimer in male rats. Cell Mol Bio 2004; 50:543-51.

Numagami Y, Ohnishi ST. S-allylcysteine inhibits free radical production, lipid peroxidation and neuronal damage in rat brain ischemia. J Nutr 2001; 131:1100-5.

Yamasaki T, Li L, Lau BHS. Garlic compounds protect vascular endothelial cells from hydrogen peroxide-induced oxidant injury. Phytother Res 1994; 8:408-12.

Ide N, Lau BHS. Garlic compounds protect vascular endothelial cells from oxidized low density lipoprotein-induced injury. J Pharm Pharmacol. 1997; 49:908-11.

Medina-Campos ON, Barrera D, Segoviano-Murillo S, Rocha D, Maldonado PD, Mendoza-Patiño N, et al. S-allylcysteine scavenges singlet oxygen and hypochlorous acid and protects LLC-PK1 cells of potassium dichromate-induced toxicity. Food Chem Toxicol 2007; 45:2030-9.

Chung LY. The antioxidant properties of garlic compounds: alyl cysteine, alliin, allicin, and allyl disulfide. J Med Food. 2006; 9:205-13.

Maldonado PD, Alvarez-Idaboy JR, Aguilar-González A, Lira-Rocha A, Jung-Cook H, Medina-Campos ON, et al. Role of allyl group in the hydroxyl and peroxyl radical scavenging activity of s-allylcysteine. J Phys Chem B. 2011; 115:13408-17.

Maldonado PD, Barrera D, Medina-Campos ON, Hernández-Pando R, Ibarra-Rubio ME, Pedraza-Chaverrí J. Aged garlic extract attenuates gentamicin induced renal damage and oxidative stress in rats. Life Sci 2003; 73:2543-56.

Wei Z, Lau BHS. Garlic inhibits free radical generation and augments antioxidant enzyme activity in vascular endothelial cells. Nutr Res 1998; 18:61-70.

Ide N, Lau BHS, Ryu K, Matsuura H, Itakura Y. Antioxidant effects of fructosyl arginine, a maillard reaction product in aged garlic extract. J Nutr Biochem 1999; 10:372-6.

Ide N, Matsuura H, Itakura Y. Scavenging effect of aged garlic extract and its constituents on active oxygen species. Phytother Res 1996; 10:340-1.

Kim JM, Lee JC, Chang N, Chun HS, Kim WK. S-Allyl-l-cysteine attenuates cerebral ischemic injury by scavenging peroxynitrite and inhibiting the activity of extracellular signal-regulated kinase. Free Radical Res 2006; 40:827-35.

Author biographies is not available.