Inhibitory Effect of 6-shogaol on Fructose-Induced Protein Glycation and Oxidation in Vitro
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Published
Apr 26, 2017
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Abstract
Advanced glycation end product (AGEs), the final products derived from the non enzymatic modification of proteins by reducing sugars, plays an important role in the development of diabetic complications. Therefore, the inhibition of AGE formation may be an important therapeutic strategy to prevent the development of AGEs related diseases. The aim of this study was to investigate the in vitro effect of 6-shogaol on fructose-induced the formation of AGEs and protein oxidation. Antioxidant activity of 6-shogaol was determined by 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. The protein glycation inhibitory potential was evaluated using in vitro BSA/ fructose model. 6-shogaol (0.1-10 mM) was incubated with BSA and fructose (0.1 M) at 37° C for 21 days. Antiglycation activity of 6-shogaol was investigated by measuring the formation of AGE-specific fluorescence and Nε-(carboxymethyl) lysine (CML). In addition glycation induced protein oxidation was examined using the protein carbonyl assays. 6-shogaol exhibited an effective antioxidant activity, Where the results that 6-shogaol inhibited the formation of both fluorescent AGEs and non-fluorescent AGE (CML) in BSA/fructose solution. In addition an increase in protein carbonyl content of BSA incubated with fructose was attenuated by 6-shogaol (10 mM). In conclusion, These results suggest that 6-shogaol has a inhibitory effect on the formation of AGEs and protein oxidation in vitro, which may be mediated through its antioxidant activity.
Keywords: 6-shogaol, Advanced glycation end products, Protein glycation, Protein oxidation
References
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Ahmad, M. S., Pischetsrieder, M., & Ahmed, N. (2007). Aged garlic extract and S-allyl cysteine prevent formation of advanced glycation endproducts. Eur J Pharmacol, 561(1-3), 32-38.
Ahmed, N. (2005). Advanced glycation endproducts-role in pathology of diabetic complications. Diabetes Res Clin Pract, 67(1), 3-21.
Ardestani, A., & Yazdanparast, R. (2007). Cyperus rotundus suppresses AGE formation and protein oxidation in a model of fructose-mediated protein glycoxidation. Int J Biol Macromol, 41(5), 572-578.
Dugasani, S., Pichika, M. R., Nadarajah, V. D., Balijepalli, M. K., Tandra, S., & Korlakunta, J.N. (2010). Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]- gingerol, [10]-gingerol and [6]-shogaol. J Ethnopharmacol, 127(2), 515-520.
Ghasemzadeh, A., Jaafar, H. Z., & Rahmat, A. (2015). Optimization protocol for the extraction of 6-gingerol and 6-shogaol from Zingiber officinale var. rubrum Theilade and improvingantioxidant and anticancer activity using response surface methodology. BMC Complement Altern Med, 15, 258.
Goh, S. Y., & Cooper, M. E. (2008). Clinical review: The role of advanced glycation end products in progression and complications of diabetes. J Clin Endocrinol Metab, 93(4), 1143-1152.
Jariyapamornkoon, N., Yibchok-anun, S., & Adisakwattana, S. (2013). Inhibition of advanced glycation end products by red grape skin extract and its antioxidant activity. BMC Complement Altern Med, 13, 171.
Jolad, S. D., Lantz, R. C., Chen, G. J., Bates, R. B., & Timmermann, B. N. (2005). Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production. Phytochemistry, 66(13), 1614-1635.
Jolad, S. D., Lantz, R. C., Solyom, A. M., Chen, G. J., Bates, R. B., & Timmermann, B. N. (2004). Fresh organically grown ginger (Zingiber officinale): composition and effects on LPS induced PGE2 production. Phytochemistry, 65(13), 1937-1954.
Li, F., Nitteranon, V., Tang, X., Liang, J., Zhang, G., Parkin, K. L., & Hu, Q. (2012). In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin. Food Chem, 135(2), 332-337.
Li, X., Zheng, T., Sang, S., & Lv, L. (2014). Quercetin inhibits advanced glycation end product formation by trapping methylglyoxal and glyoxal. J Agric Food Chem, 62(50), 12152-12158.
Lv, L., Shao, X., Chen, H., Ho, C. T., & Sang, S. (2011). Genistein inhibits advanced glycation end product formation by trapping methylglyoxal. Chem Res Toxicol, 24(4), 579-586.
Mashhadi, N. S., Ghiasvand, R., Askari, G., Hariri, M., Darvishi, L., & Mofid, M. R. (2013). Anti-oxidative and anti-inflammatory effects of ginger in health and physical activity: review of current evidence. Int J Prev Med, 4(Suppl 1), S36-42.
Moon, M., Kim, H. G., Choi, J. G., Oh, H., Lee, P. K., Ha, S. K., … Oh, M. S. (2014). 6-Shogaol, an active constituent of ginger, attenuates neuroinflammation and cognitive deficits in animal models of dementia. Biochem Biophys Res Commun, 449(1), 8-13.
Ok, S., & Jeong, W. S. (2012). Optimization of Extraction Conditions for the 6-Shogaol-rich Extract from Ginger (Zingiber officinale Roscoe). Prev Nutr Food Sci, 17(2), 166-171.
Ott, C., Jacobs, K., Haucke, E., Navarrete Santos, A., Grune, T., & Simm, A. (2014). Role of advanced glycation end products in cellular signaling. Redox Biol, 2, 411-429.
Peng, S., Yao, J., Liu, Y., Duan, D., Zhang, X., & Fang, J. (2015). Activation of Nrf2 target enzymes conferring protection against oxidative stress in PC12 cells by ginger principal constituent 6-shogaol. Food Funct, 6(8), 2813-2823.
Prasad, A., Bekker, P., & Tsimikas, S. (2012). Advanced glycation end products and diabetic cardiovascular disease. Cardiol Rev, 20(4), 177-183.
Schalkwijk, C. G., Stehouwer, C. D., & van Hinsbergh, V. W. (2004). Fructose-mediated non-enzymatic glycation: sweet coupling or bad modification. Diabetes Metab Res Rev, 20(5), 369-382.
Schlesier, K., Harwat, M., Bohm, V., & Bitsch, R. (2002). Assessment of antioxidant activity by using different in vitro methods. Free Radic Res, 36(2), 177-187.
Shim, S., Kim, S., Choi, D. S., Kwon, Y. B., & Kwon, J. (2011). Anti-inflammatory effects of [6]-shogaol: potential roles of HDAC inhibition and HSP70 induction. Food Chem Toxicol, 49(11), 2734-2740.
Singh, R., Barden, A., Mori, T., & Beilin, L. (2001). Advanced glycation end-products: a review. Diabetologia, 44(2), 129-146.
Sompong, W., Meeprom, A., Cheng, H., & Adisakwattana, S. (2013). A comparative study of ferulic acid on different monosaccharide-mediated protein glycation and oxidative damage in bovine serum albumin. Molecules, 18(11), 13886-13903.
Tanaka, Y., Uchino, H., Shimizu, T., Yoshii, H., Niwa, M., Ohmura, C., … Kawamori, R. (1999). Effect of metformin on advanced glycation endproduct formation and peripheral nerve function in streptozotocin-induced diabetic rats. Eur J Pharmacol, 376(1-2), 17-22.
Tappy, L., Le, K. A., Tran, C., & Paquot, N. (2010). Fructose and metabolic diseases: new findings, new questions. Nutrition, 26(11-12), 1044-1049.
Wu, C. H., & Yen, G. C. (2005). Inhibitory effect of naturally occurring flavonoids on the formation of advanced glycation endproducts. J Agric Food Chem, 53(8), 3167-3173.
Zhu, Y., Zhao, Y., Wang, P., Ahmedna, M., & Sang, S. (2015). Bioactive ginger constituents alleviate protein glycation by trapping methylglyoxal. Chem Res Toxicol, 28(9), 1842-1849.
Zick, S. M., Djuric, Z., Ruffin, M. T., Litzinger, A. J., Normolle, D. P., Alrawi, S., … Brenner, D. E. (2008). Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects. Cancer Epidemiol Biomarkers Prev, 17(8), 1930-1936.
Ahmad, M. S., Pischetsrieder, M., & Ahmed, N. (2007). Aged garlic extract and S-allyl cysteine prevent formation of advanced glycation endproducts. Eur J Pharmacol, 561(1-3), 32-38.
Ahmed, N. (2005). Advanced glycation endproducts-role in pathology of diabetic complications. Diabetes Res Clin Pract, 67(1), 3-21.
Ardestani, A., & Yazdanparast, R. (2007). Cyperus rotundus suppresses AGE formation and protein oxidation in a model of fructose-mediated protein glycoxidation. Int J Biol Macromol, 41(5), 572-578.
Dugasani, S., Pichika, M. R., Nadarajah, V. D., Balijepalli, M. K., Tandra, S., & Korlakunta, J.N. (2010). Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]- gingerol, [10]-gingerol and [6]-shogaol. J Ethnopharmacol, 127(2), 515-520.
Ghasemzadeh, A., Jaafar, H. Z., & Rahmat, A. (2015). Optimization protocol for the extraction of 6-gingerol and 6-shogaol from Zingiber officinale var. rubrum Theilade and improvingantioxidant and anticancer activity using response surface methodology. BMC Complement Altern Med, 15, 258.
Goh, S. Y., & Cooper, M. E. (2008). Clinical review: The role of advanced glycation end products in progression and complications of diabetes. J Clin Endocrinol Metab, 93(4), 1143-1152.
Jariyapamornkoon, N., Yibchok-anun, S., & Adisakwattana, S. (2013). Inhibition of advanced glycation end products by red grape skin extract and its antioxidant activity. BMC Complement Altern Med, 13, 171.
Jolad, S. D., Lantz, R. C., Chen, G. J., Bates, R. B., & Timmermann, B. N. (2005). Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production. Phytochemistry, 66(13), 1614-1635.
Jolad, S. D., Lantz, R. C., Solyom, A. M., Chen, G. J., Bates, R. B., & Timmermann, B. N. (2004). Fresh organically grown ginger (Zingiber officinale): composition and effects on LPS induced PGE2 production. Phytochemistry, 65(13), 1937-1954.
Li, F., Nitteranon, V., Tang, X., Liang, J., Zhang, G., Parkin, K. L., & Hu, Q. (2012). In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin. Food Chem, 135(2), 332-337.
Li, X., Zheng, T., Sang, S., & Lv, L. (2014). Quercetin inhibits advanced glycation end product formation by trapping methylglyoxal and glyoxal. J Agric Food Chem, 62(50), 12152-12158.
Lv, L., Shao, X., Chen, H., Ho, C. T., & Sang, S. (2011). Genistein inhibits advanced glycation end product formation by trapping methylglyoxal. Chem Res Toxicol, 24(4), 579-586.
Mashhadi, N. S., Ghiasvand, R., Askari, G., Hariri, M., Darvishi, L., & Mofid, M. R. (2013). Anti-oxidative and anti-inflammatory effects of ginger in health and physical activity: review of current evidence. Int J Prev Med, 4(Suppl 1), S36-42.
Moon, M., Kim, H. G., Choi, J. G., Oh, H., Lee, P. K., Ha, S. K., … Oh, M. S. (2014). 6-Shogaol, an active constituent of ginger, attenuates neuroinflammation and cognitive deficits in animal models of dementia. Biochem Biophys Res Commun, 449(1), 8-13.
Ok, S., & Jeong, W. S. (2012). Optimization of Extraction Conditions for the 6-Shogaol-rich Extract from Ginger (Zingiber officinale Roscoe). Prev Nutr Food Sci, 17(2), 166-171.
Ott, C., Jacobs, K., Haucke, E., Navarrete Santos, A., Grune, T., & Simm, A. (2014). Role of advanced glycation end products in cellular signaling. Redox Biol, 2, 411-429.
Peng, S., Yao, J., Liu, Y., Duan, D., Zhang, X., & Fang, J. (2015). Activation of Nrf2 target enzymes conferring protection against oxidative stress in PC12 cells by ginger principal constituent 6-shogaol. Food Funct, 6(8), 2813-2823.
Prasad, A., Bekker, P., & Tsimikas, S. (2012). Advanced glycation end products and diabetic cardiovascular disease. Cardiol Rev, 20(4), 177-183.
Schalkwijk, C. G., Stehouwer, C. D., & van Hinsbergh, V. W. (2004). Fructose-mediated non-enzymatic glycation: sweet coupling or bad modification. Diabetes Metab Res Rev, 20(5), 369-382.
Schlesier, K., Harwat, M., Bohm, V., & Bitsch, R. (2002). Assessment of antioxidant activity by using different in vitro methods. Free Radic Res, 36(2), 177-187.
Shim, S., Kim, S., Choi, D. S., Kwon, Y. B., & Kwon, J. (2011). Anti-inflammatory effects of [6]-shogaol: potential roles of HDAC inhibition and HSP70 induction. Food Chem Toxicol, 49(11), 2734-2740.
Singh, R., Barden, A., Mori, T., & Beilin, L. (2001). Advanced glycation end-products: a review. Diabetologia, 44(2), 129-146.
Sompong, W., Meeprom, A., Cheng, H., & Adisakwattana, S. (2013). A comparative study of ferulic acid on different monosaccharide-mediated protein glycation and oxidative damage in bovine serum albumin. Molecules, 18(11), 13886-13903.
Tanaka, Y., Uchino, H., Shimizu, T., Yoshii, H., Niwa, M., Ohmura, C., … Kawamori, R. (1999). Effect of metformin on advanced glycation endproduct formation and peripheral nerve function in streptozotocin-induced diabetic rats. Eur J Pharmacol, 376(1-2), 17-22.
Tappy, L., Le, K. A., Tran, C., & Paquot, N. (2010). Fructose and metabolic diseases: new findings, new questions. Nutrition, 26(11-12), 1044-1049.
Wu, C. H., & Yen, G. C. (2005). Inhibitory effect of naturally occurring flavonoids on the formation of advanced glycation endproducts. J Agric Food Chem, 53(8), 3167-3173.
Zhu, Y., Zhao, Y., Wang, P., Ahmedna, M., & Sang, S. (2015). Bioactive ginger constituents alleviate protein glycation by trapping methylglyoxal. Chem Res Toxicol, 28(9), 1842-1849.
Zick, S. M., Djuric, Z., Ruffin, M. T., Litzinger, A. J., Normolle, D. P., Alrawi, S., … Brenner, D. E. (2008). Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects. Cancer Epidemiol Biomarkers Prev, 17(8), 1930-1936.
Keywords
6-shogaol, Advanced glycation end products, Protein glycation, Protein oxidation
Section
Research Articles
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How to Cite
MALAKUL, Wachirawadee; PENGNET, Sirinat.
Inhibitory Effect of 6-shogaol on Fructose-Induced Protein Glycation and Oxidation in Vitro.
Naresuan University Journal: Science and Technology (NUJST), [S.l.], v. 25, n. 2, p. 1-9, apr. 2017.
ISSN 2539-553X.
Available at: <https://www.journal.nu.ac.th/NUJST/article/view/1769>. Date accessed: 24 apr. 2024.