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BMC Complementary Medicine and Therapies
Published in: BMC Complementary Medicine and Therapies 1/2016

Open Access 01-12-2016 | Research article

Cyanidin-3-rutinoside attenuates methylglyoxal-induced protein glycation and DNA damage via carbonyl trapping ability and scavenging reactive oxygen species

Authors: Thavaree Thilavech, Sathaporn Ngamukote, Damien Belobrajdic, Mahinda Abeywardena, Sirichai Adisakwattana

Published in: BMC Complementary Medicine and Therapies | Issue 1/2016

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Abstract

Background

Advanced glycation end-products (AGEs) play a significant role in the development and progression of vascular complication in diabetes. Anthocyanin has been recently reported to possess antiglycating activity. This study aimed to determine whether a naturally occurring anthocyanin, cyanidin-3-rutinoside (C3R) inhibits methylglyoxal (MG) induced protein glycation and oxidative protein and DNA damage.

Methods

C3R (0.125–1 mM) was incubated with bovine serum albumin and MG (1 mM) for 2 weeks. The formation of fluorescent AGEs was measured by using spectrofluorometer and thiol group content were used to detect protein oxidative damage. Gel electrophoresis was used to determine whether C3R (0.125–1 mM) reduced DNA strand breakage in a glycation model comprising lysine, MG and/or Cu2+. The generation of superoxide anions and hydroxyl radicals were detected by the cytochrome c reduction assay and the thiobarbituric acid reactive substances assay. MG-trapping capacity was assessed by high performance liquid chromatography (HPLC).

Results

C3R (0.25–1 mM) reduced the formation of fluorescent AGEs and depleted protein thiol groups in bovine serum albumin mediated by MG. At 1 mM C3R inhibited oxidative DNA damage in the glycation model (p < 0.05) and at 0.5–1 mM prevented Cu2+ induced DNA strand breakage in the presence of lysine and MG. The findings showed that C3R reduced the formation of superoxide anion and hydroxyl radicals during the glycation reaction of MG with lysine. C3R directly trapped MG in a concentration and time dependent manner (both p < 0.001).

Conclusions

These findings suggest that C3R protects against MG-induced protein glycation and oxidative damage to protein and DNA by scavenging free radicals and trapping MG.
Literature
1.
Kalapos MP. Methylglyoxal in living organisms: chemistry, biochemistry, toxicology and biological implications. Toxicol Lett. 1999;110(3):145–75.CrossRefPubMed
2.
Nowotny K, Jung T, Hohn A, Weber D, Grune T. Advanced glycation end products and oxidative stress in type 2 diabetes mellitus. Biomolecules. 2015;5(1):194–222.CrossRefPubMedPubMedCentral
3.
Ogawa S, Nakayama K, Nakayama M, Mori T, Matsushima M, Okamura M, et al. Methylglyoxal is a predictor in type 2 diabetic patients of intima-media thickening and elevation of blood pressure. Hypertension. 2010;56(3):471–6.CrossRefPubMed
4.
Phillips SA, Mirrlees D, Thornalley PJ. Modification of the glyoxalase system in streptozotocin-induced diabetic rats. Effect of the aldose reductase inhibitor Statil. Biochem Pharmacol. 1993;46(5):805–11.CrossRefPubMed
5.
6.
7.
8.
Argirova M, Breipohl W. Comparison between modifications of lens proteins resulted from glycation with methylglyoxal, glyoxal, ascorbic acid, and fructose. J Biochem Mol Toxic. 2002;16(3):140–5.CrossRef
9.
Kang JH. Oxidative damage of DNA induced by methylglyoxal in vitro. Toxicol Lett. 2003;145(2):181–7.CrossRefPubMed
10.
Suji G, Sivakami S. DNA damage during glycation of lysine by methylglyoxal: assessment of vitamins in preventing damage. Amino Acids. 2007;33(4):615–21.CrossRefPubMed
11.
Cooke MS, Evans MD, Dizdaroglu M, Lunec J. Oxidative DNA damage: mechanisms, mutation, and disease. FASEB J. 2003;17(10):1195–214.CrossRefPubMed
12.
Malik Q, Herbert KE. Oxidative and non-oxidative DNA damage and cardiovascular disease. Free Radic Res. 2012;46(4):554–64.CrossRefPubMed
13.
14.
Rahbar S, Figarola JL. Novel inhibitors of advanced glycation endproducts. Arch Biochem Biophys. 2003;419(1):63–79.CrossRefPubMed
15.
Bolton WK, Cattran DC, Williams ME, Adler SG, Appel GB, Cartwright K, et al. Randomized trial of an inhibitor of formation of advanced glycation end products in diabetic nephropathy. Am J Nephrol. 2004;24(1):32–40.CrossRefPubMed
16.
Freedman BI, Wuerth JP, Cartwright K, Bain RP, Dippe S, Hershon K, et al. Design and baseline characteristics for the aminoguanidine clinical trial in overt type 2 diabetic nephropathy (ACTION II). Control Clin Trials. 1999;20(5):493–510.CrossRefPubMed
17.
Xue M, Rabbani N, Momiji H, Imbasi P, Anwar MM, Kitteringham N, et al. Transcriptional control of glyoxalase 1 by Nrf2 provides a stress-responsive defence against dicarbonyl glycation. Biochem J. 2012;443(1):213–22.CrossRefPubMed
18.
Nagaraj RH, Sarkar P, Mally A, Biemel KM, Lederer MO, Padayatti PS. Effect of pyridoxamine on chemical modification of proteins by carbonyls in diabetic rats: characterization of a major product from the reaction of pyridoxamine and methylglyoxal. Arch Biochem Biophys. 2002;402(1):110–9.CrossRefPubMed
19.
Zhu W, Jia Q, Wang Y, Zhang Y, Xia M. The anthocyanin cyanidin-3-O-beta-glucoside, a flavonoid, increases hepatic glutathione synthesis and protects hepatocytes against reactive oxygen species during hyperglycemia: Involvement of a cAMP-PKA-dependent signaling pathway. Free Radic Biol Med. 2012;52(2):314–27.CrossRefPubMed
20.
Takikawa M, Inoue S, Horio F, Tsuda T. Dietary anthocyanin-rich bilberry extract ameliorates hyperglycemia and insulin sensitivity via activation of AMP-activated protein kinase in diabetic mice. J Nutr. 2010;140(3):527–33.CrossRefPubMed
21.
Bagchi D, Sen CK, Bagchi M, Atalay M. Anti-angiogenic, antioxidant, and anti-carcinogenic properties of a novel anthocyanin-rich berry extract formula. Biochem Mosc. 2004;9(1):75–80.CrossRef
22.
He J, Giusti MM. Anthocyanins: natural colorants with health-promoting properties. Annu Rev Food Sci Technol. 2010;1:163–87.CrossRefPubMed
23.
24.
Adisakwattana S, Yibchok-Anun S, Charoenlertkul P, Wongsasiripat N. Cyanidin-3-rutinoside alleviates postprandial hyperglycemia and its synergism with acarbose by inhibition of intestinal alpha-glucosidase. J Clin Biochem Nutr. 2011;49(1):36–41.CrossRefPubMedPubMedCentral
25.
Akkarachiyasit S, Yibchok-Anun S, Wacharasindhu S, Adisakwattana S. In vitro inhibitory effects of cyandin-3-rutinoside on pancreatic alpha-amylase and its combined effect with acarbose. Molecules. 2011;16(3):2075–83.CrossRefPubMed
26.
Matsui T, Ebuchi S, Kobayashi M, Fukui K, Sugita K, Terahara N, et al. Anti-hyperglycemic effect of diacylated anthocyanin derived from Ipomoea batatas cultivar Ayamurasaki can be achieved through the alpha-glucosidase inhibitory action. J Agric Food Chem. 2002;50(25):7244–8.CrossRefPubMed
27.
Thilavech T, Ngamukote S, Abeywardena M, Adisakwattana S. Protective effects of cyanidin-3-rutinoside against monosaccharides-induced protein glycation and oxidation. Int J Biol Macromol. 2015;75:515–20.CrossRefPubMed
28.
Elhabiri M, Figueiredo P, Fougerousse A, Brouillard R. A convenient method for conversion of flavonols into anthocyanins. Tetrahedron Lett. 1995;36(26):4611–4.CrossRef
29.
Meeprom A, Sompong W, Chan CB, Adisakwattana S. Isoferulic Acid, a new anti-glycation agent, inhibits fructose- and glucose-mediated protein glycation in vitro. Molecules. 2013;18(6):6439–54.CrossRefPubMed
30.
31.
Chan WH, Wu HJ. Protective effects of curcumin on methylglyoxal-induced oxidative DNA damage and cell injury in human mononuclear cells. Acta Pharmacol Sin. 2006;27(9):1192–8.CrossRefPubMed
32.
Peng X, Zheng Z, Cheng K-W, Shan F, Ren G-X, Chen F, et al. Inhibitory effect of mung bean extract and its constituents vitexin and isovitexin on the formation of advanced glycation endproducts. Food Chem. 2008;106(2):475–81.CrossRef
33.
Goldin A, Beckman JA, Schmidt AM, Creager MA. Advanced glycation end products: sparking the development of diabetic vascular injury. Circulation. 2006;114(6):597–605.CrossRefPubMed
34.
Jakus V, Rietbrock N. Advanced glycation end-products and the progress of diabetic vascular complications. Physiol Res. 2004;53(2):131–42.PubMed
35.
Yamagishi S, Nakamura K, Imaizumi T. Advanced glycation end products (AGEs) and diabetic vascular complications. Curr Diabetes Rev. 2005;1(1):93–106.CrossRefPubMed
36.
Wu CH, Huang SM, Lin JA, Yen GC. Inhibition of advanced glycation endproduct formation by foodstuffs. Food Funct. 2011;2(5):224–34.CrossRefPubMed
37.
Wang W, Yagiz Y, Buran TJ, Nunes CN, Gu L. Phytochemicals from berries and grapes inhibited the formation of advanced glycation end‐products by scavenging reactive carbonyls. Food Res Int. 2011;44(9):2666–73.CrossRef
38.
Hassimotto NM, Genovese MI, Lajolo FM. Absorption and metabolism of cyanidin-3-glucoside and cyanidin-3-rutinoside extracted from wild mulberry (Morus nigra L.) in rats. Nutr Res. 2008;28(3):198–207.CrossRefPubMed
39.
Jakobek L, Šeruga M, Medvidović-Kosanović M, Jovanović IN. Anthocyanin content and antioxidant activity of various red fruit juices. Dtsch Lebensmitt Rundsch. 2007;103(2):58–64.
40.
Ali A, Sharma R. Acomparative study on the role of lysine and BSA in glycation-induced damage to DNA. Biosci Bioeng Commun. 2015;1:38–43.
41.
Yim HS, Kang SO, Hah YC, Chock PB, Yim MB. Free radicals generated during the glycation reaction of amino acids by methylglyoxal. A model study of protein-cross-linked free radicals. J Biol Chem. 1995;270(47):28228–33.CrossRefPubMed
42.
Wu CH, Yen GC. Inhibitory effect of naturally occurring flavonoids on the formation of advanced glycation endproducts. J Agric Food Chem. 2005;53(8):3167–73.CrossRefPubMed
43.
Meeprom A, Sompong W, Suantawee T, Thilavech T, Chan CB, Adisakwattana S. Isoferulic acid prevents methylglyoxal-induced protein glycation and DNA damage by free radical scavenging activity. BMC Complement Altern Med. 2015;15(1):34.CrossRef
44.
Li W, Liang H, Zhang MW, Zhang RF, Deng YY, Wei ZC, et al. Phenolic profiles and antioxidant activity of litchi (Litchi Chinensis Sonn.) fruit pericarp from different commercially available cultivars. Molecules. 2012;17(12):14954–67.CrossRefPubMed
45.
Beaulieu LP, Harris CS, Saleem A, Cuerrier A, Haddad PS, Martineau LC, et al. Inhibitory effect of the Cree traditional medicine wiishichimanaanh (Vaccinium vitis-idaea) on advanced glycation endproduct formation: identification of active principles. Phytother Res. 2010;24(5):741–7.PubMed
46.
Jung H, Kwak H-K, Hwang K. Antioxidant and antiinflammatory activities of cyanidin-3-glucoside and cyanidin-3-rutinoside in hydrogen peroxide and lipopolysaccharide-treated RAW264.7 cells. Food Sci Biotechnol. 2014;23(6):2053–62.CrossRef
47.
Matsufuji H, Ochi H, Shibamoto T. Formation and inhibition of genotoxic malonaldehyde from DNA oxidation controlled with EDTA. Food Chem Toxicol. 2006;44(2):236–41.CrossRefPubMed
48.
Chen X-Y, Huang IM, Hwang LS, Ho C-T, Li S, Lo C-Y. Anthocyanins in blackcurrant effectively prevent the formation of advanced glycation end products by trapping methylglyoxal. J Funct Foods. 2014;8:259–68.CrossRef
49.
Lv L, Shao X, Wang L, Huang D, Ho CT, Sang S. Stilbene glucoside from Polygonum multiflorum thunb.: A novel natural inhibitor of advanced glycation end product formation by trapping of methylglyoxal. J Agric Food Chem. 2010;58(4):2239–45.CrossRefPubMed
50.
Hu TY, Liu CL, Chyau CC, Hu ML. Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells. J Agric Food Chem. 2012;60(33):8190–6.CrossRefPubMed
51.
Li X, Zheng T, Sang S, Lv L. Quercetin inhibits advanced glycation end product formation by trapping methylglyoxal and glyoxal. J Agric Food Chem. 2014;62(50):12152–8.CrossRefPubMed
52.
Peng X, Cheng KW, Ma J, Chen B, Ho CT, Lo C, et al. Cinnamon bark proanthocyanidins as reactive carbonyl scavengers to prevent the formation of advanced glycation endproducts. J Agric Food Chem. 2008;56(6):1907–11.CrossRefPubMed
53.
Sang S, Shao X, Bai N, Lo CY, Yang CS, Ho CT. Tea polyphenol (−)-epigallocatechin-3-gallate: a new trapping agent of reactive dicarbonyl species. Chem Res Toxicol. 2007;20(12):1862–70.CrossRefPubMed
Metadata
Title
Cyanidin-3-rutinoside attenuates methylglyoxal-induced protein glycation and DNA damage via carbonyl trapping ability and scavenging reactive oxygen species
Authors
Thavaree Thilavech
Sathaporn Ngamukote
Damien Belobrajdic
Mahinda Abeywardena
Sirichai Adisakwattana
Publication date
01-12-2016
Publisher
BioMed Central
Published in
BMC Complementary Medicine and Therapies / Issue 1/2016
Electronic ISSN: 2662-7671
DOI
https://doi.org/10.1186/s12906-016-1133-x

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