The identification of antioxidants in dark soy sauce

Soy sauce is a traditional fermented seasoning in Asian countries, that has high antioxidant activity in vitro and some antioxidant activity in vivo. We attempted to identify the major antioxidants present, using the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assay as a guide. 3-Hydroxy-2-methyl-4H-pyran-4-one (maltol) was one of several active compounds found in an ethyl acetate extract of dark soy sauce (DSS) and was present at millimolar concentrations in DSS. However, most of the antioxidant activity was present in colored fractions, two of which (CP1 and CP2) were obtained by gel filtration chromatography. Their structural characteristics based on nuclear magnetic resonance (NMR) and electrospray-ionization time-of-flight mass spectrometry (ESI-TOF-MS) analysis suggest that carbohydrate-containing pigments such as melanoidins are the major contributors to the high antioxidant capacity of DSS.

[1]  H. Greenfield,et al.  Isoflavones and Coumestrol in Soybeans and Soybean Products from Australia and Indonesia , 2001 .

[2]  H. Baek,et al.  Solid Phase Microextraction-Gas Chromatography-Olfactometry of Soy Sauce Based on Sample Dilution Analysis , 2004 .

[3]  B. Halliwell,et al.  Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. , 2005, Free radical biology & medicine.

[4]  T. Osawa,et al.  New potent antioxidative o-dihydroxyisoflavones in fermented Japanese soybean products. , 1999, Bioscience, biotechnology, and biochemistry.

[5]  C. Delgado-Andrade,et al.  Unraveling the contribution of melanoidins to the antioxidant activity of coffee brews. , 2005, Journal of agricultural and food chemistry.

[6]  S. Astley,et al.  Evidence that dietary supplementation with carotenoids and carotenoid-rich foods modulates the DNA damage:repair balance in human lymphocytes , 2004, British Journal of Nutrition.

[7]  M. González-Sanjosé,et al.  Inhibition of induced DNA oxidative damage by beers: correlation with the content of polyphenols and melanoidins. , 2005, Journal of agricultural and food chemistry.

[8]  Andrew Jenner,et al.  Characterization of antioxidant and antiglycation properties and isolation of active ingredients from traditional chinese medicines. , 2004, Free radical biology & medicine.

[9]  S. Kropf,et al.  Flavanol-rich cocoa drink lowers plasma F(2)-isoprostane concentrations in humans. , 2004, Free radical biology & medicine.

[10]  H. H. Rennhard The metabolism of ethyl maltol and maltol in the dog. , 1971, Journal of agricultural and food chemistry.

[11]  B. Halliwell,et al.  Cautions in the use of biomarkers of oxidative damage; the vascular and antioxidant effects of dark soy sauce in humans. , 2006, Biochemical and biophysical research communications.

[12]  C. Chou,et al.  Biochemical changes in soy sauce prepared with extruded and traditional raw materials , 1998 .

[13]  G. Vernin,et al.  Melanoidins in the Maillard reaction , 1998 .

[14]  B. Caemmerer,et al.  Intact carbohydrate structures as part of the melanoidin skeleton. , 2002, Journal of agricultural and food chemistry.

[15]  R. Hider,et al.  ABSORPTION OF LOW AND THERAPEUTIC DOSES OF FERRIC MALTOL, A NOVEL FERRIC IRON COMPOUND, IN IRON DEFICIENT SUBJECTS USING A SINGLE DOSE IRON ABSORPTION TEST , 1991, Journal of clinical pharmacy and therapeutics.

[16]  S. Taniuchi,et al.  Degradation of wheat allergen in Japanese soy sauce. , 2004, International journal of molecular medicine.

[17]  H. Motai,et al.  Oxidative Browning in Color of Shoyu , 1974 .

[18]  岡田崇,et al.  小麦タンパク(グルテン)を配合した醤油の褐変抑制と抗酸化活性 , 2004 .

[19]  S. Lertsiri,et al.  Comparison of determination method for volatile compounds in Thai soy sauce , 2003 .

[20]  H. Choi Antioxidative characteristics of melanoidin related products fractionated from fermented soybean sauce , 1993 .

[21]  Makio Kobayashi,et al.  Relationship between peroxyl radical scavenging capability measured by the chemiluminescence method and an aminocarbonyl reaction product in soy sauce. , 2003, International journal of molecular medicine.

[22]  Yun-Bae Kim,et al.  Neuroprotective Effect of Maltol Against Oxidative Stress in Brain of Mice Challenged with Kainic Acid , 2004, Nutritional neuroscience.

[23]  Joseph Rafter,et al.  Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: direct or indirect effects? Antioxidant or not? , 2005, The American journal of clinical nutrition.

[24]  F. Lajolo,et al.  Isoflavones in soy-based foods consumed in Brazil: levels, distribution, and estimated intake. , 2002, Journal of agricultural and food chemistry.

[25]  B. Halliwell,et al.  The antioxidant activities of seasonings used in Asian cooking. Powerful antioxidant activity of dark soy sauce revealed using the ABTS assay , 2000, Free radical research.

[26]  B. Halliwell,et al.  Free radicals in biology and medicine , 1985 .

[27]  H. Neil,et al.  The relation between dietary flavonol intake and coronary heart disease mortality: a meta-analysis of prospective cohort studies , 2003, European Journal of Clinical Nutrition.

[28]  A. Hofmann,et al.  The effect of a model melanoidin mixture on faecal bacterial populations in vitro , 1999, British Journal of Nutrition.

[29]  T. Hofmann,et al.  Structural and functional characterization of pronyl-lysine, a novel protein modification in bread crust melanoidins showing in vitro antioxidative and phase I/II enzyme modulating activity. , 2002, Journal of agricultural and food chemistry.

[30]  G. Hardy,et al.  Nutraceuticals - a pharmaceutical viewpoint: part II , 2003, Current opinion in clinical nutrition and metabolic care.

[31]  B. Halliwell,et al.  The gastrointestinal tract: A major site of antioxidant action? , 2000, Free radical research.

[32]  M. Boekel,et al.  Melanoidins extinction coefficient in the glucose/glycine Maillard reaction , 2003 .

[33]  M. Pariza,et al.  Inhibition of benzo[a]pyrene-induced mouse forestomach neoplasia and reduction of H2O2 concentration in human polymorphonuclear leucocytes by flavour components of Japanese-style fermented soy sauce. , 1997, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[34]  弘長 橋場 醤油の褐変物質(メラノイジン)について , 1973 .

[35]  D. Leblanc,et al.  Maltol and ethyl maltol: from the larch tree to successful food additive. Synthesis of a natural compound led to improved flavor- and aroma-enhancing capabilities , 1989 .

[36]  A. Apriyantono,et al.  Flavor Characteristics of Indonesian Soy Sauce (Kecap Manis) , 1999 .

[37]  Xu-xu Cai Protection of Human Neuroblastoma Cells Against Oxidative Damage by Maltol , 2003 .

[38]  Hasegawa,et al.  Tumor cell growth-inhibiting effect of melanoidins extracted from miso and soy sauce , 1997, Cancer biotherapy & radiopharmaceuticals.

[39]  A. Arnoldi,et al.  Investigations on the high molecular weight foaming fractions of espresso coffee. , 2004, Journal of agricultural and food chemistry.

[40]  Caimin Xu,et al.  Maltol inhibits apoptosis of human neuroblastoma cells induced by hydrogen peroxide. , 2006, Journal of biochemistry and molecular biology.

[41]  V. Fogliano,et al.  Thermal degradation studies of food melanoidins. , 2005, Journal of agricultural and food chemistry.

[42]  F. Hayase,et al.  Protective Effects of Melanoidins Derived from Soy Sauce and Soy Paste on NO-Induced DNA Damage , 2002 .

[43]  C. Rice-Evans,et al.  Antioxidant activity applying an improved ABTS radical cation decolorization assay. , 1999, Free radical biology & medicine.