Browse > Article

Isolation of Compounds with Antioxidative Activity from Quickly Fermented Soy-Based Foods  

Jang, Mi-Young (Department of Food Science and Technology and Functional Food Research Center, Chonnam National University)
Cho, Jeong-Yong (Department of Food Science and Technology and Functional Food Research Center, Chonnam National University)
Cho, Jeong-Il (Division of Food Science, Chosun College of Science and Technology)
Moon, Jae-Hak (Department of Food Science and Technology and Functional Food Research Center, Chonnam National University)
Park, Keun-Hyung (Department of Food Science and Technology and Functional Food Research Center, Chonnam National University)
Publication Information
Food Science and Biotechnology / v.15, no.2, 2006 , pp. 214-219 More about this Journal
Abstract
A bacterial strain, initially identified as B1-3, was isolated from cheonggukjang, a traditional Korean dish made from fermented soybeans. Using the Biolog system and 16S rRNA sequence analysis, we identified B1-3 as Bacillus mojavensis. We manufactured a quickly fermented soybean (QFS) food product using the B. mojavensis, and guided by their 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging ability. We isolated substances with antioxidative activity from it. Using mass spectrometry (MS) and nuclear magnetic resonance (NMR) techniques, we isolated 4 compounds from the ethyl acetate (EtOAc)-soluble neutral fraction of methyl alcohol (MeOH) extracts of the QFS food product (genistein, daidzein, 3R,4R-3-methyl-3,4-dihydroxy-2-pentanone, and 3S,4R-3-methyl-3,4-dihydroxy-2-pentanone) and 3 compounds from its acidic fraction (4-hydroxyphenylacetic acid, genistin, and daidzein). Two compounds from the neutral fraction (3R,4R-3-methyl-3,4-dihydroxy-2-pentanone and 3S,4R-3-methyl-3,4-dihydroxy-2-pentanone) were not detected in nonfermented soybeans (NFS) or in the filtrate of the LB broth used to culture B. mojavensis. However, they were detected in the filtrate of the same broth when it contained 2% glucose. These results suggest that these 2 compounds were derived from glucose (or other saccharides) in the soybean during fermentation. One compound that was found in the acidic fraction (4-hydroxyphenylacetic acid) was readily detected in NFS, but not in the culture broth. This suggests that 4-hydroxyphenylacetic acid was derived from NFS. We concluded that the antioxidative activity of cheonggukjang is a result of the interactions between soybean components and the microorganisms used in the fermentation of cheonggukjang.
Keywords
cheonggukjang; quickly fermented soybean; antioxidative activity; Bacillus mojavensis;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 8  (Related Records In Web of Science)
연도 인용수 순위
1 Esaki H, Onozaki H, Morimitsu Y. Potent Antioxidative isoflavones isolated from soybean fermented with Aspergillus saitoi. Biosci. Biotechnol. Biochem. 62: 740-746 (1998)   DOI   ScienceOn
2 Kim WK, Choi KH, Kim YT, Park HR, Choi JY, Lee YS, Oh HI, Kwon IB, Lee SY. Purification and characterization of a fibrinolytic enzyme produced from Bacillus sp. strain CK 11-4 screened from chungkookjang. Appl. Environ. Microbiol. 62: 2482-2488 (1996)
3 Agrawal PK. Carbon-13 NMR of flavonoids. Elsevier Science: New York 39: 207-212 (1989)
4 Esaki H, Onozaki H, Kawakishi S, Osawa T. New antioxidant isolated from tempeh. J. Agric. Food Chem. 44: 696-700 (1996)   DOI   ScienceOn
5 Desjardins RE, Canfield CJ, Haynes JD, Chulay JD. Quantitative assessment of anti-malarial activity in vitro by a semiautomated microdilution technique. AntimicroB Agents Ch. 16: 710-718 (1979)   DOI   ScienceOn
6 Nam HY, Min SG, Shin HC, Kim HY, Fukushima M, Han KH, Park WJ, Choi KD, Lee CH. The protective effects of isoflavone extracted from soybean paste in free radical initiator treated rats. Food Sci. Biotechnol. 14: 586-592 (2005)
7 Yoo SM, Chang CM. Study on the processing adaptability of soybean cultivars for Korean traditional Chonggugjang preparation. J. Korean Agric. Chem. Soc. 42: 91-98 (1999)
8 Choi YS, Lee BH, Kim JH, Kim NS. Concentration of phytoestrogens in soybeans and soybean products in Korea. J. Sci. Food Agric. 80: 1709-1712 (2000)   DOI   ScienceOn
9 Shon MY, Seo KI, Park SK, Cho YS, Sung NJ. Some biological activities and isoflavone content of Chungkookjang prepared with black beans and Bacillus Strains. J. Korean Soc. Food Sci. Nutr. 30: 662-667 (2001)   과학기술학회마을
10 Ausubel FM, Brent R, Kingston RE, Moore DD, Seidman JG, Smith JA, Struhl K. Current protocols in molecular biology. John Wiley and Sons. New York, NY, USA (1989)
11 Young JPW, Downer HL, Eardly BD. Phylogeny of the phototropic Rhizobium strain BTAiI by polymerase chain reaction-based sequencing of 16S rRNA Gene segment. J. Bacteriol. 7: 2271-2277 (1991)
12 Esaki H, Kawakishi S, Morimitsu Y, Osawa T. New potent antioxidative o-dihydroxyisoflavones in fermented Japanese soybean products. Biosci. Biotechnol. Biochem. 63: 1637-1639 (1999)   DOI   ScienceOn
13 Takao T, Kitatani F, Watanabe N, Yagi A, Sakata K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotechnol. Biochem. 58: 1780-1783 (1994)   DOI
14 Matsuom M. In vivo antioxidant activity of Okara Koji, a fermented Okara, by Aspergillus oryzae. Biosci. Biote. Biochem. 61: 1968-1972 (1997)   DOI   ScienceOn
15 Esaki H, Watanabe R, Onozaki H, Kawakishi S, Osawa T. Formation mechanism for potent antioxidative o-dihydroxyisoflavone in soybean fermented with Aspergillus saitoi. Biosci. Biote. Biochem. 63: 851-858 (1999)   DOI   ScienceOn
16 Coward L, Barnes NC, Setchell KDR, Barnes S. Genistein, daidzein, and their $\beta-glycoside$ conjugates: antitumor isoflavones in soybean foods from American and Asian diets. J. Agric. Food Chem. 41: 1961-1967 (1993)   DOI   ScienceOn
17 Wang HJ, Murphy PA. Isoflavone content in commercial soybean food. J. Agric. Food Chem. 42: 1666-1673 (1994)   DOI   ScienceOn
18 Kim SH, Yang JL, Song YS. Physiological functional of Chongkukjang. Food Ind. Nut. 4: 40-46 (1999)
19 Iwai K, Nakaya N, Kawasaki Y, Matsue H. Inhibitory effect of natto, a kind of fermented soybeans, on LDL oxidation in vitro. J. Agric. Food Chem. 50: 3592-3596 (2002)   DOI   ScienceOn
20 Heo S, Lee SK, Joo HK. Isolation and identification of fibrinolytic bacteria from Korean traditional chungkookjang. J. Korean Agric. Chem. Soc. 41: 119-124 (1998)   과학기술학회마을
21 Fukutake M, Takahashi M, Ishida K, Kawamura H, Sugimura T, Wakabayashi K. Quantification of genistein and genistin in soybeans and soybean products. Food Chem. Toxicol. 34: 457-461 (1996)   DOI   ScienceOn
22 Whalley JL, Bond Tl, Botting NP. Synthesis of $^{13}C$ labeled daidzein and formononetin. Bioorg. Med. Chem. Lett. 8: 2569-2572 (1998)   DOI   ScienceOn
23 Wang H, Nair MG, Strasburg GM, Booren AM, Bray n. Antioxidant polyphenols from tart cherrier (Prunus cerasus). J. Agric. Food Chem. 47: 840-844 (1999)   DOI   ScienceOn
24 Ui S, Hosaka T, Watanabe K, Mimura A. Discovery of a new mechanism of 2,3-butanediol stereoisomer formation in Bacillus cereus YUF-4. J. Ferment. Bioeng. 85: 79-83 (1998)   DOI   ScienceOn
25 Kwon TW, Park JM, Lee YS, Ryu BH. Antioxidative activity on human low density lipoprotein oxidation by Bacillus Sp. BH-96 isolated from fermented anchovy. Food Sci. Biotechnol. 7: 148-153 (1998)
26 Esaki H, Onozaki H, Kawakishi S, Osawa T. Antioxidant activity and isolation from soybean fermented with Aspergillus spp. J. Agric. Food Chem. 45: 2020-2024 (1997)   DOI   ScienceOn
27 Yang JL, Lee SH, Song YS. Improving effect of powers of cooked soybean and Chongkukjang on blood pressure and lipid metabolism in spontaneously hypertensive rats. J. Korean Soc. Food Sci. Nutr. 32: 899-905 (2003)   과학기술학회마을   DOI
28 Park KY, Jung KO, Rhee SH, Choi YH. Antimutagenic effects of deenjang (Korean fermented soypaste) and its active compounds. Mutat. Res. 523: 43-53 (2003)
29 Iwai K, Nakaya N, Kawasaki Y, Matsue H. Antioxidative function of natto, a kind of fermented soybeans: Effect on LDL-oxidation and lipid metabolism in cholesterol-fed rats. J. Agric. Food Chem. 50: 3597-3601 (2002)   DOI   ScienceOn
30 Sambrook J, Fritsch EF, Manistis T. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor, Cold Spring Harbor Laboratory Press, NY, USA (1989)
31 Murakami H, Asakawa T, Terao J, Matsushita S. Antioxidative stability of tempeh and liberation of isoflavones by fermentation. Agric. BioI. Chem. 48: 2971-2975 (1984)   DOI
32 Kim Y, Cho JY, Kuk JH, Moon JH, Cho n, Kim YC, Park KH. Identification and antimicrobial activity of phenylacetic acid produced by Bacillus licheniformis isolated from fermented soybean, Chungkookjang. Curr. Microbiol. 48: 312-317 (2004)   DOI
33 Park MY, Lee HJ, Choi DH. Extractives from the Bark of Sophora japonica L. Mokchae Konghak 30: 42-47 (2002)