• Bulletin of the Korean Chemical Society
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• v.19 no.1
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• pp.74-78
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• 1998

Synthesis of novel 9-fluoroanthracyclines carrying L-fucose as a sugar component is described. Compound 3 containing a fluorine at the C-9 position was synthesized from an epoxide 2 and HF/Pyr (7 : 3). Bromination and hydrolysis of compound 3 resulted in synthesis of an aglycone, 9-fluoroanthracyclinone 6. The α-(1b) and β -anomers (1a) of the final product were obtained in high yields by a coupling reaction with the L-fucose.

• Proceedings of the Korean Society of Crop Science Conference
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• 2018.10a
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• pp.290-290
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• 2018

• Archives of Pharmacal Research
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• v.20 no.5
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• pp.454-458
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• 1997

Two human liver UDP-glucuronosyltransferase cDNA clones, HLUG25 and UDPGTh2 were previously shown to encode isozymes active in the glucuronidation of hyodeoxycholic acid (HDCA) and certain estrogen derivatives (e.g., estriol and 3,4-catechol estrogens), respectively. in this study we have found that the UDPGTh2-encoded isoform (UDPGTh2) and HLUG25-encoded isoform (UDPGThl) have parallel aglycone specificities. When expressed in COS 1 cells, each isoform metabolized three types of dihydroxy- or trihydroxy-substituted ring structures, including the 3,4-catechol estrogen (4-hydroxyestrone), estriol, 17-epiestriol, and HDCA, but the UDPGTh2 isozyme was 100-fold more efficient than UDPGTh1. UDPGTh1 and UDPGTh2 were 86% identical overall (76 differences out of 528 amino acids), including 55 differences in the first 300 amino acids of the amino terminus, a domain which conferred the substrate specificity. The data indicated that a high level of conservation in the amino terminus was not required for the preservation of substrate selectivity. Analysis of glucuronidation activity encoded by UDPGTh1/UDPGTh2 chimeric cDNA constructed at their common restriction sites, Sac I (codon 297), Nco I (codon 385), and Hha I (codon 469), showed that nine amino acids between residues 385 and 469 were important for catalytic efficiency, suggesting that this region represented a domain which was critical for the catalysis but distinct from that responsible for aglycone-selection. These data indicate that UDPGTh2 is a primary isoform responsible for the detoxification of the bile salt intermediate as well as the active estrogen intermediates.

• Journal of the Korean Society of Food Culture
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• v.30 no.2
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• pp.197-205
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• 2015

This study was conducted to investigate the bioconversion of ginsenosides as well as anti-inflammatory activities of fresh ginseng Kkakdugi during fermentation. Fresh ginseng Kkakdugi reached proper ripeness, pH 4.30, and acidity 1.69% at $15^{\circ}C$ after 10 days. Lactic acid bacteria grew until reaching $1.10{\times}10^9CFU/mL$ after 20 days of fermentation, and ${\beta}$-glucosidase activity increased from 1.154 to 1.885 units/g. The bioconversion of ginsenosides was confirmed based on increased content of Rg3, an aglycone, from 0.13 to 0.17 mg/g during fermentation through HPLC. Fresh ginseng Kkakdugi did not display cytotoxicity up to the concentrations of $80{\mu}g/mL$, regardless of ripening period. Nitrite production and expression of inflammation-related proteins, iNOS and COX-2, decreased in a dose-dependent manner regardless of ripening period. From these results, fresh ginseng Kkakdugi showed the bioconversion of ginsenosides to aglycone during the lactic acid fermentation as well as an anti-inflammatory effect through the reduction of NO production and iNOS and COX-2 expression.

• The Korean Journal of Food And Nutrition
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• v.23 no.4
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• pp.556-561
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• 2010

Tomato fruits(Lycoperisicon esculentum) synthesize the glycoalkaloids dehydrotomatine and ${\alpha}$-tomatine, possibly as defense against bacteria, fungi and insects. We developed a new effective method to prepare and purify dehydrotomatine and ${\alpha}$-tomatine that exists in tomato fruits using alumina column chromatography and high performance liquid chromatography (HPLC). The tomato glycoalkaloids(TGA) in tomato was extracted with 2% acetic acid, and then precipitated with ammonium hydroxide(pH=10.5). The dry precipitate substance was applied on alumina column, and then fractionated with water saturated n-butylalcohol. The TGA(Fr. No. 26~36) were collected and dried under reduced pressure. The TGA was performed on a reverse phase HPLC(Inertsil ODS-2, $5\;{\mu}m$), eluted with acetonitrile/20mM $KH_2PO_4$(24:76, v/v) at 208 nm. Two peaks were detected on HPLC, and individual peak was collected by repeating HPLC. Furthermore, to confirm the identity dehydrotomatine and ${\alpha}$-tomatine, each peak isolated was hydrolyzed with 1N HCl into sugar and aglycone tomatidine. The sugars were converted to trimethylsilyl ester derivatives. The nature and molar ratios of sugars were identified by gas-liquid chromatography(GLC) and the aglycone by high-performance liquid chromatography(HPLC). The first peak (Rt=17.5 min) eluted from HPLC was identified as dehydrotomatine, and second peak(Rt=21.0 min) was as ${\alpha}$-tomatine. This technique has been used effectively to prepare and isolate dehydrotomatine and ${\alpha}$-tomatine from tomato fruits.

• Journal of Applied Biological Chemistry
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• v.52 no.4
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• pp.163-169
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• 2009

A total of 155 microbial strains were isolated from the Korean traditional soybean paste based on their morphological features on the growth of agar plate. Among the isolated strains, a total of 28 strains were capable of hydrolyzing isoflavone glycoside to isoflavone aglycone efficiently in the soybean paste. Finally, two strains, K123-1 and SI, were selected because of their resistance to 15% NaCl and ability to convert isoflavone glycoside to isoflavone aglycone efficiently during the fermentation of soybean paste. The isolated strains K123-1 and SI were identified to be Pichia guilliermondii and Candida fermentati, respectively, using the partial 26S rDNA sequence analysis and phylogenic analysis. Pichia guilliermondii K123-1 and Candida fermentati SI converted daidzin to daidzein up to 96% and 95%, respectively, and genistin to genistein up to 92% when soybean pastes were fermented at $30^{\circ}C$ for 20 days with a single isolated strain. Pichia guilliermondii K123-1 and Candida fermentati SI were able to grow in the presence of 15% NaCl on both liquid medium and agar plate. We think that Pichia guilliermondii K123-1 and Candida fermentati SI might be one of good candidates for making functional soybean paste because they are isolated from the Korean traditional soybean paste and have a good ability to convert isoflavone glycosides to isoflavone aglycones and a high salt tolerance.

• Nutrition Research and Practice
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• v.9 no.6
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• pp.569-578
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• 2015

BACKGROUND/OBJECTIVES: Fermentation can increase functional compounds in fermented soybean products, thereby improving antioxidant and/or anti-inflammatory activities. We investigated the changes in the contents of phenolics and isoflavones, antioxidant activity and anti-inflammatory activity of Doenjang during fermentation and aging. MATERIALS/METHODS: Doenjang was made by inoculating Aspergillus oryzae and Bacillus licheniformis in soybeans, fermenting and aging for 1, 3, 6, 8, and 12 months (D1, D3, D6, D8, and D12). Doenjang was extracted using ethanol, and sequentially fractioned by hexane, dichloromethane (DM), ethylacetate (EA), n-butanol, and water. The contents of total phenolics, flavonoids and isoflavones, 2,2-diphenyl-1 picryl hydrazyl (DPPH) radical scavenging activity, and ferric reducing antioxidant power (FRAP) were measured. Anti-inflammatory effects in terms of nitric oxide (NO), prostaglandin (PG) E2 and pro-inflammatory cytokine production and inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 expressions were also measured using LPS-treated RAW 264.7 macrophages. RESULTS: Total phenolic and flavonoid contents showed a gradual increase during fermentation and 6 months of aging and were sustained thereafter. DPPH radical scavenging activity and FRAP were increased by fermentation. FRAP was further increased by aging, but DPPH radical scavenging activity was not. Total isoflavone and glycoside contents decreased during fermentation and the aging process, while aglycone content and its proportion increased up to 3 or 6 months of aging and then showed a slow decrease. DM and EA fractions of Doenjang showed much higher total phenolic and flavonoid contents, and DPPH radical scavenging activity than the others. At $100{\mu}g/mL$, DM and EA fractions of D12 showed strongly suppressed NO production to 55.6% and 52.5% of control, respectively, and PGE2 production to 25.0% and 28.3% of control with inhibition of iNOS or COX-2 protein expression in macrophages. CONCLUSIONS: Twelve month-aged Doenjang has potent antioxidant and anti-inflammatory activities with high levels of phenolics and isoflavone aglycones, and can be used as a beneficial food for human health.

• Korean Journal of Food Science and Technology
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• v.45 no.6
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• pp.675-681
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• 2013

We assessed the quality of a bamboo shoot vinegar produced in Damyang-gun in terms of parameters that included acidity, mineral contents, amino acids, and flavonol aglycones. The flavor compounds of the bamboo shoot vinegar were also analyzed using the stir bar sorptive extraction (SBSE) method. The acidity of the bamboo shoot vinegar was 4.49%, which was the lowest value among the commercial vinegars studied. The bamboo shoot vinegar had a lower concentration of Na (8.36 mg/100 g) than the other commercial vinegars. There was a relatively large amount of tyrosine and lysine in the bamboo shoot vinegar. The concentration of quercetin, a flavonol aglycone, was 3.29 mg/100 g. The results of the flavor analysis showed that hexanal, 2-furancarboxaldehyde, and benzaldehyde were high in the bamboo shoot vinegar. Oleamide, a compound that is known to induce sleep, was first found in bamboo shoot vinegar using the SBSE method.

• Journal of the Korean Society of Food Science and Nutrition
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• v.35 no.3
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• pp.359-365
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• 2006

Changes in isoflavone and oligosaccharides, and some physicochemical properties of Chokong, a pickled and dried soybeans, were investigated during pickling in brewed vinegar at $20^{\circ}C$. The used soybeans were 24 hr germinated soybeans, which was maximumly increased in isoflavone content during germination. The isoflavone contents were significantly increased by approx. 80% in both glycosides and aglycone type of isoflavone after 20 day of pickling at $20^{\circ}C$. The isoflavone values of germinated Chokong were significantly higher than those of ungerminated ones. Pickling the soybeans in vinegar resulted in a rapid initial decrease in oligosaccharides, Particularly in raffinose and stachyose. The pH and soluble solids contents in vinegar increased markedly and L values decreased during initial pickling of 24 hr.

• Journal of Microbiology and Biotechnology
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• v.27 no.11
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• pp.1952-1960
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• 2017

Recently, soybean isoflavone aglycones (i.e., daidzein and genistein) and ${\gamma}-aminobutyric$ acid (GABA) have begun to receive considerable consumer attention owing to their potential as nutraceuticals. To produce these ingredients, multiple microorganisms and their enzymes are commonly used for catalysis in the nutraceutical industry. In this work, we introduce a novel fermentation process that uses whole-cell biocatalysis to accelerate GABA and isoflavone aglycone production in doenjang (a traditional Korean soybean paste). Microbial enzymes transform soybean isoflavone glycosides (i.e., daidzin and genistin) and monosodium glutamate into soybean isoflavone aglycones and GABA. Lactobacillus brevis GABA 100 and Aspergillus oryzae KACC 40250 significantly reduced the production time with the aid of a protease. The resulting levels of GABA and daidzein were higher, and genistein production resembled the levels in traditional doenjang fermented for over a year. Concentrations of GABA, daidzein, and genistein were measured as 7,162, 60, and $59{\mu}g/g$, respectively on the seventh day of fermentation. Our results demonstrate that the administration of whole-cell L. brevis GABA 100 and A. oryzae KACC 40250 paired with a protease treatment is an effective method to accelerate GABA, daidzein, and genistein production in doenjang.