• Food Science and Biotechnology
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• v.15 no.1
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• pp.96-101
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• 2006

Isoflavone distribution and ${\beta}$-glucosidase activity in cheonggukjang, a traditional Korean whole soybean-fermented food prepared with or without addition of Bacillus subtilis, were analyzed every 6 hr for 36 hr. Thermal cooking of raw-soaked soybeans significantly increased ${\beta}$-glucoside isoflavone level by 57.1 % and decreased malonyl-${\beta}$-glucosides by 57.6% (p<0.05). Consistent changes of isoflavone profiles in cheonggukjang without B. subtilis addition (COB) and samples with addition of B. subtilis (CWB) were not observed during 36 hr fermentation. ${\beta}$-Glucosides of isoflavones are major forms in both COB and CWB. ${\beta}$-Glucosidase activity in cheonggukjang decreased significantly compared to that of soaked soybeans due to thermal denaturation, while recovery of enzyme activity in COB was observed. Two new unidentified peaks were detected, and their relative peak areas in CWB were significantly larger than those in COB with increasing fermentation period (p<0.05), which indicates both peaks could be associated with fermentation metabolites.

• Journal of the Korean Society of Food Science and Nutrition
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• v.28 no.4
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• pp.907-911
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• 1999

To evaluate the effect of defatted sesame flour(DSF) on the oxidative stress of ethanol feeding in rats, Wistar male rats were divided into 4 groups of control, ethanol, DSF and DSF ethanol. Each group was sacrificed after feeding for 4 weeks and was examined by measuring the formation of 2 thiobarbituric acid reactive substance(TBARS), total cholesterol(TC) in serum, redox glutathione S transferase(GST) enzyme activity and the contents of glutathione(GSH) in the liver. The formation of TBARS in the liver after ethanol feeding was significantly increased comparing to the control, but the levels were significantly decreased by the DSF as compared to the ethanol feeding group(p<0.05). When compared to fed control diet, we found that serum TC levels were significantly lower in the DSF fed group than control group (p<0.05). The activity of hepatic GST was significantly increased by DSF as compared to the control and was decreased by ethanol feeding. On the other hand, the hepatic contents of GSH were unaffected by DSF feeding. Our findings suggest that feeding DSF may inhibit ethanol induced oxidative stress may be due to the stimulation of antioxidative activity by sesaminol glucosides in DSF.

• Archives of Pharmacal Research
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• v.29 no.10
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• pp.821-825
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• 2006

Two isoflavone C-glucosides, puerarin (1) and PG-3 (2), a but-2-enolide, $({\pm})-puerol$ B (3), two isoflavone O-glucosides, daidzin (4) and genistin (5), and three pterocarpans, (-)-medicarpin (6), (-)-glycinol (7) and (-)-tuberosin (8), were isolated from a MeOH extract of the roots of Pueraria Iobata, using an in vitro bioassay based on the inhibition of the formation of advanced glycation end products (AGEs) to monitor chromatographic fractionation. The structures of 1-8 were determined by spectroscopic data interpretation, particularly by 1D- and 2D-NMR studies, and by comparison of these data with values in the literature. All of the isolates (1-8) were evaluated for their inhibitory activity on AGEs formation in vitro. Of these, puerarin (1), PG-3 (2), and $({\pm})-puerol$ B (3) exhibited more potent inhibitory activity than the positive control aminoguanidine.

• Bulletin of the Korean Chemical Society
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• v.24 no.10
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• pp.1475-1477
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• 2003

Three monoterpene glucosides (1-3), including one new compound (3), have been isolated from the methanol extract of Portulaca oleracea. Structures of these compounds were determined to be (3S)-3-O-( ${\Beta}$-Dglucopyranosyl)-3,7-dimethylocta-1,6-dien-3-ol (1), (3S)-3-O-( ${\beta}$-D-glucopyranosyl)-3,7-dimethylocta-1,5-dien-3,7-diol (2) and (3S)-3-O-( ${\beta}$-D-glucopyranosyl)-3,7-dimethyl-7-hydroperoxyocta-1,5-dien-3-ol (3), respectively, by a combination of spectral analyses. Their stereochemistries were established by measurement of NOE and vicinal proton-proton coupling constants as well as comparisons of spectral data with those of previously related compounds.

• Journal of Microbiology and Biotechnology
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• v.32 no.5
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• pp.657-662
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• 2022

Glycosyltransferase (GT)-specific degenerate PCR screening followed by in silico sequence analyses of the target clone was used to isolate a member of family1 GT-encoding genes from the established fosmid libraries of soil actinomycetes Micromonospora echinospora ATCC 27932. A recombinant MeUGT1 was heterologously expressed as a His-tagged protein in E. coli, and its enzymatic reaction with semi-synthetic phenoxodiol isoflavene (as a glycosyl acceptor) and uridine diphosphate-glucose (as a glycosyl donor) created two different glycol-attached products, thus revealing that MeUGT1 functions as an isoflavonoid glycosyltransferase with regional flexibility. Chromatographic separation of product glycosides followed by the instrumental analyses, clearly confirmed these previously unprecedented glycosides as phenoxodiol-4'-α-O-glucoside and phenoxodiol-7-α-O-glucoside, respectively. The antioxidant activities of the above glycosides are almost the same as that of parental phenoxodiol, whereas their anti-proliferative activities are all superior to that of cisplatin (the most common platinum chemotherapy drug) against two human carcinoma cells, ovarian SKOV-3 and prostate DU-145. In addition, they are more water-soluble than their parental aglycone, as well as remaining intractable to the simulated in vitro digestion test, hence demonstrating the pharmacological potential for the enhanced bio-accessibility of phenoxodiol glycosides. This is the first report on the microbial enzymatic biosynthesis of phenoxodiol glucosides.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.50 no.4
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• pp.291-300
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• 2005

This study was focuses on the variation of isoflavone contents during seed development and their interaction with major chemical components such as protein, amino acids, saccaharides, lipid and fatty acids. During maturing, lipid, protein, and amino acid contents in soybean seeds showed the highest values at R7 stages, but isoflavone contents were increased until R8 stage. It was noted that malonyl glucosides $(64.2\%)$ are predominant forms among conjugated isoflavones followed by glucosides $(30.7\%)$, acetyl glucosides $(4.1\%)$ and aglycones $(0.9\%)$. Sucrose and stachyose were presented as a major saccharide in soybean seeds. As maturing days progressed, they were constantly increased and the highest contents were observed at R8 stage. While small quantities of raffinose, fructose, glucose, maltose, DP3 (DP: degree of polymerization), DP6, and DP7 were detected. These results showed that saccharide composition at the beginning of seed development is primarily monosaccharides with little sucrose and oligosaccharides, but as maturing days proceeds, sucrose and starch increase with concomitant decrease in monosaccharides. Sucrose and stachyose were positively correlated with isoflavone (r=0.780, 0.764 at p<0.01, respectively), while fructose, glucose, maltose, and DP7 were negatively correlated (r=-0.651, -0.653, -0.602, and -0.586 at p<0.05, respectively). Soybeans at R8 stage were high in protein and amino acid, but low in free amino acid contents. Protein and amino acid contents showed positively significant correlations with isoflavone (r=0.571 and 0.599 at p<0.05, respectively), but free amino acid content were negatively correlation with isoflavone (r=-0.673, p<0.01). The lipid content reaches its final content relatively early stage of seed development and remains constant as compared with other chemical components. Among the fatty acids, although varietal difference was presented, stearic acid and linolenic acid were gradually decreased, while oleic and linoleic acid were increased as seed maturing progressed. Lipid was significantly correlated (r=0.754, p<0.01) with isoflavones. However, neither saturated fatty acid nor unsaturated fatty acids significantly affected the isoflavone contents of maturing soybean seeds.

• Korean Journal of Food Science and Technology
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• v.41 no.2
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• pp.141-145
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• 2009

Cheongyukjang, a Banga food, is a heavy soy-soup prepared by boiling cheonggukjang, sea foods, and meats. Soybeans roasted at 140$^{\circ}C$ for 21.0 min and 220$^{\circ}C$ for 6.0 min, respectively, were used for cheonggukjang preparation. Distributions of isoflavones in raw soybeans, roasted soybeans, cheonggukjang, and cheongyukjang were analyzed by high performance liquid chromatography. The total isoflavones in roasted soybeans, cheonggukjang and cheongyukjang were about 79-80, 56-65, and 47-50% of those in raw soybeans, respectively. Roasting caused significant increases in acetyl derivatives and ${\beta}$-glucoside isoflavones, and significant decreases in malonyl derivatives (p < 0.05). The major isoflavones in cheonggukjang and cheongyukjang were ${\beta}$-glucosides. Succinyl-${\beta}$-daidzin and succinyl-${\beta}$-genistin, which are recognized as new metabolites of isoflavones, were not detected in raw and roasted soybeans. Peak areas of succinyl-${\beta}$-genistin were higher than thse of succinyl-${\beta}$-daidzin, in both cheongyukjang and cheonggukjang.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.66 no.4
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• pp.365-374
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• 2021

Soybean isoflavones are essential secondary metabolites synthesized through the phenylpropanoid pathway, and they play vital roles in human health. Isoflavone content is a complex quantitative trait controlled by multiple genes, and the genetic mechanisms underlying isoflavone biosynthesis remain largely unknown. Therefore, the present study analyzed the content of isoflavone and expression of six key genes involved in its biosynthesis (i.e., CHS6, HID, IF7GT, IF7MaT, GmIMaT1, and GmIMaT3) during soybean seed germination. Isoflavone content was quantified using high-performance liquid chromatography, and isoflavone biosynthetic gene expression was analyzed using quantitative real-time PCR. Two cultivars, namely 'Daepung2ho' and 'Pungsannamulkong', which are high- and low-isoflavone cultivars, respectively, were used. Isoflavone accumulation gradually increased with the progression of the germination period. As such, malonyl glucosides accounted for over 80% of the total content, whereas acetyl glucosides were present at trace amounts. Transcriptional analysis of isoflavone biosynthetic genes demonstrated expression patterns parallel to isoflavone content; however, there was no clear correlation between isoflavone content and gene expression. Moreover, most isoflavone biosynthetic genes showed different expression patterns depending on the individual gene or genotypes. Among the tested genes, HID showed consistently higher expression, except at 3 days after germination, and its expression was upregulated in 'Daepung2ho' but downregulated in 'Pungsannamulkong'. In addition, all tested genes exhibited different expression patterns between cotyledons and hypocotyls and responded differently to the germination period. These findings suggest that the expression levels of isoflavone biosynthetic genes are not consistent with the germination period and appear to be genotype-dependent.

• Korean Journal of Pharmacognosy
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• v.20 no.4
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• pp.219-222
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• 1989

Tectorigenin, irigenin, their glucosides and 5,3'-dihydroxy-4',5'-dimethoxy-6,7-methylenedioxyisoflavone were isolated from the rhizomes of Belamcanda chinensis.

• Archives of Pharmacal Research
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• v.15 no.1
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• pp.73-77
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• 1992

From the roots of Angelica dahurica Bentham et Hooker (Umbelliferae), five coumarin glucosides together with adenosine have been isolated and identified as nodakenin, 3'-hydroxymarmesinin, tert-O-$\beta$-D-glucopyranosyl-byakangelicin, sec-O-$\beta$-D-glucopyranosyl-byakangelicin and scopolin. This is the first report of the occurrence of these compounds in this plant.