• Title/Summary/Keyword: Glycosides

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Changes in Phenolic Compounds and Radical Scavenging Activity of Doenjang Prepared by Fermentation with Bacillus Subtilis HJ18-9 (Bacillus subtilis HJ18-9로 제조한 된장의 페놀성분 및 라디칼 소거 활성의 변화)

  • Lee, Kyung Ha;Song, Jin;Jang, Yeon Jeong;Lee, Eun Jun;Kim, Hyun Joo;Oh, Sea Kwan;Woo, Koan Sik
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.45 no.6
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    • pp.843-850
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    • 2016
  • This study was conducted to investigate changes in isoflavone composition (glycosides and bio-active aglycones) and evaluate the quality characteristics of doenjang prepared using different Bacillus strains (KACC15935 and HJ18-9). After 60 days of fermentation, ${\beta}-glucosidase$ activity of doenjang fermented with B. subtilis HJ18-9 was higher than those of other samples. Contents of aglycones (daidzein, genistein, and glycitein) in B. subtilis HJ18-9 significantly increased up to $703.90{\pm}11.09{\mu}g/g$. In addition, total phenolic content and 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity increased markedly during fermentation. These results suggest that fermentation with B. subtilis could be used to increase ${\beta}-glucosidase$ activity with a view towards development of functional foods.

NDP-sugar production and glycosylation of ${\varepsilon}$-rhodomycinone in Streptomyces venezuelae (Streptomyces Peucetius에서의 ${\varepsilon}$-rhodomycinone 추출 및 이종균주에서의 rhodomycin D 생산 연구)

  • Park, Sung-Hee;Cha, Min-Ho;Kim, Eun-Jung;Yoon, Yeo-Joon;Sohng, Jae-Kyung;Lee, Hee-Chan;Liou, Kwang-Kyoung;Kim, Byung-Gee
    • KSBB Journal
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    • v.23 no.1
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    • pp.44-47
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    • 2008
  • Anthracycline antibiotics doxorubicin (DXR) is clinically important cancer therapeutic agent produced by Streptomyces peucetius. DXR result by further metabolism of rhodomycin D (RHOD) and require a deoxy-sugar component for their biological activity. In this study, production of TDP-L-daunosamine and its attachment to ${\varepsilon}$-rhodomycinone (RHO) to generate RHOD has been achieved by bioconversion in Streptomyces venezuelae that bears eleven genes. S. peucetius seven genes (dnmUTJVZQS) were transformed by plasmid and S. venezuelae two genes desIII, IV and two more S. peucetius drrA, B genes were integrated into chromosomal DNA. To generate the feeding substrate RHO, 6L S. peucetius grown on agar plate was harvested, extracted with organic solvent and then purified using preparative HPLC. Recombinant S. venezuelae grown on agar plate containing RHO was harvested and its n-butanol soluble components were extracted. The glycosylated product of aromatic polyketide RHO using heterologous host S. venezuelae presents the minimal information for TDP-L-daunosamine biosynthesis and its attachment onto aglycone. Moreover, the structure of auxiliary protein, DnrQ, was predicted by fold recognition and homology modeling in this study. This is a general approach to further expand of new glycosides of antitumor anthracycline antibiotics.

Comparison of Isoflavone Contents and Antioxidant Effect in Cheonggukjang with Black Soybean Cultivars by Bacillus subtilis CSY191

  • Azizul Haque, Md.;Hwang, Chung Eun;Lee, Hee Yul;Ahn, Min Ju;Sin, Eui-Cheol;Nam, Sang Hae;Joo, Ok Soo;Kim, Hyun Joon;Lee, Shin-Woo;Kim, Yun-Geun;Ko, Keon Hee;Goo, Young-Min;Cho, Kye Man
    • Korean Journal of Environmental Agriculture
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    • v.35 no.1
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    • pp.62-71
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    • 2016
  • BACKGROUND: Soybeans are the rich sources of isoflavones. To date, the changes of isoflavone contents in various black soybeans cheonggukjang during fermentation by Bacillus subtilis CSY191 has not been investigated.METHODS AND RESULTS: This study investigated the changes of total phenolic and isoflavone contents and antioxidant effects during cheonggukjang fermentation made with four black soybean (BS) cultivars including Cheongja, Cheongja#3, Geomjeong#5, and Ilpumgeomjeong with a potential probiotic Bacillus subtilis CSY191. The total phenolic contents, isoflavone-malonylglycoside and -aglycone contents, and antioxidant activity were increased in cheonggukjang at 48 h fermentation, while the content of isoflavone-glycosides was decreased during cheonggukjang fermentation. In particular, the Cheongja#3 soybean fermented at 37℃ for 48 h displayed the highest antioxidant activities, compared to those of the other BS cultivars tested. Also, the highest levels of total phenolic, daidzein, glycitein, and genistein were present at concentrations of 17.28 mg/g, 283.7 g/g, 39.9 g/g, and 13.2 g/g at the end of Cheongja#3 soybean fermentation.CONCLUSION: The results from this study suggested that the enhanced antioxidant activity of cheonggukjang of BS might be related to increased levels of total phenolic, isoflavon-aglycone, and malonyl-glycoside contents achieved during fermentation. Furthermore, fermented Cheongja#3 soybean showed the highest levels of enhanced antioxidant activities than the other BS cultivars.

ACE Inhibitory Lignan Glycosides Isolated from Eucommia ulmoides Oliver (두충으로부터 분리한 Iignan glycoside 의 ACE 활성 억제)

  • Joo, Ok-Soo;Nam, Sang-Hae
    • Journal of Life Science
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    • v.19 no.6
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    • pp.698-704
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    • 2009
  • To evaluate a potential possibility of Eucommia ulmoides Oliver as a functional food, ACE (angiotensin converting enzyme) inhibitory activities of leaf, bark, stem and 4 compounds isolated from E. ulmoides were tested. The 4 compounds were isolated and purified by silica gel column chromatography, thin layer chromatography and reverse phase column chromatography. Compound I was pinoresinol-4,4'di-O-${\beta}$-D-glucoside (PG) and compound II was dehydrodiconiferyl alcohol 4,${\gamma}$'-di-O-${\beta}$-D-glucopyranoside (DAG) originating from Eucommial Cortex. The highest amount of PC was present at raw and roasted bark as 135.13 mg% and 163.67 mg%, and the highest amount of DAG was present at raw and roasted leaf as 117.93 mg% and 133.93 mg% respectively. In an ACE inhibition test, 10 mg/ml of roasted leaf, raw and roasted bark extracts of E. ulmoides Oliver were 77.49%, 75.72% and 75.36% respectively, and 10mg/ml of PC and DAG were shown to be 78.51 and 81.20% respectively. $IC_{50}$ values of PG and DAG were 0.6${\pm}$0.2 and 0.5${\pm}$0.2 mg/ml respectively.

A Comparative Study on the Lipid components of Barley and Malt -II. Composition of Polar Lipids- (보리와 맥아(麥芽)의 지방질(脂肪質) 성분(成分)에 관한 비교(比較) 연구 -제(第)2보(報) : 극성지질(極性脂質)의 조성(組成)-)

  • Lee, Sang-Young;Kim, Jong-Sung;Shin, Hyo-Sun
    • Korean Journal of Food Science and Technology
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    • v.13 no.1
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    • pp.37-42
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    • 1981
  • Polar lipids of the total lipid extracted from 4 representative varieties of barley grown in Korea and their corresponding malt were studied. The average content of glycolipids and phospholipids in barley were 8.9 and 17.3% and their average content of malt were 12.3 and 19.2%, respectively. Among the glycoliplds of the barley, digalactosyl diglycerides and monogalactosyl diglycerides were the major components, and the malts showed somewhat lower amounts of those components. Steryl glycosides and cerebrosides were the minor components of the glycolipids, and malts of the barley showed somewhat increased amounts of those components. Phosphatidyl cholines, lysophosphatidyl cholines, diphosphatidyl glycerols, and phosphatidyl ethanolamines were the major components of the phospholipids for the barley and represented 85 to 90% of the total phospholipids. The malts had lower amounts of phosphatidyl cholines and the lyso analog, and higher amounts of phosphatidyl ethnolamines and diphosphatidyl glycerols. The fatty acid composition in the glycolipids and phospholipids were similar to the pattern in those of the neutral lipids. But glycolipids and phospholipids fractions contained a higher percent of linoleic and palmitic acid than other lipid fractions, respectively.

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Effect of Euonymus alatus and Ulmus clavidiana var japonica on the immune system (화살나무 및 느릅나무 추출물이 면역계세포의 활성에 미치는 영향)

  • Kim, Jong-myeon;Choi, Min-soon;Cho, Jeong-gon;Jung, Young-mee;Park, Tae-wook
    • Korean Journal of Veterinary Research
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    • v.34 no.2
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    • pp.307-313
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    • 1994
  • We have previously shown that crude water extract of Euonymus alatus (EA) had strong prophylactic effect against chemically induced-and tumor cell implanted-cancer, and that the mechanisms responsible for its antitumor effects were due to nonspecific enhancement of the NK cell activities and the cell mediated immunity. However, it was unknown that any components of crude extract did work so, since it consisted of several components. In this paper, we fractionated the crude watar EA-extract into several fraction such as hexane-, ethylether-, ethyl acetate-, n-butanol- and water soluble-fraction, and screened the immune regulating activities of each fraction by the evaluation of lymphokine production and activated lymphocyte proliferation. As a result of the component fraction of EA-extract, it was found that n-butanol fraction was a potent immunostimulator, and the remained water soluble fraction also contained some stimulator, But, other fraction did not showed any remarkable effect. It is therefore suggested that EA-glycosides in n-butanol fraction may be new one of the potent biological response modifiers. The present study was also undertaken in an efforts to investigate the effects of elm-bark(EB, Ulmus clavidiana var japonica), which has been used for curing ulcer and inflammation as a folk medicine without any kind of experimental evidence to support this, on the cellular- and humoral-immune responses, lymphocyte function and NK cell activities in mice. Regardless of time and duration of EB-treatment, Arthus reaction and antibody response to SRBC were not modified by EB, but delayed hypersensitivity to SRBC was significantly enhanced only when EB was treated prior to SRBC-sensitization. EB slightly inhibited the proliferation responses of splenocytes to PHA-stimulation, but it significantly augmented the responses of these cells to S aureus Cowan 1 and Con A-activation, and these effects were manifested only when EB was added at culture initiation. EB did not influence Ig secretion of spleen cells but it significantly augmented the Con A-induced 1L 2 and MIF production of splenocytes. NK cell activities of splenocytes were markedly riled when effector cells were pretreated with EB and this augmentation was dine to the increase of binding affinity of effector cells to target cells and the target cell lytic activities of effector cells. These results led to the conclusion that EB triggers increase of cellular immune responses, such as delayed hypersensitivitiy, lymphokine production and NK cell activities. Also these results suggested that EB contains potent immune stimulants, which may provide the rational basis for their therapeutic use as one of the new biological response modifiers.

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Characterization of ent-Kaurenoic Acid 13-Hydroxylase in Steviol Biosynthesis of Stevia rebaudiana Bertoni (Stevia rebaudiana Bertoni의 Steviol 생합성 효소 ent-Kaurenoic Acid 13-Hydroxylase의 특성)

  • Shibata, Hitoshi;Kim, Keun-Ki
    • Applied Biological Chemistry
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    • v.40 no.6
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    • pp.501-507
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    • 1997
  • Chloroplasts isolated from Stevia rebaudiana Bertoni leaves contained an enzyme activity which catalyzed hydroxylation of ent-kaurenoic acid (ent-kaur-16-en-19-oic acid; ent-KA) to steviol (ent-13-hydroxy kaur-16-en-19-oic acid), the diterpenoid carboxylic alcohol which is the aglycone of sweet stevioside-related glycosides. $[^(14)C]-methylated$ ent-KA was used to localize ent-KA hydroxylase. $[^(14)C]-methyl-KA$ was most actively was transformed into methyl-steviol in chloroplast. The enzymatic activity was found in stroma fraction but not in thylakoid membrane in Stevia rebaudiana Bertoni. However, ent-KA 13-hydroxylase activity was not detected in stroma fraction of either Spinacia oleracea and Solidago altissima. The reaction products using $[^(14)C]-methyl-KA$ were purified and identified on TLC autoradiogram. The hydroxylation of ent-KA from stromal protein to form steviol required NADPH and oxygen. FAD and riboflavin stimulated the enzyme activity 1.5-and 1.7-fold, respectively. It also turned out that the activity of this enzyme using methyl-KA as a substrate was 16.7% that of ent-KA. The purified ent-KA 13-hydroxylase did not act on t-cinnamic acid, 4-hydroxyphenyl acetic acid, choline and resorcinol, known as monooxygenase and hydroxylase substrates.

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Lipid Class and Fatty Acid Composition of Starch-Lipid in Naked Barley (쌀보리의 전분지방질에 관한 연구)

  • Kim, Hae-Gyoung;Cheigh, Hong-Sik
    • Korean Journal of Food Science and Technology
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    • v.21 no.4
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    • pp.515-520
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    • 1989
  • The composition of lipid class and fatty acid of free lipids(FL) as non-starch lipid and bound lipids(BL) as starch-lipid extracted from starch In naked barley(Hordeum vulgare L.) was investigated with the chromatographic procedures. FL were extracted from barley starch by petroleum ether(PE) and then BL were reextracted from PE extracted starch by the solvent systems of water-saturated butanol (WSB) at $25^{\circ}C$ and at $95^{\circ}C$ respectively. The contents of neutral lipid(NL), glycolipids(GL) and phospholipids(PL) in FL were 69.9%, 27.3%, and 2.8%, on the other hand those of BL were 34.9-54.6%, 30-45.5% and 15.4-19.6%, respectively. The identified components of NL in starch-lipid were triglycerides (70.4-82.4%), free fatty acid (8.4-26.2%), esterified sterols and free sterols, and also the major GL in starch-lipid was monogalactos-yldiglycerides(87.2-91.1%). Of the PL in FL and BL, diphosphatidyl glycerols, lysophosphatidyl choline, phosphatidyl choline & phosphatidyl serine were the major components. The predominent fatty acids found in NL, GL and PL of barley starch were palmitic acid and linoleic acid, and also myristic, stearic, oleic, linolenic acids were determined.

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Identification of a Neolignan Glycoside from the Pine Tree, Pinus densiflora Showed Antithrombotic Activity (Pinus densiflora 유래의 항트롬빈 활성을 나타내는 Neolignan Glycoside의 동정)

  • Seo, Min-Jeong;Kang, Byoung-Won;Jeong, Yong-Kee
    • Journal of Life Science
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    • v.24 no.8
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    • pp.873-879
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    • 2014
  • The constituents from the needles of the pine tree, Pinus densiflora, were purified and investigated for antithrombotic activity. The needles were initially extracted three times with 70% ethanol, and the extract was sequentially fractionated with chloroform and n-butanol. The aqueous layer formed after n-butanol fractionation was subjected to purification by medium pressure and high pressure liquid chromatography. The two neolignans, 2, 3-dihydro-7-hydroxyl-3-hydroxymethyl-2-(4'-hydroxyl -3-methoxyphenyl)-5-benzofuranpropanol-3-O-${\alpha}$-rhamnopyranoside (a neolignan glycoside) and 2, 3-dihyro-3-hydroxymethyl-7-methoxy-2-(4'-hydroxyphenyl-3'-methoxy)-5-benxofuran propanol 4'-O-${\alpha}$-rhamnopyranoside (icariside $E_4$) were identified by $^1H$ and $^{13}C$ NMR spectra. The effect of the purified compounds, the neolignan glycoside and icariside $E_4$ on thrombin inhibition were investigated by measuring thrombin clotting time in plasma. As a result, the clotting of the neolignan glycoside was delayed four times compared to that of icariside $E_4$. In addition, an analysis of the inhibition effect by changing the concentration showed that the clotting time was delayed in accordance with an increase in the concentration of the neolignan glycoside. Furthermore, we examined the interaction of thrombin and fibrinogen to clarify the action mechanism. As a result, the delay of clotting time in the response of thrombin and pure fibrinogen may indicate that neolignan glycosides inhibit the thrombin action in a direct manner, leading to the suppression of fibrin generation.

Biological Activities of Flavonoid Glycosides Isolated from Angelica keiskei (신선초에서 분리된 flavonoid glycosides의 생리활성)

  • Shim, Jae-Seok;Kim, Seung-Deok;Kim, Tae-Seok;Kim, Kyung-Nam
    • Korean Journal of Food Science and Technology
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    • v.37 no.1
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    • pp.78-83
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    • 2005
  • Recently, much attention has been focused on plant antioxidants, because they are expected to protect against oxidative damage, possibly preserving biological functions of cells. Antioxidant compounds were isolated from Angelica keiskei through extraction with 80% EtOH, and fractionations were carried out sequentially with n-hexane, chloroform, ethyl acetate, n-butanol, and water. Two active compounds were isolated from ethyl acetate fraction by silica gel column chromatography, and were identified as isoquercitrin ($quercetin-3-O-{\beta}-D-glucose$) and hyperoside ($quercetin-3-O-{\beta}-D-glucose$). Isoquercitrin and hyperoside showed strong antioxidative potency, as revealed by evaluation of their ABTS, DPPH, OH, and $H_{2}O_{2}$ radical-scavenging activities, and ex vivo DNA damage-protecting effects.