• Title/Summary/Keyword: Glycosides

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Chemical Constituents of Domestic Quercus spp. Leaves (국내산 참나무속 수종 잎의 추출성분)

  • Kim, Jin-Kyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.6
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    • pp.61-71
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    • 2006
  • This study was carried out to investigate chemotaxonomical correlation an d the chemical constituents of domestic Quercus sp. leaves. The leaves of Q. mongolica, Q. aliena, Q. serrata, Q. acutissima, Q. dentata and Q. variabilis were collected in the experimental forest of Kangwon National University. The combined extracts were successively fractionated with n -hexane, methylene chloride and ethyl acetate using a separation funnel. A portion of the ethyl acetate and $H_2O$ soluble materials of each species were chromatographed on a Sephadex LH-20 column using various aqueous MeOH and EtOH-hexane as washing solvents. Spectrometric analysis such as NMR and MS, including TLC, were performed to characterize the structures of the isolated compounds. Gallic acid, (+)-catechin, (-)-epicatechin, (+)-gallocatechin, kaempferol, astragalin, astragalin-6"-O-gallate, isoquercitrin, isoquercitrin-6"-O-gallate and myricetin were isolated from Q. mongolic a leaves. Gallic acid, kaempferol and quercetin were characterized from Q. acutissima leaves. Gallic acid, (+)-catechin, (-)-epicatechin, (+)-gallocatechin, (-)-epigallocatechin, kaempferol, quercetin, guajaverin and tamarixin were identified from Q. dentata leaves. Gallic acid, (+)-catechin, (-)-epicatechin, kaempferol, quercitrin, isoquercitrin and myricetin were purified from Q. serrata leaves. Gallic acid, (+)-catechin, astragalin, astragalin-6"-O-gallate and isoquercitrin were isolated from Q. variabilis leaves. Gallic acid was isolated from all the leaves and could be a taxonomic index on Quercus spp..

Active Component of Fatsia japonica Enhances the Transduction Efficiency of Tat-SOD Fusion Protein both In Vitro and In Vivo

  • Lee, Sun-Hwa;Kim, So-Young;Kim, Dae-Won;Jang, Sang-Ho;Lim, Soon-Sung;Kwon, Hyung-Joo;Kang, Tae-Cheon;Won, Moo-Ho;Kang, Il-Jun;Lee, Kil-Soo;Park, Jin-Seu;Eum, Won-Sik;Choi, Soo-Young
    • Journal of Microbiology and Biotechnology
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    • v.18 no.9
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    • pp.1613-1619
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    • 2008
  • It has been reported that Tat-SOD can be directly transduced into mammalian cells and skin and acts as a potential therapeutic protein in various diseases. To isolate the compound that can enhance the transduction efficiency of Tat-SOD, we screened a number of natural products. 3-O-[$\beta$-D-Glucopyranosyl(1$\rightarrow$4)-$\alpha$-L-arabinopyranosyll-hederagenin (OGAH) was identified as an active component of Fatsia japonica and is known as triterpenoid glycosides (hederagenin saponins). OGAH enhanced the transduction efficiencies of Tat-SOD into HeLa cells and mice skin. The enzymatic activities in the presence of OGAH were markedly increased in vitro and in vivo when compared with the controls. Although the mechanism is not fully understood, we suggest that OGAH, the active component of Fatsia japonica, might change the conformation of the membrane structure and it may be useful as an ingredient in anti-aging cosmetics or as a stimulator of therapeutic proteins that can be used in various disorders related to reactive oxygen species (ROS).

Bioconverted Jeju Hallabong tangor (Citrus kiyomi × ponkan) peel extracts by cytolase enhance antioxidant and anti-inflammatory capacity in RAW 264.7 cells

  • Chang, Yun-Hee;Seo, Jieun;Song, Eunju;Choi, Hyuk-Joon;Shim, Eugene;Lee, Okhee;Hwang, Jinah
    • Nutrition Research and Practice
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    • v.10 no.2
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    • pp.131-138
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    • 2016
  • BACKGROUND/OBJECTIVES: Citrus and its peels have been used in Asian folk medicine due to abundant flavonoids and usage of citrus peels, which are byproducts from juice and/or jam processing, may be a good strategy. Therefore, the aim of this study was to examine antioxidant and anti-inflammatory effects of bioconversion of Jeju Hallabong tangor (Citrus kiyomi ${\times}$ ponkan; CKP) peels with cytolase (CKP-C) in RAW 264.7 cells. MATERIALS/METHODS: Glycosides of CKP were converted into aglycosides with cytolase treatment. RAW 264.7 cells were pre-treated with 0, 100, or $200{\mu}g/ml$ of citrus peel extracts for 4 h, followed by stimulation with $1{\mu}g/ml$ lipopolysaccharide (LPS) for 8 h. Cell viability, DPPH radical scavenging activity, nitric oxide (NO), and prostagladin $E_2$ ($PGE_2$) production were examined. Real time-PCR and western immunoblotting assay were performed for detection of mRNA and/or protein expression of pro-inflammatory mediators and cytokines, respectively. RESULTS: HPLC analysis showed that treatment of CKP with cytolase resulted in decreased flavanone rutinoside forms (narirutin and hesperidin) and increased flavanone aglycoside forms (naringenin and hesperetin). DPPH scavenging activities were observed in a dose-dependent manner for all of the citrus peel extracts and CKP-C was more potent than intact CKP. All of the citrus peel extracts decreased NO production by inducible nitric oxide synthase (iNOS) activity and $PGE_2$ production by COX-2. Higher dose of CKP and all CKP-C groups significantly decreased mRNA and protein expression of LPS-stimulated iNOS. Only $200{\mu}g/ml$ of CKP-C markedly decreased mRNA and protein expression of cyclooxygenase-2 in LPS-stimulated RAW 264.7 cells. Both 100 and $200{\mu}g/ml$ of CKP-C notably inhibited mRNA levels of $interleukin-1{\beta}$ ($IL-1{\beta}$) and IL-6, whereas $200{\mu}g/ml$ CKP-C significantly inhibited mRNA levels of $TNF-{\alpha}$. CONCLUSIONS: This result suggests that bioconversion of citrus peels with cytolase may enrich aglycoside flavanones of citrus peels and provide more potent functional food materials for prevention of chronic diseases attributable to oxidation and inflammation by increasing radical scavenging activity and suppressing pro-inflammatory mediators and cytokines.

Biotransformation of Pregnane Glycosides from Cynanchum wilfordii Roots by β-Glucosidase (당 분해효소를 이용한 백하수오 뿌리로부터 분리한 Pregnane Glycosides의 생전환)

  • Yoon, Mi-Young;Cuong, Mai Nguyen;Choi, Gyung-Ja;Choi, Yong-Ho;Jang, Kyoung-Soo;Cha, Byeong-Jin;Kim, Jin-Cheol
    • Research in Plant Disease
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    • v.18 no.3
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    • pp.186-193
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    • 2012
  • Biotransformation is an eco-friendly and efficient method for enhancing the bioavailability of biopesticide. To increase the antifungal activity of the crude extract of Cynanchum wilfordii roots against barely powdery mildew, we performed biotransformation of wilfoside C1G using ${\beta}$-glucosidase (cellobiase from Aspergillus niger). The mixture (G sample) of partially purified wilfoside C1G and cynauricuoside A (K1G) was treated with ${\beta}$-glucosidase to remove a glucopyranosyl moiety. The enzyme completely converted C1G to C1N and K1G to K1N. Optimal conditions for enzymatic biotransformation of G sample were determined to be 10% ethanol, 1,555 ${\mu}U$ ${\beta}$-glucosidase/ml, pH 5, and $45^{\circ}C$. In in vivo experiment, the G sample transformed by ${\beta}$-glucosidase showed stronger antifungal activity against barley powdery mildew than the non-treated G sample. These results suggest that ${\beta}$-glucosidase biotransformation can be applied to increase the antifungal activity of the crude extract of C. wilfordii roots against powdery mildews.

Characterization of Three Extracellular β-Glucosidases Produced by a Fungal Isolate Aspergillus sp. YDJ14 and Their Hydrolyzing Activity for a Flavone Glycoside

  • Oh, Jong Min;Lee, Jae Pil;Baek, Seung Cheol;Jo, Yang Do;Kim, Hoon
    • Journal of Microbiology and Biotechnology
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    • v.28 no.5
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    • pp.757-764
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    • 2018
  • A cellulolytic fungus, YDJ14, was isolated from compost and identified as an Aspergillus sp. strain. Three extracellular ${\beta}$-glucosidases, BGL-A1, BGL-A2, and BGL-A3, were separated using ultrafiltration, ammonium sulfate fractionation, and High-Q chromatography. The molecular masses of the three enzymes were estimated to be 100, 45, and 40 kDa, respectively, by SDS-PAGE. The optimum pH and temperature of BGL-A3 were 5.0 and $50^{\circ}C$, respectively, whereas the optimum pH and temperature of BGL-A1 and BGL-A2 were identical (4.0 and $60^{\circ}C$, respectively). The half-life of BGL-A3 at $70^{\circ}C$ (2.8 min) was shorter than that of BGL-A1 and BGL-A2 (12.1 and 8.8 min, respectively). All three enzymes preferred p-nitrophenyl-${\beta}$-$\text\tiny{D}$-glucopyranoside (pNPG) and hardly hydrolyzed cellobiose, suggesting that these enzymes were aryl ${\beta}$-glucosidases. The $K_m$ of BGL-A3 (1.26 mM) for pNPG was much higher than that of BGL-A1 and BGL-A2 (0.25 and 0.27 mM, respectively). These results suggested that BGL-A1 and BGL-A2 were similar in their enzymatic properties, whereas BGL-A3 differed from the two enzymes. When tilianin (a flavone glycoside of acacetin) was reacted with the three enzymes, the inhibitory activity for monoamine oxidase, a target in the treatment of neurological disorders, was similar to that shown by acacetin. We conclude that these enzymes may be useful in the hydrolysis of flavone glycosides to improve their inhibitory activities.

Anti-cancer Activity of Flavonoids from Aceriphyllum rossii (돌단풍(Aceriphyllum rossii)에서 분리한 플라보노이드의 항암활성)

  • Ahn, Eun-Mi;Han, Jae-Taek;Kwon, Byoung-Mog;Kim, Sung-Hoon;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.51 no.4
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    • pp.309-315
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    • 2008
  • The methanol extract from the aerial parts of Aceriphyllum rossii was fractionated into ethyl acetate, n-BuOH and $H_2O$ layers through solvent fractionation. Repeated silica gel column chromatography of EtOAc and n-BuOH layers afforded five flavonol glycosides. They were identified as astragalin (1), kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (2), rutin (3), kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$4)-${\alpha}$-L-rhamnopyranosyl 1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (4), and quercetin 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$4)-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (5) on the basis of spectroscopic data. All of them showed an inhibition in farnesyl protein tranferase (FPTase) activity, and rutin (3) inhibited the growth of rat H-ras cell and the cell migration of human umbilical vein endothelial cells (HUVECs).

Component Analysis and Study on Anti-elastase Activity of Equisetum arvense Extracts(II) (쇠뜨기 추출물의 성분 분석과 엘라스타제 활성 저해 효과 연구(II))

  • Park, Soo-Nam;Yang, Hee-Jung
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.33 no.3
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    • pp.139-144
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    • 2007
  • In the previous study, we reported the antioxidative activity of Equisetum arvense extracts. In this study, its inhibitory effect on elastase and components were investigated. Aglycone fractions obtained from the deglycosylation reaction of ethylacetate fraction among the Equisetum arvense extracts, showed 4 bands and 4 peaks in TLC and HPLC experiments, respectively. Four components were identified as luteolin(composition ratio, 19.12%), quercetin(12.87), apigenin(15.81) and kaempferol(52.20). TLC chromatogram of ethylacetate fraction of Equisetum arvense extract revealed 7 bands and HPLC chromatogram showed 8 peaks, which were identified as kaempferol-3,7-O-diglucoside(composition ratio, 15.74%), luteolin-5-O-glucoside(galuteolin, 11.91), apigenin-5-O-glucoside(12.91), kaempferol-3-O-glucoside(astragalin, 27.94), quercetin-glycoside(10.81, structure was not determined), kaempferol-glycoside (12.33, structure was not determined), luteolin(3.72) and apigenin(4.62) in the order of elution time. The inhibitory effect of aglycone fraction on elastase($IC_{50}$, $9.8{\mu}g/mL$) was very high. But ethylacetate fraction(flavonoid glycosides) rarely exhibited the inhibitory activity on elastase. Combined with the previous results of the antioxidative activity of Equisetum arvense extracts, it is concluded that the inhibitory activity on elastase of the aglycone fraction could be applicable to new functional cosmetics for smoothing wrinkles.

Isoflavonoid Contents, Antibacterial Activities, and Physiological Activities of Cheonggukjang Made from Sword Bean (작두콩 첨가 청국장의 Isoflavonoids 함량과 항균력 및 생리활성)

  • Kim, Un-Sung;Kim, Jae-Young;Kim, Seong-Jo;Moon, Kwang-Hyun;Baek, Seung-Hwa
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.41 no.2
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    • pp.174-181
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    • 2012
  • This research aimed to examine the isoflavonoid contents, antibacterial activities, and physiological activities of Cheonggukjang made from sword bean (CS). The effects of adding sword bean were compared with those of raw materials (RM), steamed materials (SM), and traditional Cheonggukjang (TC). In the case of the antibacterial activity on Gram-positive bacteria, the result of CS in ethanol extract was the highest in Bacillus cereus, and the result of water extract was the highest in Staphylococcus aureus. However, in the case of Gram-negative bacteria, Salmonella Typhimurium was the highest in all the extraction. Antioxidant activity and total flavonoid contents were present in the order of TC

The Transformation of Saponin Platycodi Radix by Aspergillus niger and Anti-oxidation Evaluation of the Transformed Metabolites (Aspergillus niger 효소에 의한 길경 사포닌(플라티코딘)의 전환 및 항산화 활성 비교)

  • Kang, Ju-Hui;Ji, Gnu-Uk;Wui, Hye-Jung;Hwang, In-Kyeung
    • Korean journal of food and cookery science
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    • v.24 no.6
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    • pp.729-734
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    • 2008
  • The principal objective of this study was to assess the possibility of transforming platycodin glycosides using various strains of probiotic bateria and edible fungi. Among the experimental microorganisms assess herein, Aspergillus niger KCTC 6909 evidenced the highest level of platycodin glycoside hydrolysis during fermentation. Particularly in cases in which the organism was incubated in the presence of rhamnose and platycodins. In order to produce the enzyme from Aspergillus niger effectively, various incubation conditions were assessd in order to determine the optimal conditions. The cytotoxicity on V79-4 (Chinese- hamster lung fibroblasts, normal cells) of platycodin was reduced significantly after conversion (concentration on $500{\mu}g/mL$, $1000{\mu}g/mL$); DPPH radical scavenging activity before conversion was 35.05%, and was 57.44% afterward. We noted significantly higher conversion activity inhibiting oxidative degradation. In conclusion, these results indicate that the proper combination of food microorganisms -and fermentation conditions can result in an increase in the glycoside hydrolysis of platycodin the resultant products of which reduce cytotoxicity- and increase anti-oxidant activity.

Changes in Quality Characteristics of Soybean Paste Doenjang with Addition of Garlic during Fermentation (마늘 첨가 된장의 숙성 중 품질특성 변화)

  • Kang, Jae-Ran;Kim, Gyeong-Min;Hwang, Cho-Rong;Cho, Kye-Man;Hwang, Chung-Eun;Kim, Jeong-Hwan;Kim, Jong-Sang;Shin, Jung-Hye
    • Korean journal of food and cookery science
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    • v.30 no.4
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    • pp.435-443
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    • 2014
  • In this study, we investigated the quality characteristics of Korean soybean paste, Doenjang, fermented for 6 weeks at room temperature with the addition of 0, 10, 20 and 30% garlic. Samples were analyzed in one-week intervals. The lightness decreased in all samples as the fermentation period and garlic concentration increased. Yellow index decreased in weeks 5~6 compared with weeks 0-1, for which the values were lower for the garlic-added Doenjang than the control. The pH increased, greatly reducung the acidity in week 1 compared with week 0. Significant differences in the pH and acidity were not observed among the sample groups. Amino type nitrogen contents increased continuously up to weeks 5, displaying no significant differences among the sample groups at weeks 5 and 6. In addition, reduction in the sugar content increased depending on the fermentation period. It increased in all sample groups by about 2.5 times after 6 weeks compared with the initial levels. Isoflavone content was also reduced generally depending on the fermentation period. In the early fermentation periods, the aglycone contents were the higher than the glycosides, while the glycoside contents increased over the fermentation period. The presence of Bacillus was not significantly different among the garlic added groups, but yeast was lower in the Doenjang with high garlic content.