• Title/Summary/Keyword: quercetin-3-O-rutinoside

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Acceptor Specificity of Amylosucrase from Deinococcus radiopugnans and Its Application for Synthesis of Rutin Derivatives

  • Kim, Myo-Deok;Jung, Dong-Hyun;Seo, Dong-Ho;Jung, Jong-Hyun;Seo, Ean-Jeong;Baek, Nam-In;Yoo, Sang-Ho;Park, Cheon-Seok
    • Journal of Microbiology and Biotechnology
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    • v.26 no.11
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    • pp.1845-1854
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    • 2016
  • The transglycosylation activity of amylosucrase (ASase) has received significant attention owing to its use of an inexpensive donor, sucrose, and broad acceptor specificity, including glycone and aglycone compounds. The transglycosylation reaction of recombinant ASase from Deinococcus radiopugnans (DRpAS) was investigated using various phenolic compounds, and quercetin-3-O-rutinoside (rutin) was found to be the most suitable acceptor molecule used by DRpAS. Two amino acid residues in DRpAS variants (DRpAS Q299K and DRpAS Q299R), assumed to be involved in acceptor binding, were constructed by site-directed mutagenesis. Intriguingly, DRpAS Q299K and DRpAS Q299R produced 10-fold and 4-fold higher levels of rutin transglycosylation product than did the wild-type (WT) DRpAS, respectively. According to in silico molecular docking analysis, the lysine residue at position 299 in the mutants enables rutin to more easily position inside the active pocket of the mutant enzyme than in that of the WT, due to conformational changes in loop 4.

Radical Scavenging Activities of Phenolic Compounds Isolated from Mulberry (Morus spp.) Cake

  • Shin, Young-Woong;Lee, Seong-Kwon;Kwon, Yun-Ju;Rhee, Soon-Jae;Choi, Sang-Won
    • Preventive Nutrition and Food Science
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    • v.10 no.4
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    • pp.326-332
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    • 2005
  • A methanol extract of mulberry cake prepared from mulberry fruits (Morus spp.) was shown to have strong scavenging activities against DPPH, superoxide and hydroxyl radicals. Eleven phenolic compounds were isolated from the mulberry cake by a combination of Diaion HP-20, silica gel (or polyamide), Sephadex LH-20 column chromatographies, preparative HPLC and TLC. Their chemical structures were characterized as procatechuic acid (PCA), caffeic acid (CA), cyanidin 3-O-$\beta$-D-glucopyranoside (CyG) and cyanidin $3-O-\beta­D-rutinoside$ (CyR), rutin (RT), isoquercitrin (IQT), astragalin (AG), quercetin (QT), morin (MR), di-hydroquercetin (DHQ), and 4-prenylmoracin (PM) by spectral analysis and the published data. Most of the phenolic constituents were effective scavengers of DPPH, superoxide and hydroxyl radicals, and especially caffeic acid and 4-prenylmoracin showed potent superoxide and hydroxyl radical scavenging activity, in which their activities were higher than that of the well-known antioxidant, BHT (p< 0.05). Dehydroquercetin and quercetin also exhibited strong superoxide and hydroxyl radical scavenging activities. These results suggest that mulberry cake containing antioxidant phenolic compounds may be useful as natural antioxidants in functional foods and cosmetics.

Antioxidative Effects and Component Analysis of Graviola (Annona muricata) Leaf Extract/Fractions (그라비올라(Annona muricata) 잎 추출물 및 분획물의 항산화 활성과 성분 분석)

  • Park, So Hyun;Kim, Ji Min;Kim, Jin Hwan;Oh, Yoon Soo;Joo, Dong Hee;Lee, Eun Young;Shin, Hyuk Soo;Kim, A Rang;Lee, Sang Lae;Park, Soo Nam
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.43 no.4
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    • pp.309-320
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    • 2017
  • In this study, the antioxidative effects and component analysis of 50% ethanol extract, ethyl acetate fraction and aglycone fraction obtained from Annona muricata leaf were investigated. Free radical scavenging activities were performed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, total antioxidant capacities were estimated using luminol-dependent chemiluminescence assay and $^1O_2$ quenching effects were estimated. Free radical scavenging activities ($FSC_{50}$) of 50% ethanol extract, ethyl acetate fraction and aglycone fraction were 45.6, 29.8 and $18.0{\mu}g/mL$, and total antioxidant capacities ($OSC_{50}$) were 4.4, 1.1 and $2.8{\mu}g/mL$, respectively. As a result of $^1O_2$ quenching experiment, ethyl acetate and aglycone fraction showed similar activities to L-ascorbic acid used as a comparative control. The cellular protective effects of 50% ethanol extract on the $^1O_2-induced$ cellular damage of human erythrocytes were exhibited at concentration-dependent ($5-50{\mu}g/mL$). TLC and HPLC were used to analyse components in the ethyl acetate fraction and aglycone fraction of Annona muricata leaf. In ethyl acetate fraction, rutin (quercetin-3-O-rutinoside), kaempferol-3-O-neohesperidoside, nicotiflorin (kaempferol-3-O-rutinoside), p-coumaric acid were identified. In aglycone fraction, kaempferol was identified. These results suggest that the extracts of Annona muricata leaf have the applicability as antioxidant cosmeceutical ingredients.

DPPH Free Radical Scavenging Effect of the Aerial Parts of Desmodium oldhami (큰도둑놈의갈고리 지상부의 DPPH Free Radical 소거효과)

  • Yang, Seo-Kwon;Park, Sae-Rom;Ahn, Dal-Rae;Yang, Jae-Heon;Cho, Chong-Hyeon;Hwang, Yong-Hun;Park, Jong-Han;Kim, Dae-Keun
    • Korean Journal of Pharmacognosy
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    • v.41 no.3
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    • pp.180-184
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    • 2010
  • The antioxidant activity of Desmodium oldhami (Leguminosae) was determined by measuring the radical scavenging effect on DPPH (1,1-diphenyl-2-picrylhydrazyl). The methanolic extract of D. oldhami showed the strong antioxidant activity. Five compounds, kaempferol-3-O-rhamnopyranoside (afzeline) (1), quercetin-3-O-[$\alpha$-L-rhamnopyranosyl($1{\rightarrow}6$)-$\beta$-Dglucopyranoside] (rutin) (2), kaempferol-3-O-glucopyranoside (astragalin) (3), genistein-7-O-$\beta$-D-glucopyranoside (genistin) (4), kaempferol-3-O-rutinoside (5) were isolated from the active ethyl acetate soluble fraction of D. oldhami through repeated silica gel and Sephadex LH-20 column chromatography. Among them, compound 2 showed the most significant antioxidative effect on DPPH free radical scavenging test. Compounds 1-5 are reported for the first time from this plant.

Antioxidative Activity and Component Analysis of Prunella vulgaris L. Extract/Fractions (하고초 추출물의 항산화 활성 및 성분 분석)

  • Suh, Ji Young;Seong, Joon Seob;Yun, Mid Eum;Lee, Ye Seul;Ha, Ji Hoon;Park, Dong Soon;Park, Soo Nam
    • Journal of the Korean Applied Science and Technology
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    • v.33 no.4
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    • pp.647-657
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    • 2016
  • In this study, the antioxidative effects and active component analysis of 50% ethanol extract, ethyl acetate fraction and aglycone fraction obtained from Prunella vulgaris L. were investigated. The free radical scavenging activities ($FSC_{50}$) was investigated at 50% ethanol extract ($15.25{\mu}g/mL$), ethyl acetate fraction ($8.68{\mu}g/mL$), and aglycone fraction ($8.25{\mu}g/mL$) respectively. Reactive oxygen species (ROS) scavenging activities ($OSC_{50}$) in $Fe^{3+}-EDTA/H_2O_2$ system using the luminol-dependent chemiluminescence assay was investigated at 50% ethanol extract ($4.68{\mu}g/mL$), ethyl acetate fraction ($1.00{\mu}g/mL$), and aglycone fraction($1.02{\mu}g/mL$) respectively. In the cellular protective effect against $^1O_2$ induced cellular damage of human erythrocytes, extract/fractions of P. vulgaris L. were increased in a concentration dependent manner($1{\sim}25{\mu}g/mL$). Especially, ${\tau}_{50}$ of aglycone fraction at concentrations of $25{\mu}g/mL$ showed the most protective effects at 337.9 min. It's showed nine times higher (+)-${\alpha}$-tocopherol (${\tau}_{50}=38.7min$) as typical antioxidant in the $^1O_2$-induced photohemolysis of human erythrocytes. TLC and HPLC were used to analyse active components in the ethyl acetate fraction and aglycone fraction of P. vulgaris L. In ethyl acetate fraction, caffeic acid, rosmarinic acid, quercetin 3-${\beta}$-D-glucoside, rutin, kaempferol-3-O-rutinoside, astragalin (kaempferol-3-O-glucoside) were identified. In aglycone fraction, caffeic acid, rosmarinic acid, quercetin, kaempferol were identified. These results indicated that extract/fraction of P. vulgaris L. is may be used in cosmetics industry as natural antioxidants by quenching and/or scavenging $^1O_2$ and other ROS, and protecting cellular membranes.

Profiling of flavonoid glycosides in fruits and leaves of jujube (Zizyphus jujuba var. inermis (Bunge) Rehder) using UPLC-DAD-QTOF/MS (UPLC-DAD-QTOF/MS를 이용한 대추나무(Zizyphus jujuba var. inermis (Bunge) Rehder) 잎과 열매의 플라보노이드 배당체 분석)

  • Lee, Min-Ki;Kim, Heon-Woong;Kim, Young Jin;Lee, Seon-Hye;Jang, Hwan-Hee;Jung, Hyun-Ah;Kim, Sook-Bae;Lee, Sung-Hyen;Choe, Jeong-Sook;Kim, Jung-Bong
    • Food Science and Preservation
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    • v.23 no.7
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    • pp.1004-1011
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    • 2016
  • Flavonoids, non-nutrient secondary metabolites of plants, are widely distributed in commonly consumed agro-food resources. Flavonoids include aglycones, and their glycosides are reported to have potential health-promoting compounds. The aim of this study was to investigate flavonoid glycosides in the fruit and leaves of Zizyphus jujuba var. inermis (Bunge) Rehder (jujube). A total of six flavonoids (five flavonols and one chalcone) were identified in jujube fruit and leaves by using ultra-performance liquid chromatography-diode array detector-quadrupole time of flight mass spectrometry along with chemical library and an internal standard. In positive ion mode, six flavonoids were linked to the C- and O-glycosides which were conjugated with sugar moieties based on kaempferol, quercetin, and phloretin aglycones. Total flavonoid contents of leaves (8,356.5 mg/100 g dry weight (DW)) was approximately 900-fold higher than that of fruit (fresh fruit, 13.6 mg/100 g dry DW; sun-dried fruits, 9.2 mg/100 g dry DW). Quercetin 3-O-rutinoside (rutin) and quercetin 3-O-robinobioside were the predominant flavonols in fruit and leaves of jujube. In particular, rutin had the highest content (6,735.2 mg/100 g DW) in leaves, and rutin is a widely reported bioactive compound. Phloretin 3',5'-di-C-glucoside (chalcone type) was detected only in leaves. The leaves of jujube contain a high content of flavonoids and the results of this study indicate that jujube leaves may be a source of bioactive flavonoids.

Phytochemical Constituents of Polytrichum commune (솔이끼로부터 플라보노이드 성분의 분리)

  • Nam, Jung-Hwan;Kim, Min-Young;Yoo, Young-Min;Cho, In-Sook;Kim, Su-Jeong;Yoo, Dong-Lim;Nam, Chun-Woo;Seo, Jong-Taek;Lee, Eung-Ho;Park, Hee-Juhn
    • Korean Journal of Plant Resources
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    • v.21 no.1
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    • pp.83-86
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    • 2008
  • Four compounds, luteolin(1), quercetin(2) astragalin(3), rutin(4), were isolated from the methanol extract of the all part of Polytrichum commune. on the basis of chemical and spectroscopic evidence. These compounds have not been isolated from this plant.

Analysis of Free Amino Acids and Polyphenol Compounds from Lycopene Variety of Cherry Tomatoes (방울토마토 라이코펜 품종의 유리아미노산 및 폴리페놀 화합물의 분석)

  • Kim, Hyen-Ryung;Ahn, Jun-Bae
    • Culinary science and hospitality research
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    • v.20 no.3
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    • pp.37-49
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    • 2014
  • In order to elucidate the usefulness of Lycopene, a cherry tomato variety, as a food material, the compositions of free amino acids, amino acid metabolites and polyphenol compounds were analyzed using HPLC and LC-MS/MS method. Lycopene contained eighteen free amino acids except for L-Cys and L-Try. L-Glu was the most abundant free amino acid, followed by L-Gln and L-Asp. The percentages of L-Glu, L-Gln and L-Asp of total free amino acid were 55.5%, 15.9% and 9.9% respectively. Lycopene contained essential amino acids with the exception of tryptophan. The following amino acid metabolites were found : ${\gamma}$-aminobutyric acid(GABA), carnitine(L-Car), o-phosphoethanolamine(o-Pea), hydroxylysine(Hyl) phosphoserine (p-Ser), N-methyl-histidine(Me-His), ethanolamine($EtNH_2$). Especially, GABA known as a neurotransmitter was present at a high level(305.99 mg/100 g dry weight). We identified the following polyphenol compounds in the cherry tomatoes : caffeic acid-hexose isomer I (CH I), caffeic acid-hexose isomer II (CH II), 3-caffeoylquinic acid(3-CQA), 5-caffeoylquinic acid(5-CQA), caffeoylquinic acid isomer(CQAI), quercetin-hexose-deoxyhexose-pentose(QTS), quercetin-3-rutinoside(Q-3-R), di-caffeoylquinic acid(di-CQA), tri-caffeoylquinic acid(tri-CQA), naringenin chalcone(NGC). Large quantities of Q-3-R and NGC known as bioactive compounds were found. These results revealed that Lycopene variety contained various nutritional and bioactive compounds and would be a potent functional food material.

Comparison of Anthocyanin Content in Seed Coats of Black Soybean [Glycine max(L.) Merr.] Cultivars Using Liquid Chromatography Coupled to Tandem Mass Spectrometry

  • Shin, Sung-Chul;Lee, Soo-Jung;Lee, Sung-Joong;Chung, Jong-Il;Bae, Dong-Won;Kim, Soo-Taek;Sung, Nak-Ju
    • Food Science and Biotechnology
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    • v.18 no.6
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    • pp.1470-1475
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    • 2009
  • The seed coat of the black soybean contains 3 main anthocyanins such as delphinidin-3-O-$\beta$-glucoside, cyanidin-3-O-$\beta$-glucoside, and petunidin-3-O-$\beta$-glucoside. As a part of our effort on discovering and breeding new black soybean cultivars which possesses specific anthocyanin component rich, we determined the anthocyanin profiles of the 2 cultivars recently developed soybean cv. Gaechuck #1 and cv. Gyeongsang #1, using liquid chromatography-tandem mass spectrometry (LC-MS/MS) and compared their content and identity with those of previously known 10 cultivar controls. The Cosmosil-$5C_{18}$-AR-II column were selected for the analysis because of the best peak separation. The column temperature was set up at $35^{\circ}C$. The mobile phase consisting of water containing 0.5%(v/v) formic acid and methanol gave good separation between the 3 anthocyanin analytes and internal standard (quercetin 3-O-$\beta$-rutinoside) and peaks with suppressed tail. The MS/MS spectra of each individual anthocyanin standard were detected in positive electron spray ionization (ESI) modes. It was disclosed that the anthocyanin contents of the soybean cv. Gaechuck#1 and cv. Gyeongsang#1 are roughly higher than those of the 10 controls.

Inhibitory Effects of Mulberry Fruit on Intestinal Disaccharidase Activity and Hyperglycemia in Streptozotocin-Induced Diabetic Rats

  • Hong, Jung-Hee;Kim, Sang-Woon;Choi, Kyung-Ho;Choi, Sang-Won;Rhee, Soon-Jae
    • Nutritional Sciences
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    • v.7 no.4
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    • pp.201-207
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    • 2004
  • The current study examined the effects of freeze-dried mulberry fruit on disaccharidase activity in the small intestine and the lowering of blood glucose in streptozotocin (STZ)-induced diabetic rats. Sprague-Dawley male rats were randomly assigned to one normal and three streptozotocin (STZ)-induced diabetic groups. The diabetic groups were fed a mulberry fruit-free diet (DM-group), 0.3% mulberry fruit diet (DM-F group) or 0.6% mulberry fruit diet (DM-2F group). After they were fed the experimental diets for three weeks, diabetes was induced with an intraperitoneal injection of streptozotocin 50 mg/kg b.w before sacrificing 9 days later using the same experimental treatments. Analyses of anthocyanins, flavonoid and 1-deoxynojirimycin (DNJ) of lyophilized mulberry fruit were carried out and the major anthocyanins were rutin (142.5 mg), isoquercitrin (10.3 mg), quercetin (5.8 mg), morin (1.6 mg) dihydroquercetin (3.83 mg), cy-3-O-glucopyranoside (230.45 mg) and cy-3-O-rutinoside (131.5 mg) on the basis of 100 g dry weight. Total DNJ content was 2.39 mg/g dry weight of lyophilized mulberry fruit. Blood glucose level decreased in the diabetic mts fed the mulberry fruit supplement. The content of the liver glycogen increased in the diabetic mts fed the mulberry fruit supplement. Disaccharidase activity in the proximal part of the intestine, such as that of maltase, sucrase and lactase in the mulberry fruit supplementation groups, were lower than that of the DM group. These results suggest that mulberry fruit possess a suppressive effect on hyperglycemia, possibly by inhibiting the activity of disaccharidase in the small intestine of rats.