• Title/Summary/Keyword: ${\beta}$-glucosides

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Isolation of (+)-Catechin fro the Roots of Rosa rugosa

  • Young, Han-Suk;Park, Jong-Cheol;Choi, Jae-Sue
    • Korean Journal of Pharmacognosy
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    • v.18 no.3
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    • pp.177-179
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    • 1987
  • From the roots of Rosa rugosa(Rosaceae), (+)-catechin, and a mixture of ${\beta}-sitosterol$ and campesterol glucosides were isolated and characterized by the physicochemical and spectral data.

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Changes in Isoflavone Profiles during Cheongyukjang Preparation, A Traditional Banga Food (반가 식품인 청육장 제조 중 아이소플라본 분포 변화)

  • Lee, Seung-Wook;Park, Yong-Woo;Han, Yang-Sun;Chang, Pahn-Shick;Lee, Jong-Mee;Kim, Young-Suk;Lee, Jae-Hwan
    • 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.

Coumarin Glycosides from the Roots of Angelica dahurica

  • Kim, Seoung-Han;Kang, Sam-Sik;Kim, Chang-Min
    • 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.

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Glucosylation of Isoflavonoids in Engineered Escherichia coli

  • Pandey, Ramesh Prasad;Parajuli, Prakash;Koirala, Niranjan;Lee, Joo Ho;Park, Yong Il;Sohng, Jae Kyung
    • Molecules and Cells
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    • v.37 no.2
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    • pp.172-177
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    • 2014
  • A glycosyltransferase, YjiC, from Bacillus licheniformis has been used for the modification of the commercially available isoflavonoids genistein, daidzein, biochanin A and formononetin. The in vitro glycosylation reaction, using UDP-${\alpha}$-D-glucose as a donor for the glucose moiety and aforementioned four acceptor molecules, showed the prominent glycosylation at 4' and 7 hydroxyl groups, but not at the $5^{th}$ hydroxyl group of the A-ring, resulting in the production of genistein 4'-O-${\beta}$-D-glucoside, genistein 7-O-${\beta}$-D-glucoside (genistin), genistein 4',7-O-${\beta}$-D-diglucoside, biochanin A-7-O-${\beta}$-D-glucoside (sissotrin), daidzein 4'-O-${\beta}$-D-glucoside, daidzein 7-O-${\beta}$-D-glucoside (daidzin), daidzein 4', 7-O-${\beta}$-D-diglucoside, and formononetin 7-O-${\beta}$-D-glucoside (ononin). The structures of all the products were elucidated using high performance liquid chromatography-photo diode array and high resolution quadrupole time-of-flight electrospray ionization mass spectrometry (HR QTOF-ESI/MS) analysis, and were compared with commercially available standard compounds. Significantly higher bioconversion rates of all four isoflavonoids was observed in both in vitro as well as in vivo bioconversion reactions. The in vivo fermentation of the isoflavonoids by applying engineered E. coli $BL21(DE3)/{\Delta}pgi{\Delta}zwf{\Delta}ushA$ overexpressing phosphoglucomutase (pgm) and glucose 1-phosphate uridyltransferase (galU), along with YjiC, found more than 60% average conversion of $200{\mu}M$ of supplemented isoflavonoids, without any additional UDP-${\alpha}$-D-glucose added in fermentation medium, which could be very beneficial to large scale industrial production of isoflavonoid glucosides.

A New Monoterpene Glucoside from Portulaca oleracea

  • Seo, Young-Wan;Shin, Jong-Heon;Cha, Hyo-Jun;Kim, You-Ah;Ahn, Jong-Woong;Lee, Burm-Jong;Lee, Dong-Seok
    • 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.

Phytochemical Studies on Epimedii Herba (II)$^1$ -Studies on the Underground Parts of Epimedium koreanum- (음양곽의 성분에 관한 연구(II)$^1$ -삼지구엽초 지하부의 성분-)

  • Kang, Sam-Sik;Kim, Ju-Sun;Kang, Yoon-Jung;Han, Hye-Kyoung
    • Korean Journal of Pharmacognosy
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    • v.21 no.1
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    • pp.56-59
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    • 1990
  • n-Alkanes (n-nonacosane and n-hentriacontane), phytosterols (campesterol and ${\beta}$-sitosterol) and phytosteryl glucosides (${\beta}$-sitosterol 3-O-${\beta}$-D-glucopyranoside and campesterol 3-O-${\beta}$-D-glucopyranoside) were isolated from the underground parts of Epimedium koreanum (Berberidaceae) and characterized by spectral data.

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Retro-synthesis of Analogues of Ginsenosides (역합성법에 의한 진세노사이드 유사체의 합성)

  • Chang, Eun-Ha;Je, Nam-Gyung;Im, Kwang-Sik
    • YAKHAK HOEJI
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    • v.40 no.2
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    • pp.163-169
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    • 1996
  • Glycosidation of 20(S)-protopanaxadiol obtained by the alkaline hydrolysis of total ginsenosides with 2,3,4,6-tetra-O-acetyl-${\alpha$-D-glucopyranosyl bromide in the presence of $CdCO_3$ in benzene-dioxane gave a mixture of acetylated monoglucosides and diglucosides in a total yield of 68%. Under the same condenstion condition, 20-dehydroxyglucosides were formed by dehydration of 12-O-glucosides. The structures of produced glycosides were elucidated as 3-O-${\beta$-D-glucopyranosyl-20(S)-protopanaxadiol, 12-O-${\beta$-D-glucopyranosyl-dammar-20(22), 24-dien-$3{\beta},12{\beta}$-diol, 3,12-di-O-${\beta}$-D-glucopyranosyl-dammar-20(22), 24-dien-$3{\beta},\;12{\beta}$-diol, respectively.

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Isolation of Steroids and Flavonoids from the Herbs of Hypericum ascyron L. (물레나물로부터 Steroid 및 Flavonoid 성분의 분리)

  • Kwon, Sang-Hyuk;Yun, Sei-Young;Lee, Kyung-Tae;Park, Hee-Juhn
    • Korean Journal of Pharmacognosy
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    • v.31 no.1
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    • pp.39-44
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    • 2000
  • A sterol mixture, 3-O-glucosides of these sterols, 6'-O-fattyacyl ester of these sterol glucosides, kaempferol, quercetin and isoquercitrin were isolated from the whole plants of Hypericum ascyron L. The sterols were found to be a mixture of ${\beta}-sitosterol$, campesterol and stigmasterol by GC-MS. The kinds of fatty acids linked at 6'-OH of sterol glucoside ester mixture were shown to be palmitic acid, stearic acid, oleic acid and linoleic acid by GC-MS. Three flavonoids were identified by spectroscopic methods and comparisons of mixed mp and co-TLC with authentic specimens.

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Antioxidant Activity of Flavonoids and Their Glucosides from Sonchus oleraceus L.

  • Yin, Jie;Si, Chuan-Ling;Wang, Myeong-Hyeon
    • Journal of Applied Biological Chemistry
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    • v.51 no.2
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    • pp.57-60
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    • 2008
  • Eight compounds, including 2 flavones, luteolin (1) and apigenin (2), 2 flavonols, kaempferol (3) and quercetin (4), and 4 flavonoid glucosides, luteolin-7-O-${\beta}$-D-glucoside (5), apigetrin (6), astragalin (7), and isoquercitrin (8), isolated from the whole herb of Sonchus oleraceus L. were analyzed on the basis of chemical and spectroscopic evidence. This was the first time to report compounds 3, 4, 6, 7 and 8 from the Sonchus oleraceus L. The antioxidant activities of the isolated flavonoids and their glucoside derivatives were evaluated by DPPH free radical-scavenging assay, showing that compounds 1, 3, 4 and 8 exhibited stronger antioxidant activities compared with ${\alpha}$, tocopherol and curcumin. Flavonoids containing more hydroxyl groups exhibited better antioxidant activities. The antioxidant activity of flavonols was superior to their corresponding flavones, and that of aglycone are more potent than their glucoside derivatives.