• Title/Summary/Keyword: C-glycosides

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A Novel Ginsenosidase from an Aspergillus Strain Hydrolyzing 6-O-Multi-Glycosides of Protopanaxatriol-Type Ginsenosides, Named Ginsenosidase Type IV

  • Wang, Dong-Ming;Yu, Hong-Shan;Song, Jian-Guo;Xu, Yu-Feng;Liu, Chun-Ying;Jin, Feng-Xie
    • Journal of Microbiology and Biotechnology
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    • v.21 no.10
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    • pp.1057-1063
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    • 2011
  • Herein, a novel ginsenosidase, named ginsenosidase type IV, hydrolyzing 6-O-multi-glycosides of protopanaxatriol-type ginsenosides (PPT), such as Re, R1, Rf, and Rg2, was isolated from the Aspergillus sp. 39g strain, purified, and characterized. Ginsenosidase type IV was able to hydrolyze the 6-O-${\alpha}$-L-($1{\rightarrow}2$)-rhamnoside of Re and the 6-O-${\beta}$-D-($1{\rightarrow}2$)-xyloside of R1 into ginsenoside Rg1. Subsequently, it could hydrolyze the 6-O-${\beta}$-D-glucoside of Rg1 into F1. Similarly, it was able to hydrolyze the 6-O-$_{\alpha}$-L-($1{\rightarrow}2$)-rhamnoside of Rg2 and the 6-O-${\beta}$-D-($1{\rightarrow}2$)-glucoside of Rf into Rh1, and then further hydrolyze Rh1 into its aglycone. However, ginsenosidase type IV could not hydrolyze the 3-O- or 20-O-glycosides of protopanaxadiol-type ginsenosides (PPD), such as Rb1, Rb2, Rb3, Rc, and Rd. These exhibited properties are significantly different from those of glycosidases described in Enzyme Nomenclature by the NC-IUBMB. The optimal temperature and pH for ginsenosidase type IV were $40^{\circ}C$ and 6.0, respectively. The activity of ginsenosidase type IV was slightly improved by the $Mg^{2+}$ ion, and inhibited by $Cu^{2+}$ and $Fe^{2+}$ ions. The molecular mass of the enzyme, based on SDS-PAGE, was noted as being approximately 56 kDa.

Simultaneous Determination of Asperosaponins and Iridoid Glycosides from Dipsaci Radix by Using LC-ESI-MS Spectrometry (속단(Dipsaci Radix) 중 Asperosaponins 및 Iridoid glycosides의 LC-ESI-MS에 의한 동시분석)

  • Cho, Hwang-Eui;Son, In-Seop;Kim, Sun-Cheun;Son, Kun-Ho;Woo, Mi-Hee;Moon, Dong-Cheul
    • Korean Journal of Pharmacognosy
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    • v.43 no.2
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    • pp.137-146
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    • 2012
  • Dipsaci Radix (Dipsacaceae) has been used as a tonic, an analgesic, anti-inflammatory and anti-complement agents in traditional herbal medicine for the therapy of low back pain, knee pain, rheumatic arthritis, traumatic hematoma, and bone fractures. A high-performance liquid chromatography-electrospray ionization-mass spectrometric method (HPLC-ESI-MS) was developed for the simultaneous quantitation method of the five compounds from the herbal drug: asperosaponin VI and asperosaponin XII (terpene glycosides), sweroside, loganin and dipsacus A(iridoid glycosides). HPLC separation of the analytes was achieved on a C18 column ($150{\times}2.0$ mm i.d., 5 ${\mu}m$) using the aqueous methanol containing 5 mM ammonium acetate with gradient flow of the mobile phase. Detection of the analytes was performed by positive ion electrospray ionization, and selected ion monitoring was used for data acquisition using m/z corresponding molecular adduct ion, $[M+NH_4]^+$ and $[M+H]^+$. Calibration graphs showed good linearity ($r^2$=0.9997) over the wide range of the analytes; intra- and inter-day precisions (RSD, %) were within 9.1% and the accuracy between 94.0-111.0%. Recoveries of the analytes through the assay procedure were in the range of 93.7-110.8%. Analytical results of the herbal drugs of Dipsaci Radix (17 samples) show wide distribution of the five marker compounds and clear difference of the species from Phlomidis Radix (4 samples). The developed method would provide a practical guide for the quality control of the herbal drug.

Studies on Synthesis and Accumulation Pattern of Cyannogenic Glycosides in Sorghum Piants (Sorghum 식물에 있어서 Cyanogenic Glycosides의 합성 및 축적에 관한 연구)

  • ;G. Voigtlaender
    • Journal of The Korean Society of Grassland and Forage Science
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    • v.5 no.2
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    • pp.121-126
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    • 1985
  • Phytotron and field experiments were conducted to determine the influence of morphological growth stage and environmental temperature on synthesis and accumulation pattern of cyanogenic glycosides in sorghum cv. Pioneer 931 and Sioux at Munich technical university from 1979 to 1980. Various growth stages of sorghum plants were grown in phytotron at 4 different temperature regimes of 30/25, 25/20, 28/18 and 18/8 degree C with 35,000 Lux over 13-h days. The results obtained are summarized as follows: 1. Cyanogenic glycosides in sorghum plants were shown to have a great synthetic rate at early growth stages. The highest concentrations of hydrocyanic acid (HCN) were found at 2-leaf stage with 2384 and 1800ppm (DM basis) for Pioneer 931 and Sioux respectively. The contents of HCN were, however, however decreased markedly as morphological development, which shows a value of 173ppm (Pioneer 931) and 70ppm (Sioux) at heading stages. 2. Changes of hydrocyanic acid in sorghum plants were positive correlated with leaf weight ratio and leaf area ratio ($P{\leqq}0.1%$), while plant height shows a negative correlation with HCN contents ($P{\leqq}0.1%$). 3. Cyanogenic glycosides were accumulated in young plants mainly in leaves. During the late maturities, the contents of HCN in leaves and stalks were shown, however, a similar distribution. 4. Synthesis rates of cyanogenic glycosides were increased under high temperature. Accumulated hydrocyanic acid in the plants was, however declined when temperature exceeded 30 degree C. 5. Synthesis rates of cyanogenic glycosides were affected by nitrogen reductase activity (NRA). The concentration of hydrocyanic acid in sorghum plants was associated with increasing of nitrate-N accumulation.

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Flavonoids from the Leaves of Betula platyphylla var. latifolia

  • Lee, Min-Won
    • Korean Journal of Pharmacognosy
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    • v.25 no.3
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    • pp.199-203
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    • 1994
  • Chemical examination of the leaves of Betula platyphylla var. latifolia has led to the isolation and characterization of five flavonoid glycosides including two C-glucosyl flavonoids. The structures of these compounds were elucidated as myricetin $3-O-{\alpha}-_L-rhamnoside$ (myricitrin), $quercetin-3-O-{\beta}-_D-glucopyranoside$ (isoquercitrin), $quercetin-3-O-{\beta}-_D-glucopyranoside$ (hyperoside), $nalingenin-6-C-{\beta}-_D-glucopyranoside$ (hemiphloin) and $aromadendrin-6-C-{\beta}-_D-glucopyranosidre(6-C-glucosyldihydrokaempferol)$ on the basis of physico-chemical and spectroscopic evidences.

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A Study on the Chemical Constituents of Acanthopanax koreanum Nakai and Its Pharmaco-biological Activities (Acanthopanax koreanum Nakai의 약효성분에 관한 연구)

  • 한덕룡;김창종;김정희
    • YAKHAK HOEJI
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    • v.29 no.6
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    • pp.357-361
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    • 1985
  • Two glycosides, assumed to be one of the potential active principles, is isolate from the root bark of Acanthopanax koreanu Nakai, identified to be acanthoside D, $C_{34}H_{46}O_{18}$, mp $242^{\circ}C$, and syringo side, $C_{17}H_{24}O_{9}$ mp $192^{\circ}C$. Acanthoside D has been found to have s-GPT, s-GOT lowering effect, BSP-retention rate and survival rate in the toxic state through the bio-pharmacological experiments.

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Flavone Glycosides from the Aerial Parts of Lespedeza cuneata G. Don (비수리 지상부로부터 분리한 Flavone glycosides)

  • Kwon, Dong-Joo;Kim, Jin-Kyu;Ham, Yeon-Ho;Bae, Young-Soo
    • Applied Biological Chemistry
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    • v.50 no.4
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    • pp.344-347
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    • 2007
  • The aerial parts of Lespedeza cuneata were collected, air-dried and extracted with 95% aqueous EtOH. Then it was successively partitioned with n-hexane, $CH_2Cl_2$, EtOAc and $H_2O$. Repeated Sephadex LH-20 column chromatography on the EtOAc- and $H_2O-soluble$ fractions gave four compounds. Their structures were elucidated as quercetin (1), kaempferol (2), desmodin (3) and homoadonivernith (4) on the basis of spectroscopic evidences such as $^{1}H-NMR$, $^{13}C-NMR$, 2D-NMR and MS spectrum. Desmodin (3) and homoadonivernith (4) have not been reported from this plant so far.

Synthesis of Glycosides by Transglycosylation of α-Amylase from Starch (전분으로부터 α-amylase에 의한 배당체의 합성)

  • Park, Jong Yi;Lee, Tae Ho
    • Korean Journal of Microbiology
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    • v.34 no.3
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    • pp.137-143
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    • 1998
  • Glycosides were synthesized using transglycosylation reaction of amylase in water system. The glycosides synthesized in water phase by a-amylase with starch as a glycosyl donor and benzylalcohol as an acceptor were identified as benzylalcohol-${\alpha}$-glucoside (BG) and benzylalcohol-${\alpha}$-maltoside (BM) of which one molecule of benzylalcohol was bound to 1-OH of glucose. The final products were BG in reaction system of pH 5.0, and BM in that of pH 8.0. The transglycosylation reaction by ${\alpha}$-amylase were carried out in water system containing 50 mg starch, 50 mg benzylalcohol, and 10 units enzyme at $30-35^{\circ}C$ for 3 days. The synthesized BG was hydrolyzed to glucose and benzylalcohol by ${\alpha}$-glucosidase, while ${\alpha}$-amylase hydrolyzed BM to glucose and benzylalcohol-${\alpha}$-glucoside in pH 5.0. Maltotriose resemble structurally to BM was rapidly hydrolyzed to glucose and maltose by ${\alpha}$-amylase at pH 5.0, being slightly hydrolyzed at pH 8.0, but not transglycosylated in present of benzylalcohol.

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Flvonoids and Their Glycosides from the Bark of Salix rorida (분버들(Salix rorida) 수피의 후라보노이드 및 배당체 화합물)

  • Ham, Yeon-Ho;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.30 no.1
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    • pp.56-62
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    • 2002
  • The air-dried bark of Salix rorida was extracted with acetone-water(7:3, v/v) and its extractives were concentrated with a vacuum evaporator. The extractives were fractionated with a series of n-hexane, chloroform, ethylacetate(EtOAc) and water on a separatory funnel. Each fraction was freeze-dried to give some dark brown powder. The EtOAc and water soluble fractions were chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. The isolated compounds were tested with a cellulose TLC developed with TBA and 6% acetic acid and then visualized on UV lamp or sprayed with vanillin-HCl-EtOH. The purified compounds were flavonoids and their glycosides as follows:(+)-catechin, naringenin, salipurposide, aromadendrin, isosalipurposide, aromadendrin-7-O-𝛽-D-glucopy- ranoside and taxifolin-7-O-𝛽-D-glucopyranoside. The structures of each compounds were confirmed by 1H-NMR, 13C-NMR and mass spectra.

Glycosides from the Flower of Clerodendrum trichotomum (누리장나무 꽃의 배당체 성분)

  • Lee, Jong-Wook;Bae, Jong Jin;Kwak, Jong Hwan
    • Korean Journal of Pharmacognosy
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    • v.47 no.4
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    • pp.301-306
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    • 2016
  • Four phenylpropanoid glycosides and a monoterpene glycoside were isolated from the flower of Clerodendrum trichotomum. Structures of the isolated compounds were identified as acteoside (1), martynoside (2), leucosceptoside A (3), isoacteoside (4) and neohancoside A (5) by spectroscopic analysis. Compounds 1-4 were isolated from the flower of C. trichotomum for the first time. Compound 5 was first obtained from genus Clerodendrum as well as family Verbenaceae. The antioxidant activity of compounds 1-5 were evaluated by the DPPH free radical scavenging assay. Compounds 1-4 exhibited strong antioxidant activity.

Synthesis and Antibacterial Activities of New S-glycosides Bearing 1,2,4-Triazole (1,2,4-Triazole기를 가지고 있는 S-glycoside들의 합성 및 항균활성시험)

  • Chao, Shu-Jun;Geng, Ming-Jiang;Wang, Ying-Ling
    • Journal of the Korean Chemical Society
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    • v.54 no.6
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    • pp.731-736
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    • 2010
  • Several new 5-aryl-3-($\beta$-D-glucopyranosylthio)-1,2,4-triazoles have been synthesized. The structures of these new compounds were confirmed by $^1H$ NMR, $^{13}C$ NMR and elemental analyses.The antibacterial activities of the compounds were also evaluated.