• Title/Summary/Keyword: Glycosides

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Pharmacological Activities and Applications of Spicatoside A

  • Ramalingam, Mahesh;Kim, Sung-Jin
    • Biomolecules & Therapeutics
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    • v.24 no.5
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    • pp.469-474
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    • 2016
  • Liriopogons (Liriope and Opiopogon) species are used as a main medicinal ingredient in several Asian countries. The Liriopes Radix (tuber, root of Liriope platyphylla) has to be a promising candidate due to their source of phytochemicals. Steroidal saponins and their glycosides, phenolic compounds, secondary metabolites are considered of active constituents in Liriopes Radix. Spicatoside A, a steroidal saponin, could be more efficacious drug candidate in future. In this review, we summarized the available knowledge on phytochemical and pharmacological activities for spicatoside A. It significantly suppressed the level of NF-${\kappa}B$, NO, iNOS, Cox-2, IL-$1{\beta}$, IL-6 and MAPKs in LPS-stimulated inflammation. The production of MUC5AC mucin was increased. MMP-13 expression was down-regulated in IL-$1{\beta}$-treated cells and reduced glycosaminoglycan release from IL-$1{\alpha}$-treated cells. The neurite outgrowth activity, PI3K, Akt, ERK1/2, TrkA and CREB phosphorylation and neurotropic factors such as NGF and BDNF were upregulated with increased latency time. It also showed cell growth inhibitory activity on various carcinoma cells. From this, spicatoside A exerts anti-inflammation, anti-asthma, anti-osteoclastogenesis, neurite outgrowth, memory consolidation and anticancer activities. Further studies are needed on spicatoside A in order to understand mechanisms of action to treat various human diseases.

The Glycosides of Araliaceaus Drugs and their Biological Activities

  • Hahn, Dug-Ryong;Kasai, Ryoji;Kim, Jeung-Hee;Taniyasu, Shigenori;Tanaka, Osamu;Kim, Chang-Johng;Park, Myong-Ja
    • Korean Journal of Pharmacognosy
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    • v.17 no.1
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    • pp.78-84
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    • 1986
  • Among the Araliaceae plants indigenous to Korea, those whose medicinal usage are comparatively high have been selected in this serial studies. Chiisanoside and acanthoside D were isolated and identified from the Acanthopanax chinensis leaves and root bark. Chiisanoside and acanthoside D have been found to have the lowering S-GPT, S-GOT value and BSP-retention rate and survival rate, anti-histaminic effect in the toxic state through the bio-pharmacological experiments. ${\alpha}-hederin$, hederagenin pentaglycoside were isolated both stem bark of Kalopanax pictum Nakai var. magnificum and Kalopanax pictum Nakai var. Max. respectively. Syringoside, acanthoside D were also isolated from the root bark of Acanthopanax koreanum. The biological activity of ginsenoside $Rb_1$, $Rg_1$, Re were examined. Ginsenoside $Rb_1$, $Rg_1$, Re promotes the antileaking effect in X-ray (Co 60) irradiated toxic state.

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Phytochemical Study of Hot-Water Extract of Perillae Folium (자소엽(Perillae Folium) 열수추출물의 식물화학성분 연구)

  • Kil, Hyun Woo;Rho, Taewoong;Yoon, Kee Dong
    • Korean Journal of Pharmacognosy
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    • v.51 no.1
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    • pp.55-64
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    • 2020
  • In this study, 15 compounds were elucidated from the hot-water extract of Perillae Folium. Fifteen isolates were determined to be protocatechuic acid (1), caffeic acid (2), (R)-rosmarinic acid (3), (S)-shisoflavanone A (4), luteolin-7-O-β-D-glucuronopyranoside (5), scutellarein-7-O-β-D-glucuronopyranoside (6), apigenin-7-O-β-D-glucuronopyranosyl(1→2)-O-β-D-glucuronopyranoside (7), luteolin-7-O-β-D-glucuronopyranosyl(1→2)-O-β-D-glucuronopyranoside (8), kelampayoside A (9), trans-N-feruloyloctopamine (10), 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl]acrylamide (11), perilloside C (12), perilloside A (13), (6S,9R)-9-hydroxy-megastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside (14) and (6S,9R)-roseoside (15) through spectroscopic evidences. The HPLC analysis revealed that hot-water extract of Perillae Folium contained caffeic acid, rosmarinic acid and glycosides of apigenin, luteolin and scutellarein as main constituents.

Structure-Activity Relationship of Triterpenoids Isolated from Mitragyna stipulosa on Cytotoxicity

  • Tapondjou, Leon Azefack;Lontsi, David;Sondengam, Beiham Luc;Choudhary, Muhammad Iqbal;Park, Hee-Juhn;Choi, Jong-Won;Lee, Kyung-Tae
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.270-274
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    • 2002
  • Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid $3-O-{\beta}-D-glucopyranoside$ (3, quinovin glycoside C), quinovic acid 3-O-[$(2-O-sulfo)-{\beta}-D-quinovopyranoside$] (4, zygophyloside D) and quinovic acid $3-O-{\beta}-D-quinovopyranosyl-27-O-{\beta}-D-glucopyranosyl$ ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.

Antioxidative Flavonoids from Leaves of Carthamus tinctorius

  • Lee, Jun-Young;Chang, Eun-Ju;Kim, Hyo-Jin;Park, Jun-Hong;Choi, Sang-Won
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.313-319
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    • 2002
  • A total of eight flavonoids (1-8), including a novel $quercetin-7-o-(6"-o-acetyl)-{\beta}-D-glucopyranoside$ (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin $7-o-{\beta}-D-glucopyranoside$ (3), $luteolin-7-o-(6"-Ο-acetyl)-{\beta}-D-glucopyranoside$ (4) quercetin $7-o-{\beta}-D-glucopyranoside$ (5), acacetin 7-o-{\beta}-D-glucuronide (7) and apigenin-6-C-{\beta}-D-glucopyrano $syl-8-C-{\beta}-D-glucopyranoside$ (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.

Cytotoxic Phenolic Constituents of Acer tegmentosum Maxim

  • Park, Ki-Myun;Yang, Min-Cheol;Lee, Kyu-Ha;Kim, Kyung-Ran;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.29 no.12
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    • pp.1086-1090
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    • 2006
  • The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-${\alpha}$-L-lyxoside (5), p-hydroxy phenylethyl-O-${\beta}$-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-${\beta}$-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-${\beta}$-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl ${\beta}$-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with $ED_{50}$ values ranging from $1.32\;to\;3.85\;{\mu}M$.

Studies on the Constituents of Ulmus parvifolia (참느릅나무의 성분에 관한 연구)

  • Moon, Young-Hee;Rim, Gi-Ryong
    • Korean Journal of Pharmacognosy
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    • v.26 no.1
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    • pp.1-7
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    • 1995
  • The bark of Ulmus parvifolia Jacq. (Ulmaceae) has been used for the treatment of gonorhea, edema, scabies and eczema marginatum. Previous investigations conducted with the heartwood and leaves have demonstrated it to contain sesquiterpenes as well as fat acids from the heartwood and flavonol glycosides from leaves. However, no phytochemical work has been done on the bark parts of this plant. Investigation of the phytochemical constituents in the barks of U. parvifolia has resulted in the isolation of sterols, sterol glucoside and a catechin glycoside, $(+)-catechin\;7-O-{\alpha}-{_L}-rhamnopyranoside$, all of which were isolated for the first time from this plant. Sterols were consisted of the three components, ${\beta}-sitosterol$, stigmasterol and campesterol in a ratio of 92.1:4.1:3.8, and sterol glucoside was identified as ${\beta}-sitosterol\;3-O-{\beta}-{_D}-glucoside$. The structure of the catechin $7-O-{\alpha}-{_L}-rhamnoside$ was established primarily by analysis of $^1H-and$ COSY-45 NMR, HMQC and HMBC and EI mass spectra of the heptaacetate. Especially, HMBC spectrum provides effective way for the determination of the point of attachment of the rhamnosyl group to catechin moiety.

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Advances in the Field of Thermal Procedures in Direct Combination with Thin-layer Chromatography

  • Stahl, Egon
    • Korean Journal of Pharmacognosy
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    • v.7 no.1
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    • pp.3-13
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    • 1976
  • The hitherto existing gap in the field of chromatographic methods has been filled by the direct coupling of a suitable oven (TAS-oven) with TLC. The sample to be examined is heated either isothermally or linearly within the temperature gradient of $50{\sim}450^{\circ}C$. The volatile and/or thermolytically evolved substances are fractionated on the TLC-layer and subsequently chromatographed under standard conditions. Transport mechanisms from the sample to the TLC-layer, applications of the TAS-procedure and further developments are discussed. Thermofractography, developed from the TAS-procedure, is demonstrated on different groups of natural substances such as alkaloids, amino acids, nucleic acids. nucleosides, nucleotides, triglycerides and other lipids, pyrone glycosides and aglycon. Experimental work and results on the thermolysis of macromolecular natural and synthetic substances, natural polyphenols, tanning agents and leather and the possibilities of differentiating various lignins, carbohydrate and synthetic polymers are reported. Further, it is shown that classical reactions in the microgram range, e.g. zinc dust distillation, sulphur-and selenium dehydrogenation and catalytic dehydrogenation, can be coupled directly with TLC. Also described is a method which allows to investigate the gaseous compounds evolved during thermofractography in the range of up to $450^{\circ}C$. Thermal procedures coupled with TLC open up the following new possibilities for chemical microanalysis: fractionated separation of distillable and sublimable components, fractionated thermolysis and carrying out of thermal reactions in the ultra micro range.

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Distribution of chitinases and characterization of two chitinolytic enzymes from one-year-old Korean Ginseng (Panax ginseng C.A. Meyer) roots

  • Moon, Jong-Kook;Han, Beom-Ku;Kim, T. Doo-Hun;Jo, Do-Hyun
    • BMB Reports
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    • v.43 no.11
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    • pp.726-731
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    • 2010
  • We report the tissue-specific distribution of chitinolytic activity in Korean ginseng root and characterize two 31-kDa chitinolytic enzymes. These two enzymes (SBF1 and SBF2) were purified 70- and 81-fold with yields of 0.75 and 1.25%, respectively, and exhibited optimal pH and temperature ranges of 5.0-5.5 and 40-$50^{\circ}C$. With [$^3H$]-chitin as a substrate, $K_m$ and $V_{max}$ values of SBF1 were 4.6 mM and 220 mmol/mg-protein/h, respectively, while those of SBF2 were 7.14 mM and 287 mmol/mg-protein/h. The purified enzymes showed markedly less activity with p-nitrophenyl-N-acetylglucosaminide and fluorescent 4-methylumbelliferyl glycosides of D-N-acetylglucosamine oligomers than with [$^3H$]-chitin. End-product inhibition of both enzymes demonstrated that both are endochitinases with different N-acetylglucosaminidase activity. Furthermore, the $NH_2$-terminal sequence of SBF1 showed a high degree of homology with other plant chitinases whereas the $NH_2$-terminal amino acid of SBF2 was blocked.

Cloning and Expression of Glucose-1-Phosphate Thymidylyltransferase Gene (schS6) from Streptomyces sp. SCC-2136

  • Han, Ji-Man;Kim, Su-Min;Lee, Hyo-Jung;Yoo, Jin-Cheol
    • Journal of Microbiology and Biotechnology
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    • v.17 no.4
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    • pp.685-690
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    • 2007
  • The deoxysugar biosynthetic gene cluster of Sch 47554/Sch 47555 was cloned from Streptomyces sp. SCC-2136. One of the ORFs, schS6, appeared to encode glucose-1-phosphate thymidylyltransferase, which converts dTTP and glucose-1-phosphate to TDP-D-glucose and pyrophosphate. The dTDP-D-glucose is a key metabolite in prokaryotics as a precursor for a large number of modified deoxysugars, and these deoxysugars are a maj or part of various antibiotics, ranging from glycosides to macrolides. SchS6 was expressed in E. coli vector pSCHS6 and the expressed protein was purified to apparent homogeneity by ammonium sulfate precipitation and Ni-NTA affinity column chromatography. The specific activity of the purified enzyme increased 4.7-fold with 17.5% recovery. It migrated as a single band on SDS-PAGE with an apparent molecular mass of 56kDa. The purified protein showed glucose-1-phosphate thymidylyltransferase activity, catalyzing a reversible bimolecular group transfer reaction. In the forward reaction, the highest activity was obtained with combination of dTTP and ${\alpha}-D-glucose-1-phosphate$, and only 12% of that activity was obtained with the substrates $UTP/{\alpha}-D-glucose-1-phosphate$. In the opposite direction, the purified protein was highly specific for dTDP-D-glucose and pyrophosphate.