• Title/Summary/Keyword: C-glycosides

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C-Glycoside-Metabolizing Human Gut Bacterium, Dorea sp. MRG-IFC3

  • Huynh Thi Ngoc Mi;Santipap Chaiyasarn;Heji Kim;Jaehong Han
    • Journal of Microbiology and Biotechnology
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    • v.33 no.12
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    • pp.1606-1614
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    • 2023
  • Biochemical gut metabolism of dietary bioactive compounds is of great significance in elucidating health-related issues at the molecular level. In this study, a human gut bacterium cleaving C-C glycosidic bond was screened from puerarin conversion to daidzein, and a new, gram-positive C-glycoside-deglycosylating strain, Dorea sp. MRG-IFC3, was isolated from human fecal sample under anaerobic conditions. Though MRG-IFC3 biotransformed isoflavone C-glycoside, it could not metabolize other C-glycosides, such as vitexin, bergenin, and aloin. As evident from the production of the corresponding aglycons from various 7-O-glucosides, MRG-IFC3 strain also showed 7-O-glycoside cleavage activity; however, flavone 3-O-glucoside icariside II was not metabolized. In addition, for mechanism study, C-glycosyl bond cleavage of puerarin by MRG-IFC3 strain was performed in D2O GAM medium. The complete deuterium enrichment on C-8 position of daidzein was confirmed by 1H NMR spectroscopy, and the result clearly proved for the first time that daidzein is produced from puerarin. Two possible reaction intermediates, the quinoids and 8-dehydrodaidzein anion, were proposed for the production of daidzein-8d. These results will provide the basis for the mechanism study of stable C-glycosidic bond cleavage at the molecular level.

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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Quercetin Glycosides from Bark of Maple (Acer komarovii Pojark.)

  • Kwon, Dong-Joo;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.37 no.2
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    • pp.171-176
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    • 2009
  • The chemical constituents of Acer komarovii Pojark. which belongs to Aceraceae has never been reported. The bark of A. komarovii was extracted with 70% aqueous acetone, and the concentrated extract was successively partitioned with n-hexane, dichloromethane, ethyl acetate and $H_2O$. From the ethyl acetate soluble fraction, four compounds were isolated by the repeated Sephadex LH-20 and RP C-18 column chromatography. From the results of spectroscopic methods including FAB-MS, 1D and 2D NMR, the structures of the compounds were determined as quercetin (1), guaijaverin (2), hirsutrin (3) and hyperin (4). These compounds (1-4) have not been reported in this tree yet.

A New Steroidal Glycoside from Allium macrostemon Bunge

  • Kim, Yun Sik;Cha, Joon Min;Kim, Dong Hyun;Lee, Tae Hyun;Lee, Kang Ro
    • Natural Product Sciences
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    • v.24 no.1
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    • pp.54-58
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    • 2018
  • A phytochemical investigation of Allium macrostemon Bunge (Liliaceae) afforded the new pregnane steroidal glycoside, named allimacroside F (1), along with three known glycosides, benzyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (2), phenylethyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (3), (Z)-3-hexenyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (4). The identification and structural elucidation of a new compound (1) was carried out based on spectral data analyses ($^1H-NMR$, $^{13}C-NMR$, $^1H-^1H$ COSY, HSQC, HMBC, and NOESY) and HR-FAB-MS.

In vivo Anti-metastatic Action of Ginseng Protopanaxadiol saponins is Based on Their Intestinal Bacterial Metabolites After Oral Administration

  • Saiki, Ikuo
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1998.11a
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    • pp.95-98
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    • 1998
  • Ginseng (the root of Panax ginseng C. A. MEYER, Araliaceae) has been used for traditional medicine in China, Korea, Japan and other Asian countries for the treatment of various diseases including psychiatric and neurologic diseases as well as diabetes mellitus. So far, ginseng saponins (ginsenosides) have been regarded as the principal components responsible for the pharmacological activities of ginseng. Ginsenosides are glycosides containing an aglycone (protopanaxadiol or protopanaxatriol) with a dammarane skeleton and have been shown to possess various biological activities including the enhancement of cholesterol biosynthesis, stimulation of serum protein synthesis, immuno- modulatory effects and anti-inflammatory activity. Several studies using ginsenosides have also reported anti-tumor effects, particularly the inhibition of tumor-induced angiogenesis, tumor invasion and metastasis, and the control of phenotypic expression and differentiation of tumor cells.

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Phytochemistry and Pharmacology of Moringa oleifera Lam

  • Paikra, Birendra Kumar;Dhongade, Hemant kumar J.;Gidwani, Bina
    • Journal of Pharmacopuncture
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    • v.20 no.3
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    • pp.194-200
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    • 2017
  • Moringa oleifera Lam. or munga is one of the most important plant widely cultivated in India. It belongs to family Moringaceae. This plant is widely used as nutritional herb and contains valuable pharmacological action like anti-asthmatic, anti-diabetic, hepatoprotective, anti-inflammatory, anti-fertility, anti-cancer, anti-microbial, anti-oxidant, cardiovascular, anti-ulcer, CNS activity, anti-allergic, wound healing, analgesic, and antipyretic activity, Moringa oleifera Lam. The plant is also known as Horse - radish tree, Drumstick tree. Every part of this plant contains a valuable medicinal feature. It contain rich source of the vitamin A, vitamin C and milk protein. Different types of active phytoconstituents like alkaloids, protein, quinine, saponins, flavonoids, tannin, steroids, glycosides, fixed oil and fats are present. This plant is also found in the tropical regions. Some other constituents are niazinin A, niazinin B and niazimicin A, niaziminin B. The present review discusses the phytochemical composition, medicinal uses & pharmacological activity of this plant.

Studies on the Effect of Ginseng Extract on Chick Embryonic Nerve and Muscle Cells (인삼이 신경 및 근육 세포에 미치는 영향에 대한 연구)

  • 김영중;김은경
    • YAKHAK HOEJI
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    • v.24 no.3_4
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    • pp.143-150
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    • 1980
  • The effect of ginseng saponin on chick embryonic dorsal root ganglia organ culture and brain, spinal cord, muscle dissociation cultures was studied. The fiber outgrowth in explanted chick embryonic dorsal root ganglia was markedly induced by water and alcohol extracts of ginseng, total ginseng saponin, protopanaxadiol and protopanaxatriol glycosides as well as ginsenosides R/sub b1/, R/sub d/, R/sub 0/+R/sub a/+R/sub b1/, and R/sub b2/+R/sub c/+R/sub e/ mixtures. The life span of the cultured chick embryonic dorsal root ganglia and potentiation of nerve cell density were also observed with all of these ginseng saponins. The effect of ginseng saponin on chick embryonic dorsal root ganglia organ culture was more marked in the absence of the chick embryonic extract which was known to contain nerve growth factor-like material in the culture media. However, the ginseng saponin did not influence the cultured central nervous system such as brain and spinal cord cells and cultured skeletal muscle cells with respect to the morphological changes, maturation and life span of these cells.

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Chemical Composition and Pharmacological Activities of Vietnamese Ginseng, Panax viehamensis

  • Duc, Nguyen-Minh;Nham, Nguyen-Thoi
    • Proceedings of the Ginseng society Conference
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    • 1998.06a
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    • pp.127-137
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    • 1998
  • From the underground part of Panax vietnamensis Ha et Grushv., commonly known as Vietnamese ginseng, 50 triterpene glycosides including 24 new dammarane saponins named visa-ginsenosides-Rl-24 were isolated and identified. The structure of the new saponins was elucidated based on chemical and spectroscopic evidence. The saponin composition of Vietnamese ginseng is almost similar to that of ginseng (Panax ginseng C.A. Meyer) and other cultivated Panax spp. However, the content of ocotillos-type saponins, especially that of the major saponin, majonoside-R2 (5.29% yield), was surprisingly very high. The pharmacological activities of Vietnamese ginseng are essentially similar to those of ginseng. In addition, it has marked antibacterial activity against pathogenic Streptococcus app. and is effective in treatment of granular angina. The chemical composition and pharmacological activities have made Vietnamese ginseng an interesting member of Panax spp. from chemotaxonomical and pharmacological points of view,

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A Modified Alkaline Hydrolysis of Total Ginsenosides Yielding Genuine Aglycones nad Prosapogenols

  • Im, kwang-Sik;Chang, Eun-Ha;Je, Nam-Gyung
    • Archives of Pharmacal Research
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    • v.18 no.6
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    • pp.454-457
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    • 1995
  • To improve the yield of genuine aglycones from glycosides, the conditions of alkaline hydrolysis were investigated, and a modified method was established. The modified method empolyed pyridine as an aprotic solvent. To complete the hydrolysis and obtain 20(S)-protopanaxadiol (1) and 20(S)-protopanaxatriol(2), which are the genuine aglycones of ginsenosides, total ginsenosides were refluxed with sodium methoxide in pyridine. Addition of methanol, a protic polar solvent to the reaction miuxture, led partial hydrolysis yielding a mixture of the genuine prosapogenols. Of the prosapogenols compound 3 and 6 characteristically possessed D-glucopyranosyl moiety attached at the sterically hindered C-20 hydroxyl group. 3 and 6 were not obtaijned by other hydrolysisw methods except by the soil bacterial hydrolysis.

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Post-coital antiimplantation and pregnancy interruption potency of the seeds of Crotalaria juncea Linn

  • Malashetty, Vijaykumar B.;A., Sharanabasappa;Patil, Saraswati B.
    • Advances in Traditional Medicine
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    • v.4 no.2
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    • pp.70-76
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    • 2004
  • Petroleum ether, benzene and alcohol extracts of the seeds of C. juncea were tested for antiimplantation and pregnancy interruption activities in female albino rats. Of these three extracts, the alcohol extract was found to be the most effective in causing antiimplantation and pregnancy interruption activities. These adverse effects on fertility are reversible upon withdrawal of the extract treatments. The alcohol extract was found to possess estrogenic activity. After subjecting to preliminary phytochemical screening, the alcohol extract showed positive tests for alkaloids, steroids, glycosides, saponins, flavonoides, fixed oils, phenols and tannins.