- PHENOL GLYCOSIDES AND THEIR USE IN THE TREATMENT OF UROLITHIASIS
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The present invention relates to novel derivatives of polyphenol glycoside or polyalcohols of formula (1), wherein R1, R2, R3 is selected from the group consisting of H, OH, C(O)R4, C(0) OR4, 0 (Gly H3)n, wherein n = 0 1, 2, 3, and R4 is selected from the group consisting of H, alkyl, and Gly is a mono- or disaccharide residue. The present invention also relates to novel derivatives of glycoside polyphenols or polyalcohols, as pharmaceutical composition comprising a novel polyphenol glycoside or polyalcohols and the use of novel polyphenol glycoside or polyalcohols for the treatment of urolithiasis.
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Page/Page column 26; 27; 28; 29
(2017/01/26)
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- A simple synthesis of 3-deoxyanthocyanidins and their O-glucosides
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This work deals with the chemical synthesis of simple analogs of anthocyanins, the main class of water-soluble natural pigments. Flavylium ions with hydroxyl, methoxyl and β-D-glucopyranosyloxyl substituents at positions 4′ and 7 have been prepared by straightforward chemical procedures. Moreover, the two 3-deoxyanthocyanidins of red sorghum apigeninidin (4′,5,7-trihydroxyflavylium) and luteolinidin (3′,4′,5,7-tetrahydroxyflavylium) were synthesized in a one-step protocol. Attempts to synthesize luteolinidin O-β-D-glucosides resulted in a mixture of the 5-O- and 7-O-regioisomers in low yield. A preliminary study of the 4′-β-D-glucopyranosyloxy-7-hydroxyflavylium and 7-β-D-glucopyranosyloxy-4′-hydroxy-flavylium ions shows that simply changing the glucosidation site can profoundly affect the color intensity and stability.
- Al Bittar, Sheiraz,Mora, Nathalie,Loonis, Michèle,Dangles, Olivier
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p. 4294 - 4302
(2016/07/06)
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- 6″-Galloylpicein and other phenolic compounds from Arctostaphylos uva-ursi
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Phenolic compounds from leafy shoots of A. uva-ursi (Ericaceae) were studied. The new phenolic glycoside 6″-galloylpicein and 40 known compounds were isolated. Roots of A. uva-ursi afforded 16 compounds. A C-glycoside of bergenin was found for the first time in the family Ericaceae. The dominant components of A. uva-ursi leaves according to HPLC were arbutin, (+)-catechin, and corilagin; of stems, picein and (+)-gallocatechingallate; of roots, (-)-epicatechin, (-)-epicatechingallate, and (+)-catechin.
- Olennikov,Chekhirova
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- Effective friedel-crafts acylations of O- and C-arylglycosides with triflic acid
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Triflic acid is well known not only as a Friedel-Crafts promoter, but also as a deglycosidation reagent. In this study, we promote effective Friedel-Crafts acylations for O- or C-arylglucosides without deglycosidation and check their inhibitory activities for β-glucosidase.
- Hashimoto, Makoto,Takahashi, Miho
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scheme or table
p. 227 - 231
(2009/09/06)
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- A mild and selective method for cleavage of O-acetyl groups with dibutyltin oxide
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A mild and efficient neutral method for the cleavage of O-acetyl groups with dibutyltin oxide has been developed. This method is especially useful in the synthesis of glycosides containing base- or acid-sensitive multifunctional groups.
- Liu, Hong-Min,Yan, Xuebin,Li, Wen,Huang, Conghai
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p. 1763 - 1767
(2007/10/03)
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- Structure and reactivity of glycosides: IV. Koenigs-Knorr synthesis of aryl β-D-glucopyranosides using phase-transfer catalysts
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A series of acetylated aryl β-D-glucopyranosides were prepared in 12-63% yields from tetra-O-acetyl-α-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols. 2001 MAIK "Nauka/Interperiodica".
- Pavlov,Sokolov,Zakharov
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p. 1811 - 1814
(2007/10/03)
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- Phenolic and triterpenoid glycosides from Aster batangensis
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A new phenolic glycoside, asterbatanoside A [p-hydroxyacetophenone-4-O-β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside], and two new triterpenoid saponins, asterbatanoside B [2α,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside] and asterbatanoside C [3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28- oicacid-28-O-β-D-glucopyranoside] were isolated from the roots of Aster batangensis. Their structures were determined by spectroscopic methods and chemical evidence. The total synthesis of asterbatanoside A is also reported. Copyright
- Shao, Yu,Li, Yun Long,Zhou, Bing Nan
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p. 1593 - 1598
(2007/10/03)
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- GLYCOSYLATION OF PHENOLIC COMPOUNDS BY ROOT CULTURE OF PANAX GINSENG
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A root culture of Panax ginseng was able to convert 3,5-dimethoxyphenol (taxicatigenin) into its glucoside (taxicatin), primeveroside and gentiobioside, methyl salicylate into its glucoside and gentiobioside, p-hydroxyacetophenone into its glucoside (picein), and coniferyl alcohol into dihydroconiferin propan-1-ol>.The conversion ratio and the excretion ratio of the conversion products from methyl salicylate were higher than those from the more polar p-hydroxyacetophenone, 3,5-dimethoxyphenol and coniferyl alcohol.Among the conversion products, in particular, the excretion ratio (ER) of a glucoside into the medium decreased in proportion to the quotient of substrate's Mr divided by its RRt on reversed phase HPLC (-ERMr/RRt).Key Word Index - Panax ginseng; Araliaceae; ginseng; root culture; biotransformation; glycosylation; glucoside; primeveroside; gentiobioside; 3,5-dimethoxyphenol; methyl salicylate; p-hydroxyacetophenone.
- Ushiyama, Masashi,Furuya, Tsutomu
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p. 3009 - 3014
(2007/10/02)
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- STRUCTURES AND ACCUMULATION PATTERNS OF SOLUBLE AND INSOLUBLE PHENOLICS FROM NORWAY SPRUCE NEEDLES
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Key Word Index - Picea abies; Pinaceae; Norway spruce; phenolics; identification; seasonal accumulation pattern; turnover; translocation; cell wall localization; flavonol glucosyltransferase. - Abstract - Twenty-two soluble phenolics have been isolated from Norway spruce needles and their structures elucidated on the basis of chromatographic (TLC, HPLC), chemical (hydrolysis), enzymic and spectroscopic (UV, NMR, MS) techniques.These phenolics have been quantified by HPLC during the first year of needle development from a forest near Bad Muenstereifel (F.R.G.) and showed a differential accumulation pattern.Kaempferol 3-O-glucoside showed an interesting metabolism, indicating rapid turnover and/or translocation from a soluble to an insoluble (cell wall bound) pool.The enzyme involved in the formation of this flavonoid, UDP-glucose:flavonol glucosyltransferase, showed a marked transient increase in activity that correlated with the possible kaempferol 3-O-glucoside translocation.
- Strack, Dieter,Heilemann, Juergen,Wray, Victor,Dirks, Herbert
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p. 2071 - 2078
(2007/10/02)
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