- High-Field Formation of Arbutin from Hydroquinone by Cell-Suspension Cultures of Rauwolfia serpentina
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High-density cell-suspension cultures of Rauwolfia serpentina cultivated in a nutrition medium optimized for the production of the glucoalkaloid raucaffricine synthesize hydroquinone glycosides from continuously added hydroquinone with a total yield of 23.87 g/l (18 g/l of arbutin and 5.87 g/l of a hydroquinone diglycoside) in 7 days.This arbutin production is by far the highest formation of a natural product by plant-cell-culture systems reported to date.
- Lutterbach, Ralf,Stoeckigt, Joachim
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Read Online
- α-Glucosidic hydroquinone derivatives from Viburnum erosum
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Six undescribed compounds (1–6) were isolated from the leaves of Viburnum erosum along with four known compounds 7–10. The structures were determined by NMR and MS spectroscopic analyses, and their absolute configurations were established by chemical and
- Choi, Seong Yeon,Jang, Hyeon Seok,Jeong, Birang,Kim, Juyeol,Kwon, Yong Soo,Lee, Jiho,Park, Jinyoung,Yang, Heejung
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- Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates
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Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.
- Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi
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p. 838 - 847
(2021/02/09)
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- Preparation method of glucoside and derivatives thereof
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The invention discloses a preparation method of glucoside and derivatives thereof. According to the method, all hydroxyl groups on a sugar molecule structure are acetylated, a ligand containing phenolic hydroxyl groups is prepared at the same time, then boron trifluoride-diethyl ether is used as a catalyst, the two substances are condensed to obtain tetraacetylated glucoside, and finally acetyl protecting groups are removed to obtain the required glucoside. The method can selectively catalyze hemiacetal hydroxyl of monosaccharide to react with hydroxyl to obtain glucoside, and the product is single. The method is simple in production operation and low in equipment requirement, can be used for synthesizing glucoside and derivatives thereof with similar structures, is green and environment-friendly, and can be used for large-scale production.
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Paragraph 0040; 0043
(2020/04/02)
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- Method for chemically synthesizing beta-arbutin
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The invention provides a method for chemically synthesizing beta-arbutin. The synthesis method includes the following steps: using D-glucose and acetic anhydride as raw materials, and carrying out reaction under the catalysis of molecular iodine to obtain a penta-acetyl glucose anomer mixture; subjecting the mixture without isolation and 4-Methoxyphenol to reaction under the catalysis of boron trifluoride diethyl etherate to obtain 4-Methoxyphenyl-2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside, dissolving the 4-Methoxyphenyl-2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside in anhydrous methanol, andremoving the acetyl group on the sugar ring and the methoxy group on the benzene ring under the conditions of sodium methoxide and cuprous oxide, thereby obtaining beta-arbutin. The method has the advantages of convenient operation, less discharge of the three wastes (waste gas, waste water and industrial residue), high yield and low cost, and the method is suitable for industrial production.
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Paragraph 0004; 0006-0010
(2020/02/10)
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- Preparation of salidroside with n-butyl β-D-glucoside as the glycone donor via a two-step enzymatic synthesis catalyzed by immobilized β-glucosidase from bitter almonds
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β-Glucosidase from bitter almonds was immobilized on epoxy group-functionalized beads for catalyzing salidroside synthesis in a two-step process with n-butyl-β-D-glucoside (BG) as the glucosyl donor. The formation of salidroside ((0.59 ± 0.02) M) at a yield of 39.04%±1.25% was accomplished in 8 h by the transglucosylation of immobilized β-glucosidase at pH?8.0 and 50 °C when the ratio of BG to tyrosol was 1:2 (mol/mol). A study on the influence of different glycosyl acceptors demonstrated that the yield of the glucosylation reaction of phenylmethanol and cyclohexanol was higher than that of either phenol or cyclohexanol. This may account for the selectivity of the immobilized enzyme towards the alcoholic hydroxyl group of tyrosol in the salidroside synthesis reaction. A study on the synthesis of BG via the reverse hydrolysis of immobilized β-glucosidase showed that a yield of 78.04%±2.2% BG can be obtained with a product concentration of (0.23 ± 0.015) M.
- Wang, Feng,Huang, Dengfa,Ma, Yong,Zhang, Fuming,Linhardt, Robert J.
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p. 246 - 260
(2019/02/03)
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- Chemo- and Regioselective Dihydroxylation of Benzene to Hydroquinone Enabled by Engineered Cytochrome P450 Monooxygenase
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Hydroquinone (HQ) is produced commercially from benzene by multi-step Hock-type processes with equivalent amounts of acetone as side-product. We describe an efficient biocatalytic alternative using the cytochrome P450-BM3 monooxygenase. Since the wildtype enzyme does not accept benzene, a semi-rational protein engineering strategy was developed. Highly active mutants were obtained which transform benzene in a one-pot sequence first into phenol and then regioselectively into HQ without any overoxidation. A computational study shows that the chemoselective oxidation of phenol by the P450-BM3 variant A82F/A328F leads to the regioselective formation of an epoxide intermediate at the C3=C4 double bond, which departs from the binding pocket and then undergoes fragmentation in aqueous medium with exclusive formation of HQ. As a practical application, an E. coli designer cell system was constructed, which enables the cascade transformation of benzene into the natural product arbutin, which has anti-inflammatory and anti-bacterial activities.
- Zhou, Hangyu,Wang, Binju,Wang, Fei,Yu, Xiaojuan,Ma, Lixin,Li, Aitao,Reetz, Manfred T.
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supporting information
p. 764 - 768
(2018/12/13)
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- Arbutin Derivatives Isolated from Ancient Proteaceae: Potential Phytochemical Markers Present in Bellendena, Cenarrhenes, and Persoonia Genera
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Extensive phytochemical studies of the paleoendemic Tasmanian Proteaceae species Bellendena montana, Cenarrhenes nitida, and Persoonia gunnii were conducted employing pressurized hot water extraction. As part of these studies, six novel glycosides were is
- Deans, Bianca J.,Kilah, Nathan L.,Jordan, Gregory J.,Bissember, Alex C.,Smith, Jason A.
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p. 1241 - 1251
(2018/05/31)
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- Chemical synthetic method for beta-arbutin
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The invention provides a chemical synthetic method for beta-arbutin, which includes: 1) performing a reaction to pentaacetyl-beta-D-glucose with a 70% hydrofluoric acid pyridine solution at 10-30 DEGC to obtain tetraacetyl-alpha-fluoroglucose; 2) performing a reaction to the tetraacetyl-alpha-fluoroglucose with p-hydroxyacetophenone in a mixed solvent under catalysis of tetrabutylammonium bromidewith Ca(OH)2 being an accelerant at 20-30 DEG C to prepare p-acetylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside; 3) performing a reaction to the p-acetylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside with 40% peroxyacetic acid in an organic solvent at 5-20 DEG C to obtain p-acetoxylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside; 4) performing a reaction to the p-acetoxylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside at 15-25 DEG C in the presence of anhydrous methanol-sodium methoxide to obtain the beta-arbutin. The method is high in yield, low in cost, gentle in conditions and less in emission of waste liquid, waste gas and waste solids, and is suitable for industrial production.
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Paragraph 0006; 0009; 0013; 0018
(2019/01/08)
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- Synthesis method for beta-arbutin
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The invention discloses a synthesis method for beta-arbutin and belongs to the field of synthesis of daily chemical additives. The invention aims to provide a synthesis method of which the yield can reach 81 to 90 percent. According to the method, tetra-acetyl arbutin is acetylated, and then a product is de-acetylated, wherein the tetra-acetyl arbutin is obtained by reaction among penta-acetyl glucopyranose, hydroquinone and derivatives thereof under ionic liquid. The synthesis method for the beta-arbutin can be used for synthesizing the beta-arbutin in daily chemical products.
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Paragraph 0022; 0023; 0024; 0025; 0026; 0027
(2017/10/13)
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- A method of preparing α-arbutine
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The invention provides a method for preparing alpha-arbutin. A glycosyl donor 2,3,4,6-tetra-O-trimethylsilyl-1-iodo-alpha-D-glucose, hydroquinone and its derivative undergo a glycosylation reaction, and protection groups are removed under acidic or alkaline conditions to obtain pure alpha-arbutin. Compared with present methods for preparing alpha-arbutin, the method has the advantages of realization of the synthesis of alpha-arbutin through a one-pot process, and high selectivity and high yield obtaining of alpha-arbutin under simple and mild conditions.
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Paragraph 0030-0031
(2017/06/29)
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- Preparation method of beta-arbutin
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The invention relates to the field of fine chemical industry, and provides a preparation method of beta-arbutin. The method employs anhydrous-glucose as a raw material, acetic anhydride is used as an acetylation agent, acetic acid and acetic anhydride are evaporated from reaction products, ethyl alcohol is employed for directly carrying out crystallization treatment, and beta-pentacetylglucose is prepared. Boron trifluoride etherate and triethylamine are used as catalysts, toluene and dichloromethane are used as solvents, beta-pentacetylglucose and hydroquinone are condensed, beta-tetraacetyl-arbutin is prepared, acetylation is carried out, and beta-pentaacetyl-arbutin is obtained. Methanol and sodium methoxide are used for deacetylation of beta-pentaacetyl-arbutin, a beta-arbutin crude product is prepared, active carbon is used for decolouring, petroleum ether is used for washing, a composite solvent of ethyl alcohol and water is used for recrystallization treatment, and the product beta-arbutin is obtained. The content and purity of beta-arbutin reaches 99.8%, the content of xylenol is equal to or less than 2ppm, and the content of heavy metal is equal to or less than 10ppm.
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Paragraph 0023; 0026; 0027; 0028; 0031; 0032; 0033; 0036-37
(2017/06/02)
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- Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization
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Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing α/β-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.
- De Winter, Karel,Dewitte, Griet,Dirks-Hofmeister, Mareike E.,De Laet, Sylvie,Pelantová, Helena,K?en, Vladimír,Desmet, Tom
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p. 10131 - 10139
(2016/02/03)
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- Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum
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Abstract Over the past decade, disaccharide phosphorylases have been successfully applied for the synthesis of numerous α-glucosides. In contrast, much less research has been done with respect to the production of β-glucosides. Although cellobiose phosphorylase was already successfully used for the synthesis of various disaccharides and branched trisaccharides, its glycosylation potential towards small organic compounds has not been explored to date. Unfortunately, disaccharide phosphorylases typically have a very low affinity for non-carbohydrate acceptors, which urges the addition of solvents. The ionic liquid AMMOENGTM 101 and ethyl acetate were identified as the most promising solvents, allowing the synthesis of various β-glucosides. Next to hexyl, heptyl, octyl, nonyl, decyl and undecyl β-D-glucopyranosides, also the formation of vanillyl 4-O-β-D-glucopyranoside, 2-phenylethyl β-D-glucopyranoside, β-citronellyl β-D-glucopyranoside and 1-O-β-D-glucopyranosyl hydroquinone was confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Moreover, the stability of cellobiose phosphorylase could be drastically improved by creating cross-linked enzyme aggregates, while the efficiency of the biocatalyst for the synthesis of octyl β-D-glucopyranoside was doubled by imprinting with octanol. The usefulness of the latter system was illustrated by performing three consecutive batch conversions with octanol imprinted cross-linked enzyme aggregates, yielding roughly 2 g of octyl β-D-glucopyranoside.
- De Winter, Karel,Van Renterghem, Lisa,Wuyts, Kathleen,Pelantová, Helena,K?en, Vladimír,Soetaert, Wim,Desmet, Tom
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p. 1961 - 1969
(2015/06/02)
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- Biphasic catalysis with disaccharide phosphorylases: Chemoenzymatic synthesis of α- D -glucosides using sucrose phosphorylase
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Thanks to its broad acceptor specificity, sucrose phosphorylase (SP) has been exploited for the transfer of glucose to a wide variety of acceptor molecules. Unfortunately, the low affinity (Km > 1 M) of SP towards these acceptors typically urges the addition of cosolvents, which often either fail to dissolve sufficient substrate or progressively give rise to enzyme inhibition and denaturation. In this work, a buffer/ethyl acetate ratio of 5:3 was identified to be the optimal solvent system, allowing the use of SP in biphasic systems. Careful optimization of the reaction conditions enabled the synthesis of a range of α-d-glucosides, such as cinnamyl α-d-glucopyranoside, geranyl α-d-glucopyranoside, 2-O-α-d-glucopyranosyl pyrogallol, and series of alkyl gallyl 4-O-α-d-glucopyranosides. The usefulness of biphasic catalysis was further illustrated by comparing the glucosylation of pyrogallol in a cosolvent and biphasic reaction system. The acceptor yield for the former reached only 17.4%, whereas roughly 60% of the initial pyrogallol was converted when using biphasic catalysis.
- De Winter, Karel,Desmet, Tom,Devlamynck, Tim,Van Renterghem, Lisa,Verhaeghe, Tom,Pelantova, Helena,Kren, Vladimir,Soetaert, Wim
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p. 781 - 787
(2014/07/08)
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- Purification, characterization, and gene identification of an α-glucosyl transfer enzyme, a novel type α-glucosidase from Xanthomonas campestris WU-9701
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The α-glucosyl transfer enzyme (XgtA), a novel type α-glucosidase produced by Xanthomonas campestris WU-9701, was purified from the cell-free extract and characterized. The molecular weight of XgtA is estimated to be 57 kDa by SDS-PAGE and 60 kDa by gel filtration, indicating that XgtA is a monomeric enzyme. Kinetic properties of XgtA were determined for α-glucosyl transfer and maltose-hydrolyzing activities using maltose as the α-glucosyl donor, and if necessary, hydroquinone as the acceptor. The Vmax value for α-glucosyl transfer activity was 1.3 × 10-2 (mM/s); this value was 3.9-fold as much as that for maltose-hydrolyzing activity. XgtA neither produced maltooligosaccharides nor hydrolyzed sucrose. The gene encoding XgtA that contained a 1614-bp open reading frame was cloned, identified, and highly expressed in Escherichia coli JM109 as the host. Site-directed mutagenesis identified Asp201, Glu270, and Asp331 as the catalytic sites of XgtA, indicating that XgtA belongs to the glycoside hydrolase family 13.
- Sato, Toshiyuki,Hasegawa, Nobukazu,Saito, Jun,Umezawa, Satoru,Honda, Yuki,Kino, Kuniki,Kirimura, Kohtaro
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experimental part
p. 20 - 27
(2012/09/05)
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- A new synthesis of α-arbutin via Lewis acid catalyzed selective glycosylation of tetra-O-benzyl-α-d-glucopyranosyl trichloroacetimidate with hydroquinone
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α-Arbutin has huge application potentials in the cosmetic industry, as its inhibitory effect on human tyrosinase is stronger than that of its naturally occurring anomer arbutin (4-hydroxyphenyl β-d-glucopyranoside). Enzymatic synthesis was preferred for α-arbutin previously, and now a new chemical synthesis is reported. The reaction of tetra-O-benzyl-α-d-glucopyranosyl trichloroacetimidate, as glycosyl donor, with hydroquinone was initiated by catalytic amounts of trimethylsilyl trifluoromethanesulfonate (TMSOTf), resulting in 4-hydroxyphenyl 2,3,4,6-tetra-O-benzyl-α-d-glucopyranoside with high stereoselectivity and yield, and then to α-arbutin quantitatively after deprotection.
- Wang, Zhao-Xia,Shi, Xiao-Xin,Chen, Guo-Rong,Ren, Zhi-Hua,Luo, Lei,Yan, Jing
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p. 1945 - 1947
(2007/10/03)
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- Syntheses of arbutin-α-glycosides and a comparison of their inhibitory effects with those of α-arbutin and arbutin on human tyrosinase
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The effects of 4-hydroxyphenyl α-glucopyranoside (α-arbutin) and 4-hydroxyphenyl β-glucopyranoside (arbutin) on the activity of tyrosinase from human malignant melanoma cells were examined. The inhibitory effect of α-arbutin on human tyrosinase was stronger than that of arbutin. The Ki value for α-arbutin was calculated to be 1/20 that for arbutin. We then synthesized arbutin- α-glycosides by the transglycosylation reaction of cyclomaltodextrin glucanotransferase using arbutin and starch, respectively, as acceptor and donor molecules. The structural analyses using 13C- and 1H-NMR proved that the transglycosylated products were 4-hydroxyphenyl β-maltoside (β-Ab-α-G1) and 4-hydroxyphenyl β-maltotrioside (β-Ab-α-G2). These arbutin-α-glycosides exhibited competitive type inhibition on human tyrosinase, and their Ki values were calculated to be 0.7mM and 0.9mM, respectively. These arbutin-α-glycosides posessed stronger inhibitory activity than arbutin, but less activity than α-arbutin. These results suggested that the α-glucosidic linkage of hydroquinone-glycosides plays an important role in the inhibitory effect on human tyrosinase.
- Sugimoto, Kazuhisa,Nishimura, Takahisa,Nomura, Koji,Sugimoto, Kenji,Kuriki, Takashi
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p. 798 - 801
(2007/10/03)
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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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- Process for the preparation of tetrahydropyran derivatives
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A process of making arbutin and its derivatives comprises solvolyzing an acylated precursor of arbutin or its derivative in a solution comprising an organic solvent and a base, neutralizing the solution with an acid, and crystillizing the product arbutin or its derivative. The process may be employed on an industrial scale and avoids the use of ion exchange columns. The process has the advantages of not requiring ion exchange columns and peripheral devices, which leads to cost and time savings, due to the elimination of column regeneration steps. Waste water from column regeneration is also eliminated.
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- Arbutin synthase, a novel member of the NRD1β glycosyltransferase family, is a unique multifunctional enzyme converting various natural products and xenobiotics
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Plant glucosyltransferases (GTs) play a crucial role in natural product biosynthesis and metabolization of xenobiotics. We expressed the arbutin synthase (AS) cDNA from Rauvolfia serpentina cell suspension cultures in Escherichia coli with a 6xHis tag and purified the active enzyme to homogeneity. The recombinant enzyme had a temperature optimum of 50°C and showed two different pH optima (4.5 and 6.8 or 7.5, depending on the buffer). Out of 74 natural and synthetic phenols and two cinnamyl alcohols tested as substrates for the AS, 45 were accepted, covering a broad range of structural features. Converting rates comparable to hydroquinone were not achieved. In contrast to this broad acceptor substrate specificity, only pyrimidine nucleotide activated glucose was tolerated as a donor substrate. Nucleotide and amino acid sequence analysis revealed AS to be a new member of the NRD1β family of glycosyl transferases and placed the enzyme into the group of plant secondary product GTs. Arbutin synthase is therefore the first example of a broad spectrum multifunctional glucosyltransferase.
- Hefner, Tobias,Arend, Joachim,Warzecha, Heribert,Siems, Karsten,St?ckigt, Joachim
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p. 1731 - 1741
(2007/10/03)
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- Cosmetic composition containing retinol and dioic acid
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A composition for topical application to human skin in order to promote the repair of photo-damaged skin and/or to reduce or prevent the damaging effects of ultra-violet light on skin and/or to lighten the skin comprising retinol or a derivative thereof and a dioic acid.
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- Cosmetic composition
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A composition for topical application to the skin in order to promote the repair of photo-damaged or aged skin and/or to reduce or prevent damaging effects of ultra-violet light on skin and/or to lighten the skin comprising a hydrocalchone of general structure: STR1 wherein R1, R2 and R3, which may be the same or different, represent H, --OH, --OR or --COR (where R is a C1-20 alkyl group); R4, R5, R6 and R7, which may be the same or different, represent H or --COR (where R is as herein before defined). Optional additional ingredients include sunscreens and other skin lightening skin lightening agents, particularly retinol or derivatives thereof.
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- Effects of alpha- and beta-arbutin on activity of tyrosinases from mushroom and mouse melanoma.
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The effects of alpha- and beta-arbutin on the activity of tyrosinases from mushroom and mouse melanoma were examined. alpha-Arbutin was synthesized from hydroquinone and starch using glucoside synthetase (GSase). beta-Arbutin inhibited both tyrosinase activities from mushroom and mouse melanoma. alpha-Arbutin inhibited only the tyrosinase from mouse melanoma, 10 times as strongly as beta-arbutin. The IC50 of alpha-arbutin was 0.48 mM and its inhibitory mechanism was speculated to be mixed type inhibition, while that of beta-arbutin was noncompetitive.
- Funayama,Arakawa,Yamamoto,Nishino,Shin,Murao
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p. 143 - 144
(2007/10/02)
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- Cosmetic composition
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Topical compositions for preventing or at least reducing the damaging effects of ultra-violet light on skin comprise 1-hydroxycholecalciferol and/or 1,25 dihydroxycholecalciferol in combination with a sunscreen material and preferably also retinol and/or a derivative thereof. The compositions may also be used for promoting repair of photodamaged skin.
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- DIRECT CONDENSATION OF POLYHYDRIC PHENOLS WITH GLUCOSE
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Acid-catalyzed direct condensation reaction of polyhydric phenols with free glucose in DMSO gave O-α-D-glucopyranoside in preference to its β-anomer; however, phloroglucinol and phloroacetophenone gave C-β-D-glucopyranoside instead.
- Onodera, Jun-ichi,Takano, Mitsuru,Kishi, Yuji,Yokoyama, Noriko,Ishida, Ryosuke
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p. 1487 - 1488
(2007/10/02)
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- A BITTER MONOTERPENE GLUCOSIDE FROM VIBURNUM PHLEBOTRICHUM
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From the methanol extract of the leaves of Viburnum phlebotrichum, a new bitter monoterpene glucoside has been isolated in addition to three known compounds, p-hydroquinone, arbutin and glucoluteolin.The structures were elucidated by spectroscopic and chemical methods. - Key Word Index:Viburnum phlebotrichum; Caprifoliaceae; monoterpene glucoside; phlebotricoside.
- Hase, Tsunao,Iwagawa, Tetsuo,Munesada, Kiyotaka
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p. 1435 - 1437
(2007/10/02)
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