- Neuroprotective activity of different monosaccharide-modified gastrodin analogs
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Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.
- Xu, Kun-Lun,Yu, Lan
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p. 1263 - 1269
(2020/01/21)
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- DUAL PROTECTED PRO-COELENTERAZINE SUBSTRATES
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Described are coelenterazine analogues, methods for making the analogues, kits comprising the analogues, and methods of using the compounds for the detection of luminescence in luciferase-based assays.
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- Gastrodine drug and its composition and use thereof
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The invention relates to a gastrodin medicine, and a composition and a use thereof, and also relates to a gastrodin derivative, and a preparation method and a use thereof. The gastrodin derivative has good storage stability, and is suitable for preparing medicines for increasing the cerebral blood flow, alleviating the cerebral vasospasm, calming, sleeping, easing pains, and treating or preventing Alzheimer's syndrome.
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Paragraph 0072; 0073; 0074
(2018/09/20)
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- Synthesis method of gastrodin
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The invention discloses a synthesis method of gastrodin. The synthesis method of the gastrodin comprises the following steps: putting 4-formylphenyl-2,3,4,6-tetra-0-acetyl-beta-D-glucopyranoside and a reducing agent into a solvent, and conducting reaction at 0 to 30 DEG C for 0 to 3 hours; after complete reaction, adding water and performing quenching reaction; separating and taking an organic phase, concentrating the organic phase under the vacuum condition, and adding methanol in amount which is 2 to 5 times that of the organic phase; adding organic amine, performing refluxing reaction and performing alcoholysis; after complete reaction, adding activated carbon to decolor, filtering, concentrating, crystallizing and drying. By adoption of the synthesis method provided by the invention, the processes of the production process are reduced, and the method is safe, simple and convenient in operation, low in cost, low in pollution and suitable for large-scale production; furthermore, the prepared gastrodin product has stable quality and the purity is 99.9 percent or higher.
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Paragraph 0031; 0032; 0033; 0034
(2017/07/19)
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- First and efficient synthesis of 4-[((3,4-dihydroxybenzoyl)-oxy)methyl]phenyl β-D-glucopyranoside, an antioxidant from Origanum vulgare
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4-[((3,4-Dihydroxybenzoyl)oxy)methyl]phenyl β-D-glucopyranoside (DBPG, 1), a polyphenolic glycoside previously isolated from oregano (Origanum vulgare L.) in 0.08 % isolated yield, was synthesized in five chemical steps with 41.4 % overall yield. First, 4-(hydroxymethyl)phenyl ?-D-glucopyranoside 2,3,4,6-tetraacetate (4) was obtained in 53.2 % yield by selective glycosylation of 4-hydroxybenzyl alcohol (3) with 2,3,4,6-tetra-O-acetyl-a-D- -glucopyranosyl bromide (2) in a mixture of chlorobenzene and aqueous CsOH using triethylbenzylammonium chloride (TEBAC) as a phase transfer catalyst. Then, this product was esterified with 3,4-diacetoxybenzoyl chloride (7) to generate 4-[((3,4-diacetoxybenzoyl)oxy)methyl]phenyl ?-D-glucopyranoside 2,3,4,6-tetraacetate (8) in 95 % yield. Finally, selectively global deacetylation of 8 was performed in a mixture of dibutyltin oxide and methanol under reflux to afford 1 in 94.8 % yield.
- Li, Yu-Wen,Ma, Cui-Li
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- A high-purity, high-stability Gastrodin semi-synthetic method
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The invention discloses a semi-synthesis method for high-purity and high-stability gastrodin. The semi-synthesis method comprises the following steps: carrying out a reduction reaction by taking tetraacethyl as a raw material; concentrating and adding a suitable amount of water into concentrated liquid; filtering and drying to obtain acethyl gastrodin; recycling a filtering solution which is used as a mother solution a; adding an alcohol solvent into the acethyl gastrodin to carry out a reflowing reaction, and concentrating; repeatedly reflowing and concentrating to obtain a concentrated solution; adding a non-polar solvent and filtering; drying solids to obtain a gastrodin rough product; recycling a filtering solution which is used as a mother solution b; adding alcohol and/or an ester solvent into the rough product of gastrodin; heating and completely dissolving; filtering and separating out crystals to obtain a refined product of gastrodin; recycling a filtering solution which is used as a mother solution c; mixing the mother solution b and the mother solution c; filtering and drying to obtain the rough product of gastrodin; and refining to obtain the refined product of gastrodin. The acethyl gastrodin prepared by the semi-synthesis method disclosed by the invention is stable, can be directly used as a crude drug, and can also be used as an intermediate to synthesize the high-purity gastrodin; the semi-synthesis method for the high-purity and high-stability gastrodin is very good for meeting the clinical demands on gastrodin and acethyl gastrodin.
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Page/Page column 8; 12
(2017/05/13)
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- Gastrodin Gastrodin and method for the preparation of intermediates for the synthesis of
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The invention discloses a method for preparing a gastrodin intermediate compound III. The method comprises the following steps: (1) reducing an initial raw material compound I through hydrogen, and obtaining a compound II; (2) reacting the compound II with an acetylation reagent, and obtaining a crude product of a compound III; and (3) recrystallizing the compound III obtained in the step (2), and obtaining a crude product of the compound III. In addition, the invention also provides a method for synthesizing gastrodin. The compound III prepared by the method provided in the invention is easy to recrystallize and high in purity, and a high-purity gastrodin finished product can be obtained.
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Paragraph 0079-0080
(2017/05/23)
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- Improved synthesis of gastrodin, a bioactive component of a traditional chinese medicine
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Highly practical, four-step synthesis of gastrodin was developed using penta- O-acetyl-β-D-glucopyranose and p-cresol as glycosyl donor and glycosyl acceptor, respectively, in 58.1% overall yield. As the initial step, the penta-O-acetyl-β-D-glucopyranose was treated with p-cresol in the presence of BF3 ?Et2O as catalyst to generate 4-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D- -glucopyranoside in 76.3% yield. Further, this product was subjected to radical bromination with N-bromosuccinimide (NBS) to provide 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 91% yield. Subsequently, reaction of 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside with a solution of acetone and saturated aqueous sodium bicarbonate led to 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 93% yield. Finally, global deprotection of 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O- -acetyl-β- D-glucopyranoside under Zemplen conditions furnished gastrodin in 90% yield. Compared to the previously reported methods, this protocol has the advantages of operational simplicity, chromatography-free separation, high overall yield, inexpensive and common reagents as well as less waste pollutants, rendering it an alternative suitable for industrial production.
- Li, Yu-Wen,Ma, Cui-Li
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p. 1205 - 1212
(2015/01/30)
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- Highly chemoselective hydrogenation of active benzaldehydes to benzyl alcohols catalyzed by bimetallic nanoparticles
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By using novel Pd/Ni bimetallic nanoparticles as a catalyst, the active benzaldehydes were hydrogenated to the corresponding benzyl alcohols as unique products in practical quantitative yields. The undesired catalytic hydrogenolysis of the benzyl alcohol was inhibited completely. By using this hydrogenation as a key step, the total synthesis of the natural product gastrodin was achieved with less total steps and a higher total yield.
- Liu, Chulong,Bao, Hailin,Wang, Dingsheng,Wang, Xinyan,Li, Yadong,Hu, Yuefei
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p. 6460 - 6462
(2015/11/16)
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- Molecular interactions between Barley and Oat β-glucans and phenolic derivatives
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Equilibrium dialysis, molecular modeling, and multivariate data analysis were used to investigate the nature of the molecular interactions between 21 vanillin-inspired phenolic derivatives, 4 bile salts, and 2 commercially available β-glucan preparations, Glucagel and PromOat, from barley and oats. The two β-glucan products showed very similar binding properties. It was demonstrated that the two β-glucan products are able to absorb most phenolic derivatives at a level corresponding to the absorption of bile salts. Glucosides of the phenolic compounds showed poor or no absorption. The four phenolic derivatives that showed strongest retention in the dialysis assay shared the presence of a hydroxyl group in para-position to a CHO group. However, other compounds with the same structural feature but possessing a different set of additional functional groups showed less retention. Principal component analysis (PCA) and partial least-squares regression (PLS) calculations using a multitude of diverse descriptors related to electronic, geometrical, constitutional, hybrid, and topological features of the phenolic compounds showed a marked distinction between aglycon, glucosides, and bile salt retention. These analyses did not offer additional information with respect to the mode of interaction of the individual phenolics with the β-glucans. When the barley β-glucan was subjected to enzyme degradation, the ability to bind some but not all of the phenolic derivatives was lost. It is concluded that the binding must be dependent on multiple characteristics that are not captured by a single molecular descriptor.
- Simonsen, Henrik Toft,Nielsen, Mette S.,Christensen, Niels J.,Christensen, Ulla,Cour, Thomas V. La,Motawia, Mohammed Saddik,Jespersen, Birthe P.M.,Engelsen, Soren B.,Moller, Birger Lindberg
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experimental part
p. 2056 - 2064
(2010/07/02)
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- Studies on the synthesis and antiproliferative activities of 13-cis-retinoyl sugar derivatives
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New retinoyl sugar derivatives of 13-cis-retinoic acid were synthesized in three ways in this paper in order to enhance pharmacal effects, especially antiproliferative activities of 13-cis-retinoic acid. Their structures were confirmed by IR, 1H-NMR, 13C-NMR, and MS spectra and their antiproliferative activities were determined in vitro using human cancer lines. Results showed that some compounds possessed potential antitumor activities. Copyright Taylor & Francis Group, LLC.
- Xiang, Jian-Nan,Jiang, Li-Hui,Chen, Chao-Yue,Fu, Zhi-Ying,Duan, Jun-Fei,He, Xiao-Xiao,Wang, Ke-Min
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p. 595 - 614
(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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- SYNTHESIS OF FLUORINE-CONTAINING NATURAL GASTRODIN AND ITS ANALOGUES
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Reactions of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (2) with p-hydroxybenzaldehyde, trifluoromethyl and fluoro substituted aniline and 2-amino-6-fluorobenzoic acid gave 1-O-(p-formylphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (3), 1-N-(m-trifluoromethylphenylamino)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4a), 1-N-(2-carboxyl-3-fluorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4b) and 1-N-(p-fluorophenyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4c) respectively. 1-O-(perfluoro-2-propoxypropionyl)-O-benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7) and 1-O-(m-trifluoromethylphenylaminobenzylidene)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (8) were also prepared in subsequent reactions.Conversion of the acetyl group to the hydroxyl group yielded the corresponding deprotected product.The compounds formed have been characterized by analysis, IR, 1H and 19F NMR and mass spectroscopy.The influence of phase-transfer catalysts on the reactions is discussed.
- Lin, Yong-Da,Liang, Yu-Da,Liang, Shi-Gin,Zhang, Shi-Xiang,Chi, Ching-Sung
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p. 367 - 374
(2007/10/02)
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- A New Antioxidative Glucoside Isolated from Oregano (Origanum vulgare L.)
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A new antioxidative glucoside (1a) was isolated from the leaves of oregano (Origanum vulgare L.), one of the herbal species belonging to the Family Labiatae.The structure of 1a was determined as 4-(3,4-dihydroxybenzoyloxymethyl)phenyl-β-D-glucopyranoside, on the basis of chemical and spectroscopic evidence.In addition, the structure was confirmed by synthesizing its acetyl derivative (1b).
- Nakatani, Nobuji,Kikuzaki, Hiroe
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p. 2727 - 2732
(2007/10/02)
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