497-76-7Relevant academic research and scientific papers
High-Field Formation of Arbutin from Hydroquinone by Cell-Suspension Cultures of Rauwolfia serpentina
Lutterbach, Ralf,Stoeckigt, Joachim
, p. 2009 - 2011 (1992)
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.
α-Glucosidic hydroquinone derivatives from Viburnum erosum
Choi, Seong Yeon,Jang, Hyeon Seok,Jeong, Birang,Kim, Juyeol,Kwon, Yong Soo,Lee, Jiho,Park, Jinyoung,Yang, Heejung
, (2021/05/03)
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
Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates
Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi
, p. 838 - 847 (2021/02/09)
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.
Preparation method of glucoside and derivatives thereof
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Paragraph 0040; 0043, (2020/04/02)
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.
Method for chemically synthesizing beta-arbutin
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Paragraph 0004; 0006-0010, (2020/02/10)
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.
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
Wang, Feng,Huang, Dengfa,Ma, Yong,Zhang, Fuming,Linhardt, Robert J.
, p. 246 - 260 (2019/02/03)
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.
Chemo- and Regioselective Dihydroxylation of Benzene to Hydroquinone Enabled by Engineered Cytochrome P450 Monooxygenase
Zhou, Hangyu,Wang, Binju,Wang, Fei,Yu, Xiaojuan,Ma, Lixin,Li, Aitao,Reetz, Manfred T.
supporting information, p. 764 - 768 (2018/12/13)
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.
Chemical synthetic method for beta-arbutin
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Paragraph 0006; 0009; 0013; 0018, (2019/01/08)
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.
Arbutin Derivatives Isolated from Ancient Proteaceae: Potential Phytochemical Markers Present in Bellendena, Cenarrhenes, and Persoonia Genera
Deans, Bianca J.,Kilah, Nathan L.,Jordan, Gregory J.,Bissember, Alex C.,Smith, Jason A.
, p. 1241 - 1251 (2018/05/31)
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
Synthesis method for beta-arbutin
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Paragraph 0022; 0023; 0024; 0025; 0026; 0027, (2017/10/13)
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.
