Literature DB >> 9075196

Synthesis of a novel vitamin E derivative, 2-(alpha-D-glucopyranosyl) methyl-2,5,7,8-tetramethylchroman-6-ol, by alpha-glucosidase-catalyzed transglycosylation.

H Murase1, R Yamauchi, K Kato, T Kunieda, J Terao.   

Abstract

A novel derivative of vitamin E, vitamin E glucoside, was synthesized from 2-hydroxymethyl-2,5,7,8-tetramethylchroman-6-ol and maltose in a solution containing DMSO by transglycosylation with alpha-glucosidase from Saccharomyces species. The glycosylated product was identified as 2-(alpha-D-glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol (TMG) by mass spectrometry and nuclear magnetic resonance spectroscopy. The optimal pH of transglycosylation was 5.5, and the yield of TMG increased as the concentration of maltose increased. TMG has high solubility in water (> 1 x 10(3) mg/mL). The 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity of TMG was found to be nearly the same as those of alpha-tocopherol, Trolox (2-carboxy-2,5,7,8-tetramethylchroman-6-ol), and ascorbic acid.

Entities:  

Mesh：

Substances：

Year:  1997        PMID： 9075196     DOI： 10.1007/s11745-997-0011-6

Source DB:  PubMed          Journal:  Lipids        ISSN： 0024-4201            Impact factor:   1.880


  16 in total

1.  Enzymatic formation of 4G-alpha-D-glucopyranosyl-rutin.

Authors:  Y Suzuki; K Suzuki
Journal:  Agric Biol Chem       Date:  1991-01

2.  Studies of the mechanism of vitamin E action. IV. Lipide peroxidation in the vitamin E-deficient rabbit.

Authors:  H ZALKIN; A L TAPPEL
Journal:  Arch Biochem Biophys       Date:  1960-05       Impact factor: 4.013

Review 3.  Vitamin E: antioxidant activity, biokinetics, and bioavailability.

Authors:  G W Burton; M G Traber
Journal:  Annu Rev Nutr       Date:  1990       Impact factor: 11.848

4.  Effect of phytyl side chain of vitamin E on its antioxidant activity.

Authors:  E Niki; A Kawakami; M Saito; Y Yamamoto; J Tsuchiya; Y Kamiya
Journal:  J Biol Chem       Date:  1985-02-25       Impact factor: 5.157

Review 5.  Antioxidants in relation to lipid peroxidation.

Authors:  E Niki
Journal:  Chem Phys Lipids       Date:  1987 Jul-Sep       Impact factor: 3.329

6.  L-ascorbic acid alpha-glucoside formed by regioselective transglucosylation with rat intestinal and rice seed alpha-glucosidases: its improved stability and structure determination.

Authors:  I Yamamoto; N Muto; K Murakami; S Suga; H Yamaguchi
Journal:  Chem Pharm Bull (Tokyo)       Date:  1990-11       Impact factor: 1.645

7.  Oxidation by superoxide of tocopherols dispersed in aqueous media with deoxycholate.

Authors:  M Nishikimi; H Yamada; K Yagi
Journal:  Biochim Biophys Acta       Date:  1980-01-03

8.  Oxidation of alpha-tocopherol in micelles and liposomes by the hydroxyl, perhydroxyl, and superoxide free radicals.

Authors:  K Fukuzawa; J M Gebicki
Journal:  Arch Biochem Biophys       Date:  1983-10-01       Impact factor: 4.013

9.  Membrane peroxidation: inhibiting effects of water-soluble antioxidants on phospholipids of different charge types.

Authors:  L R Barclay; M R Vinqvist
Journal:  Free Radic Biol Med       Date:  1994-06       Impact factor: 7.376

10.  α-D-Glucosyl Transfer to Phenolic Compounds by Sucrose Phosphorylase from Leuconostoc mesenteroides and Production of α-Arbutin.

Authors:  S Kitao; H Sekine
Journal:  Biosci Biotechnol Biochem       Date:  1994-01       Impact factor: 2.043
View more
  10 in total

1.  Novel alpha-glucosidase from Aspergillus nidulans with strong transglycosylation activity.

Authors:  Naoki Kato; Sachie Suyama; Masao Shirokane; Masashi Kato; Tetsuo Kobayashi; Norihiro Tsukagoshi
Journal:  Appl Environ Microbiol       Date:  2002-03       Impact factor: 4.792

2.  A novel vitamin E derivative (TMG) protects against gastric mucosal damage induced by ischemia and reperfusion in rats.

Authors:  Hiroshi Ichikawa; Norimasa Yoshida; Hiroshisa Takano; Takeshi Ishikawa; Osamu Handa; Tomohisa Takagi; Yuji Naito; Hironobu Murase; Toshikazu Yoshikawa
Journal:  Dig Dis Sci       Date:  2003-01       Impact factor: 3.199

3.  Hydrosoluble antioxidants by enzymatic glucosylation of a vitamin E derivative using marine α-D-glucosidase from Aplysia fasciata.

Authors:  Annabella Tramice; Giuseppina Andreotti; Antonio Trincone
Journal:  Mar Biotechnol (NY)       Date:  2011-01-06       Impact factor: 3.619

4.  Characterization of Halomonas sp. strain H11 α-glucosidase activated by monovalent cations and its application for efficient synthesis of α-D-glucosylglycerol.

Authors:  Teruyo Ojima; Wataru Saburi; Takeshi Yamamoto; Toshiaki Kudo
Journal:  Appl Environ Microbiol       Date:  2012-01-06       Impact factor: 4.792

5.  Novel vitamin E derivative with 4-substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties.

Authors:  K Shimizu; R Kondo; K Sakai; N Takeda; T Nagahata; T Oniki
Journal:  Lipids       Date:  2001-12       Impact factor: 1.880

6.  Crystallization and preliminary X-ray crystallographic analysis of α-glucosidase HaG from Halomonas sp. strain H11.

Authors:  Xing Shen; Wataru Saburi; Zuo-Qi Gai; Keisuke Komoda; Jian Yu; Teruyo Ojima-Kato; Yusuke Kido; Hirokazu Matsui; Haruhide Mori; Min Yao
Journal:  Acta Crystallogr F Struct Biol Commun       Date:  2014-03-25       Impact factor: 1.056

Review 7.  Vitamin E: tocopherols and tocotrienols as potential radiation countermeasures.

Authors:  Vijay K Singh; Lindsay A Beattie; Thomas M Seed
Journal:  J Radiat Res       Date:  2013-05-08       Impact factor: 2.724

Review 8.  Targeting Evolutionary Conserved Oxidative Stress and Immunometabolic Pathways for the Treatment of Respiratory Infectious Diseases.

Authors:  Jonathan R Erlich; Eunice E To; Stella Liong; Robert Brooks; Ross Vlahos; John J O'Leary; Doug A Brooks; Stavros Selemidis
Journal:  Antioxid Redox Signal       Date:  2020-05-01       Impact factor: 8.401

Review 9.  Vitamin E Analogs as Radiation Response Modifiers.

Authors:  Pankaj K Singh; Sunil Krishnan
Journal:  Evid Based Complement Alternat Med       Date:  2015-08-20       Impact factor: 2.629

10.  Maltose deterioration approach: Catalytic behavior optimization and stability profile of maltase from Bacillus licheniformis KIBGE-IB4.

Authors:  Muhammad Asif Nawaz; Sidra Pervez; Muhsin Jamal; Tour Jan; Wali Khan; Abdur Rauf; Afsheen Aman; Shah Ali Ul Qader
Journal:  Biotechnol Rep (Amst)       Date:  2019-11-12
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.