Literature DB >> 24170092

Enzymatic synthesis of apigenin glucosides by glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13.

Rit Bahadur Gurung1, Eun-Hee Kim, Tae-Jin Oh, Jae Kyung Sohng.   

Abstract

Apigenin, a member of the flavone subclass of flavonoids, has long been considered to have various biological activities. Its glucosides, in particular, have been reported to have higher water solubility, increased chemical stability, and enhanced biological activities. Here, the synthesis of apigenin glucosides by the in vitro glucosylation reaction was successfully performed using a UDP-glucosyltransferase YjiC, from Bacillus licheniformis DSM 13. The glucosylation has been confirmed at the phenolic groups of C-4' and C-7 positions ensuing apigenin 4'-O-glucoside, apigenin 7-O-glucoside and apigenin 4',7-O-diglucoside as the products leaving the C-5 position unglucosylated. The position of glucosylation and the chemical structures of glucosides were elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The parameters such as pH, UDP glucose concentration and time of incubation were also analyzed during this study.

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Year:  2013        PMID: 24170092      PMCID: PMC3887987          DOI: 10.1007/s10059-013-0164-0

Source DB:  PubMed          Journal:  Mol Cells        ISSN: 1016-8478            Impact factor:   5.034


  43 in total

1.  The flavonoid apigenin suppresses vitamin D receptor expression and vitamin D responsiveness in normal human keratinocytes.

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Journal:  Biochem Biophys Res Commun       Date:  2000-02-05       Impact factor: 3.575

Review 2.  Enzymatic glycosylation of small molecules: challenging substrates require tailored catalysts.

Authors:  Tom Desmet; Wim Soetaert; Pavla Bojarová; Vladimir Křen; Lubbert Dijkhuizen; Vanessa Eastwick-Field; Alexander Schiller
Journal:  Chemistry       Date:  2012-08-08       Impact factor: 5.236

Review 3.  Recent structures, evolution and mechanisms of glycosyltransferases.

Authors:  Christelle Breton; Sylvie Fournel-Gigleux; Monica M Palcic
Journal:  Curr Opin Struct Biol       Date:  2012-07-19       Impact factor: 6.809

4.  Enzymatic synthesis of novel phloretin glucosides.

Authors:  Ramesh Prasad Pandey; Tai Feng Li; Eun-Hee Kim; Tokutaro Yamaguchi; Yong Il Park; Joong Su Kim; Jae Kyung Sohng
Journal:  Appl Environ Microbiol       Date:  2013-03-29       Impact factor: 4.792

5.  In situ UDP-glucose regeneration unravels diverse functions of plant secondary product glycosyltransferases.

Authors:  Kazuyoshi Terasaka; Yuki Mizutani; Akito Nagatsu; Hajime Mizukami
Journal:  FEBS Lett       Date:  2012-11-15       Impact factor: 4.124

6.  Proteomic study of granulocytic differentiation induced by apigenin 7-glucoside in human promyelocytic leukemia HL-60 cells.

Authors:  Eri Nakazaki; Soninkhishig Tsolmon; Junkyu Han; Hiroko Isoda
Journal:  Eur J Nutr       Date:  2011-11-24       Impact factor: 5.614

7.  Vitexin and isovitexin from the Leaves of Ficus deltoidea with in-vivo α-glucosidase inhibition.

Authors:  C Y Choo; N Y Sulong; F Man; T W Wong
Journal:  J Ethnopharmacol       Date:  2012-06-07       Impact factor: 4.360

Review 8.  Apigenin: a promising molecule for cancer prevention.

Authors:  Sanjeev Shukla; Sanjay Gupta
Journal:  Pharm Res       Date:  2010-03-20       Impact factor: 4.200

9.  Enzymatic glycosylation of nonbenzoquinone geldanamycin analogs via Bacillus UDP-glycosyltransferase.

Authors:  Cheng-Zhu Wu; Jae-Hyuk Jang; Mihee Woo; Jong Seog Ahn; Joong Su Kim; Young-Soo Hong
Journal:  Appl Environ Microbiol       Date:  2012-08-24       Impact factor: 4.792

Review 10.  Flavonoids and the CNS.

Authors:  Anna K Jäger; Lasse Saaby
Journal:  Molecules       Date:  2011-02-10       Impact factor: 4.411

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  16 in total

1.  Modification of emodin and aloe-emodin by glycosylation in engineered Escherihia coli.

Authors:  Gopal Prasad Ghimire; Niranjan Koirala; Ramesh Prasad Pandey; Hye Jin Jung; Jae Kyung Sohng
Journal:  World J Microbiol Biotechnol       Date:  2015-02-07       Impact factor: 3.312

2.  Engineering co-culture system for production of apigetrin in Escherichia coli.

Authors:  Nguyen Huy Thuan; Amit Kumar Chaudhary; Duong Van Cuong; Nguyen Xuan Cuong
Journal:  J Ind Microbiol Biotechnol       Date:  2018-01-24       Impact factor: 3.346

3.  Microbial production of astilbin, a bioactive rhamnosylated flavanonol, from taxifolin.

Authors:  Nguyen Huy Thuan; Sailesh Malla; Nguyen Thanh Trung; Dipesh Dhakal; Anaya Raj Pokhrel; Luan Luong Chu; Jae Kyung Sohng
Journal:  World J Microbiol Biotechnol       Date:  2017-01-24       Impact factor: 3.312

Review 4.  Chemotherapeutic effects of Apigenin in breast cancer: Preclinical evidence and molecular mechanisms; enhanced bioavailability by nanoparticles.

Authors:  Moein Adel; Masoumeh Zahmatkeshan; Abolfazl Akbarzadeh; Navid Rabiee; Sepideh Ahmadi; Peyman Keyhanvar; Seyed Mahdi Rezayat; Alexander Marcus Seifalian
Journal:  Biotechnol Rep (Amst)       Date:  2022-04-12

5.  OleD Loki as a Catalyst for Hydroxamate Glycosylation.

Authors:  Ryan R Hughes; Khaled A Shaaban; Larissa V Ponomareva; Jamie Horn; Chunhui Zhang; Chang-Guo Zhan; S Randal Voss; Markos Leggas; Jon S Thorson
Journal:  Chembiochem       Date:  2019-11-26       Impact factor: 3.164

6.  Synthesis of umbelliferone derivatives in Escherichia coli and their biological activities.

Authors:  Luan Luong Chu; Ramesh Prasad Pandey; Haet Nim Lim; Hye Jin Jung; Nguyen Huy Thuan; Tae-Su Kim; Jae Kyung Sohng
Journal:  J Biol Eng       Date:  2017-04-05       Impact factor: 4.355

7.  Glucosylation of isoflavonoids in engineered Escherichia coli.

Authors:  Ramesh Prasad Pandey; Prakash Parajuli; Niranjan Koirala; Joo Ho Lee; Yong Il Park; Jae Kyung Sohng
Journal:  Mol Cells       Date:  2014-02-19       Impact factor: 5.034

8.  Glycosylation of 6-methylflavone by the strain Isaria fumosorosea KCH J2.

Authors:  Monika Dymarska; Jakub Grzeszczuk; Monika Urbaniak; Tomasz Janeczko; Elżbieta Pląskowska; Łukasz Stępień; Edyta Kostrzewa-Susłow
Journal:  PLoS One       Date:  2017-10-05       Impact factor: 3.240

9.  Enzymatic Synthesis of Unnatural Ginsenosides Using a Promiscuous UDP-Glucosyltransferase from Bacillus subtilis.

Authors:  Ting-Ting Zhang; Ting Gong; Zong-Feng Hu; An-Di Gu; Jin-Ling Yang; Ping Zhu
Journal:  Molecules       Date:  2018-10-28       Impact factor: 4.411

Review 10.  Role of Plant-Derived Flavonoids and Their Mechanism in Attenuation of Alzheimer's and Parkinson's Diseases: An Update of Recent Data.

Authors:  Ghulam Hussain; Longbin Zhang; Azhar Rasul; Haseeb Anwar; Muhammad Umar Sohail; Aroona Razzaq; Nimra Aziz; Asghar Shabbir; Muhammad Ali; Tao Sun
Journal:  Molecules       Date:  2018-04-02       Impact factor: 4.411

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