Skip to main content

Research Repository

Advanced Search

Biotransformation of Chrysin to Baicalein: Selective C6-Hydroxylation of 5,7-Dihydroxyflavone Using Whole Yeast Cells Stably Expressing Human CYP1A1 Enzyme

Nuthakki, Vijay K.; Bharate, Sandip B.; Williams, Ibidapo S.; Chib, Shifali; Gatchie, Linda; Joshi, Prashant; Narkhede, Niteen A.; Vishwakarma, Ram A.; Saran, Saurabh; Chaudhuri, Bhabatosh

Authors

Vijay K. Nuthakki

Sandip B. Bharate

Ibidapo Williams Ibidapo.Williams@uwe.ac.uk
Research Fellow- Cell Cultural Monitoring Technology

Shifali Chib

Linda Gatchie

Prashant Joshi

Niteen A. Narkhede

Ram A. Vishwakarma

Saurabh Saran

Bhabatosh Chaudhuri



Abstract

© 2017 American Chemical Society. Naturally occurring polyphenolic compounds are of medicinal importance because of their unique antioxidant, anticancer, and chemopreventive properties. Baicalein, a naturally occurring polyhydroxy flavonoid possessing a diverse range of pharmacological activities, has been used in traditional medicines for treatment of various ailments. Apart from its isolation from natural sources, its synthesis has been reported via multistep chemical approaches. Here, we report a preparative-scale biotransformation, using whole yeast cells stably expressing human cytochrome P450 1A1 (CYP1A1) enzyme that allows regioselective C6-hydroxylation of 5,7-dihydroxyflavone (chrysin) to form 5,6,7-trihydroxyflavone (baicalein). Molecular modeling reveals why chrysin undergoes such specific hydroxylation mediated by CYP1A1. More than 92% reaction completion was obtained using a shake-flask based process that mimics fed-batch fermentation. Such highly efficient selective hydroxylation, using recombinant yeast cells, has not been reported earlier. Similar CYP-expressing yeast cell based systems are likely to have wider applications in the syntheses of medicinally important polyphenolic compounds.

Citation

Bharate, S. B., Nuthakki, V. K., Williams, I. S., Chib, S., Gatchie, L., Joshi, P., …Chaudhuri, B. (2017). Biotransformation of Chrysin to Baicalein: Selective C6-Hydroxylation of 5,7-Dihydroxyflavone Using Whole Yeast Cells Stably Expressing Human CYP1A1 Enzyme. Journal of Agricultural and Food Chemistry, 65(34), 7440-7446. https://doi.org/10.1021/acs.jafc.7b02690

Journal Article Type Article
Acceptance Date Aug 7, 2017
Publication Date Aug 30, 2017
Deposit Date May 9, 2018
Journal Journal of Agricultural and Food Chemistry
Print ISSN 0021-8561
Electronic ISSN 1520-5118
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 65
Issue 34
Pages 7440-7446
DOI https://doi.org/10.1021/acs.jafc.7b02690
Keywords baicalein, biotransformation, chrysin, CYP1A1, hydroxylation, yeast cells
Public URL https://uwe-repository.worktribe.com/output/883199
Publisher URL http://dx.doi.org/10.1021/acs.jafc.7b02690
Related Public URLs https://pubs.acs.org/doi/10.1021/acs.jafc.7b02690
Additional Information Additional Information : This is the accepted version of the article. the final version can be found at: http://dx.doi.org/10.1021/acs.jafc.7b02690

Files








You might also like



Downloadable Citations