Publications
Detailed Information
Regioselective One-Pot Synthesis of Hydroxy-(S)-Equols Using Isoflavonoid Reductases and Monooxygenases and Evaluation of the Hydroxyequol Derivatives as Selective Estrogen Receptor Modulators and Antioxidants
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Song, Hanbit | - |
dc.contributor.author | Lee, Pyung-Gang | - |
dc.contributor.author | Kim, Junyeob | - |
dc.contributor.author | Kim, Joonwon | - |
dc.contributor.author | Lee, Sang-Hyuk | - |
dc.contributor.author | Kim, Hyun | - |
dc.contributor.author | Lee, Uk-Jae | - |
dc.contributor.author | Kim, Jin Young | - |
dc.contributor.author | Kim, Eun-Jung | - |
dc.contributor.author | Kim, Byung-Gee | - |
dc.date.accessioned | 2022-06-27T00:11:49Z | - |
dc.date.available | 2022-06-27T00:11:49Z | - |
dc.date.created | 2022-05-23 | - |
dc.date.issued | 2022-03 | - |
dc.identifier.citation | Frontiers in Bioengineering and Biotechnology, Vol.10, p. 830712 | - |
dc.identifier.issn | 2296-4185 | - |
dc.identifier.uri | https://hdl.handle.net/10371/184176 | - |
dc.description.abstract | Copyright © 2022 Song, Lee, Kim, Kim, Lee, Kim, Lee, Kim, Kim and Kim.Several regiospecific enantiomers of hydroxy-(S)-equol (HE) were enzymatically synthesized from daidzein and genistein using consecutive reduction (four daidzein-to-equol–converting reductases) and oxidation (4-hydroxyphenylacetate 3-monooxygenase, HpaBC). Despite the natural occurrence of several HEs, most of them had not been studied owing to the lack of their preparation methods. Herein, the one-pot synthesis pathway of 6-hydroxyequol (6HE) was developed using HpaBC (EcHpaB) from Escherichia coli and (S)-equol-producing E. coli, previously developed by our group. Based on docking analysis of the substrate or products, a potential active site and several key residues for substrate binding were predicted to interpret the (S)-equol hydroxylation regioselectivity of EcHpaB. Through investigating mutations on the key residues, the T292A variant was verified to display specific mono-ortho-hydroxylation activity at C6 without further 3′-hydroxylation. In the consecutive oxidoreductive bioconversion using T292A, 0.95 mM 6HE could be synthesized from 1 mM daidzein, while 5HE and 3′HE were also prepared from genistein and 3′-hydroxydaidzein (3′HD or 3′-ODI), respectively. In the following efficacy tests, 3′HE and 6HE showed about 30∼200-fold higher EC50 than (S)-equol in both ERα and ERβ, and they did not have significant SERM efficacy except 6HE showing 10% lower β/α ratio response than that of 17β-estradiol. In DPPH radical scavenging assay, 3′HE showed the highest antioxidative activity among the examined isoflavone derivatives: more than 40% higher than the well-known 3′HD. In conclusion, we demonstrated that HEs could be produced efficiently and regioselectively through the one-pot bioconversion platform and evaluated estrogenic and antioxidative activities of each HE regio-isomer for the first time. | - |
dc.language | 영어 | - |
dc.publisher | Frontiers Research Foundation | - |
dc.title | Regioselective One-Pot Synthesis of Hydroxy-(S)-Equols Using Isoflavonoid Reductases and Monooxygenases and Evaluation of the Hydroxyequol Derivatives as Selective Estrogen Receptor Modulators and Antioxidants | - |
dc.type | Article | - |
dc.identifier.doi | 10.3389/fbioe.2022.830712 | - |
dc.citation.journaltitle | Frontiers in Bioengineering and Biotechnology | - |
dc.identifier.scopusid | 2-s2.0-85128232854 | - |
dc.citation.startpage | 830712 | - |
dc.citation.volume | 10 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Kim, Byung-Gee | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
- Appears in Collections:
- Files in This Item:
- There are no files associated with this item.
Item View & Download Count
Items in S-Space are protected by copyright, with all rights reserved, unless otherwise indicated.