Cargando…

Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains

Biotransformation of the soy isoflavone genistein by sequential 3′-hydroxylation using recombinant Escherichia coli expressing tyrosinase from Bacillus megaterium and then methylation using another recombinant E. coli expressing O-methyltransferase from Streptomyces peucetius was conducted. The resu...

Descripción completa

Detalles Bibliográficos
Autores principales: Chiang, Chien-Min, Chang, Yu-Jhe, Wu, Jiumn-Yih, Chang, Te-Sheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155705/
https://www.ncbi.nlm.nih.gov/pubmed/28054996
http://dx.doi.org/10.3390/molecules22010087
_version_ 1783357949597450240
author Chiang, Chien-Min
Chang, Yu-Jhe
Wu, Jiumn-Yih
Chang, Te-Sheng
author_facet Chiang, Chien-Min
Chang, Yu-Jhe
Wu, Jiumn-Yih
Chang, Te-Sheng
author_sort Chiang, Chien-Min
collection PubMed
description Biotransformation of the soy isoflavone genistein by sequential 3′-hydroxylation using recombinant Escherichia coli expressing tyrosinase from Bacillus megaterium and then methylation using another recombinant E. coli expressing O-methyltransferase from Streptomyces peucetius was conducted. The results showed that two metabolites were produced from the biotransformation, identified as 5,7,4′-trihydroxy-3′-methoxyisoflavone and 5,7,3′-trihydroxy-4′-methoxyisoflavone, respectively, based on their mass and nuclear magnetic resonance spectral data. 5,7,4′-Trihydroxy-3′-methoxyisoflavone showed potent antiproliferative activity toward mouse B16 melanoma cells with an IC(50) value of 68.8 μM. In contrast, the compound did not show any cytotoxicity toward mouse normal fibroblast cells, even at 350 μM concentration. The results of the present study offer insight on the production of both 5,7,4′-trihydroxy-3′-methoxyisoflavone and 5,7,3′-trihydroxy-4′-methoxyisoflavone by two recombinant E. coli strains and the potential anti-melanoma applications of 5,7,4′-trihydroxy-3′-methoxyisoflavone.
format Online
Article
Text
id pubmed-6155705
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61557052018-11-13 Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains Chiang, Chien-Min Chang, Yu-Jhe Wu, Jiumn-Yih Chang, Te-Sheng Molecules Communication Biotransformation of the soy isoflavone genistein by sequential 3′-hydroxylation using recombinant Escherichia coli expressing tyrosinase from Bacillus megaterium and then methylation using another recombinant E. coli expressing O-methyltransferase from Streptomyces peucetius was conducted. The results showed that two metabolites were produced from the biotransformation, identified as 5,7,4′-trihydroxy-3′-methoxyisoflavone and 5,7,3′-trihydroxy-4′-methoxyisoflavone, respectively, based on their mass and nuclear magnetic resonance spectral data. 5,7,4′-Trihydroxy-3′-methoxyisoflavone showed potent antiproliferative activity toward mouse B16 melanoma cells with an IC(50) value of 68.8 μM. In contrast, the compound did not show any cytotoxicity toward mouse normal fibroblast cells, even at 350 μM concentration. The results of the present study offer insight on the production of both 5,7,4′-trihydroxy-3′-methoxyisoflavone and 5,7,3′-trihydroxy-4′-methoxyisoflavone by two recombinant E. coli strains and the potential anti-melanoma applications of 5,7,4′-trihydroxy-3′-methoxyisoflavone. MDPI 2017-01-04 /pmc/articles/PMC6155705/ /pubmed/28054996 http://dx.doi.org/10.3390/molecules22010087 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Chiang, Chien-Min
Chang, Yu-Jhe
Wu, Jiumn-Yih
Chang, Te-Sheng
Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains
title Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains
title_full Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains
title_fullStr Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains
title_full_unstemmed Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains
title_short Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains
title_sort production and anti-melanoma activity of methoxyisoflavones from the biotransformation of genistein by two recombinant escherichia coli strains
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155705/
https://www.ncbi.nlm.nih.gov/pubmed/28054996
http://dx.doi.org/10.3390/molecules22010087
work_keys_str_mv AT chiangchienmin productionandantimelanomaactivityofmethoxyisoflavonesfromthebiotransformationofgenisteinbytworecombinantescherichiacolistrains
AT changyujhe productionandantimelanomaactivityofmethoxyisoflavonesfromthebiotransformationofgenisteinbytworecombinantescherichiacolistrains
AT wujiumnyih productionandantimelanomaactivityofmethoxyisoflavonesfromthebiotransformationofgenisteinbytworecombinantescherichiacolistrains
AT changtesheng productionandantimelanomaactivityofmethoxyisoflavonesfromthebiotransformationofgenisteinbytworecombinantescherichiacolistrains