title: Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains.
abstract: Biotransformation of the soy isoflavone genistein by sequential 3'-hydroxylation using recombinantEscherichia coliexpressing tyrosinase fromBacillus megateriumand then methylation using another recombinantE. coliexpressingO-methyltransferase fromStreptomyces peucetiuswas 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 IC50value 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 recombinantE. colistrains and the potential anti-melanoma applications of 5,7,4'-trihydroxy-3'-methoxyisoflavone.
authors.affiliation: Department of Biotechnology, Chia Nan University of Pharmacy and Science, No. 60, Sec. 1, Erh-Jen Rd., Jen-Te District, Tainan 71710, Taiwan. cmchiang@mail.cnu.edu.tw.
authors.forename: Chien-Min
authors.initials: CM
authors.lastname: Chiang
authors.affiliation: Department of Biological Sciences and Technology, National University of Tainan, No. 33, Sec. 2, Shu-Lin St., Tainan 70005, Taiwan. roger199382@yahoo.com.tw.
authors.forename: Yu-Jhe
authors.initials: YJ
authors.lastname: Chang
authors.affiliation: Institute of Biotechnology and Chemical Engineering, I-Shou University, No. 1, Sec. 1, Syuecheng Rd., Dashu District, Kaohsiung 84001, Taiwan. wujy@nqu.edu.tw.|Center for General Education, National Quemoy University, No. 1, University Road., Jin-Ning Township, Kinmen County 892, Taiwan. wujy@nqu.edu.tw.
authors.forename: Jiumn-Yih
authors.initials: JY
authors.lastname: Wu
authors.affiliation: Department of Biological Sciences and Technology, National University of Tainan, No. 33, Sec. 2, Shu-Lin St., Tainan 70005, Taiwan. mozyme2001@gmail.com.
authors.forename: Te-Sheng
authors.initials: TS
authors.lastname: Chang
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000096:biosynthesis* / Q000302:isolation & purification / Q000494:pharmacology; D001410:Bacillus megaterium / Q000737:chemistry / Q000201:enzymology; D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism*; D001711:Biotransformation; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004926:Escherichia coli / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D005347:Fibroblasts / Q000187:drug effects; D019833:Genistein / Q000378:metabolism; D006900:Hydroxylation; D020128:Inhibitory Concentration 50; D007529:Isoflavones / Q000096:biosynthesis* / Q000302:isolation & purification / Q000494:pharmacology; D008546:Melanoma, Experimental / Q000473:pathology; D060847:Metabolic Engineering / Q000379:methods; D008745:Methylation; D008780:Methyltransferases / Q000235:genetics / Q000378:metabolism*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000235:genetics / Q000378:metabolism*; D009928:Organ Specificity; D030781:Organisms, Genetically Modified / Q000235:genetics / Q000378:metabolism; D013302:Streptomyces / Q000737:chemistry / Q000201:enzymology; D019076:Transgenes
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D001426:Bacterial Proteins; D007529:Isoflavones; D019833:Genistein; D014442:Monophenol Monooxygenase; D008780:Methyltransferases
keywords: genistein; melanoma; methoxyisoflavone; methyltransferase; tyrosinase