Identification of a multi-component berberine 11-hydroxylase from Burkholderia sp. strain CJ1

References

• Ikuta A, Itokawa H. Alkaloids of Coptis Rhizome. J Nat Prod. 1984;47(1):189–190.
   Web of Science ®Google Scholar
• Tosa S, Ishihara S, Nose Y, et al. Studies on quality control of crude drugs (I) analysis and distribution of alkaloids in Phellodendron amurense RUPRECHT. Shoyakugaku Zasshi (in Japanese). 1989;43:28–34.
   Google Scholar
• Amin AH, Subbaiah TV, Abbasi KM. Berberine sulfate: antimicrobial activity, bioassay and mode of action. Can J Microbiol. 1969;15:1067–1076.
   PubMed Web of Science ®Google Scholar
• Sun D, Abraham SN, Beachey EH. Influence of berberine sulfate on synthesis and expression of pap fimbrial adhesion in uropathogenic Escherichia coli. Antimicrob Agents Chemother. 1988;32(8):1274–1277.
   PubMed Web of Science ®Google Scholar
• Vennerstrom JL, Klayman DL. Protoberberine alkaloids as antimalarials. J Med Chem. 1988;31:1084–1087.
   PubMed Web of Science ®Google Scholar
• Vollekova A, Kostalova D, Sochorova R. Isoquinoline alkaloids from Mhonia aquifolium stem bark are active against Malassezia spp. Folia Microbiol (Praha). 2001;46:107–111.
   PubMed Web of Science ®Google Scholar
• Kim S, Lee J, You D. et al. Berberine suppresses cell motility through downregulation of TGF-b1 in triple negative breast cancer cells. Physiol Biochem. 2018;45(2):795–807.
   Google Scholar
• Agnarelli A, Natali M, Garcia-Gil M. et al. Cell-specific pattern of berberine pleiotropic effects on different human cell lines. Sci Rep. 2018;8(1):1–15.
   PubMedGoogle Scholar
• Jung HA, Yoon NY, Bae HJ, et al. Inhibitory activities of the alkaloids from Coptidis Rhizoma against aldose reductase. Arch Pharm Res. 2008;31:1405–1412.
   PubMed Web of Science ®Google Scholar
• Shi R, Xu Z, Xu X, et al. Organic cation transporter and multidrug and toxin extrusion 1 co-mediated interaction between metformin and berberine. Eur J Pharm Sci. 2019;127:282–290.
   PubMed Web of Science ®Google Scholar
• Chow YL, Sogame M, Sato F. 13-Methylberberine, a berberine analogue with stronger anti-adipogenic effects on mouse 3T3-L1 cells. Sci Rep. 2016;6:38129.
   PubMed Web of Science ®Google Scholar
• Han Y, Kim MJ, Lee KY. Berberine derivative, Q8, stimulates osteogenic differentiation. Biochem Biophys Res Commun. 2018;504:340–345.
   PubMed Web of Science ®Google Scholar
• Ishikawa K, Takeda H, Wakana D, et al. Isolation and identification of berberine and berberrubine metabolites by berberine-utilizing bacterium Rhodococcus sp. Strain BD7100. Biosci Biotechnol Biochem. 2016;80:856–862.
   PubMed Web of Science ®Google Scholar
• Takeda H, Ishikawa K, Wakana D, et al. 11-hydroxylation of protoberberine by the novel berberine-utilizing aerebic bacterium sphingobium sp. strain BD3100. J Nat Prod. 2015;78:2880–2886.
   PubMed Web of Science ®Google Scholar
• Takeda H, Ishikawa K, Yoshida H, et al. Common origin of methylenedioxy ring degradation and demethylation in bacteria. Sci Rep. 2017;7(1):1–8.
   PubMedGoogle Scholar
• Ochman H, Gerber AS, Hartl DL. Genetic applications of an inverse polymerase chain reaction. Genetics. 1988;120:621–623.
   PubMed Web of Science ®Google Scholar
• Brunel F, Davison J. Cloning and Sequencing of Pseudomonas genes encoding vanillate demethylase. J Bacteriol. 1988;170(10):4924–4930.
   PubMed Web of Science ®Google Scholar
• Priefert H, Rabenhorst J, Steinbüchel A. molecular characterization of genes of Pseudomonas sp. Strain HR199 involved in bioconversion of vanillin to protocatechuate. J Bacteriol. 1997;179(8):2595–2607.
   PubMed Web of Science ®Google Scholar
• Kim JH, Lee SJ, Kim SH. New derivatives of berberrubine and their salts for antibiotics and antifungal agents. PCT. WO2003051875A1. 2003.
   Google Scholar
• Li YH, Li Y, Yang P, et al. Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine. Bioorg Med Chem. 2010;18:6422–6428.
   PubMed Web of Science ®Google Scholar
• Herman PL, Behrens M, Chakraborty S, et al. A three-component dicamba O-demethylase from Pseudomonas maltophilia, Strain DI-6. J Biol Chem. 2005;280(26):24759–24767.
   PubMed Web of Science ®Google Scholar
• Chen Q, Wang CH, Deng SK, et al. A novel three-component rieske non-heme iron oxygenase (ROH) system catalyzing the N-dealkylation of chroloacetanilide herbicides in Sphingomonads DC-6 and DC-2. Appl Environ Microbial. 2014;80(16):5078–5085.
   Web of Science ®Google Scholar
• Kweon O, Kim SJ, Baek S, et al. A new classification system for bacterial Rieske non-heme iron aromatic ring-hydroxylating oxygenases. BMC Biochem. 2008;9(1):11.
   PubMedGoogle Scholar
• Chakraborty J, Ghosal D, Dutta A, et al. An insight into the origin and functional evolution of bacterial aromatic ring-hydroxylating oxygenases. J Biomol Struct Dyn. 2012;30(4):419–436.
   PubMed Web of Science ®Google Scholar
• Axcell BC, Geary PJ. Purification and some properties of a soluble benzene-oxidizing system from a strain of Pseudomonas. Biochem J. 1975;146:173–183.
   PubMed Web of Science ®Google Scholar
• Rosche B, Tshisuaka B, Fetzner S, et al. 2-Oxo-1, 2-dihydroquinoline 8-monooxygenase, a two-component enzyme system from Pseudomonas putida 86. J Biol Chem. 1995;270(30):17836–17842.
   PubMed Web of Science ®Google Scholar
• Schäfer F, Schuster J, Würz B, et al. Synthesis of short-chain diols and unsaturated alcohols from secondary alcoholic substrates by the Rieske non-heme mononuclear iron oxygenase MdpJ. Appl Environ Microbiol. 2012;78(17):6280–6284.
   PubMed Web of Science ®Google Scholar
• Wollam J, Magomedva L, Magner DB, et al. The rieske oxygenase DAF-36 functions as a cholesterol 7-desaturase in steroidogenic pathways governing longevity. Aging Cell. 2011;10:879–884.
   PubMed Web of Science ®Google Scholar
• Gallagher JR, Olson ES, Stanley DC. Microbial desulfurization of dibenzothiophene: A sulfur-specific pathway. FEMS Microbiol Lett. 1993;107:31–36.
   PubMed Web of Science ®Google Scholar