Glycosylation and subsequent malonylation of isoflavonoids in E. coli: strain development, production and insights into future metabolic perspectives. (1st November 2014)

• Record Type: Journal Article
• Authors: Koirala, Niranjan; Pandey, Ramesh Prasad; Van Thang, Duong; Jung, Hye Jin; Sohng, Jae Kyung
• Is Part Of: Journal of industrial microbiology & biotechnology. Volume 41:Number 11(2014)
• Page Start: 1647
• Page End: 1658
• Publication Date: 2014-11-01
• Subjects: Glycosylation -- Malonylation -- Bioconversion -- Isoflavonoids -- Anticancer; Industrial microbiology -- Periodicals; 660.62
• DOI: 10.1007/s10295-014-1504-6
• Languages: English
• ISSNs: 1367-5435

Abstract

Abstract: Genistin and daidzein exhibit a protective effect on DNA damage and inhibit cell proliferation. Glycosylation and malonylation of the compounds increase water solubility and stability. Constructed pET15b-GmIF7GT and pET28a-GmIF7MAT were used for the transformation of Escherichia coli and bioconversion of genistein and daidzein. To increase the availability of malonyl-CoA, a critical precursor of GmIF7MAT, genes for the acyl-CoA carboxylase α and β subunits ( nfa 9890 and nfa 9940), biotin ligase ( nfa 9950), and acetyl-CoA synthetase ( nfa 3550) from Nocardia farcinia were also introduced. Thus, the isoflavonoids were glycosylated at position 7 by 7- O -glycosyltranferase and were further malonylated at position 6 ″ of glucose by malonyl-CoA: isoflavone 7- O -glucoside-6 ″ - O -malonyltransferase both from Glycine max . Engineered E. coli produced 175.7 µM (75.90 mg/L) of genistin and 14.2 µM (7.37 mg/L) genistin 6″- O -malonate. Similar conditions produced 162.2 µM (67.65 mg/L) daidzin and 12.4 µM (6.23 mg/L) daidzin 6″- O -malonate when 200 µM of each substrate was supplemented in the culture. Based on our findings, we speculate that isoflavonoids and their glycosides may prove useful as anticancer drugs with added advantage of increased solubility, stability and bioavailability.