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References

  1. Chang TS. 2014. Isolation, bioactivity, and production of ortho-hydroxydaidzein and ortho-hydroxygenistein. Int. J. Mol. Sci. 15: 5699-5716.
    Pubmed PMC CrossRef
  2. Charaux C, Rabate J. 1939. Constitution chimique de l'orobol. Bull. Soc. Chim. Biol. (Paris) 21: 1330-1333.
  3. Chen QC, Zhang WY, Jin W, Lee IS, Min BS, Jung HJ, et al. 2010. Flavonoids and isoflavonoids from Sophorae Flos improve glucose uptake in vitro. Planta Med. 76: 79-81.
    Pubmed CrossRef
  4. Ding HY, Chiang CM, Chen YC, Chang TS. 2015. Identifying 3'-hydroxygenistein as potent melanogenesis inhibitor from biotransformation of genistein by recombinant Pichia pastoris. Process Biochem. 50: 1614-1617.
    CrossRef
  5. Ding HY, Lin PW, Wang HW, Chang TS. 2014. Methanol partition fraction of ethanol extract of Dioscorea nipponica Makino inhibits melanogenesis. Trop. J. Pharm. Res. 13: 719726.
    CrossRef
  6. Kiriakidis S, Hogemeier O, Starcke S, Dombrowski F, Hahne JC, Pepper M, et al. 2005. Novel tempeh (fermented soyabean) isoflavones inhibit in vivo angiogenesis in the chicken chorioallantoic membrane assay. Br. J. Nutr. 93: 317-323.
    Pubmed CrossRef
  7. Lee JY, Lee HJ, Seo J, Kim ES, Lee HS, Kim P. 2014. Artifical oxidative stress-tolerant Corynebacterium glutamicum. AMB Express 4: 15.
    Pubmed PMC CrossRef
  8. Lee JY, Seo J, Kim ES, Lee HS, Kim P. 2013. Adaptive evolutin of Corynebacterium glutamicum resistant to oxidative stress and its global gene expression profiling. Biotechnol. Lett. 35: 709-717.
    Pubmed CrossRef
  9. Ma CH, Chen B, Qi HY, Li BG, Zhang GL. 2004. Two pyranocoumarins from the seeds of Calophyllum polyanthum. J. Nat. Prod. 67: 1598-1600.
    Pubmed CrossRef
  10. Matsuda H, Morikawa T, Xu F, Ninomiya K, Yoshikawa M. 2004. New isoflavones and pterocarpane with hepatoprotective activity from the stems of Erycibe expansa. Planta Med. 70:1201-1209.
    Pubmed CrossRef
  11. Nguyen DT, Hernandez-Montes E, Vauzour D, Schonthal AH, Rice-Evans C, Cadenas E, Spencer JP. 2006. The intracellular genistein metabolite 5,7,3',4'-tetrahydroxyisoflavone mediates G2-M cell cycle arrest in cancer cells via modulation of the p38 signaling pathway. Free Radic. Biol. Med. 41: 1225-1239.
    Pubmed CrossRef
  12. Reyes LH, Gomez JM, Kao KC. 2014. Improving carotenoids production in yeast via adaptive laboratory evolution. Metab. Eng. 21: 26-33.
    Pubmed CrossRef
  13. Tewtrakul S, Subhadhirasakul S, Cheenpracha S, Karalai C. 2007. HIV-1 protease and HIV-1 integrase inhibitory substances from Eclipta prostrata. Phytother. Res. 21: 1092-1095.
    Pubmed CrossRef
  14. Tewtrakul S, Subhadhirasakul S, Tansakul P, Cheenpracha S, Karalai C. 2011. Antiinflammatory constituents from Eclipta prostrata using RAW264.7 macrophage cells. Phytother. Res. 25: 1313-1316.
    CrossRef
  15. Umezawa H, Tobe H, Shibamoto N, Nakamura F, Nakamura K. 1975. Isolation of isoflavones inhibiting DOPA decarboxylase from fungi and streptomyces. J. Antibiot. (Tokyo) 28: 947-952.
    CrossRef
  16. Vauzour D, Vafeiadou K, Rice-Evans C, Cadenas E, Spencer JP. 2007. Inhibition of cellular proliferation by the genistein metabolite 5,7,3',4'-tetrahydroxyisoflavone is mediated by DNA damage and activation of the ATR signalling pathway. Arch. Biochem. Biophys. 468: 159-166.
    Pubmed CrossRef

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Note

J. Microbiol. Biotechnol. 2016; 26(3): 498-502

Published online March 28, 2016 https://doi.org/10.4014/jmb.1509.09013

Copyright © The Korean Society for Microbiology and Biotechnology.

Improving 3’-Hydroxygenistein Production in Recombinant Pichia pastoris Using Periodic Hydrogen Peroxide-Shocking Strategy

Tzi-Yuan Wang 1, Yi-Hsuan Tsai 2, I-Zen Yu 2 and Te-Sheng Chang 2*

1Biodiversity Research Center, Academia Sinica, Taipei 115, Taiwan, Republic of China, 2Department of Biological Sciences and Technology, National University of Tainan, Tainan, 702, Taiwan, Republic of China

Received: September 4, 2015; Accepted: December 14, 2015

Abstract

3’-Hydroxygenistein can be obtained from the biotransformation of genistein by the
engineered Pichia pastoris X-33 strain, which harbors a fusion gene composed of CYP57B3 from
Aspergillus oryzae and a cytochrome P450 oxidoreductase gene (sCPR) from Saccharomyces
cerevisiae. P. pastoris X-33 mutants with higher 3’-hydroxygenistein production were selected
using a periodic hydrogen peroxide-shocking strategy. One mutant (P2-D14-5) produced
23.0 mg/l of 3’-hydroxygenistein, representing 1.87-fold more than that produced by the
recombinant X-33. When using a 5 L fermenter, the P2-D14-5 mutant produced 20.3 mg/l of 3’-
hydroxygenistein, indicating a high potential for industrial-scale 3’-hydroxygenistein
production.

Keywords: 3’-Hydroxygenistein, orobol, CYP57B3, Pichia pastoris

References

  1. Chang TS. 2014. Isolation, bioactivity, and production of ortho-hydroxydaidzein and ortho-hydroxygenistein. Int. J. Mol. Sci. 15: 5699-5716.
    Pubmed KoreaMed CrossRef
  2. Charaux C, Rabate J. 1939. Constitution chimique de l'orobol. Bull. Soc. Chim. Biol. (Paris) 21: 1330-1333.
  3. Chen QC, Zhang WY, Jin W, Lee IS, Min BS, Jung HJ, et al. 2010. Flavonoids and isoflavonoids from Sophorae Flos improve glucose uptake in vitro. Planta Med. 76: 79-81.
    Pubmed CrossRef
  4. Ding HY, Chiang CM, Chen YC, Chang TS. 2015. Identifying 3'-hydroxygenistein as potent melanogenesis inhibitor from biotransformation of genistein by recombinant Pichia pastoris. Process Biochem. 50: 1614-1617.
    CrossRef
  5. Ding HY, Lin PW, Wang HW, Chang TS. 2014. Methanol partition fraction of ethanol extract of Dioscorea nipponica Makino inhibits melanogenesis. Trop. J. Pharm. Res. 13: 719726.
    CrossRef
  6. Kiriakidis S, Hogemeier O, Starcke S, Dombrowski F, Hahne JC, Pepper M, et al. 2005. Novel tempeh (fermented soyabean) isoflavones inhibit in vivo angiogenesis in the chicken chorioallantoic membrane assay. Br. J. Nutr. 93: 317-323.
    Pubmed CrossRef
  7. Lee JY, Lee HJ, Seo J, Kim ES, Lee HS, Kim P. 2014. Artifical oxidative stress-tolerant Corynebacterium glutamicum. AMB Express 4: 15.
    Pubmed KoreaMed CrossRef
  8. Lee JY, Seo J, Kim ES, Lee HS, Kim P. 2013. Adaptive evolutin of Corynebacterium glutamicum resistant to oxidative stress and its global gene expression profiling. Biotechnol. Lett. 35: 709-717.
    Pubmed CrossRef
  9. Ma CH, Chen B, Qi HY, Li BG, Zhang GL. 2004. Two pyranocoumarins from the seeds of Calophyllum polyanthum. J. Nat. Prod. 67: 1598-1600.
    Pubmed CrossRef
  10. Matsuda H, Morikawa T, Xu F, Ninomiya K, Yoshikawa M. 2004. New isoflavones and pterocarpane with hepatoprotective activity from the stems of Erycibe expansa. Planta Med. 70:1201-1209.
    Pubmed CrossRef
  11. Nguyen DT, Hernandez-Montes E, Vauzour D, Schonthal AH, Rice-Evans C, Cadenas E, Spencer JP. 2006. The intracellular genistein metabolite 5,7,3',4'-tetrahydroxyisoflavone mediates G2-M cell cycle arrest in cancer cells via modulation of the p38 signaling pathway. Free Radic. Biol. Med. 41: 1225-1239.
    Pubmed CrossRef
  12. Reyes LH, Gomez JM, Kao KC. 2014. Improving carotenoids production in yeast via adaptive laboratory evolution. Metab. Eng. 21: 26-33.
    Pubmed CrossRef
  13. Tewtrakul S, Subhadhirasakul S, Cheenpracha S, Karalai C. 2007. HIV-1 protease and HIV-1 integrase inhibitory substances from Eclipta prostrata. Phytother. Res. 21: 1092-1095.
    Pubmed CrossRef
  14. Tewtrakul S, Subhadhirasakul S, Tansakul P, Cheenpracha S, Karalai C. 2011. Antiinflammatory constituents from Eclipta prostrata using RAW264.7 macrophage cells. Phytother. Res. 25: 1313-1316.
    CrossRef
  15. Umezawa H, Tobe H, Shibamoto N, Nakamura F, Nakamura K. 1975. Isolation of isoflavones inhibiting DOPA decarboxylase from fungi and streptomyces. J. Antibiot. (Tokyo) 28: 947-952.
    CrossRef
  16. Vauzour D, Vafeiadou K, Rice-Evans C, Cadenas E, Spencer JP. 2007. Inhibition of cellular proliferation by the genistein metabolite 5,7,3',4'-tetrahydroxyisoflavone is mediated by DNA damage and activation of the ATR signalling pathway. Arch. Biochem. Biophys. 468: 159-166.
    Pubmed CrossRef