Skip to main content
SpringerLink
Log in

Batch-feeding whole-cell catalytic synthesis of α-arbutin by amylosucrase from Xanthomonas campestris

  • Biocatalysis - Original Paper
  • Published:
Journal of Industrial Microbiology & Biotechnology

Abstract

α-Arbutin is an effective skin-whitening cosmetic ingredient and can be synthesized through hydroquinone glycosylation. In this study, amylosucrase (Amy-1) from Xanthomonas campestris pv. campestris 8004 was newly identified as a sucrose-utilizing glycosylating hydroquinone enzyme. Its kinetic parameters showed a seven-time higher affinity to hydroquinone than maltose-utilizing α-glycosidase. The glycosylation of HQ can be quickly achieved with over 99% conversion when a high molar ratio of glycoside donor to acceptor (80:1) was used. A batch-feeding catalysis method was designed to eliminate HQ inhibition with high productivity (> 36.4 mM h−1). Besides, to eliminate the serious inhibition caused by the accumulated hydroquinone oxidation products, the whole-cell catalysis was further proposed. 306 mM of α-arbutin was finally achieved with 95% molar conversion rate within 15 h. Hence, the batch-feeding whole-cell biocatalysis by Amy-1 is a promising technology for α-arbutin production with enhanced yield and molar conversion rate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Desmedt B, Van Hoeck E, Rogiers V, Courselle P, De Beer JO, De Paepe K, Deconinck E (2014) Characterization of suspected illegal skin whitening cosmetics. J Pharm Biomed 90:85–91

    Article  CAS  Google Scholar 

  2. He YQ, Zhang L, Jiang BL, Zhang ZC, Xu RQ, Tang DJ, Qin J, Jiang W, Zhang X, Liao J, Cao JR, Zhang SS, Wei ML, Liang XX, Lu GT, Feng JX, Chen B, Cheng J, Tang JL (2007) Comparative and functional genomics reveals genetic diversity and determinants of host specificity among reference strains and a large collection of Chinese isolates of the phytopathogen Xanthomonas campestris pv. campestris. Genome Biol 8:R218

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Kazuhisha S, Takahisha N, Takahashi K (2007) Development of alpha-arbutin: production at industrial scale and application for a skin-lightening cosmetic ingredient. Trends Glycosci Glycotechnol 19:235–246

    Article  Google Scholar 

  4. Kelebek H, Selli S, Canbas A, Cabaroglu T (2009) HPLC determination of organic acids, sugars, phenolic compositions and antioxidant capacity of orange juice and orange wine made from a Turkish cv. Kozan. Microchem J 91:187–192

    Article  CAS  Google Scholar 

  5. Kim MD, Seo DH, Jung JH, Jung DH, Joe MH, Lim S, Lee JH, Park CS (2014) Molecular cloning and expression of amylosucrase from highly radiation-resistant Deinococcus radiopugnans. Food Sci Biotechnol 23:2007–2012

    Article  CAS  Google Scholar 

  6. Kitao S, Sekine H (1994) Alpha-D-glucosyl transfer to phenolic-compounds by sucrose phosphorylase from Leuconostoc mesenteroides and production of alpha-arbutin. Biosci Biotechnol Biochem 58:38–42

    Article  CAS  PubMed  Google Scholar 

  7. Kurosu J, Sato T, Yoshida K, Tsugane T, Shimura S, Kirimura K, Kino K, Usami S (2002) Enzymatic synthesis of alpha-arbutin by alpha-anomer-selective-glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701. J Biosci Bioeng 93:328–330

    Article  CAS  PubMed  Google Scholar 

  8. Liu CQ, Deng L, Zhang P, Zhang SR, Liu L, Xu T, Wang F, Tan TW (2013) Screening of high alpha-arbutin producing strains and production of alpha-arbutin by fermentation. World J Microbiol Biotechnol 29:1391–1398

    Article  CAS  PubMed  Google Scholar 

  9. Liu CQ, Deng L, Zhing P, Zhang SR, Xu T, Wang F, Tan TW (2013) Efficient production of alpha-arbutin by whole-cell biocatalysis using immobilized hydroquinone as a glucosyl acceptor. J Mol Catal B Enzym 91:1–7

    Article  CAS  Google Scholar 

  10. Mathew S, Adlercreutz P (2013) Regioselective glycosylation of hydroquinone to alpha-arbutin by cyclodextrin glucanotransferase from Thermoanaerobacter sp. Biochem Eng J 79:187–193

    Article  CAS  Google Scholar 

  11. Migas P, Krauze-Baranowska M (2015) The significance of arbutin and its derivatives in therapy and cosmetics. Phytochem Lett 13:35–40

    Article  CAS  Google Scholar 

  12. Nakagawa H, Dobashi Y, Sato T, Yoshida K, Tsugane T, Shimura S, Kirimura K, Kino K, Usami S (2000) alpha-anomer-selective glucosylation of menthol with high yield through a crystal accumulation reaction using lyophilized cells of Xanthomonas campestris WU-9701. J Biosci Bioeng 89:138–144

    Article  CAS  PubMed  Google Scholar 

  13. Nishimura T, Kometani T, Takii H, Terada Y, Okada S (1994) Purification and some properties of alpha-amylase from Bacillus subtilis X-23 that glucosylates phenolic-compounds such as hydroquinone. J Ferment Bioeng 78:31–36

    Article  CAS  Google Scholar 

  14. Park MO, Chandrasekaran M, Yoo SH (2018) Expression, purification, and characterization of a novel amylosucrase from Neisseria subflava. Int J Biol Macromol 109:160–166

    Article  CAS  PubMed  Google Scholar 

  15. Prodanovic R, Milosavic N, Sladic D, Zlatovic M, Bozic B, Velickovic TC, Vujcic Z (2005) Transglucosylation of hydroquinone catalysed by alpha-glucosidase from baker’s yeast. J Mol Catal B Enzym 35:142–146

    Article  CAS  Google Scholar 

  16. Sato T, Hasegawa N, Saito J, Umezawa S, Honda Y, Kino K, Kirimura K (2012) Purification, characterization, and gene identification of an alpha-glucosyl transfer enzyme, a novel type alpha-glucosidase from Xanthomonas campestris WU-9701. J Mol Catal B Enzym 80:20–27

    Article  CAS  Google Scholar 

  17. Seo DH, Jung JH, Ha SJ, Cho HK, Jung DH, Kim TJ, Baek NI, Yoo SH, Park CS (2012) High-yield enzymatic bioconversion of hydroquinone to alpha-arbutin, a powerful skin lightening agent, by amylosucrase. Appl Microbiol Biotechnol 94:1189–1197

    Article  CAS  PubMed  Google Scholar 

  18. Seo DH, Jung JH, Ha SJ, Song MC, Cha J, Yoo SH, Kim TJ, Baek NI, Park CS (2009) Highly selective biotransformation of arbutin to arbutin-alpha-glucoside using amylosucrase from Deinococcus geothermalis DSM 11300. J Mol Catal B Enzym 60:113–118

    Article  CAS  Google Scholar 

  19. Seo DH, Jung JH, Lee JE, Jeon EJ, Kim W, Park CS (2012) Biotechnological production of arbutins (alpha- and beta-arbutins), skin-lightening agents, and their derivatives. Appl Microbiol Biotechnol 95:1417–1425

    Article  CAS  PubMed  Google Scholar 

  20. Seo ES, Kang J, Lee JH, Kin GE, Kim GJ, Kim D (2009) Synthesis and characterization of hydroquinone glucoside using Leuconostoc mesenteroides dextransucrase. Enzyme Microbiol Technol 45:355–360

    Article  CAS  Google Scholar 

  21. Sugimoto K, Nishimura T, Nomura K, Sugimoto K, Kuriki T (2004) Inhibitory effects of alpha-arbutin on melanin synthesis in cultured human melanoma cells and a three-dimensional human skin model. Biol Pharm Bull 27:510–514

    Article  CAS  PubMed  Google Scholar 

  22. Tian YQ, Xu W, Zhang WL, Zhang T, Guang CE, Mu WM (2018) Amylosucrase as a transglucosylation tool: from molecular features to bioengineering applications. Biotechnol Adv 36:1540–1552

    Article  CAS  PubMed  Google Scholar 

  23. Wei M, Ren Y, Liu CX, Liu RC, Zhang P, Wei Y, Xu T, Wang F, Tan TW, Liu CQ (2016) Fermentation scale up for alpha a-arbutin production by Xanthomonas BT-112. J Biotechnol 233:1–5

    Article  CAS  PubMed  Google Scholar 

  24. Yu SH, Wang YC, Tian YQ, Xu W, Bai YX, Zhang T, Mu WM (2018) Highly efficient biosynthesis of alpha-arbutin from hydroquinone by an amylosucrase from Cellulomonas carboniz. Process Biochem 68:93–99

    Article  CAS  Google Scholar 

  25. Zhu LJ, Dong HJ, Zhang YP, Li Y (2011) Engineering the robustness of Clostridium acetobutylicum by introducing glutathione biosynthetic capability. Metab Eng 13:426–434

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Nature Science Foundation of China (No. 31601445, No. 31601390 and No. 21572206) and Key Research and Development Programs in Zhejiang (No. 2019C01085 and No. 2019C02088) and the Natural Science Foundation of Zhejiang (No. LY19B060008).

Author information

Authors and Affiliations

  1. Institute of Fermentation Engineering, Zhejiang University of Technology, No. 18, Chaowang Road, 310014, Hangzhou, China

    Linjiang Zhu, Dan Jiang, Yaoyao Zhou, Yuele Lu & Xiaolong Chen

  2. College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, China

    Linjiang Zhu, Dan Jiang, Yaoyao Zhou, Yuele Lu & Xiaolong Chen

  3. College of Chemical Engineering, Zhejiang University of Technology, 310014, Hangzhou, China

    Yongxian Fan

Authors
  1. Linjiang Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dan Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yaoyao Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yuele Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yongxian Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xiaolong Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xiaolong Chen.

Ethics declarations

Conflict of interest

No conflict of interest declared.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1437 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhu, L., Jiang, D., Zhou, Y. et al. Batch-feeding whole-cell catalytic synthesis of α-arbutin by amylosucrase from Xanthomonas campestris. J Ind Microbiol Biotechnol 46, 759–767 (2019). https://doi.org/10.1007/s10295-019-02143-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10295-019-02143-z

Keywords

Search

Navigation