Skip to main content
SpringerLink
Log in

Preparation of trehalase inhibitor validoxylamine A by biocatalyzed hydrolysis of validemycin a with honeybee (Apis cerana fabr.) β-glucosidase

  • Original Research Articles
  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

Validoxylamine A is structurally similar to trehalose and acts a potent competivive inhibitor of trehalase. It has recently been receiving increased attention as a potential material for the development of new insecticides or drugs. In this study, β-glucosidase extracted from honeybees (Apis cerana Fabr.) was used as a catalyst to produce validoxylamine A through enzymatic hydrolysis of validamycin A. β-Glucosidase was separated and purified from honeybees, and its characteristics were examined. The results showed that β-glucosidase was stable across a range of temperatures from 30 to 40°C and across a relatively wide range of pH values from 5.0 to 7.5. Investigation of the biocatalyzed hydrolysis process from validamycin A to validoxylamine A with β-glucosidase revealed that both the substrate (validamycin A) and the product (validoxylamine A) inhibited β-glucosidase activity. The inhibition constant of the substrate K value was 5.01 mM, and that of the product K ip value was 1.32 mM. This product inhibition was competitive.

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

Similar content being viewed by others

References

  1. Iwasa, T., Higashide, E., and Shibato, M. (1971), J. Antibiot. 24, 107–113.

    CAS  Google Scholar 

  2. Agricultural Antibiotic Group in Shanghai Pesticide Institute (1975), Acta Microb. 15, 110–114 (in Chinese).

    Google Scholar 

  3. Asano, N., Yamaguchi, T., Kameda, Y., and Matsui, K. (1987), J. Antibiot. 40, 526–532.

    CAS  Google Scholar 

  4. Elbein, A. (1974), Adv. Carbohydr. Chem. Biochem. 30, 227–256.

    Article  CAS  Google Scholar 

  5. Asano, N., Takeuchi, M., Kameda, Y., Matsui, K., and Kono, Y. (1990), J. Antibiot. 43, 722–725.

    CAS  Google Scholar 

  6. Chiara, J. L., Storch de Gracia, I., Garcia, A., Bobo, S., and Martin-Ortega, M. D. (2005), Chem BioChem. 6, 186–191.

    CAS  Google Scholar 

  7. Kameda, Y., Asano, N., Yamaguchi, T., and Matsui, K. (1987), J. Antibiot. 40, 563–565.

    CAS  Google Scholar 

  8. Takeda, S., Kono, Y., and Kameda, Y. (1988), Ent. Exp. Appl. 46, 291–294.

    Article  CAS  Google Scholar 

  9. Kono, Y., Takahashi, M., Matshushita, K., Nishina, M., Kameda, Y., and Hori, E. (1994), J. Insect. Physiol. 40, 455–461.

    Article  CAS  Google Scholar 

  10. Takahashi, M., Kono, Y., Kurahashi, H., Matshushita, K., Nishina, M., and Kameda, Y. (1995), Appl. Entomol. Zool. 30, 231–239.

    CAS  Google Scholar 

  11. Kameda, Y., Asno, N., Yoshikawa, M., and Matsui, K. (1980), J. Antibiot. 33, 1575–1578.

    CAS  Google Scholar 

  12. Takeuchi, M., Takai, N., Asano, N., Kameda, Y., and Matsui, K. (1990), Chem. Pharm. Bull. 38, 1970–1975.

    CAS  Google Scholar 

  13. Takeuchi, M., Kamata, K., Yoshida, M., Kameda, Y., and Matsui, K. (1990), J. Antibiot. 108, 41–45.

    Google Scholar 

  14. Chen, X. L., Fan, Y. X., Zheng, Y. G., and Shen, Y. C. (2003), Chem. Rev. 103, 1955–1977.

    CAS  Google Scholar 

  15. Zheng, Y. G., Shentu, X. P., and Shen, Y. C. (2003), J. Enzyme inhib. Med. Chem. 20, 49–53.

    Article  CAS  Google Scholar 

  16. Ogawa, S., Miyamoto, Y., and Nakajima, A. (1989), Chem. Lett. 725–729.

  17. Ogawa, S., Nakajima, A., and Miyamoto, Y. (1991), J. Chem. Soc. Perkin Trans. I. 3287–3290.

    Article  Google Scholar 

  18. Zheng, Y. G., Jin, L. Q., and Shen, Y. C. (2004), Catal. Commun. 5, 519–525.

    Article  CAS  Google Scholar 

  19. Zhang, X. F., Zheng, Y. G., and Shen, Y. C. (2004), Chin. J. Antibiot. 29(4), 206–208 (in Chinese).

    CAS  Google Scholar 

  20. Low, N. H., Vong, K. V., and Sporns, P. (1986), J. Apicultural Res. 25, 178–181.

    CAS  Google Scholar 

  21. Bradford, M. (1976), Anal. Biochem. 72, 248–254.

    Article  CAS  Google Scholar 

  22. Zheng, Y. G., Zhang, X. F., and Shen, Y. C. (2005), Biocatal. Biotransform. 23, 71–77.

    Article  CAS  Google Scholar 

  23. Pontoh, J. and Low, N. H. (2002), Insect Biochem. Mol. Biol. 32, 679–690.

    Article  CAS  Google Scholar 

  24. Laemmli, U. K. (1970), Nature 227, 680–685.

    Article  CAS  Google Scholar 

  25. Hsieh, M. C. and Graham, T. L. (2001), Phytochemistry 58, 995–1005.

    Article  CAS  Google Scholar 

  26. Peralta, R. M., Kadowaki, M. K., Terenzi, H. F., and Jorge, J. A. (1997), FEMS Microbiol. Lett. 146, 291–295.

    Article  CAS  Google Scholar 

  27. Ohnishi, N. and Tanaka, T. (1996), J. Ferment. Bioeng. 82, 439–443.

    Article  Google Scholar 

  28. Nunoura, N., Ohdan, K., Yano, T., Yamamoto, K., and Kumagai, H. (1996), Biosci. Biotech. Biochem. 60, 188–193.

    Article  CAS  Google Scholar 

  29. Akiyama, T., Kaku, H., and Shibuya, N. (1998), Phystochemistry 48, 49–54.

    Article  CAS  Google Scholar 

  30. Goyal, K., Selvakumar, P., and Hayashi, K. (2001), J. Mol. Catal. B: Enzym. 15, 45–53.

    Article  CAS  Google Scholar 

  31. Terra, W. R. and Ferreira, C. (1994), Comp. Biochem. Physiol. 109B 1–62.

    CAS  Google Scholar 

  32. Goyal, K., Kim, Y. K., Kitaoka, M., and Hayashi, K. (2001), J. Mol. Catal. B: Enzym. 16, 43–51.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Bioengineering, Zhejiang University of Technology, 310014, Hangzhou, People's Republic of China

    Ya-Ping Xue, Yu-Guo Zheng & Yin-Chu Shen

Authors
  1. Ya-Ping Xue
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu-Guo Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yin-Chu Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu-Guo Zheng.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xue, YP., Zheng, YG. & Shen, YC. Preparation of trehalase inhibitor validoxylamine A by biocatalyzed hydrolysis of validemycin a with honeybee (Apis cerana fabr.) β-glucosidase. Appl Biochem Biotechnol 127, 157–171 (2005). https://doi.org/10.1385/ABAB:127:3:157

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1385/ABAB:127:3:157

Index Entries

Search

Navigation