High efficiency production of ginsenoside compound K by catalyzing ginsenoside Rb1 using snailase

doi:10.1016/j.cjche.2018.02.004

Chinese Journal of Chemical Engineering ›› 2018, Vol. 26 ›› Issue (7): 1591-1597.DOI: 10.1016/j.cjche.2018.02.004

• Materials and Product Engineering • 上一篇下一篇

High efficiency production of ginsenoside compound K by catalyzing ginsenoside Rb1 using snailase

Zhiguang Duan, Chenhui Zhu, Jingjing Shi, Daidi Fan, Jianjun Deng, Rongzhan Fu, Rong Huang, Cuiying Fan

Shaanxi Key Laboratory of Degradable Biomedical Materials, School of Chemical Engineering, Northwest University, Taibai North Road 229, Xi'an 710069, China;Shanxi R & D Center of Biomaterials and Fermentation Engineering, School of Chemical Engineering, Northwest University, Taibai North Road 229, Xi'an 710069, China

收稿日期:2017-10-30 修回日期:2018-01-22 出版日期:2018-07-28 发布日期:2018-08-16
通讯作者: Daidi Fan,E-mail address:fandaidi@nwu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China (21476182, 21776227, 21776228); Shaanxi Key Laboratory of Degradable Biomedical Materials Program (2014SZS07-K04, 2014SZS07-P05, 15JS106, 2014SZS07-Z01, 2014SZS07-Z02, 2016SZSj-35, 2014SZS07-K03) and Shaanxi R&D Center of Biomaterials and Fermentation Engineering Program (2015HBGC-04).

High efficiency production of ginsenoside compound K by catalyzing ginsenoside Rb1 using snailase

Zhiguang Duan, Chenhui Zhu, Jingjing Shi, Daidi Fan, Jianjun Deng, Rongzhan Fu, Rong Huang, Cuiying Fan

Shaanxi Key Laboratory of Degradable Biomedical Materials, School of Chemical Engineering, Northwest University, Taibai North Road 229, Xi'an 710069, China;Shanxi R & D Center of Biomaterials and Fermentation Engineering, School of Chemical Engineering, Northwest University, Taibai North Road 229, Xi'an 710069, China

Received:2017-10-30 Revised:2018-01-22 Online:2018-07-28 Published:2018-08-16
Contact: Daidi Fan,E-mail address:fandaidi@nwu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China (21476182, 21776227, 21776228); Shaanxi Key Laboratory of Degradable Biomedical Materials Program (2014SZS07-K04, 2014SZS07-P05, 15JS106, 2014SZS07-Z01, 2014SZS07-Z02, 2016SZSj-35, 2014SZS07-K03) and Shaanxi R&D Center of Biomaterials and Fermentation Engineering Program (2015HBGC-04).

摘要/Abstract

摘要： The rare ginsenoside Compound K (C-K) is attracting more attention because of its good physiological activity and urgent need. There are many pathways to obtain ginsenoside C-K, including chemical and biological methods. Among these, the conversion of PPD-type ginsenosides by enzymatic hydrolysis is a trend due to its high efficiency and mild conditions. For effectively extracting from the other panaxadiol saponins, the conversion process for ginsenoside C-K was investigated using snailases in this study. The univariate experimental design and response surface methodology were used to determine the optimal hydrolysis conditions for the conversion of ginsenoside Rb1 into ginsenoside C-K by snailases. The optimum conditions were as follows:pH 5.12, temperature 51℃, ratio of snailase/substrate 0.21, and reaction time 48 h. On the basis of these parameters, the addition of 1.0 mmol·L^-1 ferric ion was found to significantly improve the enzymolysis of snailases for the first time. With the above conditions, the maximum conversion rate reached 89.7%, suggesting that the process can obviously increase the yield of ginsenoside C-K. The bioassay tests indicated that the ginsenoside C-K showed anti-tumor activity in a series of tumor cell lines. Based on these results, we can conclude that the process of rare ginsenoside CK production by enzymolysis with snailase is feasible, efficient, and suitable for the industrial production and application.

关键词: Ginsenoside Rb1, Ginsenoside Compound K, Snailase, Enzymolysis

Abstract: The rare ginsenoside Compound K (C-K) is attracting more attention because of its good physiological activity and urgent need. There are many pathways to obtain ginsenoside C-K, including chemical and biological methods. Among these, the conversion of PPD-type ginsenosides by enzymatic hydrolysis is a trend due to its high efficiency and mild conditions. For effectively extracting from the other panaxadiol saponins, the conversion process for ginsenoside C-K was investigated using snailases in this study. The univariate experimental design and response surface methodology were used to determine the optimal hydrolysis conditions for the conversion of ginsenoside Rb1 into ginsenoside C-K by snailases. The optimum conditions were as follows:pH 5.12, temperature 51℃, ratio of snailase/substrate 0.21, and reaction time 48 h. On the basis of these parameters, the addition of 1.0 mmol·L^-1 ferric ion was found to significantly improve the enzymolysis of snailases for the first time. With the above conditions, the maximum conversion rate reached 89.7%, suggesting that the process can obviously increase the yield of ginsenoside C-K. The bioassay tests indicated that the ginsenoside C-K showed anti-tumor activity in a series of tumor cell lines. Based on these results, we can conclude that the process of rare ginsenoside CK production by enzymolysis with snailase is feasible, efficient, and suitable for the industrial production and application.

Key words: Ginsenoside Rb1, Ginsenoside Compound K, Snailase, Enzymolysis

Zhiguang Duan, Chenhui Zhu, Jingjing Shi, Daidi Fan, Jianjun Deng, Rongzhan Fu, Rong Huang, Cuiying Fan. High efficiency production of ginsenoside compound K by catalyzing ginsenoside Rb1 using snailase[J]. Chinese Journal of Chemical Engineering, 2018, 26(7): 1591-1597.

参考文献

[1] T. Li, G. Mazza, A.C. Cottrell, et al., A Gisenosides in roots and leaves of American ginseng, J. Agric. Food Chem. 44(1996) 717-720.

[2] H. Hasegawa, M. Uchiyama, Antimetastatic efficacy of orally administered ginsenoside Rbl independence on intestinal bacterial hydrolyzing potential and significance of treatment with an active bacterial metabolite, Planta Med. 64(1998) 696-700.

[3] J. Xiao, D. Chen, X.X. Lin, et al., Screening of drug metabolizing enzymes for the ginsenoside compound K in vitro:An efficient anti-cancer substance originating from Panax ginseng, PLoS One 11(2016), e0147183..

[4] C.Z. Zhang, D. Li, H.S. Yu, et al., Purification and characterization of picied-β-glucosidase from Aspergillus niger, Process Biochem. 42(2007) 83-88.

[5] C.Z. Zhang, H.S. Yu, Y.M. Bao, et al., Purification and characterization of ginsenoside- β-glucosidase from ginseng, Chem. Pharm. Bull. 49(2001) 795-798.

[6] H.S. Yu, C.Z. Zhang, M. Lu, et al., Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I, Chem. Pharm. Bull. 55(2007) 231-235.

[7] J. Chen, H. Wu, Q. Wang, Y. Chang, K. Liu, et al., Ginsenoside metabolite compound K suppresses T-cell priming via modulation of dendritic cell trafficking and costimulatory signals, resulting in alleviation of collagen-induced arthritis, J. Pharmacol. Exp. Ther. 353(2015) 71-79.

[8] K. Kobashi, Glycosides are natural prodrugs-Evidence using germ-free and gnotobiotic rats associated with a human intestinal bacterium, J. Trad. Med. 15(1998) 1-13.

[9] E.A. Bae, J.E. Shin, D.H. Kim, Metabolism of ginsenoside Re by human intestinal microflora and its estrogenic effect, Biol. Pharm. Bull. 28(2005) 1903-1908.

[10] X.D. Yang, Y.Y. Yang, D.S. Ouyang, G.P. Yang, A review of bioconversion and pharmacology of ginsenoside compound K, Fitoterapia 100(2015) 208-220.

[11] Y. Chen, Y. Xu, Y. Zhu, X. Li, Anti-cancer effects of ginsenoside compound k on pediatric acute myeloid leukemia cells, Cancer Cell Int. 13(2013) 24.

[12] Z. Zhang, G.J. Du, C.Z. Wang, X.D. Wen, T. Calway, et al., Compound K, a ginsenoside metabolite, inhibits colon cancer growth via multiple pathways including p53-p21 interactions, Int. J. Mol. Sci. 14(2013) 2980-2995.

[13] J. Li, W. Zhong, W. Wang, S. Hu, J. Yuan, et al., Ginsenoside metabolite compound K promotes recovery of dextran sulfate sodium-induced colitis and inhibits inflammatory responses by suppressing NF-kappaB activation, PLoS One 9(2014), e87810..

[14] S. Chae, K.A. Kang, W.Y. Chang, et al., Effect of Compound K, a metabolite of ginseng saponin, combined with γ-ray radiation in human lung cancer cells in vitro and in vivo, J. Agric. Food Chem. 57(2009) 5777-5778.

[15] H. Hasegawa, J.H. Sung, J.H. Huh, et al., Ginseng intestinal bacterial metabolite IH 901 as a new anti-metastatic agent, Arch. Pharm. Res. 20(1997) 539-544.

[16] H. Hasegawa, Metabolic activation of ginsenoside against cancer intestinal bacterial deglycosylation and hepatic fatty-acid esterification, J. Trad. Med. 18(2001) 217-228.

[17] J.S. Park, E.M. Park, D.H. Kim, et al., Anti-inflammatory mechanism of ginseng saponins in activated microglia, J. Neuroimmunol. 209(2009) 40-49.

[18] L. Yu, S. Yu, Advance on research of ginsenoside C-K, Biotechnol. Bull. 1(2013) 31-35.

[19] X.S. Zhao, H.U. Yanbo, F.L. Meng, Enzymatic conversion of protopanoxadiol type saponins to minor ginsenoside C-K, Sci. Technol. Food Ind. 34(2013) 205-208.

[20] V. Flari, M. Matoub, C. Rouland, Purification and characterization of a β-mannanase from the digestive tract of the edible snail Helix lucorum L, Carbohydr. Res. 275(1995) 207-213.

[21] R. Got, A. Marnay, P. Jarrige, J. Font, Beta-galactosidase of Helix pomatia, Nature 204(1964) 686-687.

[22] X. Liu, Y. Cui, L. Yang, et al., Purification of a ginsenoside-Rb1 hydrolase from Helix snailase, Chin. J. Biotechnol. 21(2005) 929-933.

[23] Y.U. Zhaohui, Q.Y. Liu, C. Li, et al., Conversion of rare ginsenoside compound K from ginsenoside Rb_1 catalyzed by snailase immobilization onto microspheres, Chin. Tradit. Herb. Drugs 45(2014) 3092-3097.

[24] T. Mosmann, Rapid colorimetric assay for cellular growth and survival:Application to proliferation and cytotoxicity assays, J. Immunol. Methods 65(1983) 55-63.

[25] W. Jian, Effect of metal ions on enzyme function, J. Yibin Univ. 2(1993) 67-73.

[26] C.Z. Wang, G.J. Du, Z. Zhang, et al., Ginsenoside compound K, not Rb1, possesses potential chemopreventive, activities in human colorectal cancer, Int. J. Oncol. 40(2012) 1970-1976.

[27] C.S. Yang, S.R. Ko, B.G. Cho, et al., The ginsenoside metabolite compound K, a novel agonist of glucocorticoid receptor, induces tolerance to endotoxin-induced lethal shock, J. Cell. Mol. Med. 12(2008) 1739-1753.

[28] C.Y. Liu, R.X. Zhou, C.K. Sun, et al., Preparation of minor ginsenosides C-Mc, C-Y, F2, and C-K from American ginseng PPD-ginsenoside using special ginsenosidase type-I from Aspergillus niger g.848, J. Ginseng Res. 39(3) (2015) 221-229.

[29] J.S. Park, J.A. Shin, J.S. Jung, et al., Anti-inflammatory mechanism of compound K in activated microglia and its neuroprotective effect on experimental stroke in mice, J. Pharmacol. Exp. Ther. 341(2012) 59-67.

[30] H.U. Li, E.A. Bae, M.J. Han, D.H. Kim, Hepatoprotective effect of ginsenoside Rb1 and compound K on tert-butyl hydroperoxide-induced liver injury, Liver Int. 25(2005) 1069-1073.

High efficiency production of ginsenoside compound K by catalyzing ginsenoside Rb1 using snailase

High efficiency production of ginsenoside compound K by catalyzing ginsenoside Rb1 using snailase

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 0

编辑推荐

Metrics

本文评价