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 |
Liu, Chun-Ying
(College of Biotechnology, Dalian Polytechnic University)
Zhou, Rui-Xin (College of Biotechnology, Dalian Polytechnic University) Sun, Chang-Kai (Institute for Brain Disorders, Dalian Medical University) Jin, Ying-Hua (Key Laboratory for Molecular Enzymology and Engineering of the Ministry of Education, College of Life Science, Jilin University) Yu, Hong-Shan (College of Biotechnology, Dalian Polytechnic University) Zhang, Tian-Yang (College of Biotechnology, Dalian Polytechnic University) Xu, Long-Quan (College of Biotechnology, Dalian Polytechnic University) Jin, Feng-Xie (College of Biotechnology, Dalian Polytechnic University) |
1 | Cui CH, Kim SC, Im WT. Characterization of the ginsenoside transforming recombinant -glucosidase from Actinosynnema mirum and bioconversion of major ginsenosides into minor ginsenosides. Appl Microbiol Biotech 2013;97: 649-59. DOI |
2 | Cui CH, Liu QM, Kim JK, Sung BH, Kim SG, Kim SC, Im WT. Identification and characterization of Mucilaginibacter sp. QM49 -glucosidase and its use in producing the pharmaceutically active minor ginsenosides, Rh1(S) and Rg2(S). Appl Environ Microbiol 2013;79:5788-98. DOI |
3 | Tanaka I, Kasai R. Saponins of ginseng and related plants. Progress in the chemistry of organic natural products, vol. 46. Berlin: Springer; 1984. p. 1-76. |
4 | Popovich DG, Kitts DD. Structure-function relationship exists for ginsenosides in reducing cell proliferation and inducing apoptosis in the human leukemia (THP-1) cell line. Arch Biochem Biophys 2002;406:1-8. DOI |
5 | Jin XF, Yu HS, Wang DM, Liu TQ, Liu CY, An DS, Im WT, Kim SG, Jin FX. Kinetics of a cloned special ginsenosidase hydrolyzing 3-O-glucoside of multiprotopanaxadiol- type ginsenosides, named ginsenosidase type III. J Microbiol Biotechnol 2012;22:343-51. DOI |
6 | Yu HS, Zhang CZ, Lu MC, Sun F, Fu YY, Jin FX. Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I. Chem Pharm Bull 2007;55:231-5. DOI |
7 | Liu CY, Jin YH, Yu HS, Sun CK, Gao P, Xiao YK, Zhang TY, Xu LQ, Im WT, Jin FX. Biotransformation pathway and kinetics of ginsenosidase type I hydrolyzing 3-O- and 20-O-multi- glucosides of PPD type ginsenosides. Process Biochem 2014;49:813-20. DOI |
8 | Yu HS, Liu QM, Zhang CZ, Lu MC, Fu YY, Im WT, Lee ST, Jin FX. A new ginsenosidase from Aspergillus strain hydrolyzing 20-O-multi-glycoside of PPD ginsenoside. Process Biochem 2009;44:772-5. DOI |
9 | Wang DM, Yu HS, Song JG, Xu YF, Jin FX. Enzyme kinetics of ginsenosidase type IV hydrolyzing 6-O-multi-glycosides of protopanaxatriol type ginsenosides. Process Biochem 2012;47:133-8. DOI |
10 | Li JW. Methods for biochemistry. Beijing: University Press; 1997. p. 189-96 [in Chinese]. |
11 | Wang JY. Biochemistry. Beijing: Higher Education Press; 2002. p. 356-61 [in Chinese]. |
12 | Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. J Biol Chem 1951;193:265-75. |
13 | Kobashi K. Glycosides are natural prodrugs - evidence using germ-free and gnotobiotic rats associated with a human intestinal bacterium. J Trad Med 1998;15:1-13. |
14 | Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc 1934;56:658-66. DOI |
15 | Jin FX. Biotransformation of natural products. Beijing: Chemical Industry Press; 2009. p. 74-113 [in Chinese]. |
16 | Attele AS, Wu JA, Yuan CS. Ginseng pharmacology: multiple constituents and multiple actions. Biochem Pharmacol 1999;58:1685-93. DOI |
17 | Christensen LP. Ginsenosides chemistry, biosynthesis, analysis, and potential health effects. Adv Food Nutr Res 2009;55:1-99. |
18 | Liu CY, Song JG, Li PF, Yu HS, Jin FX. Ginsenoside contents in three different ginseng. J Dalian Polytechnic Univ 2011;30:79-82. |
19 | Bae EA, Shin JE, Kim DH. Metabolism of ginsenoside Re by human intestinal microflora and its estrogenic effect. Bio Pharm Bull 2005;28:1903-8. DOI |
20 | Tawab MA, Bahr U, Karas M, Wurglics M, Schubert-Zsilavecz M. Degradatin of ginsenosides in humans after administration. Drug Metab Dispos 2003;31: 1065-71. DOI |
21 | Hasegawa H, Sung JH, Matsumiya S, Uchiyama M. Main ginseng saponin metabolites formed by intestinal bacteria. Planta Med 1996;62:453-7. DOI |
22 | Park CS, Yoo MH, Noh KH, Oh DK. Biotransformation of ginsenosides by hydrolyzing sugar moieties of ginsenosides using microbial glycosidases. Appl Microbiol Biotechnol 2010;87:9-19. DOI |
23 | Leung KW, Wong AS. Pharmacology of ginsenosides: a literature review. Chin Med 2010;5:20-2. DOI |
24 | Kim SJ, Kang BY, Cho SY, Sung DS, Chang HK, Yeom MH, Kim DH, Sim YC, Lee YS. Compound K induces expression of hyaluronan synthase 2 gene in transformed human keratinocytes and increases hyaluronan in hairless mouse skin. Biochem Biophys Res Commun 2004;316:348-55. DOI |
25 | Choi S, Kim TW, Singh SV. Ginsenoside Rh2-mediated G1 phase cell cycle arrest in human breast cancer cells is caused by p15 Ink4B and p27 Kip1- dependent inhibition of cyclin-dependent kinases. Pharm Res 2009;26: 2280-8. DOI |
26 | Choi SH, Shin TJ, Hwang SH, Lee BH, Kang J, Kim HJ. Differential effects of ginsenoside metabolites on HERG k channel currents. J Ginseng Res 2011;35: 191-9. DOI |
27 | Kim YJ, Yamabe N, Choi P, Lee JW, Ham J, Kang KS. Efficient thermal deglycosylation of ginsenoside Rd and its contribution to the improved anticancer activity of ginseng. J Agric Food Chem 2013;61:9185-91. DOI |
28 | Kim M, Ahn BY, Lee JS, Chung SS, Lim S, Park SG, Jung HS, Lee HK, Park KS. The ginsenoside Rg3 has a stimulatory effect on insulin signaling in L6 myotubes. Biochem Biophys Res Commun 2009;389:70-3. DOI |
29 | Lee JH, Ahn JY, Shin TJ, Choi SH, Lee BH, Hwang SH. Effects of minor ginsenosides, ginsenoside metabolites, and ginsenoside epimers on the growth of Caenorhabditis elegans. J Ginseng Res 2011;35:375-83. DOI |
30 | Sala F, Mulet J, Choi S, Jung SY, Nah SY, Rhim H, Valor LM, Criado M, Sala S. Effects of ginsenoside Rg2 on human neuronal nicotinic acetylcholine receptors. J Pharmacol Exp Ther 2002;301:1052-9. DOI |
31 | Hasegawa H. Proof of the mysterious efficacy of ginseng: basic and clinical trials: metabolic activation of ginsenoside: deglycosylation by intestinal bacteria and esterification with fatty acid. J Pharmacol Sci 2004;95:153-7. DOI |