Enzymatic Transformation of the Major Ginsenoside Rb2 to Minor Compound Y and Compound K by a Ginsenoside-hydrolyzing β-glycosidase from Microbacterium Esteraromaticum

Overview

Journal J Ind Microbiol Biotechnol

Publisher Oxford University Press

Specialty Biotechnology

Date 2012 Jun 22

PMID 22717707

Citations 19

Authors

Lin-Hu Quan

Yan Jin

Chao Wang

Jin-Woo Min

Yeon-Ju Kim

Deok-Chun Yang

Affiliations

Soon will be listed here.

Abstract

The ginsenoside-hydrolyzing β-glycosidase (Bgp3) derived from Microbacterium esteraromaticum transformed the major ginsenoside Rb2 to more pharmacologically active minor ginsenosides including compounds Y and K. The bgp3 gene consists of 2,271 bp encoding 756 amino acids which have homology to the glycosyl hydrolase family 3 protein domain. Bgp3 is capable of hydrolyzing beta-glucose links and arabinose links. HPLC analysis of the time course of ginsenoside Rb2 hydrolysis by Bgp3 (0.1 mg enzyme ml(-1) in 20 mM sodium phosphate buffer at 40 °C and pH 7.0) showed that the glycosidase first hydrolyzed the inner glucose moiety attached to the C-3 position and then the arabinopyranose moiety attached to the C-20 position. Thus, Bgp3 hydrolyzed the ginsenoside Rb2 via the following pathway: Rb2 → compound Y → compound K.

Citing Articles

Research progress on chemical diversity of saponins in .

Geng X, Wang J, Liu Y, Liu L, Liu X, Zhao Y Chin Herb Med. 2024; 16(4):529-547.

PMID: 39606259 PMC: 11589341. DOI: 10.1016/j.chmed.2024.08.005.

Bioconversion, Pharmacokinetics, and Therapeutic Mechanisms of Ginsenoside Compound K and Its Analogues for Treating Metabolic Diseases.

Morshed M, Akter R, Karim M, Iqbal S, Kang S, Yang D Curr Issues Mol Biol. 2024; 46(3):2320-2342.

PMID: 38534764 PMC: 10968794. DOI: 10.3390/cimb46030148.

Kinetic conversion of BIOGF1K enriched in compound K from 3-D human tissue model.

Kim W, Choi W, Kim J, Choi J, Hong Y, Nam J Curr Res Pharmacol Drug Discov. 2023; 5:100165.

PMID: 37869704 PMC: 10589745. DOI: 10.1016/j.crphar.2023.100165.

Diversity and Isolation of Endophytic Fungi in and Biotransformation Activity on Saponins.

Li P, Ling X, Zhao S, Xu L, Wang R Curr Pharm Biotechnol. 2023; 25(9):1199-1208.

PMID: 37767797 DOI: 10.2174/0113892010247700230919053439.

Compound K Production: Achievements and Perspectives.

Chu L, Hanh N, Quyen M, Nguyen Q, Lien T, Van Do K Life (Basel). 2023; 13(7).

PMID: 37511939 PMC: 10381408. DOI: 10.3390/life13071565.

References

Shin H, Park S, Sung J, Kim D . Purification and characterization of alpha-L-arabinopyranosidase and alpha-L-arabinofuranosidase from Bifidobacterium breve K-110, a human intestinal anaerobic bacterium metabolizing ginsenoside Rb2 and Rc. Appl Environ Microbiol. 2003; 69(12):7116-23. PMC: 309963. DOI: 10.1128/AEM.69.12.7116-7123.2003. View

Wakabayashi C, Hasegawa H, Murata J, Saiki I . In vivo antimetastatic action of ginseng protopanaxadiol saponins is based on their intestinal bacterial metabolites after oral administration. Oncol Res. 1997; 9(8):411-7. View

Christensen L . Ginsenosides chemistry, biosynthesis, analysis, and potential health effects. Adv Food Nutr Res. 2008; 55:1-99. DOI: 10.1016/S1043-4526(08)00401-4. View

Mochizuki M, Yoo Y, Matsuzawa K, Sato K, Saiki I, Samukawa K . Inhibitory effect of tumor metastasis in mice by saponins, ginsenoside-Rb2, 20(R)- and 20(S)-ginsenoside-Rg3, of red ginseng. Biol Pharm Bull. 1995; 18(9):1197-202. DOI: 10.1248/bpb.18.1197. View

Song X, Zang L, Hu S . Amplified immune response by ginsenoside-based nanoparticles (ginsomes). Vaccine. 2009; 27(17):2306-11. DOI: 10.1016/j.vaccine.2009.02.040. View

Ni H, Yu N, Yang X . The study of ginsenoside on PPARgamma expression of mononuclear macrophage in type 2 diabetes. Mol Biol Rep. 2009; 37(6):2975-9. DOI: 10.1007/s11033-009-9864-0. View

Lee H, Bae E, Joo Han M, Kim N, Kim D . Hepatoprotective effect of ginsenoside Rb1 and compound K on tert-butyl hydroperoxide-induced liver injury. Liver Int. 2005; 25(5):1069-73. DOI: 10.1111/j.1478-3231.2005.01068.x. View

Liu Z, Luo X, Liu G, Chen Y, Wang Z, Sun Y . In vitro study of the relationship between the structure of ginsenoside and its antioxidative or prooxidative activity in free radical induced hemolysis of human erythrocytes. J Agric Food Chem. 2003; 51(9):2555-8. DOI: 10.1021/jf026228i. View

Mark Stavro P, Woo M, Heim T, Leiter L, Vuksan V . North American ginseng exerts a neutral effect on blood pressure in individuals with hypertension. Hypertension. 2005; 46(2):406-11. DOI: 10.1161/01.HYP.0000173424.77483.1e. View

10.

Noh K, Oh D . Production of the rare ginsenosides compound K, compound Y, and compound Mc by a thermostable beta-glycosidase from Sulfolobus acidocaldarius. Biol Pharm Bull. 2009; 32(11):1830-5. DOI: 10.1248/bpb.32.1830. View

11.

Varghese J, Hrmova M, Fincher G . Three-dimensional structure of a barley beta-D-glucan exohydrolase, a family 3 glycosyl hydrolase. Structure. 1999; 7(2):179-90. DOI: 10.1016/s0969-2126(99)80024-0. View

12.

Chae S, Kang K, Chang W, Kim M, Lee S, Lee Y . Effect of compound K, a metabolite of ginseng saponin, combined with gamma-ray radiation in human lung cancer cells in vitro and in vivo. J Agric Food Chem. 2009; 57(13):5777-82. DOI: 10.1021/jf900331g. View

13.

Chi H, Kim D, Ji G . Transformation of ginsenosides Rb2 and Rc from Panax ginseng by food microorganisms. Biol Pharm Bull. 2005; 28(11):2102-5. DOI: 10.1248/bpb.28.2102. View

14.

Son J, Kim H, Oh D . Ginsenoside Rd production from the major ginsenoside Rb(1) by beta-glucosidase from Thermus caldophilus. Biotechnol Lett. 2007; 30(4):713-6. DOI: 10.1007/s10529-007-9590-4. View

15.

Oh S, Yin H, Lee B . Role of the Fas/Fas ligand death receptor pathway in ginseng saponin metabolite-induced apoptosis in HepG2 cells. Arch Pharm Res. 2004; 27(4):402-6. DOI: 10.1007/BF02980081. View

16.

Wakabayashi C, Murakami K, Hasegawa H, Murata J, Saiki I . An intestinal bacterial metabolite of ginseng protopanaxadiol saponins has the ability to induce apoptosis in tumor cells. Biochem Biophys Res Commun. 1998; 246(3):725-30. DOI: 10.1006/bbrc.1998.8690. View

17.

Noh K, Son J, Kim H, Oh D . Ginsenoside compound K production from ginseng root extract by a thermostable beta-glycosidase from Sulfolobus solfataricus. Biosci Biotechnol Biochem. 2009; 73(2):316-21. DOI: 10.1271/bbb.80525. View

18.

Bae E, Park S, Kim D . Constitutive beta-glucosidases hydrolyzing ginsenoside Rb1 and Rb2 from human intestinal bacteria. Biol Pharm Bull. 2001; 23(12):1481-5. DOI: 10.1248/bpb.23.1481. View