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2.4.1.314

Accepted name:

ginsenoside Rd glucosyltransferase

Reaction:

UDP-α-D-glucose + ginsenoside Rd = UDP + ginsenoside Rb1

For diagram of protopanaxadiol ginsenosides ginsenosidases, click here

Glossary:

ginsenoside Rd = 20-(β-D-glucopyranosyl)oxy-3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rb1 = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]dammar-24-en-12β-ol

Other name(s):

UDPG:ginsenoside Rd glucosyltransferase; UDP-glucose:ginsenoside Rd glucosyltransferase; UGRdGT

Systematic name:

UDP-glucose:ginsenoside-Rd β-1,6-glucosyltransferase

Comments:

The glucosyl group forms a 1→6 bond to the glucosyloxy moiety at C-20 of ginsenoside Rd. Isolated from sanchi ginseng (Panax notoginseng).

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Yue, C.-J. and Zhong J.-J. Purification and characterization of UDPG:ginsenoside Rd glucosyltransferase from suspended cells of Panax notoginseng. Process Biochem. 40 (2005) 3742–3748.

[EC 2.4.1.314 created 2013]

3.2.1.191

Accepted name:

ginsenosidase type III

Reaction:

a protopanaxadiol-type ginsenoside with two glucosyl residues at position 3 + 2 H₂O = a protopanaxadiol-type ginsenoside with no glycosidic modification at position 3 + 2 D-glucopyranose (overall reaction)
(1a) a protopanaxadiol-type ginsenoside with two glucosyl residues at position 3 + H₂O a protopanaxadiol-type ginsenoside with one glucosyl residue at position 3 + D-glucopyranose
(1b) a protopanaxadiol-type ginsenoside with one glucosyl residue at position 3 + H₂O = a protopanaxadiol-type ginsenoside with no glycosidic modification at position 3 + D-glucopyranose

For diagram of protopanaxadiol ginsenosides ginsenosidases, click here

Glossary:

ginsenoside Rb1 = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]dammar-24-en-12β-ol
gypenoside XVII = 3β-(β-D-glucopyranosyloxy)-20-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]dammar-24-en-12β-ol
gypenoside LXXV = 20-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]dammar-24-ene-3β,12β-diol

Systematic name:

protopanaxadiol-type ginsenoside 3-β-D-hydrolase

Comments:

Ginsenosidase type III catalyses the sequential hydrolysis of the 3-O-β-D-(1→2)-glucopyranosyl bond followed by hydrolysis of the 3-O-β-D-glucopyranosyl bond of protopanaxadiol ginsenosides. When acting for example on ginsenoside Rb1 the enzyme first generates ginsenoside XVII, and subsequently ginsenoside LXXV.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Jin, X.F., Yu, H.S., Wang, D.M., Liu, T.Q., Liu, C.Y., An, D.S., Im, W.T., Kim, S.G. and Jin, F.X. Kinetics of a cloned special ginsenosidase hydrolyzing 3-O-glucoside of multi-protopanaxadiol-type ginsenosides, named ginsenosidase type III. J. Microbiol. Biotechnol. 22 (2012) 343–351. [PMID: 22450790]
2.	An, D.S., Cui, C.H., Lee, H.G., Wang, L., Kim, S.C., Lee, S.T., Jin, F., Yu, H., Chin, Y.W., Lee, H.K., Im, W.T. and Kim, S.G. Identification and characterization of a novel Terrabacter ginsenosidimutans sp. nov. β-glucosidase that transforms ginsenoside Rb1 into the rare gypenosides XVII and LXXV. Appl. Environ. Microbiol. 76 (2010) 5827–5836. [DOI] [PMID: 20622122]
3.	Hong, H., Cui, C.H., Kim, J.K., Jin, F.X., Kim, S.C. and Im, W.T. Enzymatic Biotransformation of Ginsenoside Rb1 and Gypenoside XVII into Ginsenosides Rd and F2 by Recombinant β-glucosidase from Flavobacterium johnsoniae. J Ginseng Res 36 (2012) 418–424. [DOI] [PMID: 23717145]

[EC 3.2.1.191 created 2014]

3.2.1.192

Accepted name:

ginsenoside Rb1 β-glucosidase

Reaction:

ginsenoside Rb1 + 2 H₂O = ginsenoside Rg3 + 2 D-glucopyranose (overall reaction)
(1a) ginsenoside Rb1 + H₂O = ginsenoside Rd + D-glucopyranose
(1b) ginsenoside Rd + H₂O = ginsenoside Rg3 + D-glucopyranose

For diagram of protopanaxadiol ginsenosides ginsenosidases, click here

Glossary:

ginsenoside Rb1 = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rd = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-(β-D-glucopyranosyloxy)dammar-24-en-12β-ol
ginsenoside F2 = 3β,20-bis(β-D-glucopyranosyloxy)dammar-24-en-12β-ol

Systematic name:

ginsenoside Rb1 glucohydrolase

Comments:

Ginsenosidases catalyse the hydrolysis of glycosyl moieties attached to the C-3, C-6 or C-20 position of ginsenosides. They are specific with respect to the nature of the glycosidic linkage, the position and the order in which the linkages are cleaved. Ginsenoside Rb1 β-glucosidase specifically and sequentially hydrolyses the 20-[β-D-glucopyranosyl-(1→6)-β-D glucopyranosyloxy] residues attached to position 20 by first hydrolysing the (1→6)-glucosidic bond to generate ginsenoside Rd as an intermediate, followed by hydrolysis of the remaining 20-O-β-D-glucosidic bond.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Yan, Q., Zhou, W., Li, X., Feng, M. and Zhou, P. Purification method improvement and characterization of a novel ginsenoside-hydrolyzing β-glucosidase from Paecilomyces Bainier sp. 229. Biosci. Biotechnol. Biochem. 72 (2008) 352–359. [DOI] [PMID: 18256474]

[EC 3.2.1.192 created 2014]

3.2.1.193

Accepted name:

ginsenosidase type I

Reaction:

(1) a protopanaxadiol-type ginsenoside with two glucosyl residues at position 3 + H₂O = a protopanaxadiol-type ginsenoside with one glucosyl residue at position 3 + D-glucopyranose
(2) a protopanaxadiol-type ginsenoside with one glucosyl residue at position 3 + H₂O = a protopanaxadiol-type ginsenoside with no glycosidic modifications at position 3 + D-glucopyranose
(3) a protopanaxadiol-type ginsenoside with two glycosyl residues at position 20 + H₂O = a protopanaxadiol-type ginsenoside with a single glucosyl residue at position 20 + a monosaccharide

For diagram of protopanaxadiol ginsenosides ginsenosidases, click here

Glossary:

ginsenoside Rb1 = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rb2 = 3β-[β-D-glucopyranosyl-(1→2)-β-D glucopyranosyloxy]-20-[α-L-arabinopyranosyl-(1→6)-β-D glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rb3 = 3β-[β-D-glucopyranosyl-(1→2)-β-D glucopyranosyloxy]-20-[β-D-xylopyranosyl-(1→6)-β-D glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rc = 3β-[β-D-glucopyranosyl-(1→2)-β-D glucopyranosyloxy]-20-[α-L-arabinofuranosyl-(1→6)-β-D glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rd = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-(β-D-glucopyranosyloxy)dammar-24-en-12β-ol
ginsenoside F2 = 3β,20-bis(β-D-glucopyranosyloxy)dammar-24-en-12β-ol
ginsenoside C-K = 20β-(β-D-glucopyranosyloxy)dammar-24-ene-3β,12β-diol
ginsenoside Rh2 = 3β-(β-D-glucopyranosyloxy)dammar-24-ene-12β,20-diol

Systematic name:

ginsenoside glucohydrolase

Comments:

Ginsenosidase type I is slightly activated by Mg²⁺ or Ca²⁺ [1]. The enzyme hydrolyses the 3-O-β-D-(1→2)-glucosidic bond, the 3-O-β-D-glucopyranosyl bond and the 20-O-β-D-(1→6)-glycosidic bond of protopanaxadiol-type ginsenosides. It usually leaves a single glucosyl residue attached at position 20 and one or no glucosyl residues at position 3. Starting with a ginsenoside that is glycosylated at both positions (e.g. ginsenoside Rb1, Rb2, Rb3, Rc or Rd), the most common products are ginsenoside F2 and ginsenoside C-K, with low amounts of ginsenoside Rh2.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Yu, H., Zhang, C., Lu, M., Sun, F., Fu, Y. and Jin, F. Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I. Chem Pharm Bull (Tokyo) 55 (2007) 231–235. [PMID: 17268094]

[EC 3.2.1.193 created 2014]

3.2.1.195

Accepted name:

20-O-multi-glycoside ginsenosidase

Reaction:

a protopanaxadiol-type ginsenoside with two glycosyl residues at position 20 + H₂O = a protopanaxadiol-type ginsenoside with a single glucosyl residue at position 20 + a monosaccharide

For diagram of protopanaxadiol ginsenosides ginsenosidases, click here

Glossary:

ginsenoside Rb1 = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rb2 = 3β-[β-D-glucopyranosyl-(1→2)-β-D glucopyranosyloxy]-20-[α-L-arabinopyranosyl-(1→6)-β-D glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rb3 = 3β-[β-D-glucopyranosyl-(1→2)-β-D glucopyranosyloxy]-20-[β-D-xylopyranosyl-(1→6)-β-D glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rc = 3β-[β-D-glucopyranosyl-(1→2)-β-D glucopyranosyloxy]-20-[α-L-arabinofuranosyl-(1→6)-β-D glucopyranosyloxy]dammar-24-en-12β-ol
ginsenoside Rd = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-(β-D-glucopyranosyloxy)dammar-24-en-12β-ol
ginsenoside Rg3 = 3β-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-20-(β-D-glucopyranosyloxy)dammar-24-ene-12β,20-diol

Other name(s):

ginsenosidase type II (erroneous)

Systematic name:

protopanaxadiol-type ginsenoside 20-β-D-glucohydrolase

Comments:

The 20-O-multi-glycoside ginsenosidase catalyses the hydrolysis of the 20-O-α-(1→6)-glycosidic bond and the 20-O-β-(1→6)-glycosidic bond of protopanaxadiol-type ginsenosides. The enzyme usually leaves a single glucosyl residue attached at position 20, although it can cleave the remaining glucosyl residue with a lower efficiency. Starting with a ginsenoside that is glycosylated at positions 3 and 20, such as ginsenosides Rb1, Rb2, Rb3 and Rc, the most common product is ginsenoside Rd, with a low amount of ginsenoside Rg3 also formed.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Yu, H., Liu, Q., Zhang, C., Lu, M., Fu, Y., Im, W.-T., Lee, S.-T. and Jin, F. A new ginsenosidase from Aspergillus strain hydrolyzing 20-O-multi-glycoside of PPD ginsenoside. Process Biochem. 44 (2009) 772–775.

[EC 3.2.1.195 created 2014]