The Enzyme Database

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EC 1.14.13.184      
Transferred entry: protopanaxadiol 6-hydroxylase. Now EC 1.14.14.121, protopanaxadiol 6-hydroxylase
[EC 1.14.13.184 created 2013, deleted 2018]
 
 
EC 1.14.14.121     
Accepted name: protopanaxadiol 6-hydroxylase
Reaction: protopanaxadiol + [reduced NADPH—hemoprotein reductase] + O2 = protopanaxatriol + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of dammarenediol II and tirucalla-7,24-dien-3β-ol biosynthesis, click here
Glossary: protopanaxadiol = dammar-24-ene-3β,12β,20-triol
protopanaxatriol = dammar-24-ene-3β,6α,12β,20-tetrol
Other name(s): protopanaxatriol synthase; P6H; CYP716A53v2
Systematic name: protopanaxadiol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (6α-hydroxylating)
Comments: A cytochrome P-450 (heme-thiolate) protein isolated from the rhizomes of ginseng (Panax ginseng). Involved in the biosynthetic pathway of ginsenosides.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Yue, C.J., Zhou, X. and Zhong, J.J. Protopanaxadiol 6-hydroxylase and its role in regulating the ginsenoside heterogeneity in Panax notoginseng cells. Biotechnol. Bioeng. 100 (2008) 933–940. [DOI] [PMID: 18351680]
2.  Han, J.Y., Hwang, H.S., Choi, S.W., Kim, H.J. and Choi, Y.E. Cytochrome P450 CYP716A53v2 catalyzes the formation of protopanaxatriol from protopanaxadiol during ginsenoside biosynthesis in Panax ginseng. Plant Cell Physiol. 53 (2012) 1535–1545. [DOI] [PMID: 22875608]
[EC 1.14.14.121 created 2013 as EC 1.14.13.184, transferred 2018 to EC 1.14.14.121]
 
 
EC 2.4.1.363     
Accepted name: ginsenoside 20-O-glucosyltransferase
Reaction: UDP-α-D-glucose + (20S)-protopanaxadiol = UDP + ginsenoside C-K
Glossary: (20S)-protopanaxadiol = (3β,12β)-dammar-24-ene-3,12,20-triol
ginsenoside C-K = (3β,12β)-3,12-dihydroxydammar-24-en-20-yl β-D-glucopyranoside
Other name(s): UGT71A27 (gene name)
Systematic name: UDP-α-D-glucose:(20S)-protopanaxadiol 20-O-glucosyltransferase (configuration-inverting)
Comments: The enzyme, characterized from the plant Panax ginseng, transfers a glucosyl moiety to the free C20(S)-OH group of dammarane derivative substrates, including protopanaxatriol, dammarenediol II, (20S)-ginsenoside Rh2, and (20S)-ginsenoside Rg3. It does not act on the 20R epimer of protopanaxadiol, or on ginsenosides that are glucosylated at the C-6 position, such as ginsenoside Rh1 or ginsenoside Rg2.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Yan, X., Fan, Y., Wei, W., Wang, P., Liu, Q., Wei, Y., Zhang, L., Zhao, G., Yue, J. and Zhou, Z. Production of bioactive ginsenoside compound K in metabolically engineered yeast. Cell Res. 24 (2014) 770–773. [PMID: 24603359]
2.  Wei, W., Wang, P., Wei, Y., Liu, Q., Yang, C., Zhao, G., Yue, J., Yan, X. and Zhou, Z. Characterization of Panax ginseng UDP-glycosyltransferases catalyzing protopanaxatriol and biosyntheses of bioactive ginsenosides F1 and Rh1 in metabolically engineered yeasts. Mol. Plant 8 (2015) 1412–1424. [PMID: 26032089]
[EC 2.4.1.363 created 2019]
 
 
EC 2.4.1.366     
Accepted name: ginsenoside F1 6-O-glucosyltransferase
Reaction: UDP-α-D-glucose + ginsenoside F1 = UDP + (20S)-ginsenoside Rg1
Glossary: ginsenoside F1 = 3β,6α,12β-trihydroxydammar-24-en-20-yl β-D-glucopyranoside
Other name(s): UGTPg101 (gene name)
Systematic name: UDP-α-D-glucose:ginsenoside F1 6-O-glucosyltransferase
Comments: The enzyme, characterized from the plant Panax ginseng, glucosylates the C-6 position of ginsenoside F1. The enzyme also glucosylates the C-20 position of protopanaxatriol, which forms ginsenoside F1 (cf. EC 2.4.1.363, ginsenoside 20-O-glucosyltransferase). However, unlike EC 2.4.1.367, ginsenoside 6-O-glucosyltransferase, it is not able to glucosylate the C-6 position of protopanaxatriol when position C-20 is not glucosylated.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Wei, W., Wang, P., Wei, Y., Liu, Q., Yang, C., Zhao, G., Yue, J., Yan, X. and Zhou, Z. Characterization of Panax ginseng UDP-glycosyltransferases catalyzing protopanaxatriol and biosyntheses of bioactive ginsenosides F1 and Rh1 in metabolically engineered yeasts. Mol. Plant 8 (2015) 1412–1424. [PMID: 26032089]
[EC 2.4.1.366 created 2019]
 
 
EC 2.4.1.367     
Accepted name: ginsenoside 6-O-glucosyltransferase
Reaction: (1) UDP-α-D-glucose + protopanaxatriol = UDP + ginsenoside Rh1
(2) UDP-α-D-glucose + ginsenoside F1 = UDP + (20S)-ginsenoside Rg1
Glossary: protopanaxatriol = (3β,6α,12β)-dammar-24-ene-3,6,12,20-tetrol
ginsenoside F1 = (3β,6α,12β)-trihydroxydammar-24-en-20-yl β-D-glucopyranoside
Other name(s): UGTPg100 (gene name)
Systematic name: UDP-α-D-glucose:ginsenoside 6-O-glucosyltransferase
Comments: The enzyme, characterized from the plant Panax ginseng, glucosylates the C-6 position of protopanaxatriol and ginsenoside F1.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Wei, W., Wang, P., Wei, Y., Liu, Q., Yang, C., Zhao, G., Yue, J., Yan, X. and Zhou, Z. Characterization of Panax ginseng UDP-glycosyltransferases catalyzing protopanaxatriol and biosyntheses of bioactive ginsenosides F1 and Rh1 in metabolically engineered yeasts. Mol. Plant 8 (2015) 1412–1424. [PMID: 26032089]
[EC 2.4.1.367 created 2019]
 
 
EC 3.2.1.194     
Accepted name: ginsenosidase type IV
Reaction: a protopanaxatriol-type ginsenoside with two glycosyl residues at position 6 + 2 H2O = a protopanaxatriol-type ginsenoside with no glycosidic modification at position 6 + D-glucopyranose + a monosaccharide (overall reaction)
(1a) a protopanaxatriol-type ginsenoside with two glycosyl residues at position 6 + H2O = a protopanaxatriol-type ginsenoside with a single glucosyl at position 6 + a monosaccharide
(1b) a protopanaxatriol-type ginsenoside with a single glucosyl at position 6 + H2O = a protopanaxatriol-type ginsenoside with no glycosidic modification at position 6 + D-glucopyranose
For diagram of protopanaxatriol ginsenosides ginsenosidases, click here
Glossary: ginsenoside Re = 20-(β-D-glucopyranosyl)oxy-6α-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]dammar-24-en-3β,12β-diol
ginsenoside Rg1 = 6α,20-bis(β-D-glucopyranosyl)oxy-dammar-24-en-3β,12β-diol
ginsenoside F1 = 20-(β-D-glucopyranosyloxy)dammar-24-en-3β,6α,12β-triol
Systematic name: protopanaxatriol-type ginsenoside 6-β-D-glucohydrolase
Comments: Ginsenosidase type IV catalyses the sequential hydrolysis of the 6-O-β-D-(1→2)-glycosidic bond or the 6-O-α-D-(1→2)-glycosidic bond in protopanaxatriol-type ginsenosides with a disacchride attached to the C6 position, followed by the hydrolysis of the remaining 6-O-β-D-glycosidic bond (e.g. ginsenoside Re → ginsenoside Rg1 → ginsenoside F1).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Wang, D.M., Yu, H.S., Song, J.G., Xu, Y.F., Liu, C.Y. and Jin, F.X. A novel ginsenosidase from an Aspergillus strain hydrolyzing 6-O-multi-glycosides of protopanaxatriol-type ginsenosides, named ginsenosidase type IV. J. Microbiol. Biotechnol. 21 (2011) 1057–1063. [PMID: 22031031]
2.  Wang, D, Yu, H., Song, J., Xu, Y., Jin, F. Enzyme kinetics of ginsenosidase type IV hydrolyzing 6-O-multi-glycosides of protopanaxatriol type ginsenosides. Process Biochem. 47 (2012) 133–138.
[EC 3.2.1.194 created 2014]
 
 


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