3.2.1.189: dioscin glycosidase (diosgenin-forming)

This is an abbreviated version!
For detailed information about dioscin glycosidase (diosgenin-forming), go to the full flat file.

Reaction

Synonyms

dioscin glycosidase (aglycone-forming), GiGly

ECTree

     3 Hydrolases

         3.2 Glycosylases

             3.2.1 Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds

                3.2.1.189 dioscin glycosidase (diosgenin-forming)

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7	Inhibitors
4	Metals/Ions
1	Molecular Weight [Da]
4	Natural Substrates/ Products (Substrates)
4	Organism
2	pH Optimum
1	pH Range
1	pH Stability
2	Purification (Commentary)
1	Reaction
4	Reference
2	Source Tissue
2	Specific Activity [micromol/min/mg]
16	Substrates and Products (Substrate)
6	Subunits
4	Synonyms
1	Systematic Name
2	Temperature Optimum [°C]
1	Temperature Range [°C]
1	Temperature Stability [°C]

Substrates Products

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Substrates Products on EC 3.2.1.189 - dioscin glycosidase (diosgenin-forming)

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SUBSTRATE

PRODUCT                       

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

3-O-[alpha-L-Ara-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucopyranose + L-arabinose + L-rhamnopyranose + diosgenin

2 entries

3-O-[alpha-L-Ara-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + H2O

D-glucose + L-rhamnose + L-arabinose + diosgenin

2 entries

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucopyranose + 2 L-rhamnopyranose + diosgenin

4 entries

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucose + 2 L-rhamnose + diosgenin

2 entries

polyphyllin VII + 4 H2O

3 L-rhamnose + D-glucose + (22zeta,25R)-9zeta-spirost-5-en-3beta,17-diol

2 entries

additional information

?

-

4 entries

3-O-[alpha-L-Ara-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucopyranose + L-arabinose + L-rhamnopyranose + diosgenin

Absidia sp. (in: Fungi)

-

-

722930

-

-

?

3-O-[alpha-L-Ara-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucopyranose + L-arabinose + L-rhamnopyranose + diosgenin

Absidia sp. (in: Fungi) d38

-

-

722930

-

-

?

3-O-[alpha-L-Ara-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + H2O

D-glucose + L-rhamnose + L-arabinose + diosgenin

Fusarium proliferatum

-

i.e. sinodiosgenin or trillin

754439

-

-

?

3-O-[alpha-L-Ara-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + H2O

D-glucose + L-rhamnose + L-arabinose + diosgenin

Fusarium proliferatum WX12

-

i.e. sinodiosgenin or trillin

754439

-

-

?

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucopyranose + 2 L-rhamnopyranose + diosgenin

Absidia sp. (in: Fungi)

-

-

722930

-

-

?

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucopyranose + 2 L-rhamnopyranose + diosgenin

Absidia sp. (in: Fungi)

-

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin is the the main dioscin in the rhizome of Dioscorea nipponica. The dioscin-glycosidase gradually hydrolyzes either the 3-O-alpha-L-(1->4)-Rha or the 3-O-alpha-L-(1->2)-Rha from dioscin into 3-O-alpha-L-Rha-(1->2)-beta-D-diosgenin or 3-O-alpha-L-Rha-(1->4)-beta-D-diosgenin, further rapidly hydrolyzes the other alpha-L-Rha into the main intermediate products of 3-O-beta-D-Glc-diosgenin, and subsequently hydrolyzes these intermediate product into aglycone as the final product

722930

-

-

?

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucopyranose + 2 L-rhamnopyranose + diosgenin

Absidia sp. (in: Fungi) d38

-

-

722930

-

-

?

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucopyranose + 2 L-rhamnopyranose + diosgenin

Absidia sp. (in: Fungi) d38

-

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin is the the main dioscin in the rhizome of Dioscorea nipponica. The dioscin-glycosidase gradually hydrolyzes either the 3-O-alpha-L-(1->4)-Rha or the 3-O-alpha-L-(1->2)-Rha from dioscin into 3-O-alpha-L-Rha-(1->2)-beta-D-diosgenin or 3-O-alpha-L-Rha-(1->4)-beta-D-diosgenin, further rapidly hydrolyzes the other alpha-L-Rha into the main intermediate products of 3-O-beta-D-Glc-diosgenin, and subsequently hydrolyzes these intermediate product into aglycone as the final product

722930

-

-

?

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucose + 2 L-rhamnose + diosgenin

Fusarium proliferatum

-

-

754439

-

-

?

3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin + 3 H2O

D-glucose + 2 L-rhamnose + diosgenin

Fusarium proliferatum WX12

-

-

754439

-

-

?

polyphyllin VII + 4 H2O

3 L-rhamnose + D-glucose + (22zeta,25R)-9zeta-spirost-5-en-3beta,17-diol

Fusarium proliferatum

-

-

754439

-

-

?

polyphyllin VII + 4 H2O

3 L-rhamnose + D-glucose + (22zeta,25R)-9zeta-spirost-5-en-3beta,17-diol

Fusarium proliferatum WX12

-

-

754439

-

-

?

additional information

?

-

Fusarium proliferatum

-

strain WX12 has ability to hydrolyze dioscin, trillin and polyphyllin VII into diosgenin as the final product. But it is inactive toward the terminal rhamnosyl, glucosyl and galactosyl of ginsenoside Re and saikosaponin A

754439

-

-

?

additional information

?

-

Fusarium proliferatum

-

enzyme GiGly shows high substrate specificity for multi-3-O-glycosides of spirostanol saponins such as dioscin, trillin and polyphyllin VII, and is inactive toward substrates with terminal groups of rhamnosyl, glucosyl, galactosyl of ginsenoside Re and saikosaponin A. It can only hydrolyze glycosidic bonds at the C-3 position on steroidal saponins, which have similar structure with dioscin, and can be transformed into diosgenin. Substrate specificity, overview. GiGly is able tohydrolyze the terminal alpha-1,2-linked rhamnosyl residues, alpha-1,4-linked rhamnosyl residues, alpha-1,4-linked arabinosyl residues and beta-D-glucosyl residues at C-3 position.. The hydrolyzed substrates of GiGly have a double bond between carbons 5 and 6 position. By contrast, the non-substrates lack the said double bond and have substituents at carbon 4 position

754439

-

-

?

additional information

?

-

Fusarium proliferatum WX12

-

strain WX12 has ability to hydrolyze dioscin, trillin and polyphyllin VII into diosgenin as the final product. But it is inactive toward the terminal rhamnosyl, glucosyl and galactosyl of ginsenoside Re and saikosaponin A

754439

-

-

?

additional information

?

-

Fusarium proliferatum WX12

-

enzyme GiGly shows high substrate specificity for multi-3-O-glycosides of spirostanol saponins such as dioscin, trillin and polyphyllin VII, and is inactive toward substrates with terminal groups of rhamnosyl, glucosyl, galactosyl of ginsenoside Re and saikosaponin A. It can only hydrolyze glycosidic bonds at the C-3 position on steroidal saponins, which have similar structure with dioscin, and can be transformed into diosgenin. Substrate specificity, overview. GiGly is able tohydrolyze the terminal alpha-1,2-linked rhamnosyl residues, alpha-1,4-linked rhamnosyl residues, alpha-1,4-linked arabinosyl residues and beta-D-glucosyl residues at C-3 position.. The hydrolyzed substrates of GiGly have a double bond between carbons 5 and 6 position. By contrast, the non-substrates lack the said double bond and have substituents at carbon 4 position

754439

-

-

?