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Literature summary extracted from

  • Okamoto, S.; Yu, F.; Harada, H.; Okajima, T.; Hattan, J.; Misawa, N.; Utsumi, R.
    A short-chain dehydrogenase involved in terpene metabolism from Zingiber zerumbet (2011), FEBS J., 278, 2892-2900.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.1.1.326 pharmacology zerumbone is a predominating potential multi-anticancer agent Zingiber zerumbet

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.326 gene ZSD1, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression of wild-type and mutant enzymes in Escherichia coli strain BL21(DE3) Zingiber zerumbet

Protein Variants

EC Number Protein Variants Comment Organism
1.1.1.326 K159A site-directed mutagenesis, inactive mutant Zingiber zerumbet
1.1.1.326 S142A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Zingiber zerumbet
1.1.1.326 S144A site-directed mutagenesis, the mutant shows increased activity compared to the wild-type enzyme Zingiber zerumbet
1.1.1.326 Y155A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Zingiber zerumbet

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.326 additional information
-
 additional information kinetics with borneol as substrate Zingiber zerumbet
1.1.1.326 0.0161
-
 NAD+ recombinant mutant S144A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.0273
-
 NAD+ recombinant wild-type enzyme, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.028
-
 10-hydroxy-alpha-humulene recombinant mutant S144A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.0437
-
 NAD+ recombinant mutant Y155A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.0585
-
 10-hydroxy-alpha-humulene recombinant wild-type enzyme, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.0782
-
 10-hydroxy-alpha-humulene recombinant mutant Y155A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.121
-
 NAD+ recombinant mutant S142A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.138
-
 10-hydroxy-alpha-humulene recombinant mutant S142A, pH 8.0, 37°C Zingiber zerumbet

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.14.14.113 Fe2+ cytochrome P450 enzyme Zingiber zerumbet

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
1.1.1.326 28700
-
 x * 28700, sequence calculation Zingiber zerumbet

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.326 10-hydroxy-alpha-humulene + NAD+ Zingiber zerumbet
-
 zerumbone + NADH + H+
-
 ?
1.14.14.113 alpha-humulene + O2 + [reduced NADPH-hemoprotein reductase] Zingiber zerumbet
-
 10-hydroxy-alpha-humulene + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.326 Zingiber zerumbet F1SWA0 gene ZSD1
-
1.14.14.113 Zingiber zerumbet
-
 gene CYP71BA1
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.326 recombinant wild-type and mutant enzymes from Escherichia coli strain Bl21(DE3) Zingiber zerumbet

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.326 leaf
-
 Zingiber zerumbet
-
1.1.1.326 rhizome contains an exceptionally high level of sesquiterpenoids with zerumbone Zingiber zerumbet
-
1.1.1.326 stem
-
 Zingiber zerumbet
-
1.14.14.113 rhizome transcripts of ZSS1 and CYP71BA1 encoding the two upstream enzymes of zerumbone biosynthesis are almost exclusively accumulated in rhizomes Zingiber zerumbet
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.326 10-hydroxy-alpha-humulene + NAD+
-
 Zingiber zerumbet zerumbone + NADH + H+
-
 ?
1.1.1.326 10-hydroxy-alpha-humulene + NAD+ the enzyme possesses a flexible substrate-binding pocket and converts 10-hydroxy-alpha-humulene into zerumbone Zingiber zerumbet zerumbone + NADH + H+
-
 ?
1.1.1.326 additional information the enzyme also converts borneol to camphor in vitro with Km and kcat values of 0.0228 mM and 4.1/s Zingiber zerumbet ?
-
 ?
1.14.14.113 alpha-humulene + O2 + [reduced NADPH-hemoprotein reductase]
-
 Zingiber zerumbet 10-hydroxy-alpha-humulene + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Subunits

EC Number Subunits Comment Organism
1.1.1.326 ? x * 28700, sequence calculation Zingiber zerumbet
1.1.1.326 More a 3D structure model of ZSD1 reveals a large, flexible substrate-binding pocket, molecular modeling, overview Zingiber zerumbet

Synonyms

EC Number Synonyms Comment Organism
1.1.1.326 ZSD1
-
 Zingiber zerumbet
1.14.14.113 alpha-humulene-8-hydoxylase
-
 Zingiber zerumbet
1.14.14.113 CYP71BA1
-
 Zingiber zerumbet

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.326 37
-
 assay at Zingiber zerumbet

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.1.1.326 0.1
-
 NAD+ recombinant mutant S142A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.1
-
 10-hydroxy-alpha-humulene recombinant mutant S142A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.1
-
 NAD+ recombinant mutant Y155A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.1
-
 10-hydroxy-alpha-humulene recombinant mutant Y155A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 1.3
-
 10-hydroxy-alpha-humulene recombinant wild-type enzyme, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 2.9
-
 10-hydroxy-alpha-humulene recombinant mutant S144A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 3.8
-
 NAD+ recombinant wild-type enzyme, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 4.4
-
 NAD+ recombinant mutant S144A, pH 8.0, 37°C Zingiber zerumbet

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.326 8
-
 assay at Zingiber zerumbet

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.326 NAD+ ZSD1 contains an NAD+-binding motif TGxxxGxG Zingiber zerumbet
1.14.14.113 cytochrome P450
-
 Zingiber zerumbet

pI Value

EC Number Organism Comment pI Value Maximum pI Value
1.1.1.326 Zingiber zerumbet sequence calculation
-
 5.63

General Information

EC Number General Information Comment Organism
1.1.1.326 evolution ZSD1 is a member of the short-chain dehydrogenase/reductase superfamily, SDR, and shares high identities with other plant SDRs involved in secondary metabolism, stress responses and phytosteroid biosynthesis Zingiber zerumbet
1.1.1.326 metabolism ZSD1 is an alcohol dehydrogenase capable of catalyzing the final step of zerumbone biosynthesis, but ZSD1 is also be involved in other biological processes Zingiber zerumbet
1.1.1.326 additional information the enzyme contains an active site sequence 155Y-X-X-X-K159, Ser142 completes the Ser-Tyr-Lys triad responsible for the catalysis of ZSD1 Zingiber zerumbet
1.1.1.326 physiological function ZSD1 is involved in secondary metabolism, stress responses and phytosteroid biosynthesis Zingiber zerumbet
1.14.14.113 evolution the enzyme belongs to the cytochrome P450 monooxygenases Zingiber zerumbet
1.14.14.113 metabolism CYP71BA1 catalyzes the second step of zerumbone biosynthesis Zingiber zerumbet

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.1.1.326 0.0000007
-
 10-hydroxy-alpha-humulene recombinant mutant S142A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.0000008
-
 NAD+ recombinant mutant S142A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.000001
-
 10-hydroxy-alpha-humulene recombinant mutant Y155A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.000002
-
 NAD+ recombinant mutant Y155A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.000022
-
 10-hydroxy-alpha-humulene recombinant wild-type enzyme, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.000103
-
 10-hydroxy-alpha-humulene recombinant mutant S144A, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.000139
-
 NAD+ recombinant wild-type enzyme, pH 8.0, 37°C Zingiber zerumbet
1.1.1.326 0.000262
-
 NAD+ recombinant mutant S144A, pH 8.0, 37°C Zingiber zerumbet