The Enzyme Database

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EC 4.2.1.133     
Accepted name: copal-8-ol diphosphate hydratase
Reaction: (13E)-8α-hydroxylabd-13-en-15-yl diphosphate = geranylgeranyl diphosphate + H2O
For diagram of labdane diterpenoids biosynthesis, click here
Glossary: (13E)-8α-hydroxylabd-13-en-15-yl diphosphate = 8-hydroxycopalyl diphosphate
Other name(s): CcCLS
Systematic name: geranylgeranyl-diphosphate hydro-lyase [(13E)-8α-hydroxylabd-13-en-15-yl diphosphate forming]
Comments: Requires Mg2+. The enzyme was characterized from the plant Cistus creticus subsp. creticus.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Falara, V., Pichersky, E. and Kanellis, A.K. A copal-8-ol diphosphate synthase from the angiosperm Cistus creticus subsp. creticus is a putative key enzyme for the formation of pharmacologically active, oxygen-containing labdane-type diterpenes. Plant Physiol. 154 (2010) 301–310. [DOI] [PMID: 20595348]
[EC 4.2.1.133 created 2012]
 
 
EC 4.2.3.140     
Accepted name: cis-abienol synthase
Reaction: (13E)-8α-hydroxylabd-13-en-15-yl diphosphate = cis-abienol + diphosphate
For diagram of labdane diterpenoids biosynthesis, click here
Glossary: cis-abienol = (12Z)-labda-12,14-dien-8α-ol
(13E)-8α-hydroxylabd-13-en-15-yl diphosphate = 8-hydroxycopalyl diphosphate
Other name(s): Z-abienol synthase; CAS; ABS
Systematic name: (13E)-8α-hydroxylabd-13-en-15-yl-diphosphate-lyase (cis-abienol forming)
Comments: Isolated from the plants Abies balsamea (balsam fir) [1] and Nicotiana tabacum (tobacco) [2].
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Zerbe, P., Chiang, A., Yuen, M., Hamberger, B., Hamberger, B., Draper, J.A., Britton, R. and Bohlmann, J. Bifunctional cis-abienol synthase from Abies balsamea discovered by transcriptome sequencing and its implications for diterpenoid fragrance production. J. Biol. Chem. 287 (2012) 12121–12131. [DOI] [PMID: 22337889]
2.  Sallaud, C., Giacalone, C., Topfer, R., Goepfert, S., Bakaher, N., Rosti, S. and Tissier, A. Characterization of two genes for the biosynthesis of the labdane diterpene Z-abienol in tobacco (Nicotiana tabacum) glandular trichomes. Plant J. 72 (2012) 1–17. [DOI] [PMID: 22672125]
[EC 4.2.3.140 created 2012]
 
 
EC 4.2.3.141     
Accepted name: sclareol synthase
Reaction: (13E)-8α-hydroxylabd-13-en-15-yl diphosphate + H2O = sclareol + diphosphate
For diagram of labdane diterpenoids biosynthesis, click here
Glossary: sclareol = (13R)-labd-14-ene-8α,13-diol
(13E)-8α-hydroxylabd-13-en-15-yl diphosphate = 8-hydroxycopalyl diphosphate
Other name(s): SS
Systematic name: (13E)-8α-hydroxylabd-13-en-15-yl-diphosphate-lyase (sclareol forming)
Comments: Isolated from the plant Salvia sclarea (clary sage). Originally thought to be synthesized in one step from geranylgeranyl diphosphate it is now known to require two enzymes, EC 4.2.1.133, copal-8-ol diphosphate synthase and EC 4.2.3.141, sclareol synthase. Sclareol is used in perfumery.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Caniard, A., Zerbe, P., Legrand, S., Cohade, A., Valot, N., Magnard, J.L., Bohlmann, J. and Legendre, L. Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture. BMC Plant Biol. 12:119 (2012). [DOI] [PMID: 22834731]
[EC 4.2.3.141 created 2013, modified 2017]
 
 
EC 4.2.3.190     
Accepted name: manoyl oxide synthase
Reaction: (13E)-8α-hydroxylabd-13-en-15-yl diphosphate = manoyl oxide + diphosphate
For diagram of hydroxylabdenyl diphosphate derived diterpenoids, click here
Glossary: (13E)-8α-hydroxylabd-13-en-15-yl diphosphate = 8-hydroxycopalyl diphosphate
manoyl oxide = (13R)-8,13-epoxylabd-14-ene
Other name(s): GrTPS6; CfTPS3; CfTPS4; MvELS
Systematic name: (13E)-8α-hydroxylabd-13-en-15-yl-diphosphate diphosphate-lyase (manoyl-oxide-forming)
Comments: Manoyl oxide is found in many plants. This enzyme has been isolated from the plants, Grindelia hirsutula (gum weed), Plectranthus barbatus (forskohlii) and Marrubium vulgare (white horehound).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Zerbe, P., Hamberger, B., Yuen, M.M., Chiang, A., Sandhu, H.K., Madilao, L.L., Nguyen, A., Hamberger, B., Bach, S.S. and Bohlmann, J. Gene discovery of modular diterpene metabolism in nonmodel systems. Plant Physiol. 162 (2013) 1073–1091. [DOI] [PMID: 23613273]
2.  Pateraki, I., Andersen-Ranberg, J., Hamberger, B., Heskes, A.M., Martens, H.J., Zerbe, P., Bach, S.S., Moller, B.L., Bohlmann, J. and Hamberger, B. Manoyl oxide (13R), the biosynthetic precursor of forskolin, is synthesized in specialized root cork cells in Coleus forskohlii. Plant Physiol. 164 (2014) 1222–1236. [DOI] [PMID: 24481136]
3.  Zerbe, P., Chiang, A., Dullat, H., O'Neil-Johnson, M., Starks, C., Hamberger, B. and Bohlmann, J. Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare. Plant J. 79 (2014) 914–927. [DOI] [PMID: 24990389]
[EC 4.2.3.190 created 2017]
 
 


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