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Literature summary extracted from

  • Zerbe, P.; Chiang, A.; Dullat, H.; ONeil-Johnson, M.; Starks, C.; Hamberger, B.; Bohlmann, J.
    Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare (2014), Plant J., 79, 914-927 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.1.174 gene CPS1, phylogenetic analysis and tree quantitative real-time PCR enzyme expression analysis, functional expression of MvCPS1 alone or with MvELS (multifunctional betaalpha-domain class I diterpene synthase) or MvEKS (ent-kaurene synthase) in engineered Escherichia coli and Nicotiana benthamiana Marrubium vulgare
4.2.3.189 expression in Escherichia coli Marrubium vulgare
4.2.3.190 expression in Escherichia coli Marrubium vulgare
5.5.1.12 gene CPS3, phylogenetic analysis and tree, quantitative expression analysis, functional expression of MvCPS3 alone or with MvELS (multifunctional betaalpha-domain class I diterpene synthase) or MvEKS (ent-kaurene synthase) in engineered Nicotiana benthamiana Marrubium vulgare

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
4.2.3.189 ELS belongs to a subgroup of the diTPS TPS–e/f clade with unusual betaalpha-domain architecture Marrubium vulgare
4.2.3.190 ELS belongs to a subgroup of the diTPS TPS–e/f clade with unusual betaalpha-domain architecture Marrubium vulgare

Protein Variants

EC Number Protein Variants Comment Organism
4.2.1.174 additional information co-expression of MvCPS1 and MvELS in engineered Escherichia coli and Nicotiana benthamiana offers opportunities for producing precursors for an array of biologically active diterpenoids. Coexpression of MvCPS1 with MvELS results in 9,13-epoxy-labd-14-ene as the major product. In contrast, coexpression of MvCPS1 with MvEKS yields no additional product Marrubium vulgare

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.174 additional information Marrubium vulgare in contrast with previously known diterpene synthases that introduce a hydroxyl group at carbon C-8 of the labdane backbone, the MvCPS1-catalyzed reaction proceeds via oxygenation of an intermediate carbocation at C-9, yielding the bicyclic peregrinol diphosphate ?
-
 ?
4.2.1.174 peregrinol diphosphate Marrubium vulgare
-
 geranylgeranyl diphosphate + H2O
-
 ?
4.2.3.189 additional information Marrubium vulgare ELS is active in vitro and in vivo with three different prenyl diphosphate substrates forming the marrubiin precursor 9,13-epoxy-labd-14-ene, manoyl oxide, i.e. reaction of EC 4.2.3.190, and miltiradiene, reaction of EC 4.2.3.131 ?
-
 ?
4.2.3.189 peregrinol diphosphate Marrubium vulgare
-
 (13epsilon)-9,13-epoxylabda-14-ene + diphosphate
-
 ?
4.2.3.190 (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate Marrubium vulgare
-
 manoyl oxide + diphosphate
-
 ?
4.2.3.190 additional information Marrubium vulgare ELS is active in vitro and in vivo with three different prenyl diphosphate substrates forming the marrubiin precursor 9,13-epoxy-labd-14-ene, i.e. reaction of EC 4.2.3.189, manoyl oxide and miltiradiene, reaction of EC 4.2.3.131 ?
-
 ?
5.5.1.12 geranylgeranyl diphosphate Marrubium vulgare
-
 (+)-copalyl diphosphate
-
 r

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.174 Marrubium vulgare A0A075FAK4
-
-
4.2.3.189 Marrubium vulgare A0A075FBG7
-
-
4.2.3.190 Marrubium vulgare A0A075FBG7
-
-
5.5.1.12 Marrubium vulgare A0A075FA51
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.1.174 peregrinol diphosphate = geranylgeranyl diphosphate + H2O in contrast with previously known diterpene synthases that introduce a hydroxyl group at carbon C-8 of the labdane backbone, the MvCPS1-catalyzed reaction proceeds via oxygenation of an intermediate carbocation at C-9, yielding the bicyclic peregrinol diphosphate Marrubium vulgare
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
4.2.1.174 flower very low expression level of CPS1 Marrubium vulgare
-
4.2.1.174 leaf high expression level of CPS1 Marrubium vulgare
-
4.2.1.174 additional information transcript levels of MvCPS1 are 49fold higher in leaves compared with flowers Marrubium vulgare
-
4.2.3.189 flower transcript level is 4fold higher in leaf compared with flower Marrubium vulgare
-
4.2.3.189 leaf transcript level is 4fold higher in leaf compared with flower Marrubium vulgare
-
4.2.3.190 flower transcript level is 4fold higher in leaf compared with flower Marrubium vulgare
-
4.2.3.190 leaf transcript level is 4fold higher in leaf compared with flower Marrubium vulgare
-
5.5.1.12 flower very low expression level of CPS3 Marrubium vulgare
-
5.5.1.12 leaf high expression level of CPS3 Marrubium vulgare
-
5.5.1.12 additional information transcript levels of MvCPS3 are 28fold higher in leaves compared with flowers Marrubium vulgare
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.174 additional information in contrast with previously known diterpene synthases that introduce a hydroxyl group at carbon C-8 of the labdane backbone, the MvCPS1-catalyzed reaction proceeds via oxygenation of an intermediate carbocation at C-9, yielding the bicyclic peregrinol diphosphate Marrubium vulgare ?
-
 ?
4.2.1.174 additional information reaction product analysis by GC-MS Marrubium vulgare ?
-
 ?
4.2.1.174 peregrinol diphosphate
-
 Marrubium vulgare geranylgeranyl diphosphate + H2O
-
 ?
4.2.3.189 additional information ELS is active in vitro and in vivo with three different prenyl diphosphate substrates forming the marrubiin precursor 9,13-epoxy-labd-14-ene, manoyl oxide, i.e. reaction of EC 4.2.3.190, and miltiradiene, reaction of EC 4.2.3.131 Marrubium vulgare ?
-
 ?
4.2.3.189 peregrinol diphosphate
-
 Marrubium vulgare (13epsilon)-9,13-epoxylabda-14-ene + diphosphate
-
 ?
4.2.3.190 (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate
-
 Marrubium vulgare manoyl oxide + diphosphate
-
 ?
4.2.3.190 additional information ELS is active in vitro and in vivo with three different prenyl diphosphate substrates forming the marrubiin precursor 9,13-epoxy-labd-14-ene, i.e. reaction of EC 4.2.3.189, manoyl oxide and miltiradiene, reaction of EC 4.2.3.131 Marrubium vulgare ?
-
 ?
5.5.1.12 geranylgeranyl diphosphate
-
 Marrubium vulgare (+)-copalyl diphosphate
-
 r
5.5.1.12 additional information the enzyme shows substrate specificity, reaction product analysis by GC-MS. MvCPS3 does not produce ent-CPP, reaction of EC 5.5.1.13 Marrubium vulgare ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.174 CPS1
-
 Marrubium vulgare
4.2.1.174 MvCPS1
-
 Marrubium vulgare
4.2.3.189 ELS
-
 Marrubium vulgare
4.2.3.190 ELS
-
 Marrubium vulgare
5.5.1.12 (+)-copalyl diphosphate synthase
-
 Marrubium vulgare
5.5.1.12 (+)-CPS
-
 Marrubium vulgare
5.5.1.12 CPS3
-
 Marrubium vulgare
5.5.1.12 MvCPS3
-
 Marrubium vulgare

General Information

EC Number General Information Comment Organism
4.2.1.174 evolution diterpene synthases transcriptome analysis of Marrubium vulgare leaves, phylogenetic analysis, overview. CPS1 is a class II diterpene synthase, phylogenetic analysis Marrubium vulgare
4.2.1.174 metabolism enzyme CPS1 produces a precursor for marrubiin biosynthesis, pathway overview Marrubium vulgare
4.2.1.174 additional information enzyme CPS1 contains a DIDD functional motif Marrubium vulgare
4.2.1.174 physiological function in contrast with previously known diterpene synthases that introduce a hydroxyl group at carbon C-8 of the labdane backbone, the MvCPS1-catalyzed reaction proceeds via oxygenation of an intermediate carbocation at C-9, yielding the bicyclic peregrinol diphosphate. A labdane-type diterpene structure bearing an oxygen functionality at carbon C-9 is characteristic for marrubiin and many of the specialized diterpenoids in the genus Marrubium. Enzyme CPS1 produces a precursor for marrubiin biosynthesis Marrubium vulgare
4.2.3.189 physiological function in vitro, in combination with the copalyl diphosphate-producing CPS3, ELS forms miltiradiene. When coupled with TPS2, ELS converts (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate into manoyl oxide. The coupled reaction of CPS1 and ELS leads to 80% (13epsilon)-9,13-epoxylabda-14-ene Marrubium vulgare
4.2.3.190 physiological function in vitro, in combination with the copalyl diphosphate-producing CPS3, ELS forms miltiradiene. When coupled with TPS2, ELS converts (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate into manoyl oxide. The coupled reaction of CPS1 and ELS leads to 80% (13epsilon)-9,13-epoxylabda-14-ene Marrubium vulgare
5.5.1.12 evolution diterpene synthases transcriptome analysis of Marrubium vulgare leaves, overview. CPS3 is a class II diterpene synthase, phylogenetic analysis Marrubium vulgare
5.5.1.12 additional information enzyme CPS3 contains a DIDD functional motif Marrubium vulgare