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Literature summary extracted from

  • Brueckner, K.; Bozic, D.; Manzano, D.; Papaefthimiou, D.; Pateraki, I.; Scheler, U.; Ferrer, A.; de Vos, R.C.; Kanellis, A.K.; Tissier, A.
    Characterization of two genes for the biosynthesis of abietane-type diterpenes in rosemary (Rosmarinus officinalis) glandular trichomes (2014), Phytochemistry, 101, 52-64 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.3.131 gene SKL1, DNA and amino acid sequence determination and analysis, sequence comparisons, phylogenetic analysis and tree, RoKSL1 and RoKSL2 cluster into a discrete clade, together with other KSL proteins from the Lamiaceae and Solanaceae (NtABS, ShSBS and SlPHS). Functional recombinant expression in Saccharomyces cerevisiae strain AM113, and transient coexpression of RoSKL1 and RoSKL2 in Nicotiana benthamiana leaves Salvia rosmarinus
4.2.3.131 gene SKL2, DNA and amino acid sequence determination and analysis, sequence comparisons, phylogenetic analysis and tree, RoKSL1 and RoKSL2 cluster into a discrete clade, together with other KSL proteins from the Lamiaceae and Solanaceae (NtABS, ShSBS and SlPHS). Functional recombinant expression in Saccharomyces cerevisiae strain AM113, and transient coexpression of RoSKL1 and RoSKL2 in Nicotiana benthamiana leaves Salvia rosmarinus
5.5.1.12 gene CPS1, phylogenetic analysis and tree, functional recombinant expression in Saccharomyces cerevisiae strain AM113, with co-overexpressing of GGDPS1 from Cistus creticus, and Nicotiana benthamiana, heterologous expression of the RoCPS1 protein in Escherichia coli fails Salvia rosmarinus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.131 geranylgeranyl diphosphate Salvia rosmarinus
-
 (+)-copalyl diphosphate
-
 r
4.2.3.131 additional information Salvia rosmarinus substrate specificity analysis, rosemary RoKSL1/2 are functional enzymes able to convert either 8-OH-CDP or CDP into manoyl oxide or miltiradiene, respectively, and that they likely function in planta as miltiradiene synthases ?
-
 ?
5.5.1.12 geranylgeranyl diphosphate Salvia rosmarinus
-
 (+)-copalyl diphosphate
-
 r

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.131 Salvia rosmarinus W8QEG7
-
-
4.2.3.131 Salvia rosmarinus W8QMF8
-
-
4.2.3.190 Salvia rosmarinus W8QEG7 cf. EC 4.2.3.131
-
4.2.3.190 Salvia rosmarinus W8QMF8 cf. EC 4.2.3.131
-
5.5.1.12 Salvia rosmarinus W8QQT6
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
4.2.3.131 leaf young and old Salvia rosmarinus
-
4.2.3.131 additional information quantitative RT-PCR expression analysis on whole leaves shows that RoKSL2 and RoKSL1 are preferentially expressed in young leaves, with RoKSL1 being much less expressed than RoKSL2. Direct comparison of the expression levels between RoKSL1 and RoKSL2 in isolated trichomes and in the remaining leaves indicates that RoKSL1 is not specific to the trichomes and significantly less expressed than RoKSL2 (RoKSL1 transcript level about 1% of expression of RoKSL2) Salvia rosmarinus
-
4.2.3.131 trichome glandular Salvia rosmarinus
-
4.2.3.131 trichome glandular, very limited expression level Salvia rosmarinus
-
4.2.3.190 trichome glandular trichome Salvia rosmarinus
-
5.5.1.12 glandular trichome
-
 Salvia rosmarinus
-
5.5.1.12 leaf young and old Salvia rosmarinus
-
5.5.1.12 additional information quantitative RT-PCR expression analysis on whole leaves shows that RoCPS1 is preferentially expressed in in trichomes from young leaves Salvia rosmarinus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.131 (+)-copalyl diphosphate
-
 Salvia rosmarinus miltiradiene + diphosphate
-
 ?
4.2.3.131 8-hydroxy-(+)-copalyl diphosphate
-
 Salvia rosmarinus manoyl oxide + diphosphate
-
 ?
4.2.3.131 geranylgeranyl diphosphate
-
 Salvia rosmarinus (+)-copalyl diphosphate
-
 r
4.2.3.131 additional information substrate specificity analysis, rosemary RoKSL1/2 are functional enzymes able to convert either 8-OH-CDP or CDP into manoyl oxide or miltiradiene, respectively, and that they likely function in planta as miltiradiene synthases Salvia rosmarinus ?
-
 ?
4.2.3.190 (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate
-
 Salvia rosmarinus manoyl oxide + diphosphate
-
 ?
4.2.3.190 additional information bifunctional enzyme, catalyzing the reaction of (+)-copalyl diphosphate to miltiradiene, EC 4.2.3.131 and, in combination with Nicotinana tabacum CPS2 the synthesis of manoyl oxide Salvia rosmarinus ?
-
 ?
5.5.1.12 geranylgeranyl diphosphate
-
 Salvia rosmarinus (+)-copalyl diphosphate
-
 r

Synonyms

EC Number Synonyms Comment Organism
4.2.3.131 RoSKL1
-
 Salvia rosmarinus
4.2.3.131 RoSKL2
-
 Salvia rosmarinus
4.2.3.190 kaurene synthase-like 1
-
 Salvia rosmarinus
4.2.3.190 kaurene synthase-like 2
-
 Salvia rosmarinus
4.2.3.190 KSL1
-
 Salvia rosmarinus
4.2.3.190 KSL2
-
 Salvia rosmarinus
5.5.1.12 CPS1
-
 Salvia rosmarinus
5.5.1.12 RoCPS1
-
 Salvia rosmarinus

General Information

EC Number General Information Comment Organism
4.2.3.131 metabolism several stereoisomers of copalyl diphosphate (CDP) are found, among which the most common is ent-CDP, the precursor of gibberellins. Other isomers are syn-CDP and normal-CDP, the latter being utilized for the biosynthesis of diterpene resin acids in Gymnosperms and abietane-type tanshinones in Salvia miltiorrhiza. The second step of the cyclization is initiated through the formation of a carbocation upon ionization of the diphosphate linkage of CDP. This is catalyzed by class I terpene synthases which can transform CDP into a variety of polycyclic diterpenoids. By analogy to other labdane-type diterpenoids, the biosynthesis of the diterpene precursor of the carnosic acid pathway in rosemary proceeds in two sequential steps catalyzed by two distinct enzymes. The first is a class II TPS enzyme, CPS1, EC 5.5.1.12, that yields normal CDP, which then is converted by a KSL enzyme to yield an abietane diterpene, miltiradiene. Miltiradiene synthase appears in two isoforms, RoKSL1 and RoKSL2, in Rosmarinus officinalis. Hypothetical biosynthetic pathway of carnosic acid and carnosol produced in Rosmarinus officinalis, overview Salvia rosmarinus
4.2.3.190 physiological function coexpression of Nicotiana tabacum CPS2 and isoofrm KSL1 in Nicotiana benthamiana leaves results in the production of manoyl oxide Salvia rosmarinus
5.5.1.12 metabolism several stereoisomers of copalyl diphosphate (CDP) are found, among which the most common is ent-CDP, the precursor of gibberellins. Other isomers are syn-CDP and normal-CDP, the latter being utilized for the biosynthesis of diterpene resin acids in Gymnosperms and abietane-type tanshinones in Salvia miltiorrhiza. The second step of the cyclization is initiated through the formation of a carbocation upon ionization of the diphosphate linkage of CDP. This is catalyzed by class I terpene synthases which can transform CDP into a variety of polycyclic diterpenoids. By analogy to other labdane-type diterpenoids, the biosynthesis of the diterpene precursor of the carnosic acid pathway in rosemary proceeds in two sequential steps catalyzed by two distinct enzymes. The first is a class II TPS enzyme, CPS1, that yields normal CDP, which then is converted to miltiradiene by a KSL enzyme, miltiradiene synthase, EC 4.2.3.131, which apears in two isoforms, RoKSL1 and RoKSL2, in Rosmarinus officinalis. Hypothetical biosynthetic pathway of carnosic acid and carnosol produced in Rosmarinus officinalis, overview Salvia rosmarinus