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Literature summary extracted from

  • Pateraki, I.; Andersen-Ranberg, J.; Hamberger, B.; Heskes, A.M.; Martens, H.J.; Zerbe, P.; Bach, S.S.; Moller, B.L.; Bohlmann, J.; Hamberger, B.
    Manoyl oxide (13R), the biosynthetic precursor of forskolin, is synthesized in specialized root cork cells in Coleus forskohlii (2014), Plant Physiol., 164, 1222-1236 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.1.133 gene TPS2, phylogenetic analysis Plectranthus barbatus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
4.2.1.133 additional information manoyl oxide is detected in root cork and, more specifically, in oil bodies isolated from this tissue, as well as in the root cortex and stele, stem, and flowers Plectranthus barbatus
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4.2.1.133 oil body localization of forskolin and (13R)-manoyl oxide in root cork oil bodies, overview. Small amounts are located also in a small number of oil bodies in stem cork tissue Plectranthus barbatus
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Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.133 geranylgeranyl diphosphate + H2O Plectranthus barbatus
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 (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate
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 r

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.133 Plectranthus barbatus X4ZWN5 i.e. Coleus barbatus or Plectranthus barbatus
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4.2.3.190 Plectranthus barbatus X5A2Z7
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-
4.2.3.190 Plectranthus barbatus X5AHD9
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-

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.1.133 (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate = geranylgeranyl diphosphate + H2O the class II diTPS reaction, which forms the bicyclic decalin core of labdanetype diterpenoids, is terminated either by deprotonation or by water capture of the diphosphate carbocation Plectranthus barbatus
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
4.2.1.133 cork a specialized cell type containing characteristic structures with histochemical properties consistent with oil bodies Plectranthus barbatus
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4.2.1.133 root cork cell Plectranthus barbatus
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4.2.3.190 additional information expression across all tissues Plectranthus barbatus
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4.2.3.190 additional information transcripts are mostly detected in the aerial parts of the plant, especially in the leaves. Transcript level is relatively low across all tissues Plectranthus barbatus
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4.2.3.190 root low transcript level Plectranthus barbatus
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4.2.3.190 root root cork cell, high transcript level Plectranthus barbatus
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Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.133 geranylgeranyl diphosphate + H2O
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 Plectranthus barbatus (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate
-
 r
4.2.1.133 additional information compounds GC-MS analysis Plectranthus barbatus ?
-
 ?
4.2.3.190 (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate
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 Plectranthus barbatus manoyl oxide + diphosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.133 CfTPS2
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 Plectranthus barbatus
4.2.1.133 TPS2
-
 Plectranthus barbatus
4.2.3.190 TPS3
-
 Plectranthus barbatus
4.2.3.190 TPS4
-
 Plectranthus barbatus

General Information

EC Number General Information Comment Organism
4.2.1.133 evolution the enzyme is a class II diterpene synthase (diTPS), expression profiling and phylogenetic analysis of the CfTPS family. Coleus forskohlii diTPSs constitute a small gene family. Schematic overview of the biosynthetic routes from GGPP to specialized and general diterpenoids of the abietane, labdane, and ent-kaurene class Plectranthus barbatus
4.2.1.133 metabolism enzyme CfTPS2 synthesizes the intermediate copal-8-ol diphosphate,which in combination with CfTPS3 results in the stereospecific formation of (13R) manoyl oxide, while the combination of CfTPS1 an CfTPS3 or CfTPS4 leads to formation of miltiradiene, precursor of abietane diterpenoids in Coleus forskohlii, in combination with TPS14, (13R) and (13S) manoyl oxides are fomed Plectranthus barbatus
4.2.1.133 additional information analysis of diterpenoids in oil bodies from Coleus forskohlii, overview Plectranthus barbatus
4.2.1.133 physiological function involvement of CfTPS2 in the formation of (13R) manoyl oxide en route to forskolin in root cork cells Plectranthus barbatus
4.2.3.190 physiological function TPS2, which synthesizes the intermediate copal-8-ol diphosphate, in combination with TPS3 leads to the stereospecific formation of (13R) manoyl oxide. In extracts from Nicotiana benthamiana coexpressing TPS2 with TPS3, only the (13R) epimer of manoyl oxide is identified, while the combination of TPS1 and TPS3 leads to formation of miltiradiene Plectranthus barbatus
4.2.3.190 physiological function TPS2, which synthesizes the intermediate copal-8-ol diphosphate, in combination with TPS4 leads to the stereospecific formation of (13R) manoyl oxide. In extracts from Nicotiana benthamiana coexpressing TPS2 with TPS4, only the (13R) epimer of manoyl oxide is identified, while the combination of TPS1 and TPS4 leads to formation of miltiradiene Plectranthus barbatus