Biosynthesis of the diterpenoid lycosantalonol via nerylneryl diphosphate in Solanum lycopersicum

We recently reported that three genes involved in the biosynthesis of monoterpenes in trichomes, a cis-prenyltransferase named neryl diphosphate synthase 1 (NDPS1) and two terpene synthases (TPS19 and TPS20), are present in close proximity to each other at the tip of chromosome 8 in the genome of th...

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Bibliographic Details
Published in:PloS one 2015-03, Vol.10 (3), p.e0119302-e0119302
Main Authors: Matsuba, Yuki, Zi, Jiachen, Jones, A Daniel, Peters, Reuben J, Pichersky, Eran
Format: Article
Language:English
Subjects:
Alcohol
Alkyl and Aryl Transferases - genetics
Alkyl and Aryl Transferases - metabolism
Biochemistry
Biological products
Biophysics
Biosynthesis
Biosynthetic Pathways - genetics
Chemical properties
Chromosome 8
Chromosomes
Clusters
Cytochrome
Cytochrome P-450 Enzyme System - genetics
Cytochrome P-450 Enzyme System - metabolism
Cytochrome P450
Developmental biology
Dimethylallyltranstransferase - genetics
Dimethylallyltranstransferase - metabolism
Diterpenes - metabolism
E coli
Enzymes
Evolution
Flowers & plants
Fruit cultivation
Gene Expression
Genes
Genes, Plant
Genetic engineering
Genomes
Genomics
Lycopersicon esculentum - enzymology
Lycopersicon esculentum - genetics
Metabolism
Metabolites
Molecular biology
Monoterpenes
Organ Specificity
Oxidation
Oxidoreductase
Physiological aspects
Plant Leaves - metabolism
Plants, Genetically Modified
Polyisoprenyl Phosphates - metabolism
Solanaceae
Solanum lycopersicum
Tissues
Tomatoes
Transgenic plants
Trichomes
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Summary:We recently reported that three genes involved in the biosynthesis of monoterpenes in trichomes, a cis-prenyltransferase named neryl diphosphate synthase 1 (NDPS1) and two terpene synthases (TPS19 and TPS20), are present in close proximity to each other at the tip of chromosome 8 in the genome of the cultivated tomato (Solanum lycopersicum). This terpene gene "cluster" also contains a second cis-prenyltransferase gene (CPT2), three other TPS genes, including TPS21, and the cytochrome P450-oxidoreductase gene CYP71BN1. CPT2 encodes a neryneryl diphosphate synthase. Co-expression in E. coli of CPT2 and TPS21 led to the formation of the diterpene lycosantalene, and co-expression in E. coli of CPT2, TPS21 and CYP71BN1 led to the formation of lycosantalonol, an oxidation product of lycosantalene. Here we show that maximal expression of all three genes occurs in the petiolule part of the leaf, but little expression of these genes occurs in the trichomes present on the petiolules. While lycosantalene or lycosantalonol cannot be detected in the petiolules of wild-type plants (or anywhere else in the plant), lycosantalene and lycosantalonol are detected in petiolules of transgenic tomato plants expressing CPT2 under the control of the 35S CaMV promoter. These results suggest that lycosantalene and lycosantalonol are produced in the petiolules and perhaps in other tissues of wild-type plants, but that low rate of synthesis, controlled by the rate-limiting enzyme CPT2, results in product levels that are too low for detection under our current methodology. It is also possible that these compounds are further modified in the plant. The involvement of CPT2, TPS21 and CYP71BN1 in a diterpenoid biosynthetic pathway outside the trichomes, together with the involvement of other genes in the cluster in the synthesis of monoterpenes in trichomes, indicates that this cluster is further evolving into "sub-clusters" with unique biochemical, and likely physiological, roles.
ISSN:1932-6203
1932-6203
DOI:10.1371/journal.pone.0119302