Physcomitrella PpORS, Basal to Plant Type III Polyketide Synthases in Phylogenetic Trees, Is a Very Long Chain 2′-Oxoalkylresorcinol Synthase

Kim, Sun Young; Colpitts, Che C.; Wiedemann, Gertrud; Jepson, Christina; Rahimi, Mehrieh; Rothwell, Jordan R.; McInnes, Adam D.; Hasebe, Mitsuyasu; Reski, Ralf; Sterenberg, Brian T.; Suh, Dae-Yeon

doi:10.1074/jbc.m112.430686

Cited by 20 publications

(23 citation statements)

References 43 publications

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“…Similar reactions (L‐5‐A) can be performed by a bryophyte PKS (PpORS) of clade P4 (described below). However, ARASs/ARSs have active‐site architecture distinct from that of bryophyte PKSs, which indicates that Poaceae ARASs/ARSs acquired their function through a structural strategy that differs from that used by bryophyte PpORS …”

Section: Taxonomic Distribution Of Type III Pkss and Their Reaction mentioning

confidence: 99%

“…Clade P4 contains only bryophyte PKSs, including PpORS (L‐5‐A), and is located at the base of the plant clades, thus indicating that PpORS closely resembles the most recent common ancestor of the plant type III PKSs . Because no PpORS orthologues have been observed in non‐bryophyte genomes, gene losses of PpORS orthologues in tracheophyte lineages was proposed …”

Section: Taxonomic Distribution Of Type III Pkss and Their Reaction mentioning

confidence: 99%

“…However,A RASs/ARSs have active-site architecture distinct from that of bryophyte PKSs, which indicates that Poaceae ARASs/ARSs acquired their function throughas tructural strategy that differs from that used by bryophyte PpORS. [75] Clade P3 includes ASCL homologues[ Lh-4-L, Lh(b)-3-L] from angiosperms to bryophytes.T he topology of this clade is highly consistentw ith the speciesp hylogeny of land plants, which indicates that ASCLs arose early in land plant evolution and retained their function:p roduction of the sporopollenin precursor involved in pollen development. [76] Only one ASCL gene has been found in each bryophyte or fern genome, whereas each angiosperm genome has two or more ASCL genes that are divided into two distinct sister clades.…”

Section: Plantsmentioning

confidence: 99%

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Type III Polyketide Synthases: Functional Classification and Phylogenomics

2016

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Polyketide synthases (PKSs) catalyze the sequential condensation of simple acetate units to produce a large class of natural products, including pharmacologically valuable compounds. PKSs are classified into three types on the basis of their domain structures; type III PKSs have the simplest domain structure, although their products have various structures and functions. The sequence–function relationship is fundamental for predicting enzyme functions, but it has not been well investigated in type III PKSs to date. Consequently, the current methods for predicting type III PKS functions are still immature in comparison with those that target type I/II PKSs. In this review we summarize the current functional and phylogenomic knowledge about type III PKSs and propose a new classification of their enzymatic reactions. We also discuss possible directions for the development of better computational tools for functional prediction of type III PKS homologues.

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Section: Taxonomic Distribution Of Type III Pkss and Their Reaction mentioning

confidence: 99%

Section: Taxonomic Distribution Of Type III Pkss and Their Reaction mentioning

confidence: 99%

Section: Plantsmentioning

confidence: 99%

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Type III Polyketide Synthases: Functional Classification and Phylogenomics

2016

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“…The R F values of the main products ( 3a – 3h ) progressively increased with increasing chain length of the substrate, indicating that the main products are of the same chemical type. The major products, 3a – 3j , were stained yellow–orange with Fast Blue B salt on TLC, which is characteristic of triketide α‐pyrone compounds . Compounds 3a – 3j comigrated on TLC with the triketide α‐pyrones produced by Azotobacter vinelandii ArsC and/or PpASCL from the same starter CoA substrate.…”

Section: Resultsmentioning

confidence: 97%

Hypericum perforatum hydroxyalkylpyrone synthase involved in sporopollenin biosynthesis – phylogeny, site‐directed mutagenesis, and expression in nonanther tissues

et al. 2014

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Anther-specific chalcone synthase-like enzyme (ASCL), an ancient plant type III polyketide synthase, is involved in the biosynthesis of sporopollenin, the stable biopolymer found in the exine layer of the wall of a spore or pollen grain. The gene encoding polyketide synthase 1 from Hypericum perforatum (HpPKS1) was previously shown to be expressed mainly in young flower buds, but also in leaves and other tissues at lower levels. Angiosperm ASCLs, identified by sequence and phylogenetic analyses, are divided into two sister clades, the Ala-clade and the Val-clade, and HpPKS1 belongs to the Ala-clade. Recombinant HpPKS1 produced triketide and, to a lesser extent, tetraketide alkylpyrones from medium-chain (C 6 ) to very long-chain (C 24 ) fatty acyl-CoA substrates. Like other ASCLs, HpPKS1 also preferred hydroxyl fatty acyl-CoA esters over the analogous unsubstituted fatty acyl-CoA esters. To study the structural basis of the substrate preference, mutants of Ala200 and Ala215 at the putative active site and Arg202 and Asp211 at the modeled acyl-binding tunnel were constructed. The A200T/A215Q mutant accepted decanoyl-CoA, a poor substrate for the wild-type enzyme, possibly because of active site constriction by bulkier substitutions. The substrate preference of the A215V and A200T/A215Q mutants shifted toward nonhydroxylated, medium-chain to long-chain fatty acyl-CoA substrates. The R202L/D211V double mutant was selective for acyl-CoA with chain lengths of C 16 -C 18 , and showed a diminished preference for the hydroxylated acyl-CoA substrates. Transient upregulation by abscisic acid and downregulation by jasmonic acid and wounding suggested that HpPKS1, and possibly other Ala-clade ASCLs, may be involved in the biosynthesis of minor cell wall components in nonanther tissues.

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“…Genes encoding PKS have been characterized from plant, fungal and bacterial species and are shown to have a role in the biosynthesis of wide range of alkaloids (acridone, quinolone, curcuminoids), flavanoids, alkylresorcinols and antibiotics etc 222324252627…”

Section: Discussionmentioning

confidence: 99%

Transcriptomic insight into terpenoid and carbazole alkaloid biosynthesis, and functional characterization of two terpene synthases in curry tree (Murraya koenigii)

Meena

Kumar

Dwivedi

et al. 2017

Sci Rep

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Curry tree (Murraya koenigii L.) is a rich source of aromatic terpenes and pharmacologically important carbazole alkaloids. Here, M. koenigii leaf transcriptome was generated to gain insight into terpenoid and alkaloid biosynthesis. Analysis of de novo assembled contigs yielded genes for terpene backbone biosynthesis and terpene synthases. Also, gene families possibly involved in carbazole alkaloid formation were identified that included polyketide synthases, prenyltransferases, methyltransferases and cytochrome P450s. Further, two genes encoding terpene synthases (MkTPS1 and MkTPS2) with highest in silico transcript abundance were cloned and functionally characterized to determine their involvement in leaf volatile formation. Subcellular localization using GFP fusions revealed the plastidial and cytosolic localization of MkTPS1 and MkTPS2, respectively. Enzymatic characterization demonstrated the monoterpene synthase activity of recombinant MkTPS1, which produced primarily (−)-sabinene from geranyl diphosphate (GPP). Recombinant MkTPS2 exhibited sesquiterpene synthase activity and formed (E,E)-α-farnesene as the major product from farnesyl diphosphate (FPP). Moreover, mRNA expression and leaf volatile analyses indicated that MkTPS1 accounts for (−)-sabinene emitted by M. koenigii leaves. Overall, the transcriptome data generated in this study will be a great resource and the start point for characterizing genes involved in the biosynthetic pathway of medicinally important carbazole alkaloids.

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Physcomitrella PpORS, Basal to Plant Type III Polyketide Synthases in Phylogenetic Trees, Is a Very Long Chain 2′-Oxoalkylresorcinol Synthase

Cited by 20 publications

References 43 publications

Type III Polyketide Synthases: Functional Classification and Phylogenomics

Type III Polyketide Synthases: Functional Classification and Phylogenomics

Hypericum perforatum hydroxyalkylpyrone synthase involved in sporopollenin biosynthesis – phylogeny, site‐directed mutagenesis, and expression in nonanther tissues

Transcriptomic insight into terpenoid and carbazole alkaloid biosynthesis, and functional characterization of two terpene synthases in curry tree (Murraya koenigii)

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