Polyketide synthases from poison hemlock (Conium maculatum L.)

Hannu Hotti, Tuulikki Seppänen-Laakso, Mikko Arvas, Teemu H. Teeri, Heiko Rischer (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

6 Citations (Scopus)

Abstract

Coniine is a toxic alkaloid, the biosynthesis of which is not well understood. A possible route, supported by evidence from labelling experiments, involves a polyketide formed by the condensation of one acetyl-CoA and three malonyl-CoAs catalysed by a polyketide synthase (PKS). We isolated PKS genes or their fragments from poison hemlock (Conium maculatum L.) by using random amplification of cDNA ends (RACE) and transcriptome analysis, and characterized three full-length enzymes by feeding different starter-CoAs in vitro. On the basis of our in vitro experiments, two of the three characterized PKS genes in poison hemlock encode chalcone synthases (CPKS1 and CPKS2), and one encodes a novel type of PKS (CPKS5). We show that CPKS5 kinetically favours butyryl-CoA as a starter-CoA in vitro. Our results suggest that CPKS5 is responsible for the initiation of coniine biosynthesis by catalysing the synthesis of the carbon backbone from one butyryl-CoA and two malonyl-CoAs.
Original languageEnglish
Pages (from-to)4141-4156
JournalFEBS Journal
Volume282
Issue number21
DOIs
Publication statusPublished - 2015
MoE publication typeA1 Journal article-refereed

Fingerprint

Conium
Polyketide Synthases
Poisons
Starters
Biosynthesis
Genes
Polyketides
Acetyl Coenzyme A
Gene Expression Profiling
Coenzyme A
Alkaloids
Labeling
Amplification
Condensation
Carbon
Complementary DNA
Experiments
Enzymes
In Vitro Techniques

Keywords

  • alkaloids
  • coniine
  • Conium maculatum(poison hemlock)
  • polyketide synthase
  • secondary metabolites

Cite this

Hotti, Hannu ; Seppänen-Laakso, Tuulikki ; Arvas, Mikko ; Teeri, Teemu H. ; Rischer, Heiko. / Polyketide synthases from poison hemlock (Conium maculatum L.). In: FEBS Journal. 2015 ; Vol. 282, No. 21. pp. 4141-4156.
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abstract = "Coniine is a toxic alkaloid, the biosynthesis of which is not well understood. A possible route, supported by evidence from labelling experiments, involves a polyketide formed by the condensation of one acetyl-CoA and three malonyl-CoAs catalysed by a polyketide synthase (PKS). We isolated PKS genes or their fragments from poison hemlock (Conium maculatum L.) by using random amplification of cDNA ends (RACE) and transcriptome analysis, and characterized three full-length enzymes by feeding different starter-CoAs in vitro. On the basis of our in vitro experiments, two of the three characterized PKS genes in poison hemlock encode chalcone synthases (CPKS1 and CPKS2), and one encodes a novel type of PKS (CPKS5). We show that CPKS5 kinetically favours butyryl-CoA as a starter-CoA in vitro. Our results suggest that CPKS5 is responsible for the initiation of coniine biosynthesis by catalysing the synthesis of the carbon backbone from one butyryl-CoA and two malonyl-CoAs.",
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Polyketide synthases from poison hemlock (Conium maculatum L.). / Hotti, Hannu; Seppänen-Laakso, Tuulikki; Arvas, Mikko; Teeri, Teemu H.; Rischer, Heiko (Corresponding Author).

In: FEBS Journal, Vol. 282, No. 21, 2015, p. 4141-4156.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Polyketide synthases from poison hemlock (Conium maculatum L.)

AU - Hotti, Hannu

AU - Seppänen-Laakso, Tuulikki

AU - Arvas, Mikko

AU - Teeri, Teemu H.

AU - Rischer, Heiko

PY - 2015

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N2 - Coniine is a toxic alkaloid, the biosynthesis of which is not well understood. A possible route, supported by evidence from labelling experiments, involves a polyketide formed by the condensation of one acetyl-CoA and three malonyl-CoAs catalysed by a polyketide synthase (PKS). We isolated PKS genes or their fragments from poison hemlock (Conium maculatum L.) by using random amplification of cDNA ends (RACE) and transcriptome analysis, and characterized three full-length enzymes by feeding different starter-CoAs in vitro. On the basis of our in vitro experiments, two of the three characterized PKS genes in poison hemlock encode chalcone synthases (CPKS1 and CPKS2), and one encodes a novel type of PKS (CPKS5). We show that CPKS5 kinetically favours butyryl-CoA as a starter-CoA in vitro. Our results suggest that CPKS5 is responsible for the initiation of coniine biosynthesis by catalysing the synthesis of the carbon backbone from one butyryl-CoA and two malonyl-CoAs.

AB - Coniine is a toxic alkaloid, the biosynthesis of which is not well understood. A possible route, supported by evidence from labelling experiments, involves a polyketide formed by the condensation of one acetyl-CoA and three malonyl-CoAs catalysed by a polyketide synthase (PKS). We isolated PKS genes or their fragments from poison hemlock (Conium maculatum L.) by using random amplification of cDNA ends (RACE) and transcriptome analysis, and characterized three full-length enzymes by feeding different starter-CoAs in vitro. On the basis of our in vitro experiments, two of the three characterized PKS genes in poison hemlock encode chalcone synthases (CPKS1 and CPKS2), and one encodes a novel type of PKS (CPKS5). We show that CPKS5 kinetically favours butyryl-CoA as a starter-CoA in vitro. Our results suggest that CPKS5 is responsible for the initiation of coniine biosynthesis by catalysing the synthesis of the carbon backbone from one butyryl-CoA and two malonyl-CoAs.

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KW - coniine

KW - Conium maculatum(poison hemlock)

KW - polyketide synthase

KW - secondary metabolites

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