2018
DOI: 10.1038/s41467-018-06565-8
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Kauniolide synthase is a P450 with unusual hydroxylation and cyclization-elimination activity

Abstract: Guaianolides are an important class of sesquiterpene lactones with unique biological and pharmaceutical properties. They have been postulated to be derived from germacranolides, but for years no progress has been made in the elucidation of their biosynthesis that requires an unknown cyclization mechanism. Here we demonstrate the isolation and characterization of a cytochrome P450 from feverfew (Tanacetum parthenium), kauniolide synthase. Kauniolide synthase catalyses the formation of the guaianolide kauniolide… Show more

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Cited by 31 publications
(37 citation statements)
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“…One well-observed example is as the rearrangement reaction from a germacrene to a eudesmane backbone. This acid-induced rearrangement converts, for instance, germacrene A acid (10) to α-costic acid (11), β-costic acid (12), and γ-costic acid (13) [9,10,30] with the double bond positions ∆3→4 (f), ∆4→15 (g) or ∆4→5 (h). The subsequent introduction of water (i) resulting in ilicic acid (14) has also been reported [9,10], likely neutralizing a carbocationic intermediate.…”
Section: Acid-induced Rearrangementmentioning
confidence: 99%
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“…One well-observed example is as the rearrangement reaction from a germacrene to a eudesmane backbone. This acid-induced rearrangement converts, for instance, germacrene A acid (10) to α-costic acid (11), β-costic acid (12), and γ-costic acid (13) [9,10,30] with the double bond positions ∆3→4 (f), ∆4→15 (g) or ∆4→5 (h). The subsequent introduction of water (i) resulting in ilicic acid (14) has also been reported [9,10], likely neutralizing a carbocationic intermediate.…”
Section: Acid-induced Rearrangementmentioning
confidence: 99%
“…In the case of a yeast expression system, culture and extraction conditions can be altered to differentiate between specific and unspecific enzyme products. For instance, Nguyen et al (2010) could show an increase of the specific enzyme product germacrene A acid (10) and a decrease of the rearrangement products costic acids and ilicic acid (11)(12)(13)(14) by comparing extracts from buffered versus unbuffered yeast cultures on a GC-MS and a LC-MS system [10]. Co-elution of acid-induced isomers on GC-MS can be overcome by the use of chiral columns which allow the separation of α-costic acid (11) and β-costic acid (12) [10].…”
Section: Acid-induced Rearrangementmentioning
confidence: 99%
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“…TpPTS (KC954155), Tp3β-hydroxylase (KC954153) and TpKLS (MF197558) were previously cloned into the pESC-Ura vector under the control of the galactose-inducible promoter by addition of BamHI and NotI restriction sites (Liu et al, 2018(Liu et al, , 2014. Microsomal fraction isolation was performed according to the method described by Liu et al (2018).…”
Section: Plasmid Construction For Gene Expression In Yeastmentioning
confidence: 99%