Closely related to EC 2.3.1.74, naringenin-chalcone synthase. Also acts on isobutyryl-CoA as substrate to give phlorisobutyrophenone. The products are intermediates in the biosynthesis of the bitter acids in hops (Humulus lupulus) and glucosides in strawberry (Fragaria X ananassa). It is also able to generate naringenin chalcone from 4-coumaroyl-CoA.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
isovaleryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisovalerophenone
Closely related to EC 2.3.1.74, chalcone synthase. The product, 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one, is chloroisovalerophenone. Also acts on isobutyryl-CoA as substrate to give phlorisobutyrophenone. The products are intermediates in the biosynthesis of the bitter alpha-acids in hops, Humulus lupulus
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PATHWAY SOURCE
PATHWAYS
MetaCyc
adlupulone and adhumulone biosynthesis, colupulone and cohumulone biosynthesis, hyperforin and adhyperforin biosynthesis, lupulone and humulone biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
isovaleryl-CoA:malonyl-CoA acyltransferase
Closely related to EC 2.3.1.74, naringenin-chalcone synthase. Also acts on isobutyryl-CoA as substrate to give phlorisobutyrophenone. The products are intermediates in the biosynthesis of the bitter acids in hops (Humulus lupulus) and glucosides in strawberry (Fragaria X ananassa). It is also able to generate naringenin chalcone from 4-coumaroyl-CoA.
Substrates: the Fragaria vesca bifunctional chalcone synthase enzymes readily catalyze the condensation isovaleryl-Coenzyme A (CoA) and isobutyryl-CoA, with three molecules of malonyl-CoA to form phlorisovalerophenone and phlorisobutyrophenone, respectively, and form naringenin chalcone when 4-coumaroyl-CoA is used as starter molecule Products: -
following the activity through the development of the glandular trichomes on the female flowers phlorisovalerophenone synthase shows the highest activity at 21-29 days
suppression of chalcone synthase activity in both transient and stable chalcone synthase-silenced fruit results in a substantial decrease of acylphloroglucinol glucosides and anthocyanins and enhanced levels of volatiles derived from branched-chain amino acids
valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content
total enzymatic synthesis of acylphloroglucinol glucosides is achieved by co-incubation of recombinant dual functional chalcone/valerophenone synthase and UGT71K3 proteins with essential coenzyme A esters and UDP-glucose. Proteins UGT71K3a/b catalyze the glucosylation of diverse hydroxycoumarins, naphthols and flavonoids, enzymatically synthesized acylphloroglucinol aglycones and pelargonidin
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