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EC Tree
IUBMB Comments 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
Synonyms
valerophenone synthase, phlorisovalerophenone synthase, chs2-1,
more
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3-methyl-1-(trihydroxyphenyl)butan-1-one synthase
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bifunctional chalcone/(iso)valerophenone synthase
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CHS2-1
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bifunctional chalcone/(iso)valerophenone synthase
phlorisovalerophenone synthase
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valerophenone synthase
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valerophenone synthase
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6
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VPS
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VPS
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400 -
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isobutyryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisobutyrophenone
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isovaleryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisovalerophenone
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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isovaleryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisovalerophenone
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Acyl group transfer
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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.
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
isovaleryl-CoA + 3 malonyl-CoA
phloroisovalerophenone + 3 CO2 + 4 CoA
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isovaleryl-CoA is the preferred starter substrate of isoform CHS2-1
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isovaleryl-CoA + malonyl-CoA
phloroisovalerophenone + CO2 + CoA
additional information
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
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phloroglucinol derivative, intermediates in the biosynthesis of the hop bitter alpha- and beta-acids
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
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enzyme is involved in formation of the hyperforin skeleton of Hypericum calycinum
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isovaleryl-CoA + malonyl-CoA
phloroisovalerophenone + CO2 + CoA
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isovaleryl-CoA + malonyl-CoA
phloroisovalerophenone + CO2 + CoA
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isovaleryl-CoA + malonyl-CoA
phloroisovalerophenone + CO2 + CoA
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phloroglucinol derivative, intermediates in the biosynthesis of the hop bitter alpha- and beta-acids
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additional information
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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
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additional information
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the enzyme is responsible for the biosynthesis of the precursors of alpha-acid and beta-acid
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
isovaleryl-CoA + malonyl-CoA
phloroisovalerophenone + CO2 + CoA
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phloroglucinol derivative, intermediates in the biosynthesis of the hop bitter alpha- and beta-acids
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additional information
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the enzyme is responsible for the biosynthesis of the precursors of alpha-acid and beta-acid
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
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phloroglucinol derivative, intermediates in the biosynthesis of the hop bitter alpha- and beta-acids
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isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
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enzyme is involved in formation of the hyperforin skeleton of Hypericum calycinum
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additional information
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following the activity through the development of the glandular trichomes on the female flowers phlorisovalerophenone synthase shows the highest activity at 21-29 days
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7
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assay at
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brenda
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brenda
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brenda
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brenda
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SwissProt
brenda
hop
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brenda
variety AB047593
SwissProt
brenda
variety Cascade
B3GEB6
UniProt
brenda
variety Cluster
B3GEA8
UniProt
brenda
variety Eastern Gold
B3GEB0
UniProt
brenda
variety Ember
B3GEB3
UniProt
brenda
variety Golding
B3GEA9
UniProt
brenda
variety Hallertau mf
SwissProt
brenda
variety J78
B3GEB4
UniProt
brenda
variety Nugget
B3GEB1
UniProt
brenda
variety Opal
B3GEB2
UniProt
brenda
variety Saaz x
B3GEB5
UniProt
brenda
variety Symphony
B3GEB6
UniProt
brenda
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high activity is found in male flowers
brenda
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brenda
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glands
brenda
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400 at early, mid, and late stages of development
brenda
specifically expressed in
brenda
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brenda
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brenda
additional information
no expression in leaf and stem
brenda
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glandular hairs
brenda
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400 at early, mid, and late stages of development
brenda
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physiological function
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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
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CHSH1_HUMLU
389
0
42534
Swiss-Prot
other Location (Reliability: 3 )
VPS_HUMLU
394
0
43080
Swiss-Prot
other Location (Reliability: 4 )
VPS_PSINU
406
0
44562
Swiss-Prot
Chloroplast (Reliability: 4 )
B5IIM9_9CYAN
356
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37270
TrEMBL
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A0A182ALK9_9CYAN
375
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39356
TrEMBL
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110000
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native PAGE of purified VPS
45000
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homodimer, 2 * 45000, SDS-PAGE
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dimer
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homodimer, 2 * 45000, SDS-PAGE
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separation of benzophenone synthase, isobutyrophenone synthase, and chalcone synthase activities
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characterization of the VPS cDNA clone
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expression in Escherichia coli
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brewing
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400 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
nutrition
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cones of the hop plant used in the beer-brewing process
synthesis
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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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Zuurbier, K.W.M.; Leser, J.; Berger, T.; Hofte, A.J.P.; Schroder, G.; Verpoorte, R.; Schroder, J.
4-Hydroxy-2-pyrone formation by chalcone and stilbene synthase with nonphysiological substrates
Phytochemistry
49
1945-1951
1998
Humulus lupulus
brenda
Paniego, N.B.; Zuurbier, K.W.M.; Fung, S.Y.; Van der Heijden, R.; Scheffer, J.J.C.; Verpoorte, R.
Phlorisovalerophenone synthase, a novel polyketide synthase from hop (Humulus lupulus L.) cones
Eur. J. Biochem.
262
612-616
1999
Humulus lupulus
brenda
Okada, Y.; Ito, K.
Cloning and analysis of valerophenone synthase gene expressed specifically in lupulin gland of hop (Humulus lupulus L.)
Biosci. Biotechnol. Biochem.
65
150-155
2001
Humulus lupulus (O80400)
brenda
Klingauf, P.; Beuerle, T.; Mellenthin, A.; El-Moghazy, S.A.; Boubakir, Z.; Beerhues, L.
Biosynthesis of the hyperforin skeleton in Hypericum calycinum cell cultures
Phytochemistry
66
139-145
2005
Hypericum calycinum
brenda
Castro, C.B.; Whittock, L.D.; Whittock, S.P.; Leggett, G.; Koutoulis, A.
DNA sequence and expression variation of hop (Humulus lupulus) valerophenone synthase (VPS), a key gene in bitter acid biosynthesis
Ann. Bot.
102
265-273
2008
Humulus lupulus (B3GEA8), Humulus lupulus (B3GEA9), Humulus lupulus (B3GEB0), Humulus lupulus (B3GEB1), Humulus lupulus (B3GEB2), Humulus lupulus (B3GEB3), Humulus lupulus (B3GEB4), Humulus lupulus (B3GEB5), Humulus lupulus (B3GEB6), Humulus lupulus (O80400)
brenda
Flores-Sanchez, I.J.; Verpoorte, R.
PKS activities and biosynthesis of cannabinoids and flavonoids in Cannabis sativa L. plants
Plant Cell Physiol.
49
1767-1782
2008
Cannabis sativa
brenda
Song, C.; Zhao, S.; Hong, X.; Liu, J.; Schulenburg, K.; Schwab, W.
A UDP-glucosyltransferase functions in both acylphloroglucinol glucoside and anthocyanin biosynthesis in strawberry (Fragaria x ananassa)
Plant J.
85
730-742
2016
Fragaria x ananassa
brenda
Song, C.; Ring, L.; Hoffmann, T.; Huang, F.C.; Slovin, J.; Schwab, W.
Acylphloroglucinol biosynthesis in strawberry fruit
Plant Physiol.
169
1656-1670
2015
Fragaria vesca
brenda
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