adlupulone and adhumulone biosynthesis

Li H, Ban Z, Qin H, Ma L, King AJ, Wang G. A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter acid pathway. Plant Physiol. 2015 Mar;167(3):650–9. PMID: 25564559; PMCID: PMC4348772.; Paniego NB, Zuurbier KWM, Fung S, van der Heijden R, Scheffer JJC, Verpoorte R. Phlorisovalerophenone synthase, a novel polyketide synthase from hop (Humulus lupulus L.) cones. European Journal of Biochemistry. 1999 Jun;262(2):612–6. doi: 10.1046/j.1432-1327.1999.00444.x.

Metabolites

CO2

Formula: CO2 (43.98983)

CAS ID: 124-38-9

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

Multifidol

Formula: C11H14O4 (210.0892044)

CAS ID: 125074-06-8

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Adhumulone

Formula: C21H30O5 (362.209313)

CAS ID: 28374-89-2

2-methylbutyrate

Formula: C5H9O2 (101.0602514)

CAS ID:

adenosine 5'-monophosphate(2-)

Formula: C10H12N5O7P (345.0474332)

CAS ID:

ATP(4-)

Formula: C10H12N5O13P3 (502.9644492)

CAS ID:



Enzyme

EC Number name full name note
6.2.1.-
2.3.1.156 phloroisovalerophenone synthase isovaleryl-CoA:malonyl-CoA acyltransferase
2.3.1.74 chalcone synthase malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing)
2.5.1.136 2-acylphloroglucinol 4-prenyltransferase prenyl-diphosphate:2-acylphloroglucinol 4-prenyltransferase
2.5.1.137 2-acyl-4-prenylphloroglucinol 6-prenyltransferase dimethylallyl-diphosphate:2-acyl-4-prenylphloroglucinol 6-dimethylallyltransferase
6.2.1.17 propionate-CoA ligase propanoate:CoA ligase (AMP-forming)


Proteins

Protein ID name full name