(-)-medicarpin biosynthesis

Guo L, Paiva NL. Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis. Archives of Biochemistry and Biophysics. 1995 Jul;320(2):353–60. doi: 10.1016/0003-9861(95)90019-5.; Guo L, Dixon RA, Paiva NL. The 'pterocarpan synthase' of alfalfa: association and co-induction of vestitone reductase and 7,2'-dihydroxy-4'-methoxy-isoflavanol (DMI) dehydratase, the two final enzymes in medicarpin biosynthesis. FEBS Lett. 1994 Dec 19;356(2-3):221–5. doi: 10.1016/0014-5793(94)01267-9. PMID: 7805842.; Oommen A, Dixon RA, Paiva NL. The elicitor-inducible alfalfa isoflavone reductase promoter confers different patterns of developmental expression in homologous and heterologous transgenic plants. Plant Cell. 1994 Dec;6(12):1789–803. PMID: 7866024; PMCID: PMC160562.; Guo L, Dixon RA, Paiva NL. Conversion of vestitone to medicarpin in alfalfa (Medicago sativa L.) is catalyzed by two independent enzymes. Identification, purification, and characterization of vestitone reductase and 7,2‘-dihydroxy-4‘-methoxyisoflavanol dehydratase. Journal of Biological Chemistry. 1994 Sep;269(35):22372–8. doi: 10.1016/s0021-9258(17)31799-4.

Metabolites

(-)-Vestitone

Formula: C16H14O5 (286.0841194)

CAS ID: 158112-50-6

2'-Hydroxyformononetin

Formula: C16H12O5 (284.0684702)

CAS ID: 1890-99-9

Formononetin

Formula: C16H12O4 (268.0735552)

CAS ID: 485-72-3

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Medicarpin

Formula: C16H14O4 (270.0892044)

CAS ID: 32383-76-9

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
1.1.1.348 (3R)-2'-hydroxyisoflavanone reductase (3R)-2'-hydroxyisoflavanone:NADP+ 4-oxidoreductase
1.3.1.45 2'-hydroxyisoflavone reductase vestitone:NADP+ oxidoreductase


Proteins

Protein ID name full name