EC |
2.1.1.65 |
Accepted name: |
licodione 2′-O-methyltransferase |
Reaction: |
S-adenosyl-L-methionine + licodione = S-adenosyl-L-homocysteine + 2′-O-methyllicodione |
|
For diagram of licodione biosynthesis, click here |
Systematic name: |
S-adenosyl-L-methionine:licodione 2′-O-methyltransferase |
Comments: |
As well as licodione [1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione], the 2′′-hydroxy-derivative and isoliquiritigenin can act as acceptors, but more slowly. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 77000-07-8 |
References: |
1. |
Ayabe, S.-I., Yoshikawa, T., Kobayashi, M. and Furuya, T. Biosynthesis of retrochalcone, echinatin: involvement of O-methyltransferase to licodione. Phytochemistry 19 (1980) 2331–2336. |
|
[EC 2.1.1.65 created 1983] |
|
|
|
|
EC |
2.1.1.154 |
Accepted name: |
isoliquiritigenin 2′-O-methyltransferase |
Reaction: |
S-adenosyl-L-methionine + isoliquiritigenin = S-adenosyl-L-homocysteine + 2′-O-methylisoliquiritigenin |
|
For diagram of daidzein biosynthesis, click here |
Glossary: |
isoliquiritigenin = 4,2′,4′-trihydroxychalcone |
Other name(s): |
chalcone OMT; CHMT |
Systematic name: |
S-adenosyl-L-methionine:isoliquiritigenin 2′-O-methyltransferase |
Comments: |
Not identical to EC 2.1.1.65, licodione 2′-O-methyltransferase [2]. While EC 2.1.1.154, isoliquiritigenin 2′-O-methyltransferase can use licodione as a substrate, EC 2.1.1.65 cannot use isoliquiritigenin as a substrate. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 139317-14-9 |
References: |
1. |
Maxwell, C.A., Edwards, R. and Dixon, R.A. Identification, purification, and characterization of S-adenosyl-L-methionine: isoliquiritigenin 2′-O-methyltransferase from alfalfa (Medicago sativa L.). Arch. Biochem. Biophys. 293 (1992) 158–166. [DOI] [PMID: 1731632] |
2. |
Ichimura, M., Furuno, T., Takahashi, T., Dixon, R.A. and Ayabe, S. Enzymic O-methylation of isoliquiritigenin and licodione in alfalfa and licorice cultures. Phytochemistry 44 (1997) 991–995. [DOI] [PMID: 9055445] |
|
[EC 2.1.1.154 created 2004] |
|
|
|
|
EC |
2.1.1.339 |
Accepted name: |
xanthohumol 4-O-methyltransferase |
Reaction: |
S-adenosyl-L-methionine + xanthohumol = S-adenosyl-L-homocysteine + 4-O-methylxanthohumol |
|
For diagram of xanthohumol biosynthesis, click here |
Glossary: |
xanthohumol = 2′,4,4′-trihydroxy-6′-methoxy-3-prenylchalcone = (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
4-O-methylxanthohumol =2′,4′-dihydroxy-4,6′-dimethoxy-3-prenylchalcone = (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one |
Other name(s): |
OMT2 (ambiguous); S-adenosyl-L-methionine:xanthohumol 4′-O-methyltransferase (incorrect); xanthohumol 4′-O-methyltransferase (incorrect) |
Systematic name: |
S-adenosyl-L-methionine:xanthohumol 4-O-methyltransferase |
Comments: |
The enzyme from hops (Humulus lupulus) has a broad substrate specificity. The best substrates in vitro are resveratrol, desmethylxanthohumol, naringenin chalcone and isoliquiritigenin. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Nagel, J., Culley, L.K., Lu, Y., Liu, E., Matthews, P.D., Stevens, J.F. and Page, J.E. EST analysis of hop glandular trichomes identifies an O-methyltransferase that catalyzes the biosynthesis of xanthohumol. Plant Cell 20 (2008) 186–200. [DOI] [PMID: 18223037] |
|
[EC 2.1.1.339 created 2017, modified 2018] |
|
|
|
|
EC |
2.3.1.170 |
Accepted name: |
6′-deoxychalcone synthase |
Reaction: |
3 malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = 4 CoA + isoliquiritigenin + 3 CO2 + NADP+ + H2O |
|
For diagram of daidzein biosynthesis, click here |
Glossary: |
isoliquiritigenin = 4,2′,4′-trihydroxychalcone
liquiritigenin = 7,4′-dihydroxyflavanone |
Systematic name: |
malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing, reducing) |
Comments: |
Isoliquiritigenin is the precursor of liquiritigenin, a 5-deoxyflavanone. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 114308-23-5 |
References: |
1. |
Ayabe, S., Udagawa, A. and Furuya, T. NAD(P)H-dependent 6′-deoxychalcone synthase activity in Glycyrrhiza echinata cells induced by yeast extract. Arch. Biochem. Biophys. 261 (1988) 458–462. [DOI] [PMID: 3355160] |
|
[EC 2.3.1.170 created 2004] |
|
|
|
|