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2.1.1.338

Accepted name:

desmethylxanthohumol 6′-O-methyltransferase

Reaction:

S-adenosyl-L-methionine + desmethylxanthohumol = S-adenosyl-L-homocysteine + xanthohumol

For diagram of xanthohumol biosynthesis, click here

Glossary:

desmethylxanthohumol = 2′,4,4′,6′-tetrahydroxy-3-prenylchalcone = (2E)-3-(4-hydroxyphenyl)-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one
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

Other name(s):

OMT1 (ambiguous)

Systematic name:

S-adenosyl-L-methionine:desmethylxanthohumol 6′-O-methyltransferase

Comments:

Found in hops (Humulus lupulus). The enzyme can also methylate xanthogalenol.

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 2.1.1.338 created 2017]

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]

2.5.1.136

Accepted name:

2-acylphloroglucinol 4-prenyltransferase

Reaction:

prenyl diphosphate + a 2-acylphloroglucinol = diphosphate + a 2-acyl-4-prenylphloroglucinol

Glossary:

naringenin chalcone = 2′,4,4′,6′-tetrahydroxychalcone = 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
phlorisovalerophenone = 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one

Other name(s):

PT-1 (gene name); PT1L (gene name); aromatic prenyltransferase (ambiguous); dimethylallyl-diphosphate:2-acylphloroglucinol 4-dimethylallyltransferase

Systematic name:

prenyl-diphosphate:2-acylphloroglucinol 4-prenyltransferase

Comments:

The enzyme, characterized from hop (Humulus lupulus), acts on phlorisovalerophenone, phlormethylbutanophenone, and phlorisobutanophenone during the synthesis of bitter acids. It also acts with much lower activity on naringenin chalcone. Forms a complex with EC 2.5.1.137, 2-acyl-4-prenylphloroglucinol 6-prenyltransferase, which catalyses additional prenylation reactions. Requires Mg²⁺.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Tsurumaru, Y., Sasaki, K., Miyawaki, T., Uto, Y., Momma, T., Umemoto, N., Momose, M. and Yazaki, K. HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops. Biochem. Biophys. Res. Commun. 417 (2012) 393–398. [DOI] [PMID: 22166201]
2.	Li, H., Ban, Z., Qin, H., Ma, L., King, A.J. and Wang, G. A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter acid pathway. Plant Physiol. 167 (2015) 650–659. [DOI] [PMID: 25564559]

[EC 2.5.1.136 created 2017]