KEGG   ENZYME: 2.1.1.69
Entry
EC 2.1.1.69                 Enzyme                                 
Name
5-hydroxyfuranocoumarin 5-O-methyltransferase;
furanocoumarin 5-methyltransferase;
furanocoumarin 5-O-methyltransferase;
bergaptol 5-O-methyltransferase;
bergaptol O-methyltransferase;
bergaptol methyltransferase;
S-adenosyl-L-methionine:bergaptol O-methyltransferase;
BMT;
S-adenosyl-L-methionine:5-hydroxyfuranocoumarin 5-O-methyltransferase
Class
Transferases;
Transferring one-carbon groups;
Methyltransferases
Sysname
S-adenosyl-L-methionine:5-hydroxyfurocoumarin 5-O-methyltransferase
Reaction(IUBMB)
(1) S-adenosyl-L-methionine + a 5-hydroxyfurocoumarin = S-adenosyl-L-homocysteine + a 5-methoxyfurocoumarin (general reaction);
(2) S-adenosyl-L-methionine + bergaptol = S-adenosyl-L-homocysteine + bergapten [RN:R02882]
Reaction(KEGG)
R02882;
(other) R08538
Substrate
S-adenosyl-L-methionine [CPD:C00019];
5-hydroxyfurocoumarin;
bergaptol [CPD:C00758]
Product
S-adenosyl-L-homocysteine [CPD:C00021];
5-methoxyfurocoumarin;
bergapten [CPD:C01557]
Comment
Converts bergaptol into bergapten, which has therapeutic potential in the treatment of psoriasis as it has photosensitizing and antiproliferative activities [4]. The enzyme methylates the 5-hydroxy group of some hydroxy- and methylcoumarins, such as 5-hydroxyxanthotoxin [3], but has little activity on non-coumarin phenols [1]. Caffeate, 5-hydroxyferulate and daphnetin are not substrates [4]. Cu2+, Zn2+ and Co2+ cause enzyme inhibition [4]. (see also EC 2.1.1.70, 8-hydroxyfuranocoumarin 8-O-methyltransferase)
History
EC 2.1.1.69 created 1984 (EC 2.1.1.92 created 1989, incorporated 2006), modified 2006
Pathway
ec00999  Biosynthesis of various plant secondary metabolites
ec01110  Biosynthesis of secondary metabolites
Orthology
K21550  5-hydroxyfuranocoumarin 5-O-methyltransferase
Reference
1  [PMID:28084]
  Authors
Thompson HJ, Sharma SK, Brown SA.
  Title
O-methyltransferases of furanocoumarin biosynthesis.
  Journal
Arch Biochem Biophys 188:272-81 (1978)
DOI:10.1016/S0003-9861(78)80009-5
Reference
2  [PMID:156999]
  Authors
Sharma SK, Garrett JM, Brown SA.
  Title
Separation of the S-adenosylmethionine: 5- and 8-hydroxyfuranocoumarin O-methyltransferases of Ruta graveolens L. by general ligand affinity chromatography.
  Journal
Z Naturforsch [C] 34C:387-91 (1979)
DOI:10.1515/znc-1979-5-611
Reference
3
  Authors
Hauffe, K.D., Hahlbrock, K. and Scheel, D.
  Title
Elicitor-stimulated furanocoumarin biosynthesis in cultured parsley cells - S-adenosyl-L-methionine-bergaptol and S-adenosyl-L-methionine-xanthotoxol O-methyltransferases.
  Journal
Z Naturforsch C: Biosci 41:228-239 (1986)
Reference
4  [PMID:15009205]
  Authors
Hehmann M, Lukacin R, Ekiert H, Matern U
  Title
Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase.
  Journal
Eur J Biochem 271:932-40 (2004)
DOI:10.1111/j.1432-1033.2004.03995.x
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 2.1.1.69
IUBMB Enzyme Nomenclature: 2.1.1.69
ExPASy - ENZYME nomenclature database: 2.1.1.69
BRENDA, the Enzyme Database: 2.1.1.69
CAS: 67339-12-2 101637-31-4

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