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- Name help_outline 3,5-dihydroxyanisole Identifier CHEBI:136806 (CAS: 2174-64-3) help_outline Charge 0 Formula C7H8O3 InChIKeyhelp_outline HDVRLUFGYQYLFJ-UHFFFAOYSA-N SMILEShelp_outline O(C1=CC(O)=CC(O)=C1)C 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline S-adenosyl-L-methionine Identifier CHEBI:59789 Charge 1 Formula C15H23N6O5S InChIKeyhelp_outline MEFKEPWMEQBLKI-AIRLBKTGSA-O SMILEShelp_outline C[S+](CC[C@H]([NH3+])C([O-])=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12 2D coordinates Mol file for the small molecule Search links Involved in 938 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 3,5-dimethoxyphenol Identifier CHEBI:88715 Charge 0 Formula C8H10O3 InChIKeyhelp_outline XQDNFAMOIPNVES-UHFFFAOYSA-N SMILEShelp_outline C1(=CC(=CC(=C1)OC)OC)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline S-adenosyl-L-homocysteine Identifier CHEBI:57856 Charge 0 Formula C14H20N6O5S InChIKeyhelp_outline ZJUKTBDSGOFHSH-WFMPWKQPSA-N SMILEShelp_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](CSCC[C@H]([NH3+])C([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 854 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:80543 | RHEA:80544 | RHEA:80545 | RHEA:80546 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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| MetaCyc help_outline |
Publications
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O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals.
Lavid N., Wang J., Shalit M., Guterman I., Bar E., Beuerle T., Menda N., Shafir S., Zamir D., Adam Z., Vainstein A., Weiss D., Pichersky E., Lewinsohn E.
Rose (Rosa hybrida) flowers produce and emit a diverse array of volatiles, characteristic to their unique scent. One of the most prominent compounds in the floral volatiles of many rose varieties is the methoxylated phenolic derivative 3,5-dimethoxytoluene (orcinol dimethyl ether). Cell-free extra ... >> More
Rose (Rosa hybrida) flowers produce and emit a diverse array of volatiles, characteristic to their unique scent. One of the most prominent compounds in the floral volatiles of many rose varieties is the methoxylated phenolic derivative 3,5-dimethoxytoluene (orcinol dimethyl ether). Cell-free extracts derived from developing rose petals displayed O-methyltransferase (OMT) activities toward several phenolic substrates, including 3,5-dihydroxytoluene (orcinol), 3-methoxy,5-hydroxytoluene (orcinol monomethyl ether), 1-methoxy, 2-hydroxy benezene (guaiacol), and eugenol. The activity was most prominent in rose cv Golden Gate, a variety that produces relatively high levels of orcinol dimethyl ether, as compared with rose cv Fragrant Cloud, an otherwise scented variety but which emits almost no orcinol dimethyl ether. Using a functional genomics approach, we have identified and characterized two closely related cDNAs from a rose petal library that each encode a protein capable of methylating the penultimate and immediate precursors (orcinol and orcinol monomethyl ether, respectively) to give the final orcinol dimethyl ether product. The enzymes, designated orcinol OMTs (OOMT1 and OOMT2), are closely related to other plant methyltransferases whose substrates range from isoflavones to phenylpropenes. The peak in the levels of OOMT1 and OOMT2 transcripts in the flowers coincides with peak OMT activity and with the emission of orcinol dimethyl ether. << Less
Plant Physiol 129:1899-1907(2002) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.
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Two O-methyltransferases isolated from flower petals of Rosa chinensis var. spontanea involved in scent biosynthesis.
Wu S., Watanabe N., Mita S., Ueda Y., Shibuya M., Ebizuka Y.
Rosa chinensis var. spontanea predominantly emits 1,3,5-trimethoxybenzene together with methyleugenol and isomethyleugenol as minor floral scent compounds. Two O-methyltransferases (OMTs), designated as RcOMT1 and RcOMT2, were isolated from rose flower petals using homology-based screening strateg ... >> More
Rosa chinensis var. spontanea predominantly emits 1,3,5-trimethoxybenzene together with methyleugenol and isomethyleugenol as minor floral scent compounds. Two O-methyltransferases (OMTs), designated as RcOMT1 and RcOMT2, were isolated from rose flower petals using homology-based screening strategies. RcOMT1 efficiently methylated eugenol and isoeugenol to yield volatile methyleugenol and isomethyleugenol, respectively. Furthermore, the mRNA transcripts of RcOMT1 were highly expressed in floral organs and the expression pattern coincided with intracellular content changes of methyleugenol and isomethyleugenol in rose flowers. In contrast, RcOMT2, which shows 94% similarity with caffeic acid O-methyltransferase (COMT) of Prunus amygdalus, was expressed in all tissues tested and had the highest activity with caffeic acid, a typical substrate for COMT. However, this COMT-like OMT also showed some degrees of activity with all three putative precursors of 1,3,5-trimethoxybenzene. << Less
J Biosci Bioeng 96:119-128(2003) [PubMed] [EuropePMC]
This publication is cited by 4 other entries.