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- Name help_outline 3',4',5'-O-trimethylmyricetin Identifier CHEBI:194070 Charge -2 Formula C18H14O8 InChIKeyhelp_outline LHNLHJJGLDWGFS-UHFFFAOYSA-L SMILEShelp_outline C1=C(C=C(C2=C1OC(=C(C2=O)[O-])C3=CC(=C(C(=C3)OC)OC)OC)O)[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-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 3,3',4',5'-O-tetramethylmyricetin Identifier CHEBI:194076 Charge -1 Formula C19H17O8 InChIKeyhelp_outline YSXLGTWJLNLXKQ-UHFFFAOYSA-M SMILEShelp_outline C1=C(C=C(C2=C1OC(=C(C2=O)OC)C3=CC(=C(C(=C3)OC)OC)OC)O)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 1 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
Cross-references
| RHEA:74771 | RHEA:74772 | RHEA:74773 | RHEA:74774 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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| Gene Ontology help_outline | ||||
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Publications
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Characterization of a flavonol 3-O-methyltransferase in the trichomes of the wild tomato species Solanum habrochaites.
Schmidt A., Li C., Jones A.D., Pichersky E.
The glandular trichomes of the wild tomato species Solanum habrochaites accumulate the polymethylated flavonol aglycones, 3,7,3'-O-methyl myricetin, 3,7,3',5'-O-methyl myricetin, and 3,7,3',4',5'-O-methyl myricetin. Partially methylated flavonol aglycones and partially methylated flavonol glycones ... >> More
The glandular trichomes of the wild tomato species Solanum habrochaites accumulate the polymethylated flavonol aglycones, 3,7,3'-O-methyl myricetin, 3,7,3',5'-O-methyl myricetin, and 3,7,3',4',5'-O-methyl myricetin. Partially methylated flavonol aglycones and partially methylated flavonol glycones containing a methyl group at the 3 position have been previously reported from a variety of plants. The 3-O-methyltransferase (3-OMT) activity has been previously partially purified from plants, but a gene transcript encoding an enzyme capable of methylating flavonols at the 3 position has not yet been identified, nor have been such proteins purified and characterized. We previously identified two gene transcripts expressed in the glandular trichomes of S. habrochaites and showed that they encode enzymes capable of methylating myricetin at the 3' and 5' and the 7 and 4' positions, respectively. Here we report the identification of gene transcripts expressed in S. lycopersicum (cultivated tomato) and in S. habrochaites glandular trichomes that encode enzymes capable of methylating myricetin, and its partially methylated derivatives exclusively at the 3 position. The S. habrochaites gene transcript is preferentially expressed in the glandular trichomes and it encodes a protein with high similarity to the S. habrochaites, 3'/5' O-methyltransferase which is also present in glandular trichomes. Phylogenic analysis suggests that the 3-OMT activity has probably evolved from an ancestral 3'/5' methyltransferase activity. The discovery and characterization of 3-OMT provides a more complete picture of the series of reactions leading to highly methylated myricetin compounds in S. habrochaites glandular trichomes. << Less
Planta 236:839-849(2012) [PubMed] [EuropePMC]
This publication is cited by 8 other entries.