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- Name help_outline myricetin 3-O-α-L-rhamnoside Identifier CHEBI:144432 Charge -1 Formula C21H19O12 InChIKeyhelp_outline DCYOADKBABEMIQ-OWMUPTOHSA-M SMILEShelp_outline C1=C(C=C(C2=C1OC(=C(C2=O)O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)C4=CC(=C(C(=C4)O)O)O)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 UDP-α-D-glucose Identifier CHEBI:58885 (Beilstein: 3827329) help_outline Charge -2 Formula C15H22N2O17P2 InChIKeyhelp_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILEShelp_outline OC[C@H]1O[C@H](OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 272 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline myricetin 3-O-[β-D-glucosyl-(1→2)-α-L-rhamnoside] Identifier CHEBI:144429 Charge -1 Formula C27H29O17 InChIKeyhelp_outline JRHHAUSYXYDKGJ-SEDTXNTKSA-M SMILEShelp_outline [C@@H]1([C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O[C@H]2[C@@H](O[C@H]([C@@H]([C@H]2O)O)C)OC=3C(C=4C(=CC(=CC4OC3C5=CC(=C(C(=C5)O)O)O)[O-])O)=O 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKeyhelp_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILEShelp_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 711 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 10,232 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:61148 | RHEA:61149 | RHEA:61150 | RHEA:61151 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Discovery of UDP-glycosyltransferases and BAHD-acyltransferases involved in the biosynthesis of the antidiabetic plant metabolite montbretin A.
Irmisch S., Jo S., Roach C.R., Jancsik S., Man Saint Yuen M., Madilao L.L., O'Neil-Johnson M., Williams R., Withers S.G., Bohlmann J.
Plant specialized metabolism serves as a rich resource of biologically active molecules for drug discovery. The acylated flavonol glycoside montbretin A (MbA) and its precursor myricetin 3-<i>O</i>-(6'-<i>O</i>-caffeoyl)-glucosyl rhamnoside (mini-MbA) are potent inhibitors of human pancreatic α-am ... >> More
Plant specialized metabolism serves as a rich resource of biologically active molecules for drug discovery. The acylated flavonol glycoside montbretin A (MbA) and its precursor myricetin 3-<i>O</i>-(6'-<i>O</i>-caffeoyl)-glucosyl rhamnoside (mini-MbA) are potent inhibitors of human pancreatic α-amylase and are being developed as drug candidates to treat type-2 diabetes. MbA occurs in corms of the ornamental plant montbretia (<i>Crocosmia x crocosmiiflora</i>), but a system for large-scale MbA production is currently unavailable. Biosynthesis of MbA from the flavonol myricetin and MbA accumulation occur during early stages of corm development. We established myricetin 3-<i>O</i>-rhamnoside (MR), myricetin 3-<i>O</i>-glucosyl rhamnoside (MRG), and mini-MbA as the first three intermediates of MbA biosynthesis. Contrasting the transcriptomes of young and old corms revealed differentially expressed UDP-sugar-dependent glycosyltransferases (UGTs) and BAHD-acyltransferases (BAHD-ATs). UGT77B2 and UGT709G2 catalyze the consecutive glycosylation of myricetin to produce MR and of MR to give MRG, respectively. In addition, two BAHD-ATs, CcAT1 and CcAT2, catalyze the acylation of MRG to complete the formation of mini-MbA. Transcript profiles of UGT77B2, UGT709G2, CcAT1, and CcAT2 during corm development matched the metabolite profile of MbA accumulation. Expression of these enzymes in wild tobacco (<i>Nicotiana benthamiana</i>) resulted in the formation of a surrogate mini-MbA, validating the potential for metabolic engineering of mini-MbA in a heterologous plant system. << Less
Plant Cell 30:1864-1886(2018) [PubMed] [EuropePMC]
This publication is cited by 11 other entries.