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- Name help_outline (E)-caffeoyl-CoA Identifier CHEBI:87136 Charge -4 Formula C30H38N7O19P3S InChIKeyhelp_outline QHRGJMIMHCLHRG-ZSELIEHESA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)\C=C\c1ccc(O)c(O)c1 2D coordinates Mol file for the small molecule Search links Involved in 15 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 CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,468 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline myricetin 3-O-[(6-O-(E)-caffeoyl-β-D-glucosyl)-(1→2)-α-L-rhamnoside] Identifier CHEBI:144428 Charge -1 Formula C36H35O20 InChIKeyhelp_outline YHIHWLPOKDIYGF-ZLGVOOGTSA-M SMILEShelp_outline [C@@H]1([C@@H]([C@H]([C@@H]([C@H](O1)COC(/C=C/C2=CC=C(C(=C2)O)O)=O)O)O)O)O[C@H]3[C@@H](O[C@H]([C@@H]([C@H]3O)O)C)OC=4C(C=5C(=CC(=CC5OC4C6=CC(=C(C(=C6)O)O)O)[O-])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
Cross-references
| RHEA:61152 | RHEA:61153 | RHEA:61154 | RHEA:61155 | |
|---|---|---|---|---|
| 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.