Protein Variants | Comment | Organism |
---|---|---|
additional information | trans-Resveratrol has powerful antioxidant, anti-inflammatory, anticarcinogenic, and antiaging properties, but its use as a therapeutic agent is limited by its rapid metabolism into its conjugated forms by UDP-glucuronosyltransferases. The limited bioavailability of tRes can be improved by modifying its structure to create analogues which can be glucuronidated at a lower rate than tRes itself | Homo sapiens |
KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
additional information | - |
additional information | steady-state kinetics, Michaelis-Menten kinetics | Homo sapiens | |
0.0062 | - |
(E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime | pH 7.4, 37°C | Homo sapiens | |
0.063 | 0.24 | (E)-3-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid | pH 7.4, 37°C, isozyme-dependent | Homo sapiens |
Localization | Comment | Organism | GeneOntology No. | Textmining |
---|---|---|---|---|
microsome | - |
Homo sapiens | - |
- |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
additional information | Homo sapiens | no activity with (E)-4-(3,5-dimethoxystyryl)-2,6-dinitrophenol, i.e. DNR-1, glucuronide formation is verified by beta-glucuronidase hydrolysis and LC-MS/MS analysis | ? | - |
? | |
additional information | Homo sapiens | trans-Resveratrol has powerful antioxidant, anti-inflammatory, anticarcinogenic, and antiaging properties, but its use as a therapeutic agent is limited by its rapid metabolism into its conjugated forms by UDP-glucuronosyltransferases. The limited bioavailability of tRes can be improved by modifying its structure to create analogues which can be glucuronidated at a lower rate than tRes itself. Three synthetic stilbenoids ((E)-3-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid, (E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime, and (E)-4-(3,5-dimethoxystyryl)-2,6-dinitrophenol) are designed based on the structure of tRes and synthesized. UDP-glucuronosyltransferases recognize and glucuronidate trans-resveratrol at each of the 3 hydroxyl groups attached to its aromatic rings | ? | - |
? | |
UDP-glucuronate + (E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime | Homo sapiens | i.e. NI-ST-05, low activity, NI-ST-05 forms a distinct N-O-glucuronide. NI-ST-05 is primarily metabolized by an extrahepatic enzyme, UGT1A10 | UDP + 1-O-[(E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime]-beta-D-glucuronate | - |
? | |
UDP-glucuronate + (E)-3-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid | Homo sapiens | i.e. NI-12a, low activity, NI-12a is glucuronidated at both the -COOH and -OH functions. NI-12a is primarily metabolized by the hepatic and renal enzyme UGT1A9 | UDP + ? | - |
? | |
UDP-glucuronate + trans-resveratrol | Homo sapiens | - |
UDP + trans-resveratrol beta-D-glucuronoside | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Homo sapiens | - |
- |
- |
Source Tissue | Comment | Organism | Textmining |
---|---|---|---|
intestine | - |
Homo sapiens | - |
kidney | - |
Homo sapiens | - |
liver | - |
Homo sapiens | - |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
additional information | no activity with (E)-4-(3,5-dimethoxystyryl)-2,6-dinitrophenol, i.e. DNR-1, glucuronide formation is verified by beta-glucuronidase hydrolysis and LC-MS/MS analysis | Homo sapiens | ? | - |
? | |
additional information | trans-Resveratrol has powerful antioxidant, anti-inflammatory, anticarcinogenic, and antiaging properties, but its use as a therapeutic agent is limited by its rapid metabolism into its conjugated forms by UDP-glucuronosyltransferases. The limited bioavailability of tRes can be improved by modifying its structure to create analogues which can be glucuronidated at a lower rate than tRes itself. Three synthetic stilbenoids ((E)-3-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid, (E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime, and (E)-4-(3,5-dimethoxystyryl)-2,6-dinitrophenol) are designed based on the structure of tRes and synthesized. UDP-glucuronosyltransferases recognize and glucuronidate trans-resveratrol at each of the 3 hydroxyl groups attached to its aromatic rings | Homo sapiens | ? | - |
? | |
UDP-glucuronate + (E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime | i.e. NI-ST-05, low activity, NI-ST-05 forms a distinct N-O-glucuronide. NI-ST-05 is primarily metabolized by an extrahepatic enzyme, UGT1A10 | Homo sapiens | UDP + 1-O-[(E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime]-beta-D-glucuronate | - |
? | |
UDP-glucuronate + (E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime | i.e. NI-ST-05, low activity, NI-ST-05 forms a distinct N-O-glucuronide. NI-ST-05 is primarily metabolized by an extrahepatic enzyme, UGT1A10, in cooperative binding | Homo sapiens | UDP + 1-O-[(E)-2,4-dimethoxy-6-(4-methoxystyryl)benzaldehyde oxime]-beta-D-glucuronate | - |
? | |
UDP-glucuronate + (E)-3-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid | i.e. NI-12a, low activity, NI-12a is glucuronidated at both the -COOH and -OH functions. NI-12a is primarily metabolized by the hepatic and renal enzyme UGT1A9 | Homo sapiens | UDP + ? | - |
? | |
UDP-glucuronate + trans-resveratrol | - |
Homo sapiens | UDP + trans-resveratrol beta-D-glucuronoside | - |
? |
Synonyms | Comment | Organism |
---|---|---|
UDP-glucuronosyltransferase | - |
Homo sapiens |
UGT | - |
Homo sapiens |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
37 | - |
assay at | Homo sapiens |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
7.4 | - |
assay at | Homo sapiens |