Sakuranetin
 | |
| Names | |
|---|---|
| IUPAC name
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one | |
| Other names
4',5-Dihydroxy-7-methoxyflavanone Naringenin 7-methyl ether | |
| Identifiers | |
2957-21-3  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:28927  |
| ChEMBL | ChEMBL448297 |
| ChemSpider | 66249 |
| ECHA InfoCard | 100.019.073 |
| 412 | |
| PubChem | 73571 |
| |
| |
| Properties | |
| C16H14O5 | |
| Molar mass | 286.27 g/mol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Sakuranetin is a flavanone, a type of flavonoid. It can be found in Polymnia fruticosa[1] and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae.[2]
Glycosides
Sakuranin is the -O-glucoside of sakuranetin.
Metabolism
- biosynthesis
Naringenin 7-O-methyltransferase uses naringenin to yield sakuranetin, with S-adenosyl-methionine as the methyl donor.[3]
- biodegradation
In compounds like 7-methoxylated flavanones like sakuranetin, demethylation followed by sulfation occur in model organism Cunninghamella elegans.[4]
References
- ↑ Sakuranetin on home.ncifcrf.gov
- ↑ Sakuranetin, a flavonone phytoalexin from ultraviolet-irradiated rice leaves, Kodama O., Miyakawa J., Akatsuka T., Kiyosawa S, 1992
- ↑ A Methyltransferase for Synthesis of the Flavanone Phytoalexin Sakuranetin in Rice Leaves, Randeep Rakwala, Morifumi Hasegawab and Osamu Kodama, 1996
- ↑ Ibrahim, A. R.; Galal, A. M.; Ahmed, M. S.; Mossa, G. S. (2003). "O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans". Chemical & pharmaceutical bulletin. 51 (2): 203–206. doi:10.1248/cpb.51.203. PMID 12576658. INIST:14569933.
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