Sakuranetin
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| Names | |
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| IUPAC name
(2S)-4′,5-Dihydroxy-7-methoxyflavan-4-one
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| Systematic IUPAC name
(2S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one | |
| Other names
Naringenin 7-methyl ether
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.019.073 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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Sakuranetin is a flavan-on, the 7-methoxy derivative of naringenin, found in Polymnia fruticosa[1] and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae.[2]
Glycosides
[edit]Sakuranin is the 5-O-glucoside of sakuranetin.[citation needed]
Metabolism
[edit]- 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
[edit]- ^ Sakuranetin on home.ncifcrf.gov
- ^ Sakuranetin, a flavonone phytoalexin from ultraviolet-irradiated rice leaves, Kodama O., Miyakawa J., Akatsuka T., Kiyosawa S, 1992
- ^ Rakwal, Randeep; Hasegawa, Morifumi; Kodama, Osamu (1996). "A Methyltransferase for Synthesis of the Flavanone Phytoalexin Sakuranetin in Rice Leaves". Biochemical and Biophysical Research Communications. 222 (3): 732–735. doi:10.1006/bbrc.1996.0812. PMID 8651913.
- ^ 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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