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{{chembox |
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{{chembox |
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| Name = Sakuranetin |
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| ImageFile = Sakuranetin.svg |
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| verifiedrevid = 401003343 |
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| ImageSize = 250px |
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| ImageName = Sakuranetin |
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| Name = Sakuranetin |
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| ImageFile = Sakuranetin.svg |
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| IUPACName = (2''S'')-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one |
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| ImageSize = 250px |
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| OtherNames = 4',5-Dihydroxy-7-methoxyflavanone<br>Naringenin 7-methyl ether |
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| ImageName = Sakuranetin |
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| Section1 = {{Chembox Identifiers |
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| IUPACName = (2''S'')-4′,5-Dihydroxy-7-methoxyflavan-4-one |
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| CASNo = 2957-21-3 |
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| SystematicName = (2''S'')-5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4''H''-1-benzopyran-4-one |
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| EINECS = |
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| OtherNames = Naringenin 7-methyl ether |
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| SMILES = COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O |
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|Section1={{Chembox Identifiers |
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| PubChem = 73571 |
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| IUPHAR_ligand = 412 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 2957-21-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 3O38P61299 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 28927 |
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| EINECS = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 448297 |
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| SMILES = COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O |
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| PubChem = 73571 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 66249 |
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| InChI = 1/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1 |
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| InChIKey = DJOJDHGQRNZXQQ-AWEZNQCLBK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DJOJDHGQRNZXQQ-AWEZNQCLSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>16</sub>H<sub>14</sub>O<sub>5</sub> |
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| Formula = C<sub>16</sub>H<sub>14</sub>O<sub>5</sub> |
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| MolarMass = 286.27 g/mol |
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| MolarMass = 286.27 g/mol |
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| MeltingPt = <!-- °C --> |
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| ExactMass = 286.084124 |
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| Solvent = |
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| MeltingPt = <!-- °C --> |
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| Solvent = |
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| SolubleOther = |
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| SolubleOther = |
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'''Sakuranetin''' is a ], a type of flavonoid. It can be found in '']''<ref></ref> and ], where it acts as a ] against spore germination of '']''<ref>. |
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'''Sakuranetin''' is a ], the 7-methoxy derivative of naringenin, found in Polymnia fruticosa<ref></ref> and rice, where it acts as a ] against spore germination of '']''.<ref>{{Cite web |url=http://cat.inist.fr/?aModele=afficheN&cpsidt=4682303 |title=Sakuranetin, a flavonone phytoalexin from ultraviolet-irradiated rice leaves, Kodama O., Miyakawa J., Akatsuka T., Kiyosawa S, 1992 |access-date=2009-09-11 |archive-date=2012-06-16 |archive-url=https://web.archive.org/web/20120616100332/http://cat.inist.fr/?aModele=afficheN&cpsidt=4682303 |url-status=dead }}</ref> |
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__TOC__ |
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== Glycosides == |
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] is the 5-O-] of sakuranetin.{{cn|date=March 2023}} |
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==Glycosides== |
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== Metabolism == |
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; biosynthesis |
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] is the -O-] of sakuranetin. |
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] uses ] to yield sakuranetin, with ] as the methyl donor.<ref>{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S0006291X96908128 | doi=10.1006/bbrc.1996.0812 | title=A Methyltransferase for Synthesis of the Flavanone Phytoalexin Sakuranetin in Rice Leaves | date=1996 | last1=Rakwal | first1=Randeep | last2=Hasegawa | first2=Morifumi | last3=Kodama | first3=Osamu | journal=Biochemical and Biophysical Research Communications | volume=222 | issue=3 | pages=732–735 | pmid=8651913 }}</ref> |
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; biodegradation |
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==Metabolism== |
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In compounds like 7-methoxylated flavanones like sakuranetin, ] followed by ] occur in model organism '']''.<ref>{{Cite journal |
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] uses ] to yield sakuranetin, with ] as the methyl donor<ref></ref>. |
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| doi = 10.1248/cpb.51.203 |
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| last1 = Ibrahim | first1 = A. R. |
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| last2 = Galal | first2 = A. M. |
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| last3 = Ahmed | first3 = M. S. |
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| last4 = Mossa | first4 = G. S. |
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| title = O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans |
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| journal = Chemical & Pharmaceutical Bulletin |
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| volume = 51 |
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| issue = 2 |
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| pages = 203–206 |
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| year = 2003 |
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| pmid = 12576658 |
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| id= {{INIST|14569933}} |
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| doi-access = free |
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}}</ref> |
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==References== |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{Flavanone}} |
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{{Flavanone}} |
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] |
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] |
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] |
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] |
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] |
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{{ketone-stub}} |
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{{aromatic-stub}} |