Sakuranetin

Sakuranetin
Names
	IUPAC name (2S)-4′,5-Dihydroxy-7-methoxyflavan-4-one
	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
Identifiers
CAS Number	2957-21-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28927 ;
ChEMBL	ChEMBL448297 ;
ChemSpider	66249 ;
ECHA InfoCard	100.019.073
IUPHAR/BPS	412;
PubChem CID	73571;
UNII	3O38P61299 ;
CompTox Dashboard (EPA)	DTXSID10874774 ;
	InChI InChI=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 Key: DJOJDHGQRNZXQQ-AWEZNQCLSA-N ; 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 Key: DJOJDHGQRNZXQQ-AWEZNQCLBK;
	SMILES COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O;
Properties
Chemical formula	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 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

Sakuranin is the 5-O-glucoside of sakuranetin.^{[citation needed]}

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
^ 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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[1] Sakuranetin on home.ncifcrf.gov

[2] Sakuranetin, a flavonone phytoalexin from ultraviolet-irradiated rice leaves, Kodama O., Miyakawa J., Akatsuka T., Kiyosawa S, 1992

[3] 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.

[4] 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.

[1]

[2]

[3]

[4]

v t e Flavanones and their glycosides
Flavanones	Butin Eriodictyol Naringenin Pinocembrin
O-methylated flavanones	Alpinetin Hesperetin Homoeriodictyol Isosakuranetin Pinostrobin (Pinocembrin-7-methylether) Sakuranetin Sterubin
C-methylated flavanones	Poriol
Glycosides	Eriocitrin Neoeriocitrin Hesperidin Liquiritin Naringin (Narigenin 7-O-neohesperidoside) Narirutin (Naringenin 7-O-rutinoside) Poncirin Prunin (Naringenin-7-O-glucoside) Sakuranin
Acetylated	8-Prenylnaringenin Isoxanthohumol Sophoraflavanone G
Acetylated glycosides	Nirurin

Names

IUPAC name (2S)-4′,5-Dihydroxy-7-methoxyflavan-4-one
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
Identifiers
CAS Number	2957-21-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28927^N
ChEMBL	ChEMBL448297^N
ChemSpider	66249^N
ECHA InfoCard	100.019.073
IUPHAR/BPS	412
PubChem CID	73571
UNII	3O38P61299^Y
CompTox Dashboard (EPA)	DTXSID10874774
InChI InChI=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^N Key: DJOJDHGQRNZXQQ-AWEZNQCLSA-N^N 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 Key: DJOJDHGQRNZXQQ-AWEZNQCLBK
SMILES COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references

Sakuranetin

Glycosides

Metabolism

References

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