Sakuranetin

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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28927 ☒N
ChEMBL
  • ChEMBL448297 ☒N
ChemSpider
  • 66249 ☒N
ECHA InfoCard 100.019.073 Edit this at Wikidata
IUPHAR/BPS
  • 412
PubChem CID
  • 73571
UNII
  • 3O38P61299 checkY
CompTox Dashboard (EPA)
  • DTXSID10874774 Edit this at Wikidata
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
  • 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).
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Infobox references
Chemical compound

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

  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. ^ A Methyltransferase for Synthesis of the Flavanone Phytoalexin Sakuranetin in Rice Leaves, Randeep Rakwala, Morifumi Hasegawab and Osamu Kodama, 1996
  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.
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Flavanones and their glycosides
FlavanonesO-methylated flavanones
C-methylated flavanonesGlycosides
AcetylatedAcetylated glycosides
  • Nirurin


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