Sakuranetin

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.019.073
UNII
  • 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 checkY
    Key: DJOJDHGQRNZXQQ-AWEZNQCLSA-N checkY
  • COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O
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).
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.[3]

Metabolism

biosynthesis

Naringenin 7-O-methyltransferase uses naringenin to yield sakuranetin, with S-adenosyl-methionine (SAM) as the methyl donor.[4]

2D representation of the chemical structure of naringenin .
naringenin
+ SAM
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of sakuranetin .
sakuranetin
+ SAH
 
biodegradation

In compounds like 7-methoxylated flavanones like sakuranetin, demethylation followed by sulfation occur in model organism Cunninghamella elegans.[5]

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". Archived from the original on 2012-06-16. Retrieved 2009-09-11.
  3. ↑ Hasegawa, Masao; Shirato, Teruo (1955). "Flavonoids of Various Prunus Species. IV. The Flavonoids in the Wood of Prunus donarium var. spontanea". Journal of the American Chemical Society. 77 (13): 3557–3558. doi:10.1021/ja01618a039.
  4. ↑ 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. Bibcode:1996BBRC..222..732R. doi:10.1006/bbrc.1996.0812. PMID 8651913.
  5. ↑ 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.


This page is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.