Prunetin

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Prunetin
Chemical structure of prunetin
Prunetin molecule
Names
IUPAC name
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
Other names
Prunusetin
4',5-dihydroxy-7-methoxyisoflavone
5,4'-dihydroxy-7-methoxyisoflavone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.199 Edit this at Wikidata
EC Number
  • 209-018-5
KEGG
  • InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3 ☒N
    Key: KQMVAGISDHMXJJ-UHFFFAOYSA-N ☒N
  • InChI=1/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
    Key: KQMVAGISDHMXJJ-UHFFFAOYAR
  • COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O)O
Properties
C16H12O5
Molar mass 284.26 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 checkY☒N ?)

Prunetin is an O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of Prunus emarginata (the Oregon cherry).[1] Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores.[2] It is also an allosteric inhibitor of human liver aldehyde dehydrogenase.[3]

Glycosides

References

  1. ^ Isoflavones. III. The structure of prunetin and a new synthesis of genistein. R. L. Shriner, C. J. Hull, J. Org. Chem., 1945, 10 (4), pp 288–291
  2. ^ Aphanomyces euteiches zoospore attractant isolated from pea root; prunetin. Ryozo Yokosawa, Shiro Kuninaga and Harua Sekizaki, Ann. Phytopath. Soc. Japan 52:809-816 (1986)
  3. ^ Allosteric inhibition of human liver aldehyde dehydrogenase by the isoflavone prunetin. Sheikh S. and Weiner H., Biochemical pharmacology, 1997, vol. 53, no4, pp. 471-478
  4. ^ Conformational Study of 8-C-glucosyl-prunetin by Dynamic NMR Spectroscopy. Pei Cheng Zhang, Ying Hong Wang, Xin Liu, Xiang Yi, Ruo Yun Chen and De Quan Yu, Chinese Chemical Letters Vol. 13, No. 7, pp 645 – 648, 2002

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