Prunetin

Prunetin
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
CAS number 552-59-0 Y=
PubChem 5281804
ChEMBL CHEMBL491174 N
Jmol-3D images Image 1
Properties
Molecular formula C16H12O5
Molar mass 284.26 g/mol
Exact mass 284.068473 u
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Prunetin is a 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
Isoflavones and their glycosides
Isoflavones
Daidzein | Genistein | Irilone |Orobol | Pseudobaptigenin | Anagyroidisoflavone A and B
O-methylated isoflavones
Glycosides
Prenylated isoflavones
Bidwillol A | Derrubone | Luteone | Wighteone
Pyranoisoflavones
Alpinumisoflavone | Barbigerone | Di-O-methylalpinumisoflavone | 4'-methyl-alpinumisoflavone
Misc
Synthetic