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Prunetin

Prunetin
Chemical structure of prunetin
Prunetin molecule
Names
IUPAC name
4′,5-Dihydroxy-7-methoxyisoflavone
Systematic IUPAC name
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Other names
Prunusetin
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
UNII
  • 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).
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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]

Prunetin can lower blood pressure of spontaneously hypertensive rats and relax isolated rat aortic rings through calcium channel block mechanisms in vessel smooth muscles.[4]

  1. ^ Shriner, R. L.; Hull, Clarence J. (1945). "Isoflavones. III. The Structure of Prunetin and a New Synthesis of Genistein1". The Journal of Organic Chemistry. 10 (4): 288–291. doi:10.1021/jo01180a006.
  2. ^ Yokosawa, Ryozo; Kuninaga, Shiro; Sekizaki, Harua (1986). "Aphanomyces euteiches zoospore attractant isolated from pea root; prunetin". Ann. Phytopath. Soc. Japan. 52 (5): 809–816. doi:10.3186/jjphytopath.52.809.
  3. ^ Sheikh, S.; Weiner, H. (1997). "Allosteric inhibition of human liver aldehyde dehydrogenase by the isoflavone prunetin". Biochemical Pharmacology. 53 (4): 471–478. doi:10.1016/s0006-2952(96)00837-4. PMID 9105397.
  4. ^ Kim, B., Jo, C., Choi, H. Y., & Lee, K. (2018). "Prunetin relaxed isolated rat aortic rings by blocking calcium channels". Molecules, 23(9), 2372. doi:10.3390/molecules23092372 PMC 6225200 PMID 30227625 This article incorporates text from this source, which is available under the CC BY 4.0 license.
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