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Prunetin

From Wikipedia, the free encyclopedia
Prunetin
Chemical structure of 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 InfoCard100.008.199Edit 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 mass284.26 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Prunetin is anO-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark ofPrunus emarginata (the Oregon cherry).[1] Prunetin isolated frompea roots can act as an attractant forAphanomyces euteicheszoospores.[2] It is also an allosteric inhibitor of human liveraldehyde 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]

Glycosides

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See also

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References

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  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, Bumjung; Jo, Cheolmin; Choi, Ho-Young; Lee, Kyungjin (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 theCC BY 4.0 license.
  5. ^Pei Cheng Zhang, Ying Hong Wang, Xin Liu, Xiang Yi, Ruo Yun Chen and De Quan Yu (2002)."Conformational Study of 8-C-glucosyl-prunetin by Dynamic NMR Spectroscopy"(PDF).Chinese Chemical Letters.13 (7):645–648. Archived fromthe original(PDF) on 2011-07-07. Retrieved2010-02-26.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Isoflavones and theirglycosides
Isoflavones
O-methylated isoflavones
Glycosides
Prenylated isoflavones
Pyranoisoflavones
Derivatives
Synthetic
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