Prunetin

Last updated
Prunetin
Prunetin.svg
Prunetin-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-018-5
KEGG
PubChem CID
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 X mark.svgN
    Key: KQMVAGISDHMXJJ-UHFFFAOYSA-N X mark.svgN
  • 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]

Contents

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

See also

Related Research Articles

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<span class="mw-page-title-main">Acetaldehyde dehydrogenase</span> Class of enzymes

Acetaldehyde dehydrogenases are dehydrogenase enzymes which catalyze the conversion of acetaldehyde into acetic acid. The oxidation of acetaldehyde to acetate can be summarized as follows:

<span class="mw-page-title-main">Pyruvate dehydrogenase complex</span>

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<span class="mw-page-title-main">Glutamate dehydrogenase</span> Hexameric enzyme

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<span class="mw-page-title-main">Glycogen phosphorylase</span> Class of enzymes

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<span class="mw-page-title-main">ALDH2</span> Enzyme

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<span class="mw-page-title-main">Genistin</span> Chemical compound

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<span class="mw-page-title-main">TROX-1</span> Chemical compound

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References

  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" (PDF). Ann. Phytopath. Soc. Japan. 52 (5): 809–816. doi: 10.3186/jjphytopath.52.809 . Archived from the original (PDF) on 2011-07-22.
  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
  5. 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 Archived 2011-07-07 at the Wayback Machine