From Wikipedia, the free encyclopedia
Prunetin
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
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.008.199
EC Number
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
C16 H12 O5
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).
Chemical compound
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]
Glycosides
See also
References
^ 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 .
^ 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.
^ 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 .
^ 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
^
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