Prunetin

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

Names
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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8600
ChEMBL	ChEMBL491174
ChemSpider	4445116
ECHA InfoCard	100.008.199
EC Number	209-018-5
IUPHAR/BPS	6919
KEGG	C10521
PubChem CID	5281804
UNII	1TG4H5H11J
CompTox Dashboard (EPA)	DTXSID3022530
InChI 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 Key: KQMVAGISDHMXJJ-UHFFFAOYSA-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
SMILES COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O)O
Properties
Chemical formula	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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Infobox references

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

• 8-C-glucosyl prunetin, isolated from the leaves of Dalbergia hainanensis[5]

See also

• List of phytochemicals in food
• Biochanin A

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