Prunetin

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
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). verify (what is ?) Infobox references

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

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

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". Ann. Phytopath. Soc. Japan. 52 (5): 809–816. doi:10.3186/jjphytopath.52.809.
^ 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, 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 the CC BY 4.0 license.
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)Archived 2011-07-07 at the Wayback Machine

[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 the CC 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)Archived 2011-07-07 at the Wayback Machine

[1]

[2]

[3]

[4]

[5]

v t e Isoflavones and their glycosides
Isoflavones	Daidzein Genistein Orobol
O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin
Glycosides	Daidzin Genistin Iridin Mirificin Ononin Puerarin Sophoricoside Tectoridin
Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone
Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone
Derivatives	Anagyroidisoflavone A and B Irilone Pseudobaptigenin Rotenoids
Synthetic	Ipriflavone

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
CAS Number	552-59-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8600^N
ChEMBL	ChEMBL491174^N
ChemSpider	4445116^N
ECHA InfoCard	100.008.199
EC Number	209-018-5
IUPHAR/BPS	6919
KEGG	C10521^N
PubChem CID	5281804
UNII	1TG4H5H11J^Y
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^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
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). N verify (what is ^YN ?) Infobox references

Prunetin

Glycosides

See also

References