Prunetin

Prunetin
	Chemical structure of 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 ;
	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). 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]

Biosynthesis

Genistein is converted to prunetin by the enzyme isoflavone 7-O-methyltransferase. The methylation reaction requires the cofactor, S-adenosyl methionine (SAM), to provide the methyl group, and was characterised from alfalfa.^[5] The process can be induced by attack from a pathogen, with the plant responding with the synthesis of a phytoalexin.^[6]^[7]

genistein

+ SAM

prunetin

+ SAH

Glycosides

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

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.
↑ He XZ, Dixon RA (2000). "Genetic manipulation of isoflavone 7-O-methyltransferase enhances biosynthesis of 4'-O-methylated isoflavonoid phytoalexins and disease resistance in alfalfa". Plant Cell. 12 (9): 1689–702. doi:10.1105/tpc.12.9.1689. PMC 149079. PMID 11006341.
↑ Zubieta C, He XZ, Dixon RA, Noel JP (2001). "Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases". Nat. Struct. Biol. 8 (3): 271–9. doi:10.1038/85029. PMID 11224575. S2CID 36170487.
↑ Christensen AB, Gregersen PL, Olsen CE, Collinge DB (1998). "A flavonoid 7-O-methyltransferase is expressed in barley leaves in response to pathogen attack". Plant Mol. Biol. 36 (2): 219–27. doi:10.1023/A:1005985609313. PMID 9484434. S2CID 23711170.
↑ 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 from the original (PDF) on 2011-07-07. Retrieved 2010-02-26.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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] He XZ, Dixon RA (2000). "Genetic manipulation of isoflavone 7-O-methyltransferase enhances biosynthesis of 4'-O-methylated isoflavonoid phytoalexins and disease resistance in alfalfa". Plant Cell. 12 (9): 1689–702. doi:10.1105/tpc.12.9.1689. PMC 149079. PMID 11006341.

[6] Zubieta C, He XZ, Dixon RA, Noel JP (2001). "Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases". Nat. Struct. Biol. 8 (3): 271–9. doi:10.1038/85029. PMID 11224575. S2CID 36170487.

[7] Christensen AB, Gregersen PL, Olsen CE, Collinge DB (1998). "A flavonoid 7-O-methyltransferase is expressed in barley leaves in response to pathogen attack". Plant Mol. Biol. 36 (2): 219–27. doi:10.1023/A:1005985609313. PMID 9484434. S2CID 23711170.

[8] 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 from the original (PDF) on 2011-07-07. Retrieved 2010-02-26.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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[3]

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[5]

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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
Category

Biosynthesis

Glycosides

See also

References