Prunetin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 350355577

| Name = Prunetin

| ImageFile = Prunetin.svg

| ImageSize = 220px

| ImageFile1 = Prunetin-3D-balls.png

| ImageSize1 = 220

| ImageAlt1 = Prunetin molecule

| ImageName = Chemical structure of prunetin

| IUPACName = 4′,5-Dihydroxy-7-methoxyisoflavone

| SystematicName = 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one

| OtherNames = Prunusetin
5,4'-dihydroxy-7-methoxyisoflavone

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 6919

| CASNo = 552-59-0

| CASNo_Ref = {{cascite|correct|??}}

| CASNoOther =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1TG4H5H11J

| PubChem = 5281804

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 8600

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 491174

| SMILES = COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O)O

| EINECS = 209-018-5

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4445116

| 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

| InChIKey = KQMVAGISDHMXJJ-UHFFFAOYAR

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = KQMVAGISDHMXJJ-UHFFFAOYSA-N

| RTECS =

| MeSHName =

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C10521

}}

|Section2={{Chembox Properties

| Formula = C₁₆H₁₂O₅

| MolarMass = 284.26 g/mol

| Appearance =

| Density =

| MeltingPt =

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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).{{cite journal|doi=10.1021/jo01180a006 | volume=10 | issue=4 | year=1945 | journal=The Journal of Organic Chemistry | pages=288–291 | last1 = Shriner | first1 = R. L. | last2 = Hull | first2 = Clarence J.| title=Isoflavones. III. The Structure of Prunetin and a New Synthesis of Genistein1 }} Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores.{{cite journal | last1 = Yokosawa | first1 = Ryozo | last2 = Kuninaga | first2 = Shiro | last3 = Sekizaki | first3 = Harua | year = 1986 | title = Aphanomyces euteiches zoospore attractant isolated from pea root; prunetin | journal = Ann. Phytopath. Soc. Japan | volume = 52 | issue = 5| pages = 809–816 | doi = 10.3186/jjphytopath.52.809 | doi-access = free }} It is also an allosteric inhibitor of human liver aldehyde dehydrogenase.{{cite journal | last1 = Sheikh | first1 = S. | last2 = Weiner | first2 = H. | year = 1997 | title = Allosteric inhibition of human liver aldehyde dehydrogenase by the isoflavone prunetin | url = http://cat.inist.fr/?aModele=afficheN&cpsidt=2618386 | journal = Biochemical Pharmacology | volume = 53 | issue = 4| pages = 471–478 | doi=10.1016/s0006-2952(96)00837-4| pmid = 9105397 }}

Prunetin can lower blood pressure of spontaneously hypertensive rats and relax isolated rat aortic rings through calcium channel block mechanisms in vessel smooth muscles.{{cite journal | doi = 10.3390/molecules23092372 | doi-access = free | pmc = 6225200 | pmid = 30227625 | title = Prunetin Relaxed Isolated Rat Aortic Rings by Blocking Calcium Channels | date = 2018 | last1 = Kim | first1 = Bumjung | last2 = Jo | first2 = Cheolmin | last3 = Choi | first3 = Ho-Young | last4 = Lee | first4 = Kyungjin | journal = Molecules | volume = 23 | issue = 9 | page = 2372 }}{{Creative Commons text attribution notice|cc=by4|from this source=yes}}