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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
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
  • 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
  • 6919
KEGG
  • C10521 N
  • 5281804
UNII
  • 1TG4H5H11J Y
  • DTXSID3022530
  • 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
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 ?)

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 edit

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

See also edit

References edit

  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). (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 2011-07-07 at the Wayback Machine


prunetin, methylated, isoflavone, type, flavonoid, been, isolated, first, time, finnemore, 1910, bark, prunus, emarginata, oregon, cherry, isolated, from, roots, attractant, aphanomyces, euteiches, zoospores, also, allosteric, inhibitor, human, liver, aldehyde. 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 NamesIUPAC name 4 5 Dihydroxy 7 methoxyisoflavoneSystematic IUPAC name 5 Hydroxy 3 4 hydroxyphenyl 7 methoxy 4H 1 benzopyran 4 oneOther names Prunusetin5 4 dihydroxy 7 methoxyisoflavoneIdentifiersCAS Number 552 59 0 Y3D model JSmol Interactive imageChEBI CHEBI 8600 NChEMBL ChEMBL491174 NChemSpider 4445116 NECHA InfoCard 100 008 199EC Number 209 018 5IUPHAR BPS 6919KEGG C10521 NPubChem CID 5281804UNII 1TG4H5H11J YCompTox Dashboard EPA DTXSID3022530InChI 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 NKey KQMVAGISDHMXJJ UHFFFAOYSA N NInChI 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 1H3Key KQMVAGISDHMXJJ UHFFFAOYARSMILES COC1 CC C2C C1 OC C C2 O C3 CC C C C3 O OPropertiesChemical formula C16H12O5Molar mass 284 26 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N 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 edit8 C glucosyl prunetin isolated from the leaves of Dalbergia hainanensis 5 See also editList of phytochemicals in food Biochanin AReferences edit 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 amp 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 nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Prunetin amp oldid 1153518423, wikipedia, wiki, book, books, library,

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