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Nyasol

From Wikipedia, the free encyclopedia
Nyasol
Names
IUPAC name
4,4'-[(1Z,3R)-3-Ethenyl-1-propene-1,3-diyl]bis[phenol]
Other names
cis-Hinokiresinol; (Z)-Hinokiresinol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C17H16O2/c1-2-14(15-7-11-17(19)12-8-15)6-3-13-4-9-16(18)10-5-13/h2-12,14,18-19H,1H2/b6-3-/t14-/m1/s1
    Key: VEAUNWQYYMXIRB-JHAQOBCDSA-N
  • C=C[C@H](/C=C\C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
Properties
C17H16O2
Molar mass252.313 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Nyasol, also known ascis-hinokiresinol or as(Z)-hinokiresinol, is alignan that is found inAnemarrhena asphodeloides.[1][2][3][4] It hasestrogenic activity, acting as aselectiveagonist of theERβ,[5] and hence is aphytoestrogen.[6][7][4] In addition, (-)-nyasol has been found to inhibit the production ofeicosanoids andnitric oxidein vitro and showsanti-inflammatory effects.[8]

References

[edit]
  1. ^J. Buckingham (1986).Dictionary of Organic Compounds. CRC Press. pp. 3544–.ISBN 978-0-412-54090-5.
  2. ^Atta-ur-Rahman (8 July 2003).Studies in Natural Products Chemistry: Bioactive Natural Products. Elsevier. pp. 234–.ISBN 978-0-08-054205-8.
  3. ^Christophe Wiart (11 May 2012).Medicinal Plants of China, Korea, and Japan: Bioresources for Tomorrow's Drugs and Cosmetics. CRC Press. pp. 135–.ISBN 978-1-4398-9912-0.
  4. ^abKwon, J., Kondaji, G., Song, S., Kim, C., Lee, K., Kim, W. K., & Choi, Y. (2013). Synthesis of naturally occurring norlignan (±)-nyasol. Bulletin of the Korean Chemical Society, 34(4), 1247-1249.
  5. ^Yang, H; Baggett, S; Staub, R; Chow, S; Bjeldanes, LF; Leitman, D; Cohen, I (2008). "Norlignans from Anemarrhenae asphoeloides Displaying Selective Estrogen Beta (ER?) Activity".Planta Medica.74 (3).Bibcode:2008PlMed..7475274Y.doi:10.1055/s-2008-1075274.ISSN 0032-0943.
  6. ^Atta-ur- Rahman; Allen B. Reitz (1 January 2005).Frontiers in Medicinal Chemistry. Bentham Science Publishers. pp. 205–.ISBN 978-1-60805-205-9.
  7. ^Minami E, Taki M, Takaishi S, Iijima Y, Tsutsumi S, Akiyama T (2000)."Stereochemistry of cis- and trans-hinokiresinol and their estrogen-like activity".Chem. Pharm. Bull.48 (3):389–92.doi:10.1248/cpb.48.389.PMID 10726863.
  8. ^Lim H, Nam JW, Seo EK, Kim YS, Kim HP (2009). "(-)-Nyasol (cis-hinokiresinol), a norneolignan from the rhizomes of Anemarrhena asphodeloides, is a broad spectrum inhibitor of eicosanoid and nitric oxide production".Arch. Pharm. Res.32 (11):1509–14.doi:10.1007/s12272-009-2102-4.PMID 20091263.S2CID 23151318.


Types oflignans
Lignans
Lignanglycosides
Mammalian lignans (enterolignans)
Neolignans
Flavonolignans
Phytoestrogens
Flavanones
Flavones
Prenylflavonoids
Isoflavones
Isoflavanes
Dihydrochalcones
Isoflavenes
Coumestans
Lignans
Flavonolignans
Flavonols
Others
Mycoestrogens
Derivatives
Synthetic
Metalloestrogens
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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