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Nyasol

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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)
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 mass 252.313 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nyasol, also known as cis-hinokiresinol or as (Z)-hinokiresinol, is a lignan that is found in Anemarrhena asphodeloides.[1][2][3][4] It has estrogenic activity, acting as a selective agonist of the ERβ,[5] and hence is a phytoestrogen.[6][7][4] In addition, (-)-nyasol has been found to inhibit the production of eicosanoids and nitric oxide in vitro and shows anti-inflammatory effects.[8]

References

  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. ^ a b Kwon, 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). 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.



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