Nyasol
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| IUPAC name 4,4'-[(1Z,3R)-3-Ethenyl-1-propene-1,3-diyl]bis[phenol] | |
| Other names cis-Hinokiresinol; (Z)-Hinokiresinol | |
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| Properties | |
Chemical formula | 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). Infobox references | |
Chemical compound
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
- ^ J. Buckingham (1986). Dictionary of Organic Compounds. CRC Press. pp. 3544–. ISBN 978-0-412-54090-5.
- ^ Atta-ur-Rahman (8 July 2003). Studies in Natural Products Chemistry: Bioactive Natural Products. Elsevier. pp. 234–. ISBN 978-0-08-054205-8.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Atta-ur- Rahman; Allen B. Reitz (1 January 2005). Frontiers in Medicinal Chemistry. Bentham Science Publishers. pp. 205–. ISBN 978-1-60805-205-9.
- ^ 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.
- ^ 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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Types of lignans
- Arboreol
- Arctigenin
- Chamaecypanone A and B
- Eudesmin
- Globoidnan A
- Gmelanone
- Gmelinol
- Gummadiol
- Isootobanone
- Lyoniresinol
- Macelignan
- Matairesinol
- Obtulignolide
- Pinoresinol
- Pluviatilol
- Podophyllotoxin
- Secoisolariciresinol
- Sesamin
- Sesamolin
- Steganacin
- Arctiin
- Aviculin (isolariciresinol-9'-rhamnopyranoside)
- Secoisolariciresinol diglucoside (SDG)
- Balanophonin
- Eusiderin
- Honokiol
- Interiotherin
- Linderin A
- Magnolol
- Megaphone
- 4-O-Methylhonokiol
- Rhaphidecursinol A
- Rhaphidecursinol B
- Cinchonain-Ib
- Dehydrosilybin
- Deoxysilycistin
- Deoxysilydianin
- Hydnocarpin
- Hydnowightin
- Neosilyhermin
- Palstatin
- Rhodiolin
- Salcolin A
- Salcolin B
- Scutellaprostin A, B, C, D, E and F
- Silandrin
- Silyamandin
- Silibinin
- Silybinome
- Silicristin
- Silydianin
- Silyhermin
- Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether
- Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether
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