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
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
C 17 H 16 O 2
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Nyasol , also known as cis -hinokiresinol(Z )-hinokiresinol , is a lignan that is found in Anemarrhena asphodeloides [ 1] [ 2] [ 3] [ 4] estrogenic activity, acting as a selective agonist of the ERβ べーた ,[ 5] phytoestrogen .[ 6] [ 7] [ 4] eicosanoids and nitric oxide in vitro anti-inflammatory effects.[ 8]
^ J. Buckingham (1986). Dictionary of Organic Compounds ISBN 978-0-412-54090-5 ^ Atta-ur-Rahman (8 July 2003). Studies in Natural Products Chemistry: Bioactive Natural Products 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 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). Bibcode :2008PlMed..7475274Y . doi :10.1055/s-2008-1075274 . ISSN 0032-0943 . ^ Atta-ur- Rahman; Allen B. Reitz (1 January 2005). Frontiers in Medicinal Chemistry 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 .
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β べーた 3α あるふぁ 3α あるふぁ α あるふぁ 3β べーた α あるふぁ 3α あるふぁ 3β べーた 3β べーた 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α あるふぁ 7α あるふぁ 7β べーた 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β べーた 10β べーた β べーた 11β べーた 11β べーた 15α あるふぁ 16-Ketoestradiol 16-Ketoestrone 16α あるふぁ 16α あるふぁ 16α あるふぁ 16α あるふぁ 16α あるふぁ 16β べーた 16β べーた α あるふぁ β べーた α あるふぁ 17α あるふぁ (alfatradiol )17α あるふぁ 17α あるふぁ 17α あるふぁ α あるふぁ α あるふぁ 17α あるふぁ α あるふぁ 17α あるふぁ β べーた 17β べーた 17β べーた 17β べーた α あるふぁ Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol
Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β べーた β べーた β べーた Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol
Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol
Estrofurate Estrogenic substances Estromustine Estrone
Etamestrol (eptamestrol) Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )Coumestans (e.g., coumestrol , psoralidin )Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )Lavender oil Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )Metalloestrogens (e.g., cadmium )Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )Phytosterols (e.g., β べーた campesterol , stigmasterol )Resorcylic acid lactones (e.g., zearalanone , α あるふぁ β べーた zearalenone , zeranol (α あるふぁ , taleranol (teranol, β べーた )Steroid -like (e.g., deoxymiroestrol , miroestrol )Stilbenoids (e.g., resveratrol , rhaponticin )Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )Others (e.g., agnuside , rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
