From Wikipedia, the free encyclopedia
Nyasol
Names
IUPAC name
4,4'-[(1Z )-1,4-Pentadiene-1,3-diyl]diphenol
Other names
cis -Hinokiresinol; (Z )-Hinokiresinol
Identifiers
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-
Key: VEAUNWQYYMXIRB-UTCJRWHESA-N
C=CC(C=CC1=CC=C(C=C1)O)C2=CC=C(C=C2)O
Properties
C 17 H 16 O 2
Molar mass
252.313 g/mol
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 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 (03). 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 .
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
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 -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
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-sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )
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 )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown