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Glyceollin III
Names
Preferred IUPAC name
(2S ,6aS ,11aS )-2-(Prop-1-en-2-yl)-1,2-dihydro-6H -[1]benzofuro[3,2-c ]furo[3,2-g ][1]benzopyran-6a,9(11aH )-diol
Identifiers
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
InChI=1S/C20H18O5/c1-10(2)15-6-11-5-13-17(8-16(11)24-15)23-9-20(22)14-4-3-12(21)7-18(14)25-19(13)20/h3-5,7-8,15,19,21-22H,1,6,9H2,2H3/t15-,19-,20+/m0/s1
Key: MIYTVBARXCVVHZ-RYGJVYDSSA-N
CC(=C)[C@@H]1Cc2cc3c(cc2O1)OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O
Properties
C20 H18 O5
Molar mass
338.35 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Glyceollin III is a glyceollin , a type of pterocarpan , found in the soybean (Glycine max ).[ 1] [ 2] It has an antiestrogenic effect.[ 3] In soil, it has an antifungal activity against Aspergillus sojae .[ 4]
^ Zimmermann, M. Carla; Tilghman, Syreeta L.; Boué, Stephen M.; Salvo, Virgilio A.; Elliott, Steven; Williams, K. Y.; Skripnikova, Elena V.; Ashe, Hasina; Payton-Stewart, Florastina; Vanhoy-Rhodes, Lyndsay; Fonseca, Juan Pablo; Corbitt, Cynthia; Collins-Burow, Bridgette M.; Howell, Melanie H.; Lacey, Michelle; Shih, Betty Y.; Carter-Wientjes, Carol; Cleveland, Thomas E.; McLachlan, John A.; Wiese, Thomas E.; Beckman, Barbara S.; Burow, Matthew E. (2010). "Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy" . Journal of Pharmacology and Experimental Therapeutics . 332 (1): 35–45. doi :10.1124/jpet.109.160382 . PMC 2802480 . PMID 19797619 .
^ Banks, Stephen W.; Dewick, Paul M. (1983). "Biosynthesis of glyceollins I, II and III in soybean". Phytochemistry . 22 (12): 2729–2733. doi :10.1016/S0031-9422(00)97682-9 .
^ Salvo Virgilo A., Boue Stephen M., Fonseca Juan P., Elliott Steven, Corbitt Cynthia, Collins-Burow Bridgette M., Curiel Tyler J., Srivastav Sudesh K., Shih Betty Y., Carter-Wientjes Carol, Wood Charles E., Erhardt Paulw., Beckman Barbara S., McLachlan John A., Cleveland Thomas E. and Burow Matthew E. (2006). "Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis" . Clinical Cancer Research . 12 (23): 7159–7164. doi :10.1158/1078-0432.CCR-06-1426 . PMID 17145841 . {{cite journal }}
: CS1 maint: multiple names: authors list (link )
^ Kim, Hyo Jung; Suh, Hwa-Jin; Lee, Choong Hwan; Kim, Jeong Hwan; Kang, Sun Chul; Park, Sunmin; Kim, Jong-Sang (2010). "Antifungal Activity of Glyceollins Isolated from Soybean Elicited with Aspergillus sojae". Journal of Agricultural and Food Chemistry . 58 (17): 9483–9487. doi :10.1021/jf101694t . PMID 20666365 .
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β べーた -ol
3α あるふぁ -Androstanediol
3α あるふぁ ,5α あるふぁ -Dihydrolevonorgestrel
3β べーた ,5α あるふぁ -Dihydrolevonorgestrel
3α あるふぁ -Hydroxytibolone
3β べーた -Hydroxytibolone
3β べーた -Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α あるふぁ -Hydroxy-DHEA
7α あるふぁ -Methylestradiol
7β べーた -Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β べーた -VE2
10β べーた ,17β べーた -Dihydroxyestra-1,4-dien-3-one (DHED)
11β べーた -Chloromethylestradiol
11β べーた -Methoxyestradiol
15α あるふぁ -Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α あるふぁ -Fluoroestradiol
16α あるふぁ -Hydroxy-DHEA
16α あるふぁ -Hydroxyestrone
16α あるふぁ -Iodoestradiol
16α あるふぁ -LE2
16β べーた -Hydroxyestrone
16β べーた ,17α あるふぁ -Epiestriol (16β べーた -hydroxy-17α あるふぁ -estradiol)
17α あるふぁ -Estradiol (alfatradiol )
17α あるふぁ -Dihydroequilenin
17α あるふぁ -Dihydroequilin
17α あるふぁ -Epiestriol (16α あるふぁ -hydroxy-17α あるふぁ -estradiol)
17α あるふぁ -Ethynyl-3α あるふぁ -androstanediol
17α あるふぁ -Ethynyl-3β べーた -androstanediol
17β べーた -Dihydroequilenin
17β べーた -Dihydroequilin
17β べーた -Methyl-17α あるふぁ -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 べーた -epiestriol, 16β べーた -hydroxy-17β べーた -estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
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Estrofurate
Estrogenic substances
Estromustine
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Ethinylestradiol
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Lynestrenol phenylpropionate
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Noretynodrel
Orestrate
Pentolame
Prodiame
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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 -sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α あるふぁ -zearalenol , β べーた -zearalenol , zearalenone , zeranol (α あるふぁ -zearalanol) , taleranol (teranol, β べーた -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