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Glyceollin I
Names
Preferred IUPAC name
(6aS ,11aS )-2,2-Dimethyl-2H ,6H -[1]benzofuro[3,2-c ]pyrano[2,3-h ][1]benzopyran-6a,9(11aH )-diol
Other names
(−)-Glyceollin I
Identifiers
ChEBI
ChemSpider
ECHA InfoCard 100.222.666
KEGG
UNII
InChI=1S/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1
N Key: YIFYYPKWOQSCRI-AZUAARDMSA-N
N InChI=1/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1
Key: YIFYYPKWOQSCRI-AZUAARDMBS
CC1(C=Cc2c(ccc3c2OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O)O1)C
Properties
C20 H18 O5
Molar mass
338 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 I is a glyceollin , a type of prenylated pterocarpan . It is a phytoalexin found in the soybean .[ 1]
Glyceollin synthase is an enzyme responsible for the production of glyceollin.[ 2] NADPH , H+ , and O2 , whereas its three products are glyceollin, NADP+ , and H2 O .
In in vitro studies, this molecule has been shown to exhibit antiestrogenic properties.[ 3]
^ Zimmermann, M. C.; Tilghman, S. L.; Boué, S. M.; Salvo, V. A.; Elliott, S.; Williams, K. Y.; Skripnikova, E. V.; Ashe, H.; Payton-Stewart, F.; Vanhoy-Rhodes, L.; Fonseca, J. P.; Corbitt, C.; Collins-Burow, B. M.; Howell, M. H.; Lacey, M.; Shih, B. Y.; Carter-Wientjes, C.; Cleveland, T. E.; McLachlan, J. A.; Wiese, T. E.; Beckman, B. S.; Burow, M. E. (2009). "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 . ^ Welle, R.; Grisebach, H. (1988). "Induction of phytoalexin synthesis in soybean: Enzymatic cyclization of prenylated pterocarpans to glyceollin isomers". Archives of Biochemistry and Biophysics . 263 (1): 191–198. doi :10.1016/0003-9861(88)90627-3 . PMID 3369863 . ^ Payton-Stewart, F.; Khupse, R. S.; Boué, S. M.; Elliott, S.; Zimmermann, M. C.; Skripnikova, E. V.; Ashe, H.; Tilghman, S. L.; Beckman, B. S.; Cleveland, T. E.; McLachlan, J. A.; Bhatnagar, D.; Wiese, T. E.; Erhardt, P.; Burow, M. E. (2010). "Glyceollin I enantiomers distinctly regulate ER-mediated gene expression" . Steroids . 75 (12): 870–878. doi :10.1016/j.steroids.2010.05.007 . hdl :11336/58472 PMID 20493896 . S2CID 14878980 . [permanent dead link ]
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 -EstradiolEpiestriol (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 ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
