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Type of pterocarpan found in the soybean
Glyceollin III
Chemical structure of 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] antiestrogenic effect in vivo .[ 2] antifungal activity against Aspergillus sojae [ 3]
All the glyceollins are products of a pathway in soybean which starts from the amino acid L-phenylalanine . This is converted in a series of steps to the flavanone , liquiritigenin, and then by the action of isoflavonoid synthase (IFS) to the isoflavone , daidzein.[ 4] [ 5] : Supplement 1
pterocarpan ring system of the compound glycinol. The prenylation enzyme trihydroxypterocarpan dimethylallyltransferase (G4DT) and then glyceollin synthase (GS) complete the biosynthesis of glyceollin III.[ 5]
^ 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.; Boué, Stephen M.; Fonseca, Juan P.; et al. (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 . ^ Kim, Hyo Jung; Suh, Hwa-Jin; Lee, Choong Hwan; et al. (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 . ^ Lygin, Anatoliy V.; Zernova, Olga V.; Hill, Curtis B.; et al. (2013). "Glyceollin is an Important Component of Soybean Plant Defense Against Phytophthora sojae and Macrophomina phaseolina " . Phytopathology 103 (10). American Phytopathological Society : 984– 994. doi :10.1094/phyto-12-12-0328-r ISSN 0031-949X . PMID 23617338 . S2CID 12170923 . ^ a b Khatri, Praveen; Kuflu, Kuflom; McDowell, Tim; et al. (2025). "Discovery of three cytochrome P450 monooxygenase prenyl cyclases that catalyze the final step of glyceollin biosynthesis in soybean" . Molecular Plant . 18 (5): 721– 724. doi :10.1016/j.molp.2025.01.022 PMID 39891385 .
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
