GLYCEOLLIN I

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H18O5
Molecular Weight	338.3539
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)OC2=C(C=C1)C3=C(C=C2)[C@@H]4OC5=C(C=CC(O)=C5)[C@]4(O)CO3

InChI

InChIKey=YIFYYPKWOQSCRI-AZUAARDMSA-N

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

HIDE SMILES / InChI

Molecular Formula	C20H18O5
Molecular Weight	338.3539
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Glyceollin I enantiomers distinctly regulate ER-mediated gene expression.	2010-12	20493896
Antioxidant activity of glyceollins derived from soybean elicited with Aspergillus sojae.	2010-11-24	21033668
Abscisic acid deficiency causes changes in cuticle permeability and pectin composition that influence tomato resistance to Botrytis cinerea.	2010-10	20709830
Antifungal activity of glyceollins isolated from soybean elicited with Aspergillus sojae.	2010-09-08	20666365
Response of soybean pathogens to glyceollin.	2010-09	20701487
Induction of glyceollins by fungal infection in varieties of Korean soybean.	2010-08	20798587
Inhibitory effect of glyceollin isolated from soybean against melanogenesis in B16 melanoma cells.	2010-07	20663406
Effects of glyceollin I on vascular contraction in rat aorta.	2010-06	20354679
Glyceollins, one of the phytoalexins derived from soybeans under fungal stress, enhance insulin sensitivity and exert insulinotropic actions.	2010-02-10	20067288
Glyceollin I, a novel antiestrogenic phytoalexin isolated from activated soy.	2010-01	19797619
The importance of phenolic metabolism to limit the growth of Phakopsora pachyrhizi.	2009-12	19900008
Estrogen/isoflavone interactions in cynomolgus macaques (Macaca fascicularis).	2009-09	19322873
Molecular effects of soy phytoalexin glyceollins in human prostate cancer cells LNCaP.	2009-09	19263441
Systemic acquired resistance in soybean is regulated by two proteins, Orthologous to Arabidopsis NPR1.	2009-08-05	19656407
Prenylation of aromatic compounds, a key diversification of plant secondary metabolites.	2009-06-12	19819506
Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max).	2009-05	19116342
Molecular cloning and characterization of a cDNA for pterocarpan 4-dimethylallyltransferase catalyzing the key prenylation step in the biosynthesis of glyceollin, a soybean phytoalexin.	2009-02	19091879
The Phytophthora sojae avirulence locus Avr3c encodes a multi-copy RXLR effector with sequence polymorphisms among pathogen strains.	2009	19440541
Copy number variation and transcriptional polymorphisms of Phytophthora sojae RXLR effector genes Avr1a and Avr3a.	2009	19343173
Novel process of fermenting black soybean [Glycine max (L.) Merrill] yogurt with dramatically reduced flatulence-causing oligosaccharides but enriched soy phytoalexins.	2008-11-12	18831591
Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I.	2008-11-06	18817403
Soybean seed extracts preferentially express genomic loci of Bradyrhizobium japonicum in the initial interaction with soybean, Glycine max (L.) Merr.	2008-08	18511436
Fungal-stressed germination of black soybeans leads to generation of oxooctadecadienoic acids in addition to glyceollins.	2007-10-17	17892258
RNAi silencing of genes for elicitation or biosynthesis of 5-deoxyisoflavonoids suppresses race-specific resistance and hypersensitive cell death in Phytophthora sojae infected tissues.	2007-06	17416637
Mining for glyceollins.	2007-04	17450198
Modification of phenolic metabolism in soybean hairy roots through down regulation of chalcone synthase or isoflavone synthase.	2007-02	16924535
Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis.	2006-12-01	17145841
Rhizobial exopolysaccharides: genetic control and symbiotic functions.	2006-02-16	16483356
Effects of soybean glyceollins and estradiol in postmenopausal female monkeys.	2006	17176220
The diphenylether herbicide lactofen induces cell death and expression of defense-related genes in soybean.	2005-12	16299178
[Isolation and identification of glycinol from Glycine max [L.] Merri].	2005-07	16250441
Isoflavonoid accumulation in soybean hairy roots upon treatment with Fusarium solani.	2003-11-05	15331097
Effects of plant flavonoids on fecundity, survival, and feeding of the Formosan subterranean termite.	2003-11	14682534
The role of octadecanoids and functional mimics in soybean defense responses.	2003-03	12715894
Lactofen induces isoflavone accumulation and glyceollin elicitation competency in soybean.	2003-03	12590114
Induction of H(2)O(2) synthesis by beta-glucan elicitors in soybean is independent of cytosolic calcium transients.	2001-11-16	11718714
Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea.	2001-10	11600046
Bradyrhizobium japonicum mutants defective in cyclic beta-glucan synthesis show enhanced sensitivity to plant defense responses.	2001-09-04	11531093
Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor alpha and beta.	2001-04	11297613
Cross-resistance and resistance longevity as induced by bean leaf beetle, Cerotoma trifurcata and soybean looper, Pseudoplusia includens herbivory on soybean.	2001	15455065

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:53:38 GMT 2025` Edited by `admin` on `Mon Mar 31 19:53:38 GMT 2025`
Record UNII	6461TV6UCH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(-)-GLYCEOLLIN I

Preferred Name

English

GLYCEOLLIN I

Common Name

English

2H,6H-BENZOFURO(3,2-C)PYRANO(2,3-H)(1)BENZOPYRAN-6A,9(11AH)-DIOL, 2,2-DIMETHYL-, (6AS-CIS)-

Common Name

English

2H,6H-BENZOFURO(3,2-C)PYRANO(2,3-H)(1)BENZOPYRAN-6A,9(11AH)-DIOL, 2,2-DIMETHYL-, (6AS,11AS)-

Common Name

English

Code System Code Type Description

MESH

C017343