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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 of GLYCEOLLIN I

SMILES

[H][C@@]12OC3=CC(O)=CC=C3[C@]1(O)COC4=C5C=CC(C)(C)OC5=CC=C24

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Cross-resistance and resistance longevity as induced by bean leaf beetle, Cerotoma trifurcata and soybean looper, Pseudoplusia includens herbivory on soybean.
2001
Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor alpha and beta.
2001 Apr
Bradyrhizobium japonicum mutants defective in cyclic beta-glucan synthesis show enhanced sensitivity to plant defense responses.
2001 Jul-Aug
Induction of H(2)O(2) synthesis by beta-glucan elicitors in soybean is independent of cytosolic calcium transients.
2001 Nov 16
Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea.
2001 Oct
The role of octadecanoids and functional mimics in soybean defense responses.
2003 Mar
Lactofen induces isoflavone accumulation and glyceollin elicitation competency in soybean.
2003 Mar
Effects of plant flavonoids on fecundity, survival, and feeding of the Formosan subterranean termite.
2003 Nov
Isoflavonoid accumulation in soybean hairy roots upon treatment with Fusarium solani.
2004 Jul-Aug
The diphenylether herbicide lactofen induces cell death and expression of defense-related genes in soybean.
2005 Dec
[Isolation and identification of glycinol from Glycine max [L.] Merri].
2005 Jul
Effects of soybean glyceollins and estradiol in postmenopausal female monkeys.
2006
Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis.
2006 Dec 1
Rhizobial exopolysaccharides: genetic control and symbiotic functions.
2006 Feb 16
Mining for glyceollins.
2007 Apr
Modification of phenolic metabolism in soybean hairy roots through down regulation of chalcone synthase or isoflavone synthase.
2007 Feb
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 Jun
Fungal-stressed germination of black soybeans leads to generation of oxooctadecadienoic acids in addition to glyceollins.
2007 Oct 17
Soybean seed extracts preferentially express genomic loci of Bradyrhizobium japonicum in the initial interaction with soybean, Glycine max (L.) Merr.
2008 Aug
Novel process of fermenting black soybean [Glycine max (L.) Merrill] yogurt with dramatically reduced flatulence-causing oligosaccharides but enriched soy phytoalexins.
2008 Nov 12
Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I.
2008 Nov 6
The Phytophthora sojae avirulence locus Avr3c encodes a multi-copy RXLR effector with sequence polymorphisms among pathogen strains.
2009
Copy number variation and transcriptional polymorphisms of Phytophthora sojae RXLR effector genes Avr1a and Avr3a.
2009
Systemic acquired resistance in soybean is regulated by two proteins, Orthologous to Arabidopsis NPR1.
2009 Aug 5
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 Feb
Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max).
2009 May
Prenylation of aromatic compounds, a key diversification of plant secondary metabolites.
2009 Oct-Nov
Estrogen/isoflavone interactions in cynomolgus macaques (Macaca fascicularis).
2009 Sep
Molecular effects of soy phytoalexin glyceollins in human prostate cancer cells LNCaP.
2009 Sep
Induction of glyceollins by fungal infection in varieties of Korean soybean.
2010 Aug
Glyceollins, one of the phytoalexins derived from soybeans under fungal stress, enhance insulin sensitivity and exert insulinotropic actions.
2010 Feb 10
Glyceollin I, a novel antiestrogenic phytoalexin isolated from activated soy.
2010 Jan
Antioxidant activity of glyceollins derived from soybean elicited with Aspergillus sojae.
2010 Nov 24
Abscisic acid deficiency causes changes in cuticle permeability and pectin composition that influence tomato resistance to Botrytis cinerea.
2010 Oct
Name Type Language
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
(-)-GLYCEOLLIN I
Common Name English
Code System Code Type Description
MESH
C017343
Created by admin on Fri Dec 15 19:41:29 GMT 2023 , Edited by admin on Fri Dec 15 19:41:29 GMT 2023
PRIMARY
FDA UNII
6461TV6UCH
Created by admin on Fri Dec 15 19:41:29 GMT 2023 , Edited by admin on Fri Dec 15 19:41:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID10205726
Created by admin on Fri Dec 15 19:41:29 GMT 2023 , Edited by admin on Fri Dec 15 19:41:29 GMT 2023
PRIMARY
PUBCHEM
162807
Created by admin on Fri Dec 15 19:41:29 GMT 2023 , Edited by admin on Fri Dec 15 19:41:29 GMT 2023
PRIMARY
WIKIPEDIA
GLYCEOLLIN I
Created by admin on Fri Dec 15 19:41:29 GMT 2023 , Edited by admin on Fri Dec 15 19:41:29 GMT 2023
PRIMARY
CAS
57103-57-8
Created by admin on Fri Dec 15 19:41:29 GMT 2023 , Edited by admin on Fri Dec 15 19:41:29 GMT 2023
PRIMARY
CHEBI
16470
Created by admin on Fri Dec 15 19:41:29 GMT 2023 , Edited by admin on Fri Dec 15 19:41:29 GMT 2023
PRIMARY