125136-17-6Relevant articles and documents
Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups
Dutta, Sansa,Basak, Amit,Dasgupta, Swagata
experimental part, p. 6538 - 6546 (2010/10/03)
The reported ribonuclease A inhibitory activity of the green tea extracts prompted us to synthesize novel catechin/epicatechin based conjugates with resorcinol and phloroglucinol with the aim to increase the number of phenolic OH groups. These are found to be more effective inhibitors of ribonuclease A as compared to catechin and epicatechin thus indicating the importance of number of phenolic OH groups for the inhibition of ribonucleolytic activity. Fluorescence studies have been carried out to evaluate the binding parameters. The protein-ligand docking studies are also performed to gain insight into the protein-polyphenols interactions. The epicatechin based polyphenols 1 and 2 also showed inhibition of angiogenin-induced angiogenesis, as determined by chorioallantoic membrane (CAM) assay.
Spectroscopic Properties of Free Phenolic 4-Arylflavan-3-ols as Models for Natural Condensed Tannins
Zyl, Pieter W. van,Steynberg, Jan P.,Brandt, Edward V.,Ferreira, Daneel
, p. 1057 - 1063 (2007/10/02)
A unique range of free phenolic 4-arylflavan-3-ols consisting of four sets (3',4',5,7-tertrahydroxyflavan-3-ol or its 5-deoxy analogue coupled to phloroglucinol or resorcinol), each composed of three diastereomers (2,3-trans-3,4-trans, 2,3-trans-3,4-cis and 2,3-cis-3,4-trans) were synthesized to assess their spectroscopic properties. 1H and 13C NMR and circular dichroism data are related to selected structural and stereochemical features with a view to modelling natural phenolic oligoflavanoids. - Key words: 4-Arylflavan-3-ols 1H NMR 13C NMR Circular dichroism Condensed tannins
OLIGOMERIC FLAVANOIDS.PART 6.EVIDENCE SUPPORTING THE INVERSION OF ABSOLUTE CONFIGURATION AT 3-C ASSOCIATED WITH BASE CATALYSED A-/B-RING INTERCHANGE OF PRECURSORS HAVING 2,3-TRANS-3,4-CIS-FLAVAN-3-OL CONSTITUENT UNITS
Steynberg, Jan P.,Burger, Johann F. W.,Young, Desmond A.,Brandt, Edward V.,Ferreira, Daneel
, p. 923 - 935 (2007/10/02)
Whereas the enantiomeric 2,3-trans-3,4-trans-arylflavan-3-ols (10) and (12) as biflavanoid models are subject to stereospecific C-ring isomerisation under base catalysis, those with 3,4-cis configuration (11) and (13) are transformed stereoselectively via
Synthesis of Condensed Tannins. Part 2. Synthesis by Photolytic Rearrangement, Stereochemistry, and Circular Dichroism of the First 2,3-cis,3,4-cis-4-Arylflavan-3-ols
Westhuizen, Jan H. van der,Ferreira, Daneel,Roux, David G.
, p. 1220 - 1226 (2007/10/02)
Photolytic rearrangements of those 2,3-trans-3,4-trans- and 2,3-trans-3,4-cis-4-arylflavan-3-ols in which the nucleophilicity of D-ring (4-aryl group) functionality exceeds that of the A-ring, provide the first access to 2,3-cis-3,4-cis-diastereoisomers.The circular dichroism of these new isomers is at variance with the proposed general rule for assessing the absolute configuration at C-4.In terms of the aromatic quadrant rule such discrepancies correlate with deviations from the preferred C-ring conformations.
Synthesis of Condensed Tannins. Part 1. Stereoselective and Stereospecific Syntheses of Optically Pure 4-Arylflavan-3-ols, and Assessment of their Absolute Stereochemistry at C-4 by means of Circular Dichroism
Botha, Jacobus J.,Young, Desmond A.,Ferreira, Daneel,Roux, David G.
, p. 1213 - 1219 (2007/10/02)
Stereoselective and also stereospecific condensation at C-4 of flavan-3,4-diols of known absolute configuration with phloroglucinol and resorcinol in acid medium proceeds at ambient temperatures with partial retention of configuration for 2,3-trans-isomers and with inversion for 2,3-cis-analogues.Circular dichroism spectra of the resultant 4-arylflavan-3-ols all exhibit multiple Cotton effects.The sign of high intensity Cotton effects to low wavelength, contributed by aryl chromophores at C-4, may almost invariably be correlated with the absolute configuration at this chiral centre of 2,3-trans-3,4-trans, 2,3-trans-3,4-cis, and 2,3-cis-3,4-trans-isomers.