Gram-Scale Production and Applications of Optically Pure13C-Labelled (+)-Catechin and (−)-Epicatechin

Nay, Bastien; Arnaudinaud, Valérie; Vercauteren, Joseph

doi:10.1002/1099-0690(200106)2001:12<2379::aid-ejoc2379>3.0.co;2-d

Cited by 27 publications

(13 citation statements)

References 18 publications

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“…• Gallic acid (3,4,5-Trihydroxybenzoic acid, 9): 0.16% (Saito and Kawabata 2006). • (q)-Catechin (10)/(-)-Epicatechin (11) (1/1.5): 1.09% (Nay et al 2001;Mendoza-Wilson and Glossman-Mitnik 2006). Absolute configurations were tentatively assigned based on optical rotation of epicatechin derivative 12, assuming that 12 should be a derivative of wallaba epicatechin.…”

Section: Purification and Characterization Of Extractivesmentioning

confidence: 99%

Extractives of the tropical wood wallaba (Eperua falcata Aubl.) as natural anti-swelling agents

et al. 2010

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International audienceA comparative study of 9H-pyrido[3,4-b]indole (norharmane) and 1-methyl-9H-pyrido[3,4-b]indole (harmane) as inhibitors for C38 steel corrosion in 1 M HCl solution at 25 °C was carried out. Potentiodynamic polarization and electrochemical impedance spectroscopy (EIS) techniques were applied to study the metal corrosion behavior in the absence and presence of different concentrations of these inhibitors. The OCP as a function of time were also established. Cathodic and anodic polarization curves show that norharmane and harmane are a mixed-type inhibitors. Adsorption of indole derivatives on the C38 steel surface, in 1 M HCl solution, follows the Langmuir adsorption isotherm model. The ΔGads values were calculated and discussed. The potential of zero charge (PZC) of the C38 steel in inhibited solution was studied by the EIS method, and a mechanism for the adsorption process was proposed. Raman spectroscopy confirmed that indole molecules strongly adsorbed onto the steel surface. The electronic properties of indole derivates, obtained using the AM1 semi-empirical quantum chemical approach, were correlated with their experimental efficiencies using the linear resistance model (LR)

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Section: Purification and Characterization Of Extractivesmentioning

confidence: 99%

Extractives of the tropical wood wallaba (Eperua falcata Aubl.) as natural anti-swelling agents

et al. 2010

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“…Compounds 1-10 were prepared as outlined in fi gure 2, and their structure is given in fi gure l, thus the aldolic condensation between o-hydroxyacetophenones 11 and benzaldehydes 12 (step i) gave calchones 13 [24]. 3-Flavenes 14 were obtained by reductive cyclization of calchones with NaBH 4 (step ii) [20]; the conversion of compound 14 into a trialkylborane complex (step iii), and the subsequent cleavage by hydrogen peroxide gave 3-fl avanols 15 (step iv), isolated as a mixture of trans and cis diastereoisomers (trans/cis = 4/1).…”

Section: Synthesis Of Catechin Analoguesmentioning

confidence: 99%

A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate

Dell’Agli

Bellosta

Rizzi

et al. 2005

Cell. Mol. Life Sci.

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Catechins are able to modulate the gelatinolytic activity of matrix metalloproteinase-9 (MMP-9) by reducing its release from macrophages. Gallocatechins decrease MMP-9 secretion by lowering MMP-9 promoter activity and mRNA levels. The effect appears to be dependent on some structural and stereochemical requirements. In this study, the relationship between chemical structure and activity was studied by testing the effect of analogues of (+/-)-gallocatechin-3-gallate (+/-)-GCG, selectively deprived of hydroxyl groups, on MMP-9 activity, transcription, and secretion. Our results indicate that (+/-)-GCG and (+/-)-catechin-3-gallate are characterized by a substitution pattern compatible with direct inhibition of MMP-9 activity. Conversely, when transcription was the target, (+/-)-trans-3-flavanol-3-benzoate, lacking all the hydroxyl groups, was the most effective both in lowering MMP-9 promoter activity and consequently protein secretion, and in inhibiting nuclear-factor-kappaB-driven transcription. Our results suggest that the structural requirements for enzyme inhibition are different from those necessary for targeting gene expression.

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“…From a 1-BuOH-soluble fraction of the MeOH extract of leaves of E. meliaefolia, 10 megastigmane glucosides (1)(2)(3)(4)(5)(6)(7)(8)(9)(10) were isolated together with two known aliphatic [(Z)-3-hexenyl b-D-glucopyranoside (11) ) and 3,7-dimethylocte-1-en-3,6,7-triol 6-O-b-D-glucopyranoside (12) (Manns, 1995)] and three phenolic [(+)-catechin (13) (Nay et al, 2001), syringin (14) DellaGreca 0031-9422/$ -see front matter Ó 2008 Elsevier Ltd. All rights reserved. doi:10.1016/j.phytochem.2008.01.020 et al, 1998) and 1-b-D-glucopyranosyloxy-3-methoxy-5-hydroxybenzene (15) (Sakar et al, 1993)] compounds.…”

Section: Introductionmentioning

confidence: 99%

Euodionosides A–G: Megastigmane glucosides from leaves of Euodia meliaefolia

et al. 2008

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Gram-Scale Production and Applications of Optically Pure13C-Labelled (+)-Catechin and (−)-Epicatechin

Cited by 27 publications

References 18 publications

Extractives of the tropical wood wallaba (Eperua falcata Aubl.) as natural anti-swelling agents

Extractives of the tropical wood wallaba (Eperua falcata Aubl.) as natural anti-swelling agents

A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate

Euodionosides A–G: Megastigmane glucosides from leaves of Euodia meliaefolia

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