Phenylpropanoid substituted flavan-3-ols from Trichilia catigua and their in vitro antioxidative activity

Abstract

O novo flavan-3-ol contendo um substituinte fenilpropanoide apocinina E, juntamente com oito substâncias conhecidas, epicatequina, procianidina B2, procianidina B4, procianidina C1, cinchonaína Ia, cinchonaína Ib, cinchonaína IIb e cinchonaína IIa foram isoladas a partir do extrato acetona-H 2 O das cascas secas de Trichilia catigua. As substâncias cinchonaína Ib e cinchonaína IIb foram reavaliadas em relação à sua estereoquímica. Todas as substâncias foram caracterizadas por análises espectroscópicas incluindo ressonância magnética nuclear (NMR) 1D e 2D e espectrometria de massa (MS) de seus derivados acetilados. A configuração absoluta do substituinte fenilpropanoide foi determinada por espectropolarimetria de dicroísmo circular (CD) e pela análise do efeito anisotrópico empregando modelo de Dreiding, e por experimento de espectroscopia de efeito nuclear Overhauser (NOESY NMR). As nove substâncias mostraram maior atividade sobre o sequestro de radical livre e poder de redução do que o ácido ascórbico e Trolox frente ao radical livre 2,2-difenil-1-picrilhidrazila e no sistema do teste de redução do ferro (Fe 3+ -Fe 2+ ).The new phenylpropanoid substituted flavan-3-ol apocynin E, together with eight known compounds, epicatechin, procyanidin B2, procyanidin B4, procyanidin C1, cinchonain Ia, cinchonain Ib, cinchonain IIb, and cinchonain IIa were isolated from an acetone-H 2 O extract of the air-dried stem bark of Trichilia catigua. The cinchonain Ia e Ib were reevaluated to its estereochemistry. All the compounds were characterized by spectroscopic analysis including 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS) of their peracetate derivatives. The absolute configuration of the phenylpropanoid moiety was determined by circular dichroism (CD) spectra and by analyzing the anisotropic effects in the Dreiding model and nuclear Overhauser effect (NOESY NMR) experiments. The nine isolated compounds showed higher radical scavenging activity and reducing power than ascorbic acid and Trolox in the free-radical 2,2-diphenyl-1-picrylhydrazyl and Fe 3+ -Fe 2+ reduction assay systems. Keywords:Trichilia catigua, Meliaceae, cinchonains, proanthocyanidins, antioxidative activity IntroductionTrichilia catigua A. Juss. (Meliaceae), commonly known as "catuaba", is a plant native to South and Central America and widely distributed in Brazil. 1 However, the identity of the plant source is often uncertain, and stem barks from several different species of Erythroxylum or Anemopaegma, all regionally known as "catuaba", are sold commercially. Marques 2 described the differences among the species known as "catuaba" and Phenylpropanoid Substituted Flavan-3-ols from Trichilia catigua J. Braz. Chem. Soc. 2088 determined that T. catigua is the main species that is sold as "catuaba" in Brazil. The same conclusion was reached by Kletter et al. 3 and Daolio et al. 4 The bark of T. catigua has been traditionally used as a health and mental tonic, and especially as a sexual stimulant. 3,5 Some pharmacological studies o...

Quality control and TLC profile data on selected plant species commonly found in the Brazilian market

“…From the preliminary results of the chemical analyses, it was possible to determine the chemical marker for each plant drug. These data were corroborated from literature sources (Oliveira et al, 1984apud Osório & Martins, 2004Kawashty et al, 1994;Müller & Kasper, 1996;Veneziani & Oliveira, 1999;Pereira et al, 2000;De Souza, 2002;Pizzolatti et al, 2002;Yang & Lambert, 2003;Araújo-Junior et al, 2004;Polydoro et al, 2004;Chan et al, 2007;Marques et al, 2007;Resende et al, 2011;Manian et al, 2008;Silva et al, 2010).…”

“…Deionized water was prepared with a Millipore Milli-Q Plus system (Millipore, Bedford, MA, USA). Hydroquinone, epicatechin, catechin, caffeic acid, chlorogenic acid, gallic acid, o-coumaric acid, quercetin, coumarin, lupeol, and rutin (Sigma, USA), isoastilbin and cinchonain Ib (isolated and certified by spectroscopic methods at the Pharmaceutical Biology Laboratory of the Universidade Estadual de Maringá; Marques et al, 2007;Resende et al, 2011), and epicatechin-3-Ogallate (kindly provided by Dr. Frank Petereit, Institute for Pharmaceutical Biology and Phytochemistry of the Universität Münster, Germany; Danne et al, 1994) of the highest grade (purity >99.0%) were used as external standards.…”

Anti-Diabetic Effects of the Ethyl-Acetate Fraction of Trichilia catigua in Streptozo-tocin-Induced Type 1 Diabetic Rats

“…Juss., known as "catuaba" in Brazil, has been popularly used as a tonic for fatigue, impotence and memory deficits. It has been demonstrated that the ethyl-acetate fraction (EAF) of T. catigua has antioxidant and anti-inflammatory effects [10][11][12].…”

“…Previously, our group reported the antioxidant capacity of EAF from the bark of T. catigua, where nine polyphenolic constituents with antioxidant effects were found [11,13]. Furthermore, subchronic treatment with EAF promoted an antidepressant effect as well as increased hippocampal cell proliferation in mice [12].…”

Development and characterization of multiple emulsions for controlled release ofTrichilia catigua(Catuaba) extract

“…It is used in Brazilian popular medicine as a tonic for the treatment of fatigue, stress, impotence, and memory deficits, mainly due to its ability to inhibit or protect against free radicals. The crude extracts and isolated compounds (epicatechin, cinchonains Ia, Ib, IIa, IIb, catiguanins A and B, apocynin E, and procyanidins B2 and C1) from the bark of T. catigua show antioxidant activity toward the free radical 2,2-diphenyl-2-picrylhydrazyl (DPPH), and reduction of the Fe 3+ / ferricyanide complex to the ferrous form [9][10][11][12][13][14] .…”