Antioxidant Phenylpropanoid-Substituted Epicatechins from <i>Trichilia catigua</i>

Tang, Wanxia; Hioki, Hideaki; Harada, Kenichi; Kubo, Miwa; Fukuyama, Yoshiyasu

doi:10.1021/np0703895

Cited by 70 publications

(61 citation statements)

References 14 publications

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“…This suggests the presence of a phenylpropanoid linked to the A-ring of the epicatechin unit through a carbon-carbon linkage. According to Nonaka and Nishioka 13 and Tang et al, 21 the C-8 resonance (d 111.5 for 5a and d 111.1 for 6a) relative to the C-6 (d 104.8 for 5a and d 104.5 for 6a) demonstrates the occurrence of a carbon-carbon linkage at the C-8 position for both compounds. The HMBC (heteronuclear multiplebond correlation spectroscopy) spectra of 5a and 6a clearly indicated a strong correlation between H-7" and C-8 and C-9, H-8" and C-8, C-9" and C-1", and H-6 and C-5, C-7, C-8, and C-10, which would be impossible if the substituent were attached at the C-6 position, and therefore confirmed the position of the phenylpropanoid moiety at C-8.…”

Section: Structure Of Phenylpropanoid Substituted Flavan-3-olsmentioning

confidence: 81%

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

Resende¹,

Rodrigues‐Filho²,

Luftmann³

et al. 2011

J. Braz. Chem. Soc.

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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...

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Section: Structure Of Phenylpropanoid Substituted Flavan-3-olsmentioning

confidence: 81%

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

Resende¹,

Rodrigues‐Filho²,

Luftmann³

et al. 2011

J. Braz. Chem. Soc.

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“…In addition, some of biological activities of Trichilia catigua may derive from its capacity to exert protective and/or inhibitory actions against free radicals (Davydov and Krikorian, 2000). A strong antioxidant activity was described for the constituents of the methanolic extract, acetonic extract, and ethyl-acetate fraction (EAF) of the barks of Trichilia catigua by the 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging test (Beltrame et al, 2006;Brighente et al, 2007;Tang et al, 2007). It is possible that the antioxidant properties of Trichilia catigua are related to the presence of phenolic compounds such as flavonoids, tannins and phenylpropanoids (Tang et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Preclinical evaluation of Trichilia catigua extracts on the central nervous system of mice

Chassot

Longhini

Gazarini

et al. 2011

Journal of Ethnopharmacology

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“…It exhibits a variety of pharmacological properties, including antidepressive and anti-inflammatory ones, and its use has been reported to be safe with no known side effects or toxicity in healthy human volunteers (2). Phytochemical reports on T. catigua indicated that the plant contains omega-phenyl alkanes, omega-phenyl alkanoic acids, omega-phenyl--gamma-lactones, alkyl-gamma-lactones, alkenyl-gamma-lactones, fatty acids, b-sitosterol, stigmasterol, campesterol, epicatechin, cinchonains (Ia, Ib, IIa, IIb), catiguanins A and B, procyanidins B2 and C1, tannins and a mixture of flavalignans (3,4).…”

mentioning

confidence: 99%

In vitro antioxidant activity of stem bark of Trichilia catigua Adr. Juss

Kamdem¹,

Stefanello²,

Boligon³

et al. 2012

Acta Pharmaceutica

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Antioxidant activity of the ethanolic extract and fractions from the stem bark of T. catigua was investigated. IC 50 (for DPPH scavenging) by T. catigua varied from 9.17 ± 0.63 to 76.42 ± 5.87 mg mL -1 and total phenolic content varied from 345.63 ± 41.08 to 601.27 ± 42.59 mg GAE g -1 of dry extract. Fe 2+ -induced lipid peroxidation was significantly reduced by the ethanolic extract and fractions. Mitochondrial Ca 2+ -induced dichlorofluorescein oxidation was significantly reduced by the ethanolic extract in a concentration-dependent manner. Ethanolic extract reduced mitochondrial Dy m only at high concentrations (40-100 mg mL -1 ), which indicates that its toxicity does not overlap with its antioxidant effects. Results suggest involvement of antioxidant activities of T. catigua in its pharmacological properties.

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Antioxidant Phenylpropanoid-Substituted Epicatechins from Trichilia catigua

Cited by 70 publications

References 14 publications

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

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

Preclinical evaluation of Trichilia catigua extracts on the central nervous system of mice

In vitro antioxidant activity of stem bark of Trichilia catigua Adr. Juss

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