Synthesis and biological activity evaluation of lignan lactones derived from (−)-cubebin

Silva, Rosangela da; Souza, Gustavo Henrique Bianco de; Silva, Ademar A. da; Souza, Vanessa A. de; Pereira, Ana Carolina; Royo, Vanesa de A.; Silva, Márcio L A E; Donate, Paulo Marcos; Araújo, Ana Lúcia Santos de Matos; Carvalho, J.C.T.; Bastos, Jairo Kenupp

doi:10.1016/j.bmcl.2004.12.035

Cited by 81 publications

(57 citation statements)

References 16 publications

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“…Thus, lignans are biosynthesized by dimerization, via oxidative coupling of phenylpropanoids units (C6C3), forming a variety of structurally distinct subclasses. An example of these substances is cubebin (Figure 9a), a dibenzylbutyrolactone lignan obtained from the seeds of Piper cubeba (Piperaceae), which has anti-inflammatory (Souza et al, 2004;Silva et al,2005); and trypanocidal (Bastos et al, 2001) activities. Neolignans are dimers derived from condensation by oxidative coupling of allyl and /or propenyl phenols and, unlike lignans, are free of oxidation in the γ carbon atom.…”

Section: Oxidation Of Lignans By Ironporphyrinsmentioning

confidence: 99%

Green Oxidation Reactions of Drugs Catalyzed by Bio-inspired Complexes as an Efficient Methodology to Obtain New Active Molecules

Faria¹,

Ricci²,

Lemos³

et al. 2011

Biomimetic Based Applications

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Section: Oxidation Of Lignans By Ironporphyrinsmentioning

confidence: 99%

Green Oxidation Reactions of Drugs Catalyzed by Bio-inspired Complexes as an Efficient Methodology to Obtain New Active Molecules

Faria¹,

Ricci²,

Lemos³

et al. 2011

Biomimetic Based Applications

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“…Its chemical structure was confirmed by 1 H NMR and IR data, as previously reported [6]; its purity, 99%, was estimated by both HPLC and spectral data analysis. (2 )-Hinokinin, 7-hydroxy-hinokinin and (2 )-9-O-N,N-dimethylamino-ethyl-cubebin were obtained from cubebin by partial synthesis as previously described [6,7,18].…”

Section: Isolation Of Cubebin and Preparation Of Its Derivativesmentioning

confidence: 99%

“…It is a dibenzylbutyrolactone lignan, belonging to a group of compounds with considerable interest as antiviral [2,3], trypanocidal [4], anti-inflammatory [5,6], analgesic [7] and anti-cancer agents [8].…”

Section: Introductionmentioning

confidence: 99%

Cubebin and derivatives as inhibitors of mitochondrial complex I. Proposed interaction with subunit B8

Saraiva

Siqueira

Silva

et al. 2009

Journal of Enzyme Inhibition and Medicinal Chemistry

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The effects on mitochondrial respiration and complex I NADH oxidase activity of cubebin and derivatives were evaluated. The compounds inhibited the state 3 glutamate/malate-supported respiration of hamster liver mitochondria with IC 50 values ranging from 12.16 to 83.96 mM. NADH oxidase reaction was evaluated in submitochondrial particles. The compounds also inhibited this activity, showing the same order of potency observed for effects on state 3 respiration, as well as a tendency towards a non-competitive type of inhibition (K I values ranging from 0.62 to 16.1 mM). A potential binding mode of these compounds with complex I subunit B8, assessed by docking calculations, is proposed.

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“…Inú-meros estudos sobre as propriedades biológicas da P. cubeba e de seus metabólitos secundários já foram descritos na literatura incluindo a atividade antimicrobiana (Silva et al 2005, Khan & Siddiqui 2007, Silva et al 2009, Rukayadi et al 2013.…”

Section: Introductionunclassified

Parâmetros sanguíneos de frangos de corte alimentados com dietas suplementadas com sementes secas de Piper cubeba como aditivo fitogênico

et al. 2016

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RESUMO: Dois experimentos foram realizados com o objetivo de avaliar o uso das sementes secas de Piper cubeba nas dietas de frangos de corte de 1 a 21 dias de idades e seus efeitos sobre o perfil bioquímicos do sangue e na biometria dos órgãos das aves. Em cada experimento 240 pintos de corte machos, com um dia de idade da linhagem Cobb foram distribuídos em um delineamento inteiramente casualizado, com cinco tratamentos e quatro repetições de 12 aves por parcela experimental. No primeiro experimento foi avaliado o uso da Piper cubeba em dietas consideradas de alta digestibilidade, a base de milho e farelo de soja, e no segundo avaliou-se o uso da pimenta em dietas de baixa digestibilidade, as quais foram obtidas com a inclusão de farinha de carne e ossos. Com relação aos dados de perfil bioquímico sanguíneo do experimento I, com exceção da gama glutamil transferase, todos os demais níveis séricos se apresentaram dentro dos limites recomendados para aves, e apenas os níveis de triglicerídeos diferiram entre os tratamentos (P<0,05). No experimento II houve diferença significativa para os níveis de albumina, colesterol e ácido úrico, porém isso não foi resultado de desordens metabólicas, visto que com exceção da gama glutamil transferase, todos os níveis encontraram-se dentro dos limites recomendados. Em ambos os experimentos não foram observadas diferenças (P>0,05) para a biometria dos órgãos. Nas condições em que os experimentos foram realizados a inclusão das sementes de Piper cubeba na ração para frangos de corte não proporcionou alterações bioquímicas e biométricas que possam limitar seu uso como material vegetal para os estudos fitogênicos.

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Synthesis and biological activity evaluation of lignan lactones derived from (−)-cubebin

Cited by 81 publications

References 16 publications

Green Oxidation Reactions of Drugs Catalyzed by Bio-inspired Complexes as an Efficient Methodology to Obtain New Active Molecules

Green Oxidation Reactions of Drugs Catalyzed by Bio-inspired Complexes as an Efficient Methodology to Obtain New Active Molecules

Cubebin and derivatives as inhibitors of mitochondrial complex I. Proposed interaction with subunit B8

Parâmetros sanguíneos de frangos de corte alimentados com dietas suplementadas com sementes secas de Piper cubeba como aditivo fitogênico

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