Neolignans of Virola surinamensis

Barata, Lauro Euclides Soares; Baker, Paul; Gottlieb, Otto R.; Rúveda, Edmundo A.

doi:10.1016/s0031-9422(00)94227-4

Cited by 99 publications

(67 citation statements)

References 6 publications

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“…In order to determine the biological activity of neolignans, Barata et al 4 and Santos 5 synthesized eighteen analogues of neolignan compounds which were submitted to biological tests against fungi, bacteria, leishmaniasis, schistosomiasis, cancer and PAF (platelet activating factor). 6 From the eighteen neolignan compounds synthesized, five have been classified as active and thirteen have been classified as inactive against schistosomiasis (all tests in vitro).…”

Section: Introductionmentioning

confidence: 99%

“…6 From the eighteen neolignan compounds synthesized, five have been classified as active and thirteen have been classified as inactive against schistosomiasis (all tests in vitro). 4,5 In the present work we calculated selected molecular descriptors of the eighteen neolignan derivatives synthesized 4,5 and afterwards statistical methods (principal component analysis, PCA, hierarchical cluster analysis, HCA, and discriminant analysis, DA) were used in order to obtain the relationship between the molecular descriptors and the biological activity. The results obtained with PCA, HCA and DA were tested in a new set of neolignan compounds and the KNN method was used for activity prediction of these new compounds.…”

Section: Introductionmentioning

confidence: 99%

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A Structure-Activity Relationship (SAR) Study of Neolignan Compounds with Anti-schistosomiasis Activity

Alves¹,

Macedo²,

Honório³

et al. 2002

J. Braz. Chem. Soc.

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Um conjunto de dezoito compostos de neolignanas com atividade antiesquistossomose foi estudado com o método semi-empírico PM3 e outros métodos teóricos com o intuito de avaliar algumas propriedades (variáveis ou descritores) moleculares selecionadas e correlacioná-las com a atividade biológica.Análise exploratória dos dados (análise de componentes principais, PCA, e análise hierárquica de agrupamentos, HCA), análise discriminante (DA) e o método KNN foram utilizados na obtenção de possíveis correlações entre os descritores calculados e a atividade biológica em questão e na predição da atividade antiesquistossimose de algumas moléculas teste. Os descritores moleculares responsáveis pela separação entre os compostos ativos e inativos foram: energia de hidratação (HE), refratividade molecular (MR) e carga sobre o átomo C19 (Q 19 ). Estes descritores fornecem informações a respeito do tipo de interação que pode ocorrer entre os compostos e seu respectivo receptor biológico. Após a construção do modelo para compostos ativos e inativos, os métodos PCA, HCA, DA e KNN foram empregados em um estudo de predição. Foram estudados 10 novos compostos e somente 5 deles foram classificados como ativos contra esquistossomose.A set of eighteen neolignan derivative compounds with anti-schistosomiasis activity was studied by using the quantum mechanical semi-empirical method PM3 and other theoretical methods in order to calculate selected molecular properties (variables or descriptors) to be correlated to their biological activities.Exploratory data analysis (principal component analysis, PCA, and hierarchical cluster analysis, HCA), discriminant analysis (DA) and the Kth nearest neighbor (KNN) method were employed for obtaining possible relationships between the calculated descriptors and the biological activities studied and predicting the anti-schistosomiasis activity of new compounds from a test set. The molecular descriptors responsible for the separation between active and inactive compounds were: hydration energy (HE), molecular refractivity (MR) and charge on the C19 carbon atom (Q 19 ). These descriptors give information on the kind of interaction that can occur between the compounds and their respective biological receptor. The prediction study was done with a new set of ten derivative compounds by using the PCA, HCA, DA and KNN methods and only five of them were predicted as active against schistosomiasis.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Structure-Activity Relationship (SAR) Study of Neolignan Compounds with Anti-schistosomiasis Activity

Alves¹,

Macedo²,

Honório³

et al. 2002

J. Braz. Chem. Soc.

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“…In this paper, we report the neurotrophic effects of these 2,5-diaryl-3,4-dimethyltetrahydrofuran neolignans (2-7) for comparison with 1, the neuroprotective effects of neolignans (1-7) against Ab [25][26][27][28][29][30][31][32][33][34][35] -induced cell death in primary cultured rat hippocampal neurons, 15) as well as against cell death induced by 1-methyl-4-phenylpyridinium ion (MPP ϩ ), a neurotoxin used in the cellular model for Parkinson's disease. 16) 17) and its analogues, veraguensin (2), 18) galgravin (3), 19) aristolignin (4), 19) nectandrin A (5), 20) isonectandrin B (6), 20) and nectandrin B (7), 20) were isolated from a methanol extract of the root of A. arcuata as previously described. 14) Their structures were elucidated by extensive analyses of IR, MS, 1 H-, and 13 C-NMR spectra and identified by spectral data and specific rotations in the literature.…”

mentioning

confidence: 99%

“…14) Their structures were elucidated by extensive analyses of IR, MS, 1 H-, and 13 C-NMR spectra and identified by spectral data and specific rotations in the literature. [17][18][19][20] Cell culture medium and supplements were from Gibco BRL Co. Ltd. (NY, U.S.A.). Cell culture plates were purchased from Iwaki (Chiba, Japan).…”

mentioning

confidence: 99%

Neuroprotective Effects of 2,5-Diaryl-3,4-dimethyltetrahydrofuran Neolignans

Zhai

Inoue

Moriyama

et al. 2005

Biological & Pharmaceutical Bulletin

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We previously reported the neurotrophic effects of talaumidin (1) from Aristolochia arcuata MASTERS. In the present study, we compared the neurotrophic and neuroprotective effects of six other 2,5-diaryl-3,4-dimethyltetrahydrofuran neolignans isolated from the same plant, veraguensin (2), galgravin (3), aristolignin (4), nectandrin A (5), isonectandrin B (6), and nectandrin B (7), with compound 1 in primary cultured rat neurons. Compounds 3-7 promoted neuronal survival and neurite outgrowth, among which compounds 6 and 7 showed neurotrophic activity comparable with that of 1.

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“…Natural neolignans have been isolated from Virola surinamensis and found to be effective against Schistosoma mansoni (Barata et al, 1978). In studies covering infectious diseases, neolignan analogues were synthesized (Barata et al, 1978;Aveniente et al, 2007) and shown to have antimicrobial activity against Leishmania (Barata et al, 2000), Schistosoma (Alves et al, 2002), fungi (Lima et al, 1987) and Mycobacterium tuberculosis H37Rv (De Souza et al, 2011). The most effective analogue, 2-phenoxy-1-phenylethanone (LS-2), showed promising extra-and intracellular antimycobacterial activity and very weak cytotoxicity against V79 cells, J774 macrophages and rat hepatocytes.…”

Section: Research Articlementioning

confidence: 99%