Avaliação da atividade antimicobacteriana da lignana diidrocubebina extraída da Piper cubeba e de seus derivados semissintéticos

Abstract

RESUMO:A atividade antimicobacteriana de diidrocubebina (1), uma lignana dibenzilbutanodioica obtida a partir de extrato etanólico de sementes da Piper cubeba, e seus derivados foram avaliados in vitro contra três diferentes cepas de Mycobacterium utilizando o método de microdiluição. Dentre as lignanas avaliadas 3 e 4 foram as mais ativas, exibindo valores de CIM de 62,5 µg/mL contra M. avium e M. tuberculosis, respectivamente. Os derivados 2-6 obtidos por síntese parcial possuem diferentes substituintes nos carbonos 9 e 9 ', que alteram polaridade, solubilidade e limitam as rotações livres entre C8-C8' em relação de material (1) de partida. As diferenças estruturais entre estes compostos podem fornecer informações importantes sobre a relação estrutura-atividade antimicobacteriana do esqueleto dibenzilbutanodioico, obtido a partir de fonte natural, como um possível alvo para o desenvolvimento de drogas mais potentes contra a tuberculose. Palavras-chave: lignanas, diidrocubebina, atividade antimicobacteriana, Piper cubebaABSTRACT: Evaluation of antimycobacterial activity of dihydrocubebin lignan extracted from Piper cubeba and its semisynthetic derivatives. The antimycobacterial activity of the dihydrocubebin (1), a dibenzylbutanedioiclignan obtained from ethanolic extract of Piper cubeba seeds, and its derivatives were examined in vitro against three different strains of Mycobacterium using amicrodilution method. Among the lignans evaluated, the 3 and 4 samples were the most active ones, displaying MIC values of 62.5 μg/mL against M. avium and M. tuberculosis, respectively. The derivatives 2-6, obtained for partial synthesis, had different substituents in the carbons 9 and 9', fact thatalters the polarity, solubility and restricts the free rotations between the bonds C8-C8' in relation to the starting material (1). The structural differences among these compounds provide important information about the antimycobacterial structure-activity relationship of the dibenzylbutanodioic skeleton, obtained from natural source, such as a possible target for the development of more powerful drugs against tuberculosis.

Performance and Serum Biochemical Profile of Broiler Chickens Supplemented with Piper Cubeba Ethanolic Extract

“…The ethanolic extract was obtained according to the methodology described by Laurentiz et al (2015) from the seeds of Piper cubeba purchased from Floral Seed Company®, Dehradun, India.…”

COX Inhibition Profiles and Molecular Docking Studies of the Lignan Hinokinin and Some Synthetic Derivatives

“…According to the methods reported by Da Silva et al, [4] 1 was extracted from the Piper cubeba fruit and, after subsequent teratment with nitric acid, 3 was isolated. The reduction of 1 with lithium aluminum hydride in THF provided (after purification by silica gel column chromatography in hexane:ethylacetate, 1 : 1) dihydrocubebin (2), as previusly reported by Laurentiz et al [29] All compounds displayed purity > 95 %, as determined by HPLC and NMR analyses and are in agreement with data published in the literature. (supplmentary material).…”

Medicinal Attributes of Lignans Extracted from Piper Cubeba: Current Developments

“…(−)‐Hinokinin was moderately active against M. tuberculosis , with a minimum inhibitory concentration of 62.5 μg mL −1 . These are promising results that are important in the search for biologically active natural products, as they highlight the fact that new approaches for the prevention, treatment, and cure of tuberculosis are extremely important …”