ABSTRACT
Objective: To study the chemical constituents in the whole herb of Balanophora involucrate. Methods: The compounds were isolated and purified using polyamide, silica gel colimu, ODS, MCI gel, and semi-preparative HPLC, and their structures were elucidated by means of physicochemical properties and spectroscopic analysis. The anti-inflammatory activities of all the isolated compounds were evaluated using Griess method and ELISA for the determination of LPS-induced NO and IL-6 releases in inflammation cell model induced by LPS. Results: Eleven lignans were isolated from 75% ethyl alcohol extract from the whole herb of B. involucrata and identified as (+)-pinoresinol (1), (+)-5’-hydroxypinoresinol (2), isolariciresinol 4-O-β-D-glucopyranoside (3), (+)-isolariciresinol (4), burselignan (5), (+)-9-acetoxyisolariciresinol (6), yunnanensin A (7), (-)-secoisolariciresinol-4-O-β-D- glucopyranoside (8), (-)-secoisolariciresinol (9), dihydrocubebin (10), and secoisolariciresinol-9’-acetate (11). Conclusion: Among them, compound 11 is a new natural product, and compound 2, 5, 7, 8, and 10 are isolated from the genus of Balanophora for the first time. All compounds showed strong anti-inflammatory activities.
ABSTRACT
OBJECTIVE: To study the chemical constituents from the stems of Acorus tatarinowii Schott. METHODS: The chemical constituents were isolated from the 70% ethanol-soluble extract of the stems of Acorus tatarinowii Schott and purified by a series of column chromatography methods, including MCI, silica gel, Sephadex LH - 20, HPLC and so on, and their structures were identified by physical chemical constants and NMR techniques. RESULTS: A total of twelve compounds were isolated and identified as (7S, 8R) -4, 9'-dihydroxyl-3, 3'-dimethoxyl-7, 8-dihydrobenzofuran-1'-propylneolignan (1), (-) -lyoniresinol (2), dihydrocubebin (3), evofolin B(4), (+) -icariol A2 (5), β-sitosterol(6), (+) -13-hydroxyspathulenol(7), aromadendrane-4β, 10β-diol(8), anomallenodiol( 9), (9CI) -cis-4-(3, 4-dihydroxy-2, 6, 6-trimethyl-1-cyclohexen-1-yl) -2-butanone (10), (3E) -rel-4-[(3R, 4S) -3, 4-dihydroxy- 2, 6, 6 -trimethyl-1-cyclohexen-1-yl]-3-buten-2-one(11), and ixerol B(12), respectively. CONCLUSION: Compounds 2 - 4 and 7 - 12 are isolated from the genus Acorus for the first time, and compound 5 is isolated from this plant for the first time.
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
ABSTRACT: 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