RESUMO
A new compound, illiciumflavane acid (1), along with 13 known compounds (2-14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC50 values of 4.63 µM and 9.17 µM, respectively.
Assuntos
Flavonoides/isolamento & purificação , Frutas/química , Illicium/química , Antineoplásicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Dicroísmo Circular , Cisplatino/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/química , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Rotação OcularRESUMO
Four new lignans, strebluslignanol F (1), (7'R,8'S,7â³R,8â³S)-erythro-strebluslignanol G (2), isomagnaldehyde (3) and isostrebluslignanaldehyde (4), along with 12 known lignans (5-16) were isolated from the ethyl acetate-soluble part of MeOH extract of the root of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans were evaluated for their anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line. The most active lignans, (7'R,8'S,7â³R,8â³S)-erythro-strebluslignanol G, magnolol, isomagnolol and isolariciresinol, exhibited significant anti-HBV activities with IC50 values of 1.58, 2.03, 10.34 and 3.67 µM, respectively, for HBsAg with no cytotoxicity, and of 3.24, 3.76, 8.83 and 14.67 µM, respectively, for HBeAg with no cytotoxicity. (7'R,8'S,7â³R,8â³S)-erythro-Strebluslignanol G and magnolol showed significant anti-HBV activities to inhibit the replication of HBV DNA with the IC50 values of 9.02 and 8.67 µM, respectively.
Assuntos
Antivirais/farmacologia , Vírus da Hepatite B/efeitos dos fármacos , Lignanas/farmacologia , Moraceae/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Antivirais/química , Antivirais/isolamento & purificação , Relação Dose-Resposta a Droga , Células Hep G2 , Humanos , Lignanas/química , Lignanas/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Relação Estrutura-AtividadeRESUMO
Seven compounds, (7'S,8'S)-trans-streblusol A, (7'R,8'S)-erythro-streblusol B, (7'S,8'S)-threo-streblusol B, 8'R-streblusol C, streblusquinone, (8R,8'R)-streblusol D, and streblusol E, along with 15 known compounds (8-22) were isolated from the n-butanol-soluble part of the MeOH extract of stem bark of Streblus asper. Their structures were elucidated through application of extensive spectroscopic methods, including ESI-MS and 2D NMR spectroscopy (HMQC and HMBC). The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans and allylbenzene derivatives were evaluated for their anti-HBV activities in vitro using the HBV transfected Hep G2.2.15 cell line. The most active compounds, magnolol and 9-ß-xylopyranosyl-isolariciresinol, exhibited significant anti-HBV activities with IC(50) values of 2.03 and 6.58µM for secretion of HBsAg, with no cytotoxicity, and of 3.76 and 24.86µM for secretion of HBeAg, with no cytotoxicity.
Assuntos
Antivirais/isolamento & purificação , Antivirais/farmacologia , Vírus da Hepatite B/efeitos dos fármacos , Moraceae/química , Casca de Planta/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Células Hep G2 , Antígenos de Superfície da Hepatite B/metabolismo , Antígenos E da Hepatite B/metabolismo , Humanos , Concentração Inibidora 50 , Metanol/químicaRESUMO
The extracts from leaves, heartwood, barks and roots of the Streblus asper were investigated for anti-HBV activities, separately. The results suggested that the MeOH extracts of the heartwood, barks, and roots exhibited good anti-HBV activities. Further investigations displayed that ethyl acetate and n-butanol soluble parts of their MeOH extracts showed more significant anti-HBV activities. Moreover, a new lignan, together with 11 known compounds, was isolated from n-butanol-soluble part of MeOH extract of the roots of S. asper. The structures were elucidated by spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC) and HR-EI-MS experiments. Compounds 1-3 were evaluated for their anti-HBV activities. Honokiol showed significant anti-HBV activity with IC(50) values of 3.14µM and 4.74µM for HBsAg and HBeAg with no cytotoxicity respectively, while lamivudine (3TC, positive control) exhibited weak anti-HBV activity with IC(50) values of 11.81µM and 25.80µM for HBsAg and HBeAg respectively.