RESUMO
Fourteen chemical constituents, including 5-hydroxy-4-methoxy-1-tetralone(1), 4,8-dihydroxy-1-tetralone(2), 4,5-dihydroxy-α-tetralone(3), blumenol B(4), dehydrovomifoliol(5), megastigm-5-ene-3,9-diol(6), juglanin B(7), blumenol C(8), loliolide(9), oleracone B(10), syringarsinol(11), pinoresinol(12), methyl 4-hydroxy-3-methoxybenzoate(13), and isovanillic acid(14), were isolated from the dichloromethane fraction of 95% methanol extract of green walnut husks by silica gel and MCI column chromatography, and Pre-HPLC. Their structures were determined by spectroscopic methods, such as NMR, MS and so on. Among them, compounds 1, 4-6, 8-13 were isolated from the green walnut husks for the first time, and compounds 4-6, 8, 10, 12, 13 were isolated from the Juglans genus for the first time. All of isolates were detected their inhibitory activities against HeLa, HGC-27 and Ht-29 cell lines by the MTT assay. The result showed that compounds 2, 3, 7, 9 and 11 exhibited inhibitory activity against the tested cell line. The IC_(50) of 7 were 26.5, 9.0, 25.4 μmol·L~(-1), respectively.
Assuntos
Humanos , Antineoplásicos Fitogênicos , Farmacologia , Cromatografia Líquida de Alta Pressão , Células HT29 , Células HeLa , Juglans , Química , Estrutura Molecular , Compostos Fitoquímicos , Farmacologia , Extratos Vegetais , QuímicaRESUMO
Objective To study the lignans chemical constituents from Diaphragma Juglandis Fructus and their activity of inhibiting HIV. Methods The constituents were isolated from Diaphragma Juglandis Fructus and purified by column chromatography, and the structures were identified by spectra analysis and chemical methods.The activity of anti-HIV-1 were detected by LEDGF/p75-IN proteins complex ELISA kit. Results Sixteen compounds were isolated from Diaphragma Juglandis Fructus and the structures were identified as (-)-syringaresinol (1), (+)-pinoresinol (2), (+)-(7R,7’R,7″S,7’’’S,8S,8’S,8″S,8’’’S)-4″,4’’’-dihydroxy-3,3’,3″,3’’’,5,5’- hexamethoxy-7,9’;7’,9-diepoxy-4,8″;4’,8’’’-bisoxy-8,8’-dineolignan-7″,7’’’,9″,9’’’-tetraol (3), 2,3-dihydroxy-1-(4’-hydroxy-3’-methoxy- phenyl)-propan-1-one (4), 3-hydroxy-1-(4’-hydroxy-3’-methoxyphenyl)-propan-1-one (5), 3’,4’-dimethoxyphenylpropanediol (6), (2S)-3,3-di-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol (7), 3-hydroxy-1-(4’-hydroxy-3’,5’-dimethoxy phenyl)-propan-1-one (8), (1R,5R,6R)-6-{4’-O-[8″-(7″-(4″-hydroxy-3″-methoxyphenyl)) glyceol]-3’,5’-dimethoxyphenyl}-3,7-dioxabicyclo [3.3.0] octan-2-one (9), curcasinlignan B (10), evofolin-B (11), (7S,8R)-dihydrodehydrodiconiferyl alcohol (12), pinnatifidanin C I (13), (+)-(7S,8S)-4,1’-dihydroxy-3,3’,5’-trimethoxy-7,8,9-trinor-8,4’-oxyneolignan-7,9-diol (14), dysosmarol (15), and 1-(4’-hydroxy-3’-methoxyphenyl)-2- [4″-(3-hydroxypropyl)-2″,6″-dimethoxyphenoxy]-propane-1,3-diol (16). Conclusion All compounds are isolated from Diaphragma Juglandis Fructus for the first time. Compound 13 has the potential activity of inhibiting HIV-1.