分心木中的木脂素类化学成分及其抗HIV活性研究

目的研究分心木Diaphragma Juglandis Fructus中的木脂素类化学成分及其抗人免疫缺陷病毒(HIV)活性。方法运用柱色谱方法对分心木的95%甲醇提取物进行分离纯化,结合波谱技术与理化常数鉴定结构,通过LEDGF/p75-IN蛋白复合体ELISA筛选模型对化合物进行抗HIV活性筛选。结果从分心木95%甲醇提取物中分离得到16个木脂素类化合物,分别鉴定为(-)-丁香脂素(1)、(+)-松脂素(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,′-dineolignan-7″,7′′′,9″,9′′′-tetraol(3)、2,3-二羟基-1-(4′-羟基-3′-甲氧基苯基)-丙-1-酮(4)、3-羟基-1-(4′-羟基-3′-甲氧基苯基)-丙-1-酮(5)、3′,4′-二甲氧基苯丙二醇(6)、(2S)-3,3-二-(4-羟基-3-甲氧基苯基)-丙-1,2-二醇(7)、3-羟基-1-(4′-羟基-3′,5′-二甲氧基苯基)-丙-1-酮(8)、(1R,5R,6R)-6-{4′-O-8″-(7″-(4″-hydroxy-3″-methoxyphenyl))glyceol]-3′,5′-dimethoxyphenyl}-3,7-dioxabicyclo3.3.0]octan-2-one(9)、curcasinlignan B(10)、evofolin-B(11)、(7S,8R)-dihydrodehydrodiconiferyl alcohol(12)、pinnatifdanin C I(13)、(+)-(7S,8S)-4,1′-dihydroxy-3,3′,5′-trimethoxy-7,8,9-trinor-8,4′-oxyneolignan-7,9-diol(14)、八角莲醇(15)、1-(4′-羟基-3′-甲氧基苯基)-2-4″-(3-羟丙基)-2″,6″-二甲氧基苯基]-丙-1,3-二醇(16)。结论所有化合物均为首次从分心木中分离得到,其中化合物13具有潜在的抑制HIV-1的活性。

Lignans chemical constituents from Diaphragma Juglandis Fructus and activity of inhibiting HIV

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-dioxabicyclo3.3.0] 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.