Chang Su-Yen, Cheng Ming-Jen, Peng Chien-Fang, Chang Hsun-Shuo, Chen Ih-Sheng
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, R.O.C.
Chem Biodivers. 2008 Dec;5(12):2690-8. doi: 10.1002/cbdv.200890223.
Three racemic butanolides, majorenolide (1), majorynolide (2), and majoranolide (3), with 18 known compounds, including ten butanolides, i.e., litsenolide A(2) (4), litsenolide B(2) (5), litsenolide C(1) (6), litsenolide C(2) (7), hamabiwalactone A (8), hamabiwalactone B (9), litseakolide A (10), litseakolide B (11), isoobtusilactone (12), and obtusilactone (13); one lignan, i.e., (+/-)-syringaresinol (14), two flavans, i.e., (+)-catechin (15), and (-)-epicatechin (16), one coumarin, i.e., scopoletin (17), and four steroids, i.e., a mixture of beta-sitosterol (18) and stigmasterol (19), and a mixture of beta-sitosteryl-3-O-beta-D-glucoside (20) and stigmasteryl-3-O-beta-D-glucoside (21) were isolated from the root of Lindera akoensis. The structures of the isolates were elucidated by in-depth spectroscopic analysis. Compounds 1-3 were previously assigned a delta-lactone structure, which was then revised to a gamma-lactone structure, based on 1D-NMR data. The cigar-HMBC technique was used to confirm the accuracy of the gamma-lactone structure, and the zero [alpha] (20)_D value of compounds 1-3 suggested that they were considerably racemized. Nine butanolides 1-3, 4-8, and 10 showed antimycobacterial activities against M. tuberculosis H(37)Rv, with MIC values of 15-50 microg/ml.
从香叶树的根中分离出三种外消旋丁烯内酯，即大根香叶烯内酯（1）、大根香叶炔内酯（2）和大根香叶醇内酯（3），以及18种已知化合物，其中包括10种丁烯内酯，即利森内酯A(2)（4）、利森内酯B(2)（5）、利森内酯C(1)（6）、利森内酯C(2)（7）、滨玉蕊内酯A（8）、滨玉蕊内酯B（9）、乌药内酯A（10）、乌药内酯B（11）、异鹅掌楸内酯（12）和鹅掌楸内酯（13）；1种木脂素，即（±）-丁香树脂酚（14），2种黄烷，即（+）-儿茶素（15）和（-）-表儿茶素（16），1种香豆素，即东莨菪素（17），以及4种甾体，即β-谷甾醇（18）和豆甾醇（19）的混合物，以及β-谷甾醇-3-O-β-D-葡萄糖苷（20）和豆甾醇-3-O-β-D-葡萄糖苷（21）的混合物。通过深入的光谱分析阐明了分离物的结构。化合物1-3先前被指定为δ-内酯结构，然后根据一维核磁共振数据将其修订为γ-内酯结构。采用雪茄-HMBC技术确认γ-内酯结构的准确性，化合物1-3的零α_D值表明它们已大量消旋。9种丁烯内酯1-3、4-8和10对结核分枝杆菌H(37)Rv显示出抗分枝杆菌活性，最低抑菌浓度值为15-50微克/毫升。
