Department of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, N. Tesle 10/V, HR-21000 Split.
Chem Biodivers. 2011 Jun;8(6):1170-81. doi: 10.1002/cbdv.201000370.
Two different volatile isolates from the aerial parts of Cardaria draba (L.) Desv., obtained either by hydrodistillation (Extract I) or by CH(2) Cl(2) extraction subsequent to hydrolysis by exogenous myrosinase (Extract II), were characterized by GC-FID and GC/MS analyses. The main volatiles obtained by hydrodistillation, i.e., 4-(methylsulfanyl)butyl isothiocyanate (1; 28.0%) and 5-(methylsulfanyl)pentanenitrile (2; 13.8%), originated from the degradation of glucoerucin. In Extract I, also volatiles without sulfur and/or nitrogen were identified. These were mostly hexadecanoic acid (10.8%), phytol (10.2%), dibutyl phthalate (4.5%), and some other compounds in smaller percentages. Extract II contained mostly glucosinolate degradation products. They originated from glucoraphanin, viz., 4-(methylsulfinyl)butyl isothiocyanate (3; 69.2%) and 5-(methylsulfinyl)pentanenitrile (4; 4.5%), glucosinalbin, viz., 2-(4-hydroxyphenyl)acetonitrile (5; 7.2%), and glucoerysolin, viz., 4-(methylsulfonyl)butyl isothiocyanate (6; 5.0%). Moreover, the volatile samples were evaluated for their antimicrobial activity using the disc-diffusion method and determining minimum inhibitory concentrations (MIC). All volatile isolates expressed a wide range of growth inhibition activity against both Gram-positive and Gram-negative bacteria and fungi. The MIC values varied between 4 and 128 μg/ml.
从芝麻菜(Cardaria draba(L.)Desv.)的地上部分分别通过水蒸气蒸馏(提取物 I)或通过外源硫代葡萄糖苷酶水解后的 CH(2)Cl(2)提取(提取物 II)获得了两种不同的挥发性混合物,并用 GC-FID 和 GC/MS 分析进行了表征。通过水蒸气蒸馏获得的主要挥发性物质,即 4-(甲基亚磺酰基)丁基异硫氰酸酯(1;28.0%)和 5-(甲基亚磺酰基)戊腈(2;13.8%),来源于葡萄糖异硫氰酸酯的降解。在提取物 I 中,还鉴定出了不含硫和/或氮的挥发性物质。这些主要是十六烷酸(10.8%)、植醇(10.2%)、邻苯二甲酸二丁酯(4.5%)和其他一些含量较少的化合物。提取物 II 主要含有硫代葡萄糖苷降解产物。它们源自萝卜硫素,即 4-(甲基亚磺酰基)丁基异硫氰酸酯(3;69.2%)和 5-(甲基亚磺酰基)戊腈(4;4.5%)、葡萄糖芸薹素,即 2-(4-羟基苯基)乙腈(5;7.2%)和葡萄糖异硫氰酸酯,即 4-(甲基磺酰基)丁基异硫氰酸酯(6;5.0%)。此外,使用圆盘扩散法和测定最小抑菌浓度(MIC)评估了挥发性样品的抗菌活性。所有挥发性混合物对革兰氏阳性和革兰氏阴性细菌和真菌均表现出广泛的生长抑制活性。MIC 值在 4 至 128μg/ml 之间变化。