Han Yi-Feng, Zhang Qi, Gao Kun, Jia Zhong-Jian
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. China.
Planta Med. 2005 Jun;71(6):543-7. doi: 10.1055/s-2005-864156.
Four new eudesmanolides were isolated from the whole plant of Sonchus transcaspicus and their structures were elucidated by means of spectroscopic methods, including 2D-NMR (1H-1H COSY, HMQC, HMBC and NOESY) and NOEDS (NOE difference spectra) as 1beta-O-beta-D-glucopyranosyl-5alpha,6beta H-eudesma-3-en-12,6alpha-olide (1), 1beta-O-beta-D-glucopyranosyl-15-O-( p-hydroxyphenylacetyl)-5alpha,6beta H-eudesma-3,11(13)-dien-12,6alpha-olide (2), 1beta-O-beta-D-glucopyranosyl-(6'-O-p-hydroxyphenyl acetate)-15-O-(p-hydroxyphenylacetyl)-5alpha,6beta H-eudesma-3,11(13)-dien-12,6alpha-olide (3) and 1beta-hydroxy-15-O-(p-methoxyphenylacetyl)-5alpha,6beta H-eudesma-3,11(13)-dien-12,6alpha-olide (4). Compounds 1, 2 and 3 showed antibacterial activity against Escherichia coli and Staphylococcus aureus cells. Compounds 2 and 3 were evaluated for their in vitro cytotoxic activity against cultured SMMC-7721 (human hepatoma), HELA (human cervical carcinoma) and B-16 (murine melanoma) cells. The IC50 values for 2 were 108.0, 161.1 and 203.0 microM and those for 3 were 74.1, 117.3 and 135.0 microM, respectively. The structure-activity relationship is discussed.
从跨里海苦苣菜全草中分离出4个新的桉叶烷型倍半萜内酯，通过光谱方法（包括二维核磁共振谱（1H-1H COSY、HMQC、HMBC和NOESY）以及NOEDS（NOE差谱））阐明了它们的结构，分别为1β-O-β-D-吡喃葡萄糖基-5α,6βH-桉叶-3-烯-12,6α-内酯（1）、1β-O-β-D-吡喃葡萄糖基-15-O-（对羟基苯乙酰基）-5α,6βH-桉叶-3,11(13)-二烯-12,6α-内酯（2）、1β-O-β-D-吡喃葡萄糖基-（6'-O-对羟基苯乙酸酯）-15-O-（对羟基苯乙酰基）-5α,6βH-桉叶-3,11(13)-二烯-12,6α-内酯（3）和1β-羟基-15-O-（对甲氧基苯乙酰基）-5α,6βH-桉叶-3,11(13)-二烯-12,6α-内酯（4）。化合物1、2和3对大肠杆菌和金黄色葡萄球菌细胞显示出抗菌活性。对化合物2和3进行了体外细胞毒活性评价，针对培养的SMMC-7721（人肝癌）、HELA（人宫颈癌）和B-16（小鼠黑色素瘤）细胞。化合物2的IC50值分别为108.0、161.1和203.0微摩尔，化合物3的IC50值分别为74.1、117.3和135.0微摩尔。并讨论了构效关系。
