Wessels M, König G M, Wright A D
Institute for Pharmaceutical Biology, Technical University of Braunschweig, Mendelssohnstrasse 1, D-38106 Braunschweig, Germany.
J Nat Prod. 2000 Jul;63(7):920-8. doi: 10.1021/np9905721.
Three distinct samples of the sea hare Aplysia dactylomela from two different locations around Tenerife (Spain) were investigated for their secondary metabolite content. The investigation resulted in the isolation of five new natural products (1, 2, 5-7), a number of compounds known from red algae of the genera Laurencia (4, 8-14) and Plocamium (17-19), and three known sea-hare metabolites (3, 15, 16). This is the first report of monoterpenes (17-19) from A. dactylomela. All structures were determined mainly by spectroscopic methods (1D and 2D NMR, MS, IR). Compounds 11, 14, 15, and 17 demonstrated significant cytotoxicity toward three cancer cell lines (HM02, HEP G2, and MCF 7; IC(50) for 11, 7.0 to <1.0 microg/mL; 14, <1.0 microg/mL; 15, 17 to <1.0 microg/mL; 17, 1.0 to 1.5 microg/mL). Compounds 3, 8, 9, 11, 15, 18, and 19 exhibited activity in a brine shrimp bioassay in the range of 100% lethality within 24 h to 40% after 48 h. Metabolites 11, 14, 15, and 19 showed moderate antimicrobial activities (2-25 mm total/growth inhibition of several organisms), with 19 also being strongly algicidal (MIC 7-11 microg/filter disk).
对采集自西班牙特内里费岛附近两个不同地点的三种不同样本的海兔（Aplysia dactylomela）进行了次生代谢产物含量研究。研究结果分离出了五种新的天然产物（1、2、5 - 7），一些从劳伦氏藻属（Laurencia，4、8 - 14）和海索面属（Plocamium，17 - 19）红藻中已知的化合物，以及三种已知的海兔代谢产物（3、15、16）。这是首次从海兔（Aplysia dactylomela）中报道单萜类化合物（17 - 19）。所有结构主要通过光谱方法（一维和二维核磁共振、质谱、红外光谱）确定。化合物11、14、15和17对三种癌细胞系（HM02、HEP G2和MCF 7）表现出显著的细胞毒性（11的IC50为7.0至<1.0μg/mL；14为<1.0μg/mL；15为17至<1.0μg/mL；17为1.0至1.5μg/mL）。化合物3、8、9、11、15、18和19在卤虫生物测定中表现出活性，在24小时内致死率为100%，48小时后为40%。代谢产物11、14、15和19表现出中等抗菌活性（对几种生物体的总生长抑制为2 - 25mm），其中19还具有强烈的杀藻活性（最低抑菌浓度为7 - 11μg/滤纸片）。
