Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan.
Faculty of Fisheries, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan.
Fitoterapia. 2020 Sep;145:104639. doi: 10.1016/j.fitote.2020.104639. Epub 2020 May 28.
Bioassay-guided separation of a methanol extract of Tricleocarpa jejuensis by monitoring algicidal activity against the red tide phytoplankton Chattonella antiqua led to the isolation of an active fraction consisting of a mixture of four isomeric compounds. The active compounds were identified as (E)-9-hydroxyoctadec-10-enoic acid (1), (E)-10-hydroxyoctadec-8-enoic acid (2), (E)-11-hydroxyoctadec-12-enoic acid (3) and (E)-12-hydroxyoctadec-10-enoic acid (4) by NMR, IR and mass spectral data. The structures were confirmed by comparison of the NMR and MS data with those of authentic samples of 1-4 obtained by unambiguous syntheses. Synthesized hydroxy acids 1-4 and related compounds were assessed for algicidal activity against C. antiqua and it was found that all of 1-4 had high activity (>80% mortality at 24 h) at a concentration of 20 μg/mL. A structure-activity relationship study using 11 related compounds revealed that the presence of the hydroxyl group is important for the activity and the double bond may be replaced with a triple bond.
生物测定指导下分离的甲醇提取物的 Tricleocarpa jejuensis 通过监测杀藻活性对赤潮浮游植物赤潮对虾导致分离的活性部分组成的混合物的四种同分异构化合物。活性化合物被鉴定为（E）-9-羟基十八烷-10-烯酸（1），（E）-10-羟基十八烷-8-烯酸（2），（E）-11-羟基十八烷-12-烯酸（3）和（E）-12-羟基十八烷-10-烯酸（4）通过核磁共振，红外和质谱数据。结构通过比较 NMR 和 MS 数据与那些真实样品 1-4 获得明确的合成。合成的羟基酸 1-4 和相关化合物的杀藻活性对 C. antiqua 发现所有的 1-4 有高活性（>80%死亡率在 24 h）在浓度为 20 μg/mL。结构活性关系研究用 11 个相关化合物表明，羟基的存在是重要的活性和双键可能被三键取代。
