School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, People's Republic of China.
J Nat Prod. 2010 Feb 26;73(2):270-4. doi: 10.1021/np900670b.
Three unique phenylpropanoyl 2,7-anhydro-3-deoxy-2-octulosonic acid derivatives were isolated from Conyza canadensis (horseweed). Their structures were defined as rel-(1S,2R,3R,5S,7R)-methyl 7-caffeoyloxymethyl-2-hydroxy-3-feruloyloxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (1), rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (2), and rel-(1R,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-feruloyloxy-3-hydroxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (3). Compound 1 and a 5:3 mixture of compounds 2 and 3 were demonstrated to inhibit the catecholamine secretion induced by acetylcholine with IC(50) values of 94.65 and 42.35 microM, respectively, and to inhibit the catecholamine secretion induced by veratridine and high [K(+)] at a dose of 100 microM in cultured bovine adrenal medullary cells.
从加拿大飞蓬（horseweed）中分离得到三个独特的苯丙酰基 2,7-脱水-3-脱氧-2-辛糖酸衍生物。它们的结构被定义为 rel-(1S,2R,3R,5S,7R)-甲基 7-咖啡酰氧基甲基-2-羟基-3-阿魏酰氧基-6,8-二氧杂双环[3.2.1]辛烷-5-羧酸酯（1）、rel-(1S,2R,3R,5S,7R)-甲基 7-阿魏酰氧基甲基-2-羟基-3-阿魏酰氧基-6,8-二氧杂双环[3.2.1]辛烷-5-羧酸酯（2）和 rel-(1R,2R,3R,5S,7R)-甲基 7-阿魏酰氧基甲基-2-阿魏酰氧基-3-羟基-6,8-二氧杂双环[3.2.1]辛烷-5-羧酸酯（3）。化合物 1 和化合物 2 和 3 的 5:3 混合物被证明能抑制乙酰胆碱诱导的儿茶酚胺分泌，其 IC50 值分别为 94.65 和 42.35 μM，并能在 100 μM 剂量下抑制veratridine 和高 [K+] 诱导的牛肾上腺髓质细胞儿茶酚胺分泌。
