Pham Van Cuong, Ma Ji, Thomas Shannon J, Xu Zhidong, Hecht Sidney M
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901, USA.
J Nat Prod. 2005 Aug;68(8):1147-52. doi: 10.1021/np058013j.
Crude CH2Cl2-MeOH extracts prepared from Alangium javanicum and A. grisolleoides were found to induce DNA strand breakage in the presence of Cu2+ and were subjected to bioassay-guided fractionation to permit identification of the active principle(s). Javaniside (1), a novel alkaloid possessing an unusual monoterpenoid oxindole skeleton, was identified as an active principle contributing to the DNA cleavage activity observed for the crude extract of A. javanicum. Alangiside (2), a tetrahydroisoquinoline monoterpene glucoside widely distributed in the genus Alangium, was also isolated from A. grisolleoides as a new type of Cu2+-dependent DNA cleavage agent. The relative configuration of the asymmetric centers in javaniside was established by analysis of 1H-1H coupling constants and NOESY correlations. Semisynthesis of javaniside from secologanin (3) established the absolute stereochemistry of javaniside.
从爪哇八角枫和灰八角枫中制备的粗二氯甲烷 - 甲醇提取物在Cu2+存在下可诱导DNA链断裂，并进行了生物测定导向的分级分离以鉴定活性成分。爪哇八角枫碱（1）是一种具有不寻常单萜吲哚酮骨架的新型生物碱，被鉴定为对爪哇八角枫粗提物中观察到的DNA切割活性有贡献的活性成分。八角枫苷（2）是一种广泛分布于八角枫属的四氢异喹啉单萜糖苷，也从灰八角枫中分离出来，作为一种新型的Cu2+依赖性DNA切割剂。通过分析1H-1H耦合常数和NOESY相关性确定了爪哇八角枫碱中不对称中心的相对构型。从裂环马钱子苷（3）半合成爪哇八角枫碱确定了爪哇八角枫碱的绝对立体化学。
