Department of Chemistry, Centre for Analysis and Synthesis, Lund University, 22100 Lund, Sweden.
Instituto de Investigaciones Farmaco Bioquimicas, Universidad Mayor de San Andres, La Paz, Bolivia.
Molecules. 2021 Feb 15;26(4):1019. doi: 10.3390/molecules26041019.
The fractionation of an ethanol extract of the bark of yielded four novel limonoids (trichilinones A-D, -), with five fused rings and related to the hortiolide-type limonoids. Starting with an ε-lactone, which is α,β-unsaturated in trichilinones A and D ( and ), attached to a tetrahydrofuran ring that is connected to an unusual bicyclo [5.1.0] hexane system, joined with a cyclopentanone with a 3-furanyl substituent [(2-oxo)-furan-(5)-3-yl in trichilinone D ()], the four compounds isolated display a new 7/5/3/5/5 limonoid ring system. Their structures were established based on extensive analysis of NMR spectroscopic data. As the crude extract possessed anti-leishmanial properties, the compounds were assayed for cytotoxic and anti-parasitic activities in vitro in murine macrophages cells (Raw 264.7) and leishmania promastigotes ( and ), respectively. The compounds showed moderate cytotoxicity (approximately 70 μg/mL), but are not responsible for the leishmanicidal effect of the extract.
从 的树皮乙醇提取物中分离得到四个新的柠檬苦素（三藜啶酮 A-D，-），具有五个稠合环，与hortiolide 型柠檬苦素有关。从 ε-内酯开始，它在三藜啶酮 A 和 D（和）中是 α，β-不饱和的，连接到一个四氢呋喃环，与一个不寻常的双环 [5.1.0] 己烷系统相连，与一个带有 3-呋喃基取代基的环戊酮相连（在三藜啶酮 D 中为（2-氧代）呋喃-（5）-3-基 ()），分离得到的四个化合物显示出一个新的 7/5/3/5/5 柠檬苦素环系统。根据 NMR 光谱数据的广泛分析确定了它们的结构。由于粗提取物具有抗利什曼原虫的特性，因此在体外分别在鼠巨噬细胞（Raw 264.7）和利什曼原虫前鞭毛体（和）中对化合物进行了细胞毒性和抗寄生虫活性测定。这些化合物表现出中等的细胞毒性（约 70 μg/mL），但不是提取物的杀利什曼原虫作用的原因。
