State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
Org Lett. 2013 Sep 6;15(17):4450-3. doi: 10.1021/ol401992s. Epub 2013 Aug 12.
Two novel spirooliganones A (1) and (2), a pair of spiro carbon epimers, with a rare dioxaspiro skeleton were isolated from the roots of Illicium oligandrum. The structures were fully determined by spectroscopic analysis and chemical methods, especially modified Mosher's method, and X-ray diffraction analysis. Spirooliganone B was found to exhibit more potent activities against coxsackie virus B3 and influenza virus A (H3N2) (IC50 3.70-5.05 μM) than spirooliganone A. The biosynthetic pathway involving a hetero-Diels-Alder reaction of the epimers was proposed.
从八角莲根部分离得到了两种新的螺环橄榄烷酮 A（1）和（2），它们是一对具有罕见的二氧杂螺骨架的螺环碳差向异构体。通过光谱分析和化学方法，特别是改良的 Mosher 法和 X 射线衍射分析，确定了它们的结构。螺环橄榄烷酮 B 对柯萨奇病毒 B3 和甲型流感病毒（H3N2）的活性比螺环橄榄烷酮 A 更强（IC50 为 3.70-5.05 μM）。提出了涉及差向异构体的杂 Diels-Alder 反应的生物合成途径。
