Spiroalanpyrroids A and B, sesquiterpene alkaloids with a unique spiro-eudesmanolide-pyrrolizidine skeleton from Inula helenium
Spiroalanpyrroids A and B, sesquiterpene alkaloids with a unique spiro-eudesmanolide-pyrrolizidine skeleton from Inula helenium
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螺环吡咯烷 A 和 B，倍半萜生物碱，具有来自旋覆花的独特螺环-桉内酯-吡咯里西啶骨架
DOI：
10.1039/c9qo01248f
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发表时间：
2020
影响因子：
5.4
通讯作者：
Jianqing Yu
中科院分区：
文献类型：
--
作者：
You-Sheng Cai;Zi Wu;Xiao-Qin Zheng;Cong Wang;Jian-Rong Wang;Xin-Xin Zhang;Guofu Qiu;Kongkai Zhu;Shugeng Cao;Jianqing Yu
旋螺吡咯烷 A (1) 和 B (2) 是两种倍半萜生物碱，具有前所未有的 eudesmanolide-pyrrolizidine spiro[5.5] 框架，与两种新的倍半萜-氨基酸加合物 helenalanprolines A (3) 和 B (4) 一起从 Inula helenium 的根中分离出来。通过光谱数据分析、ECD 计算和单晶 X 射线衍射分析阐明了它们的结构。为1和2提出了一条合理的生物合成途径。生物测定表明，化合物3和4显着抑制脂多糖诱导的RAW264.7巨噬细胞中一氧化氮的产生，IC50值分别为15.8和13.5 μM。
Spiroalanpyrroids A (1) and B (2), two sesquiterpene alkaloids with an unprecedented eudesmanolide–pyrrolizidine spiro[5.5] framework, were isolated together with two new sesquiterpene-amino acid adducts, helenalanprolines A (3) and B (4), from the roots of Inula helenium. Their structures were elucidated by spectroscopic data analysis, ECD calculations, and single-crystal X-ray diffraction analysis. A plausible biosynthetic pathway was proposed for 1 and 2. Bioassays showed that compounds 3 and 4 significantly inhibited nitric oxide production in lipopolysaccharide-induced RAW264.7 macrophages with IC50 values of 15.8 and 13.5 μM, respectively.