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Ciliatonoids D–M, highly modified limonoids from the twigs of Toona ciliata
Tetrahedron ( IF 2.1 ) Pub Date : 2024-03-14 , DOI: 10.1016/j.tet.2024.133942
Cui-Ping Liu , Yuan Gao , Wen-Jing Li , Cheng-Hui Xu , Qun-Fang Liu , Jian Ding , Jin-Xin Zhao , Jian-Min Yue

A new ring-intact limonoid, ciliatonoid D (), five new 7,8- limonoids, ciliatonoids E–I (–), three new 7,8--29-nor limonoids, ciliatonoids J–L (–), and a new 7,8:9,11- limonoid, ciliatonoid M (), together with eleven known limonoids were isolated from the twigs of . Their structures were established by comprehensive analyses of spectroscopic, electronic circular dichroism, single-crystal X-ray diffraction data. Compound bears an uncommon 1,30-oxygen bridge. Compound represents a rare example of a structure with 9,11- limonoid from Meliaceae. The orientation of the 14,15-epoxy moiety in a known limonoid, toonayunnanae C (), was revised as in a -orientation by quantum NMR calculations with ML--DP4 probability analysis. Compound and a known analogue, toonanoronoid C (), were found to show modest in vitro cytotoxicity against HL-60 (human premyelocytic leukemia) and P-388 (murine leukemia) cell lines.

中文翻译:

Ciliatonoids D–M,高度改良的柠檬苦素类化合物,来自香椿的嫩枝

一种新的环完整柠檬苦素类纤毛素 D ()、五种新的 7,8- 柠檬苦素类、纤毛素 E–I (–)、三种新的 7,8--29-nor 柠檬苦素类、纤毛素 J–L (–) 和一种新的 7,8:9,11- 柠檬苦素类化合物、纤毛素 M () 以及 11 种已知的柠檬苦素类化合物是从 的小枝中分离出来的。通过对光谱、电子圆二色性、单晶X射线衍射数据的综合分析,确定了它们的结构。化合物具有罕见的 1,30-氧桥。该化合物代表了来自楝科的 9,11- 柠檬苦素结构的罕见实例。通过量子 NMR 计算和 ML--DP4 概率分析,将已知的柠檬苦素类香椿素 C () 中 14,15-环氧部分的取向修正为 β 取向。化合物和已知类似物 toonanoronoid C () 被发现对 HL-60(人早幼粒细胞白血病)和 P-388(鼠白血病)细胞系表现出适度的体外细胞毒性。
更新日期:2024-03-14
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