Garciyunnanimines A–C, novel cytotoxic polycyclic polyprenylated acylphloroglucinol imines from Garcinia yunnanensis,Organic Chemistry Frontiers

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Garciyunnanimines A–C, novel cytotoxic polycyclic polyprenylated acylphloroglucinol imines from Garcinia yunnanensis
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-07-28 00:00:00 , DOI: 10.1039/c7qo00485k
Dan Zheng _{1,

2,

3,

4} , Hong Zhang _{1,

2,

3,

4} , Chang-Wu Zheng _{1,

2,

3,

4,

5} , Yuan-Zhi Lao _{1,

2,

3,

4} , Dan-Qing Xu _{1,

2,

3,

4} , Lian-Bo Xiao _{3,

4,

6,

7,

8} , Hong-Xi Xu _{1,

2,

3,

4,

6}

Affiliation

Three novel polycyclic polyprenylated acylphloroglucinol imines (PPAP imines), garciyunnanimines A–C (1–3), which contain unprecedented imine functionality at C-10, together with their presumed biogenetic precursors, guttiferone K (6), garcinol (7) and oblongifolin C (8), were isolated from Garcinia yunnanensis. The imines’ synthesis pathways and structures were elucidated by conversion of the known PPAPs 6–8 to the corresponding imines 1–3 in good yields in the presence of ammonia in dioxane and acetic acid. Using the established method, two new PPAP imine derivatives, garciyunnanimines D and E (4 and 5), were easily synthesized using the corresponding PPAPs, oblongifolins A and B (9 and 10). Structures of the new compounds were assigned by spectroscopic analysis and verified by biomimetic conversion and calculations of the ECD (electron circular dichroism) spectra. In addition, the cytotoxicities of these compounds were evaluated using a CCK-8 assay against three human cancer cell lines, A549, HepG2, and RPMI-8226.

中文翻译：

Garciyunnanimines A–C，来自云南藤黄的新型细胞毒性多环多亚丙基酰基间苯三酚亚胺

三种新颖的多环多烯丙基化酰基间苯三酚亚胺（PPAP亚胺），garciyunnanimines A–C（1-3），在C-10处含有空前的亚胺官能团，以及其推测的生物遗传前体，guttiferone K（6），garcinol（7）和oblongifolin C（8），从云南藤黄中分离得到。亚胺的合成途径和结构通过在二恶烷和乙酸中存在氨的情况下，将已知的PPAP 6-8转化为相应的亚胺1-3来阐明。使用已建立的方法，两个新的PPAP亚胺衍生物garciyunnanimines D和E（4和5），很容易使用相应的PPAPs合成，长链富勒烯A和B（9和10）。通过光谱分析确定新化合物的结构，并通过仿生转化和ECD（电子圆二色性）光谱计算来验证新化合物的结构。另外，使用CCK-8测定法评估了这些化合物对三种人类癌细胞系A549，HepG2和RPMI-8226的细胞毒性。

更新日期：2017-10-25

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