氯代茶螺烷A和B，由茶树内生真菌茶拟盘多毛孢菌通过狄尔斯-阿尔德反应生成的螺缩酮类化合物
Chlorotheolides A and B, Spiroketals Generated via Diels-Alder Reactions in the Endophytic Fungus Pestalotiopsis theae.
作者信息
Liu Ling, Han Yu, Xiao Junhai, Li Li, Guo Liangdong, Jiang Xuejun, Kong Lingyi, Che Yongsheng
机构信息
State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences , Beijing 100101, People's Republic of China.
State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology , Beijing 100850, People's Republic of China.
出版信息
J Nat Prod. 2016 Oct 28;79(10):2616-2623. doi: 10.1021/acs.jnatprod.6b00550. Epub 2016 Oct 12.
Chlorotheolides A (1) and B (2), two new spiroketals possessing the unique [4,7]methanochromene and dispiro-trione skeletons, respectively, and their putative biosynthetic precursors, 1-undecen-2,3-dicarboxylic acid (3) and maldoxin (4), were isolated from the solid substrate fermentation of the plant endophytic fungus Pestalotiopsis theae (N635). Their structures were elucidated based on NMR spectroscopic data and electronic circular dichroism calculations. Biogenetically, compounds 1 and 2 could be generated from the co-isolated 3 and 4 via Diels-Alder reactions. Chlorotheolide (2) showed an antiproliferative effect against the human tumor cell line HeLa and induced an autophagic process in the cells.
从植物内生真菌茶拟盘多毛孢（N635）的固体基质发酵物中分离得到了氯硫代内酯A（1）和B（2），这两种新的螺环缩酮分别具有独特的[4,7]亚甲基色烯和双螺环三酮骨架，以及它们可能的生物合成前体1-十一碳烯-2,3-二羧酸（3）和麦多克辛（4）。基于核磁共振光谱数据和电子圆二色性计算确定了它们的结构。从生源合成角度来看，化合物1和2可能是通过双烯加成反应由共分离得到的3和4生成的。氯硫代内酯（2）对人肿瘤细胞系HeLa显示出抗增殖作用，并诱导细胞发生自噬过程。
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