Bioactive Alkaloids from Indole-3-carbinol Exposed Culture of Daldiniaeschscholzii
Bioactive Alkaloids from Indole-3-carbinol Exposed Culture of Daldiniaeschscholzii
复制标题
Daldiniaeschscholzii 暴露培养物中吲哚-3-甲醇的生物活性生物碱
DOI：
10.1002/cjoc.201800160
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发表时间：
2018-08-01
影响因子：
5.4
通讯作者：
Tan, Ren Xiang
中科院分区：
文献类型：
--
作者：
Lin, Li Ping;Tan, Ren Xiang
从经吲哚-3-甲醇（I3 C）处理的黑炭层壳（Daldinia eschscholzii）中分离得到两个新的吲哚类化合物，分别命名为dalesindoloids A（1）和B（3），以及沿着的3-（1H-吲哚-3-甲基）-2-羟吲哚（2）。2的绝对构型通过电子圆二色性（ECD）光谱的量子化学计算确定。达来吲哚类化合物A和B对HL-60细胞有细胞毒作用，IC_（50）分别为1.0和7.4 mol/L，对金黄色葡萄球菌有抑制作用（MIC：9.1 mol/L）。来自I3 C暴露的真菌培养物的生物碱的同时表征突出了2，3-环氧吲哚啉基序可以转化为内酰胺和吲哚啉-3-酮部分。这是第一次描述的2，3-环氧吲哚啉的化学多功能性和Wagner-Meerwein重排（WMR）反应在微生物培养。
Two new and rare bioactive indoles named dalesindoloids A (1) and B (3), along with 3-(1H-indole-3ylmethyl)-2-oxindole (2), were characterized from the indole-3-carbinol (I3C)-exposed culture of Daldinia eschscholzii. The absolute configuration of 2 was determined by quantum chemical calculations of the electronic circular dichroism (ECD) spectrum. Dalesindoloids A and B were cytotoxic against the leukemia HL-60 cell line with the IC50 values of 1.0 and 7.4 mol/L, respectively, with the former being inhibitory on Staphylococcus aureus (MIC: 9.1 mol/L). The simultaneous characterization of the alkaloids from the I3C-exposed fungal culture highlighted that the 2,3-epoxyindoline motif can be transformed into both lactam and indolin-3-one moieties. This is the first-time description of the 2,3-epoxyindoline chemical versatility and Wagner-Meerwein rearrangement (WMR) reaction in the microbial culture.