Isolation, Stereochemical Study, and Antioxidant Activity of Benzofuranone Derivatives from a Mangrove-derived Fungus Eurotium rubrum MA-150
Isolation, Stereochemical Study, and Antioxidant Activity of Benzofuranone Derivatives from a Mangrove-derived Fungus Eurotium rubrum MA-150
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红树林真菌红色散囊菌 MA-150 中苯并呋喃酮衍生物的分离、立体化学研究和抗氧化活性
DOI：
10.1002/chir.22613
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发表时间：
2016-08-01
期刊：
影响因子：
2
通讯作者：
Wang, Bin-Gui
中科院分区：
文献类型：
--
作者：
Meng, Ling-Hong;Mandi, Attila;Wang, Bin-Gui
从红散囊菌（Eurotium rubrum MA-150）的培养物中分离并鉴定了一种2-苯并呋喃-1（3 H）-酮衍生物[（-）-1和（+）-1]和四种已知类似物（2，3，4，5）的对映体。通过核磁共振（NMR）数据的详细解释确定了它们的结构，并且通过单晶X射线衍射分析确认了（+/-）-1的结构。通过在线高效液相色谱-电子圆二色性（HPLC-ECD）测量和时间依赖性密度泛函理论-电子圆二色性（TDDFT-ECD）计算确定对映异构体（-）-1和（+）-1的绝对构型。化合物（+/-）-1、2和3具有较强的DPPH自由基清除活性，IC 50值分别为1.23、2.26和3.99 g/mL。Chirality 28：581-584，2016. (c)2016 Wiley Periodicals，Inc.
Enantiomers of a 2-benzofuran-1(3H)-one derivative [(-)-1 and (+)-1] and four known analogs (2, 3, 4, 5) were isolated and identified from the culture extract of Eurotium rubrum MA-150, a fungus obtained from the mangrove-derived rizospheric soil. Their structures were established by detailed interpretation of nuclear magnetic resonance (NMR) data and the structure of (+/-)-1 was confirmed by single-crystal X-ray diffraction analysis. The absolute configuration of the enantiomers (-)-1 and (+)-1 was determined by means of online high-performance liquid chromatography - electronic circular dichroism (HPLC-ECD) measurements and time-dependent Density Functional Theory - electronic circular dichroism (TDDFT-ECD) calculations. Compounds (+/-)-1 as well as 2 and 3 exhibited potent DPPH radical scavenging activities with IC50 values of 1.23, 2.26, and 3.99 g/mL, respectively. Chirality 28:581-584, 2016. (c) 2016 Wiley Periodicals, Inc.