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Absolute Configurations and Bioactivities of Guaiane-Type Sesquiterpenoids Isolated from Pogostemon cablin.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-09-06 , DOI: 10.1021/acs.jnatprod.7b00690 Qin-Mei Zhou , Ming-Hua Chen 1 , Xiao-Hong Li , Cheng Peng , Da-Sheng Lin 2 , Xiao-Nian Li 3 , Yang He , Liang Xiong
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-09-06 , DOI: 10.1021/acs.jnatprod.7b00690 Qin-Mei Zhou , Ming-Hua Chen 1 , Xiao-Hong Li , Cheng Peng , Da-Sheng Lin 2 , Xiao-Nian Li 3 , Yang He , Liang Xiong
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Seven novel guaiane sesquiterpenoids (1-7) and three known seco-guaianes were isolated from the volatile oil of Pogostemon cablin. Their structures including absolute configurations were determined by spectroscopic analyses, a modified Mosher's method, and X-ray diffraction and ECD data. The results indicated that the ECD Cotton effects arising from one or two nonconjugated olefinic chromophores could be applied to define the absolute configurations of guaiane sesquiterpenoids. Compounds 3 and 6 exhibited significant vasorelaxant activity against phenylephrine-induced and KCl-induced contractions of rat aorta rings [half-maximal effective concentration (EC50) of 3 against PHE-induced contraction, 5.4 μM; EC50 of 6 against PHE- and KCl-induced contractions, 1.6 and 24.2 μM, respectively]. They also showed antifungal activity against Candida albicans (minimum inhibitory concentrations, 500 and 300 μM, respectively). In addition, 2 and 7-9 displayed a neuroprotective effect against glutamate-induced injury in PC12 cells.
中文翻译：
从Pogostemon cablin分离出的Guaiane型倍半萜类化合物的绝对构型和生物活性。
从Pogostemon cablin的挥发油中分离出了七个新颖的愈创树倍半萜类化合物（1-7）和三个已知的山核桃愈创木瓜。通过光谱分析，改进的Mosher方法以及X射线衍射和ECD数据确定了它们的结构，包括绝对构型。结果表明，由一种或两种非共轭烯烃发色团引起的ECD Cotton效应可用于确定愈创树倍半萜的绝对构型。化合物3和6对苯肾上腺素诱导的和KCl诱导的大鼠主动脉环显示出显着的血管舒张活性[3对PHE诱导的收缩的半最大有效浓度（EC50）为5.4μM; 针对PHE和KCl引起的收缩的EC50为6，分别为1.6和24.2μM]。他们还显示出对白色念珠菌的抗真菌活性（最低抑菌浓度分别为500和300μM）。此外，2和7-9对PC12细胞中谷氨酸诱导的损伤表现出神经保护作用。
更新日期：2018-09-06
中文翻译：
从Pogostemon cablin分离出的Guaiane型倍半萜类化合物的绝对构型和生物活性。
从Pogostemon cablin的挥发油中分离出了七个新颖的愈创树倍半萜类化合物（1-7）和三个已知的山核桃愈创木瓜。通过光谱分析，改进的Mosher方法以及X射线衍射和ECD数据确定了它们的结构，包括绝对构型。结果表明，由一种或两种非共轭烯烃发色团引起的ECD Cotton效应可用于确定愈创树倍半萜的绝对构型。化合物3和6对苯肾上腺素诱导的和KCl诱导的大鼠主动脉环显示出显着的血管舒张活性[3对PHE诱导的收缩的半最大有效浓度（EC50）为5.4μM; 针对PHE和KCl引起的收缩的EC50为6，分别为1.6和24.2μM]。他们还显示出对白色念珠菌的抗真菌活性（最低抑菌浓度分别为500和300μM）。此外，2和7-9对PC12细胞中谷氨酸诱导的损伤表现出神经保护作用。
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