Modified Eremophilanes from Parasenecio hastatus and Their Neuroprotective Activities
Modified Eremophilanes from Parasenecio hastatus and Their Neuroprotective Activities
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来自Parasenecio hasstatus的修饰Eremophilanes及其神经保护活性
DOI：
10.1021/acs.jnatprod.9b00217
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发表时间：
2020
影响因子：
5.1
通讯作者：
Yang Luowenlei
中科院分区：
文献类型：
--
作者：
Liu Tingting;Wu Haibo;Zhang Jing;Deng Wenjie;Yang Luowenlei
从海南拟青霉(Parasenecio Haatus)中分离得到新的改良型马齿菌素A-K(1-11)和13个已知化合物(12-24)。通过光谱分析和与文献数据的比较，确定了化合物1-24的结构。用单晶X-射线衍射法确定了化合物1和2的绝对构型，并根据电子捕获光谱数据对其他新化合物进行了归属。这项工作是首次报道了含有两个内酯单元的8，9-二环芳香内酯(1)的晶体结构。通过手性相高效液相色谱分离，确定了(−)-1和(+)-1的绝对构型。新化合物代表了四个不寻常的骨架：具有稀有的6，9；8，12-二内酯部分的修饰的8，9-二内酯部分(1)，呋喃-内酯类型的骨架(2-7，11)，罕见的C14-内酯类型的骨架(8，9)和修饰的内酯类型的骨架(10)。结果表明，化合物2-5、12、21和23在低浓度(1μM)下仍有活性，化合物6-9、13、14、17、20、22和24在10和100μM时也表现出显著的保护作用。
The new modified eremophilanes hastatusins A–K (1–11) and 13 known compounds (12–24) were isolated fromParasenecio hastatus. The structures of1–24were elucidated based on spectroscopic data analysis and comparison with literature data. The absolute configurations of compounds1and2were defined by single-crystal X-ray diffraction analysis, and the other new compounds were assigned based on ECD data. This work is the first report of the crystal structure of an 8,9-seco-eremophilanolide (1) with two lactone units. The enantiomers of1were separated by chiral-phase HPLC, and the absolute configurations of (−)-1and (+)-1were established via experimental and calculated ECD data. The new compounds represent four unusual skeletons: a modified 8,9-seco-eremophilane featuring a rare 6,9;8,12-dilactone moiety (1), a furanoeremophilane-type skeleton (2–7,11), a rare C14nor-eremophilane-type skeleton (8,9), and a modified eremophilane lactone-type skeleton (10). All isolates were assayed for their neuroprotective effects against H2O2-induced SH-SY5Y cell injury, and compounds2–5,12,21, and23exhibited activities even at a low concentration of 1 μM. Compounds6–9,13,14,17,20,22, and24also showed notable effects at 10 and 100 μM.