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Illilanceolide A, a unique seco-prezizaane sesquiterpenoid with 5/5/6 tricyclic scaffold from the fruits of Illicium lanceolatum A. C. Smith
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2021-03-23 , DOI: 10.1016/j.tetlet.2021.153022
Wei Nie , Lin-Fen Ding , Tie Lei , Zheng-Hong Pan , Liu-Dong Song , Xing-De Wu , Qin-Shi Zhao

A unique seco-prezizaane sesquiterpenoid with 5/5/6 tricyclic skeleton, illilanceolide A (1), and two rare 10,14-cycloseco-prezizaane sesquiterpenoids, 2-oxo-6-dehydroxyneoanisatinic acid (2) and 3,4-anhydro-2-oxo-6-dehydroxyneoanisatinic acid (3), together with two known sesquiterpenoids, were isolated from the fruits of Illicium lanceolatum. Their structures and absolute configurations were elucidated on the basis of extensive 1H, 13C, and 2D NMR, and HRESIMS data, as well as single-crystal X-ray diffraction analysis. Compounds 24 enhanced the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM with differentiation rates of 13.33%, 10.90%, and 11.76%, respectively. Moreover, compounds 24 were found to exhibit moderate neuroprotective effect against MPP+-induced PC12 cell damage.

中文翻译:


Illilanceolide A,一种独特的 seco-prezizaane 倍半萜类化合物,具有 5/5/6 三环支架,来自 Illicium lanceolatum AC Smith 的果实



一种独特的 seco-prezizaane 倍半萜类化合物,具有 5/5/6 三环骨架,illilanceolide A (1),和两种稀有的 10,14-环-prezizaane 倍半萜类化合物,2-氧代-6-脱羟基新茴香酸 (2) 和 3,4-脱水-2-氧代-6-脱羟基新茴香酸 (3),以及两种已知的倍半萜类化合物,是从 Illicium lanceolatum 的果实中分离出来的。它们的结构和绝对构型是在广泛的 1H、13C 和 2D NMR 和 HRESIMS 数据以及单晶 X 射线衍射分析的基础上阐明的。化合物 2-4 在 10 μM 的浓度下增强了 NGF 介导的 PC12 细胞的神经突生长,分化率分别为 13.33%、10.90% 和 11.76%。此外,发现化合物 2-4 对 MPP+ 诱导的 PC12 细胞损伤表现出中等神经保护作用。
更新日期:2021-03-23
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