Ten undescribed highly oxidized sesquiterpenes and six known sesquiterpenes were isolated from H2O-soluble part of the fruits of Illicium lanceolatum A. C. Smith. The structures of undescribed compounds were elucidated by interpretation of spectroscopic data, and the absolute configurations of 2α-hydroxyneoanisatinic acid, (1R,5R,6S,7R,9R,10R)-3,4-dehydro-12-hydroxy-floridanolide, and (1R,4S,5R,6S,7S,9S)-1-deoxy-13-hydroxymerrilactone B were determined by the single-crystal X-ray diffraction analysis. Illilanceolatin A was the first example of a seco-prezizaane type sesquiterpene with a hemiacetal moiety located at C-10. 2α-Hydroxyneoanisatinic acid and anisatinic acid were two naturally occurring undescribed seco-prezizaane type sesquiterpenes with a 5/5/6 tricyclic carbon skeleton. Plausible biosynthetic pathways of the isolated polycyclic and highly oxidized sesquiterpenes derived from the intermediate allo-cedrane were proposed. (1R,5R,6S,7R,9R,10R)-3,4-dehydro-12-hydroxy-floridanolide, 1,3-dihydroxyneoanisatin, and 2α-hydroxyneoanisatin displayed neuroprotective effects with protection rates of 19.9, 22.7 and 24.3% at 10 μM, respectively. Additionally, the preliminary acute toxicity of anisatinic acid was also evaluated.

中文翻译：

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来自 Illicium lanceolatum AC Smith 果实的高度氧化的倍半萜

从 Illicium lanceolatum AC Smith 果实的 H2O 可溶性部分中分离出 10 种未描述的高度氧化倍半萜和 6 种已知的倍半萜。未描述的化合物的结构通过光谱数据的解释和 2α-羟基新茴香酸、(1R,5R,6S,7R,9R,10R)-3,4-dehydro-12-hydroxy-floridanolide 的绝对构型阐明，以及(1R,4S,5R,6S,7S,9S)-1-脱氧-13-羟基梅里内酯B通过单晶X射线衍射分析确定。Illilanceolatin A 是第一个具有位于 C-10 处的半缩醛部分的 seco-prezizaane 型倍半萜烯的例子。2α-羟基新茴香酸和茴香酸是两种天然存在的未描述的 seco-prezizaane 型倍半萜，具有 5/5/6 三环碳骨架。提出了衍生自中间体异位雪松的分离的多环和高度氧化的倍半萜的合理生物合成途径。(1R,5R,6S,7R,9R,10R)-3,4-dehydro-12-hydroxy-floridanolide、1,3-dihydroxyneoanisatin 和 2α-hydroxyneoanisatin 显示出神经保护作用，保护率为 19.9、22.7 和 24.3%分别为 10 μM。此外，还评估了茴香酸的初步急性毒性。