New hexalactone derivatives and a pair of new oxaspiro-carbon epimeric glycosides from the fruits of Illicium lanceolatum.
New hexalactone derivatives and a pair of new oxaspiro-carbon epimeric glycosides from the fruits of Illicium lanceolatum.
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DOI：
10.1016/j.bioorg.2019.103113
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发表时间：
2019-07
影响因子：
5.1
通讯作者：
Yang-Lan Liu;Xiao-jing Wang;Ru-Bing Wang;Mi Li;Wen-Rui Li;Jian-Pei Zhang;Xiu-Qi Bao;Dan Zhang;Shuang-Gang Ma
中科院分区：
文献类型：
--
作者：
Yang-Lan Liu;Xiao-jing Wang;Ru-Bing Wang;Mi Li;Wen-Rui Li;Jian-Pei Zhang;Xiu-Qi Bao;Dan Zhang;Shuang-Gang Ma
从披针叶八角（Illicium lanceolatum）果实中分得5个新化合物（1-5），包括3个己内酯衍生物（1-3）和1对新的氧杂螺碳差向异构糖苷（4和5），以及6个已知化合物（6-11）。新化合物的结构用广泛的光谱数据进行了鉴定。化合物1 - 3的绝对构型由圆二色谱确定。化合物4和5在C-5位为差向异构体，具有相同的1-氧杂螺[4，5]癸烷-7 α，8 α，9 β-三醇部分。提出了4和5由关键前体莽草酸衍生的可能的生物发生途径。测定化合物1 - 11对谷氨酸盐诱导的人神经母细胞瘤SH-SY 5 Y细胞损伤的影响。结果表明化合物4、5和8 - 10具有潜在的神经保护作用。还评价了1 - 11的抗炎、抗病毒和细胞毒活性。
Five new compounds (1–5), including three hexalactone derivatives (1–3) and a pair of new oxaspiro-carbon epimeric glycosides (4and5), and six known compounds (6–11) were obtained from the fruits ofIllicium lanceolatum. The structures of the new compounds were elucidated using extensive spectroscopic data. The absolute configurations of compounds1–3were determined by an analysis of their CD spectra. It was determined that compounds4and5, which are epimeric at C-5, possess the same 1-oxaspiro[4,5]decane-7α,8α,9β-triol moiety. Plausible biogenetic pathways for4and5derived from the key precursor shikimic acid were proposed. Compounds1–11were all assayed on monosodium glutamate-induced human neuroblastoma SH-SY5Y cell damage. The results demonstrated that compounds4,5, and8–10possess potential neuroprotective effects. The anti-inflammatory, antiviral, and cytotoxic activities of1–11were also evaluated.