New hexalactone derivatives and a pair of new oxaspiro-carbon epimeric glycosides from the fruits of Illicium lanceolatum |
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Institution: | 1. Xiangya Hospital of Central South University, Changsha 410008, PR China;2. Xiangya School of Pharmaceutical Sciences, Central South University, Changsha 410013, PR China;1. School of Pharmaceutical Science, Zhengzhou University, Ke Xue Da Dao 100, Zhengzhou 450001, People''s Republic of China;2. Henan Key laboratory for Pharmacology of Liver Disease, Academy of Medical and Pharmaceutical Science, Zhengzhou University, 40 Daxue Road, Zhengzhou 450052, People''s Republic of China;3. College of Chemistry and Chemical Engineering, Xuchang University, Henan, Xuchang 461000, People''s Republic of China |
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Abstract: | Five new compounds (1–5), including three hexalactone derivatives (1–3) and a pair of new oxaspiro-carbon epimeric glycosides (4 and 5), and six known compounds (6–11) were obtained from the fruits of Illicium lanceolatum. The structures of the new compounds were elucidated using extensive spectroscopic data. The absolute configurations of compounds 1–3 were determined by an analysis of their CD spectra. It was determined that compounds 4 and 5, which are epimeric at C-5, possess the same 1-oxaspiro4,5]decane-7α,8α,9β-triol moiety. Plausible biogenetic pathways for 4 and 5 derived from the key precursor shikimic acid were proposed. Compounds 1–11 were all assayed on monosodium glutamate-induced human neuroblastoma SH-SY5Y cell damage. The results demonstrated that compounds 4, 5, and 8–10 possess potential neuroprotective effects. The anti-inflammatory, antiviral, and cytotoxic activities of 1–11 were also evaluated. |
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Keywords: | Hexalactone derivatives Oxaspiro carbon epimers Glycosides Neuroprotective activity |
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