Title
New hexalactone derivatives and a pair of new oxaspiro-carbon epimeric glycosides from the fruits of Illicium lanceolatum
Author
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
Year
2019
Journal
Bioorganic Chemistry
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-oxaspiro[4,5]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.
Instrument
V-650, J-815
Keywords
Circular dichroism, Absorption, Quantitation, Absolute configuration, Natural products, Medicinal, Biochemistry, Organic chemistry