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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Sesquiterpene enantiomers from Alismatis Rhizoma
Shan-Shan Liu1, Yun Li2, Yun-He An3
1Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, PR China; Institute of Analysis and Testing, Beijing Academy of Science and Technology (Beijing Center for Physical &Chemical Analysis), No.27, North Xisanhuan Road, Beijing, 100089, PR China.
Abstract:
A pair of dinor-sesquiterpene enantiomers (1a/1b), eight pairs of guaiane-type sesquiterpenes enantiomers (2a/2b, 3a/3b, 4a/4b, 5a/5b, 6a/6b, 7a/7b, 8a/8b, 9a/9b) and two guaiane-type sesquiterpenes (10, 11), including eleven undescribed ones (1a, 1b, 2a, 2b, 3a, 3b, 4a, 5b, 6a, 10, and 11), were isolated from the aqueous extract of Alismatis Rhizoma. The structures were elucidated by combining 1D and 2D NMR and HRESIMS spectroscopic data. The absolute configurations were determined by experimental and calculated ECD spectra, [Mo2(OAc)4]-induced ECD spectral analysis, and comparison of the experimental ECD spectra with those of similar analogs. Compound 5b (NO inhibition rate, 52.63%) and 8b (36.49%) showed comparable activity to indomethacin (46.36%) against LPS-induced NO production in RAW 264.7 murine macrophages at 100 μM with obvious stereoselectivity, whereas compounds 1-10 exerted no or extremely low cytotoxicities against MCF-7 and MDA-MB-231 cells (IC50 > 100 μM).
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