Sesquiterpene enantiomers from Alismatis Rhizoma

Shan-Shan Liu; Yun Li; Yun-He An; Jing-Jing Zhu; Mei Zhang; Wei Wang; Li-Hua Yan; Zhi-Min Wang

doi:10.1016/j.phytochem.2024.114359

Sesquiterpene enantiomers from Alismatis Rhizoma

Phytochemistry. 2024 Dec 12:232:114359. doi: 10.1016/j.phytochem.2024.114359. Online ahead of print.

Authors

Shan-Shan Liu¹, Yun Li², Yun-He An³, Jing-Jing Zhu⁴, Mei Zhang³, Wei Wang³, Li-Hua Yan⁵, Zhi-Min Wang⁶

Affiliations

¹ Institute 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.
² School of Pharmaceutical Sciences, Shandong University of Traditional Chinese Medicine, Jinan, 250355, PR China.
³ 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.
⁴ Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, PR China.
⁵ Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, PR China. Electronic address: [email protected].
⁶ Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, PR China. Electronic address: [email protected].

PMID: 39674245
DOI: 10.1016/j.phytochem.2024.114359

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).

Keywords: Alisma; Alismataceae; Alismatis Rhizoma; Anti-inflammatory activity; Enantiomers; Guaiane-type sesquiterpenes.