Scalemic diacetylenic spiroacetal enol ethers from the flowers of Tanacetum tatsienense

Xinqiao Liu; Yan Du; Wenli Xie; Xueni Li; Jing Xu; Yu Chen; Zhinan Mei; Guangzhong Yang

doi:10.1016/j.phytochem.2023.113619

Scalemic diacetylenic spiroacetal enol ethers from the flowers of Tanacetum tatsienense

Phytochemistry. 2023 May:209:113619. doi: 10.1016/j.phytochem.2023.113619. Epub 2023 Feb 23.

Authors

Xinqiao Liu¹, Yan Du², Wenli Xie¹, Xueni Li¹, Jing Xu¹, Yu Chen², Zhinan Mei³, Guangzhong Yang⁴

Affiliations

¹ School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, PR China.
² College of Chemistry and Material Sciences, South-Central Minzu University, Wuhan, 430074, PR China.
³ College of Plant Science & Technology, Huazhong Agricultural University, Wuhan, 430072, PR China. Electronic address: meizhinan@mail.hzau.edu.cn.
⁴ School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, PR China; Ethnopharmacology Level 3 Laboratory, National Administration of Traditional Chinese Medicine, Wuhan, 430072, PR China. Electronic address: yanggz888@126.com.

PMID: 36828098
DOI: 10.1016/j.phytochem.2023.113619

Abstract

Six scalemic mixtures of previously undescribed diacetylenic spiroacetal enol ethers (DSEEs) and six scalemic mixtures of known DSEEs were isolated from the flowers of Tanacetum tatsienense. Except for E-epidendranthemenol, Z-O-acetyl-epi dendranthemenol, and Z-O-isovaleryl-epidendranthemenol, the remaining scalemic mixtures of DSEEs were resolved by chiral HPLC, and their structures were determined through an analysis of HR-ESI-MS and NMR data. The absolute configurations of seven pairs of enantiomers and one pair of epimers were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. In addition, the inhibitory effects of all of the DSEEs on nitric oxide (NO) production were evaluated in LPS-stimulated RAW264.7 cells. The results showed that (+)-tatsienenol B had a weak inhibitory effect on NO production. The IC₅₀ value of the compound was 19.78 ± 0.78 μM. This study is the first to report that DSEEs are isolable from plants as scalemic mixtures. Moreover, this study is the first to determine the absolute configurations of DSEEs by chiral resolution and ECD calculations.

Keywords: Anti-inflammatory activity; Chiral; Diacetylenic spiroacetal enol ethers; ECD calculations; Resolution; Tanacetum tatsienense.

MeSH terms

Animals
Ethers*
Flowers
Mice
Molecular Structure
RAW 264.7 Cells
Tanacetum*

Substances

Ethers