Oxygen heterocyclic Diels-Alder-Type sesquiterpenoid dimers from Vernonia anthelmintica

Ablajan Turak; Haji Akber Aisa

doi:10.1016/j.phytochem.2022.113386

Oxygen heterocyclic Diels-Alder-Type sesquiterpenoid dimers from Vernonia anthelmintica

Phytochemistry. 2022 Nov:203:113386. doi: 10.1016/j.phytochem.2022.113386. Epub 2022 Aug 20.

Authors

Ablajan Turak¹, Haji Akber Aisa²

Affiliations

¹ State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, and the Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China. Electronic address: ablajan@ms.xjb.ac.cn.
² State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, and the Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China. Electronic address: haji@ms.xjb.ac.cn.

PMID: 35998833
DOI: 10.1016/j.phytochem.2022.113386

Abstract

Eleven undescribed oxygen heterocyclic Diels-Alder-Type sesquiterpenoid dimers, vernodalidimer I-K and M-T, along with a known one, vernodalidimer B were isolated from the seeds of Vernonia anthelmintica. The structures of them were elucidated based on 1D, 2D-NMR experiments and HRESIMS. The absolute configurations of vernodalidimer I-K and M-T were determined by comparison of their experimental and calculated electronic circular dichroism spectra. Cytotoxicity of the isolates against HCT-15, PC-3, A549, and HeLa cell lines were tested. Vernodalidimer K and Q exhibited significant cytotoxic activity against HCT-15 cell line with IC₅₀ values of 9.8 ± 5.4 μM and 9.4 ± 1.3 μM, respectively.

Keywords: Asteraceae; Cytotoxicity; Diels-alder; Sesquiterpenoid dimers; Vernonia anthelmintica.

MeSH terms

Cell Line, Tumor
HeLa Cells
Humans
Molecular Structure
Oxygen
Sesquiterpenes* / chemistry
Sesquiterpenes* / pharmacology
Vernonia* / chemistry

Substances

Sesquiterpenes
Oxygen