Guaiane-type sesquiterpenes from Curcumawenyujin

Phytochemistry. 2022 Jun:198:113164. doi: 10.1016/j.phytochem.2022.113164. Epub 2022 Mar 17.

Abstract

Eight undescribed sesquiterpenes including seven guaianes and one pseudoguaiane which were named as wenyujinols A-H, along with ten known guaianes, were isolated from rhizomes of Curcuma wenyujin Y. H. Chen et C. Ling. The structures of wenyujinols A-H were elucidated by 1D and 2D nuclear magnetic resonance (NMR) data, high resolution mass spectrum (HRMS), electronic circular dichroism (ECD) spectra, and X-ray single crystallographic analysis. All of the isolated compounds were evaluated for antioxidant activity via activation of the Nrf2-ARE pathway in human embryonic kidney (HEK) 293 cells, for inhibitory effects on NO production in RAW 264.7 cells, and for cytotoxicity against three human cancer cell lines A549, HL60, and MCF7 in vitro. The results indicated that procurcumenol (50-200 μM) and 9-oxo-neoprocurcumenol (25-200 μM) exhibited antioxidant activity via activation of the Nrf2-ARE pathway in a dose-dependent manner.

Keywords: Antioxidant activity; Curcuma wenyujin; Guaiane; Wenyujinols a-h; Zingiberaceae.

MeSH terms

  • Antioxidants / pharmacology
  • Curcuma / chemistry
  • Curcuma / metabolism
  • HEK293 Cells
  • Humans
  • Macrophages
  • Molecular Structure
  • NF-E2-Related Factor 2* / metabolism
  • Nitric Oxide
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes* / pharmacology
  • Sesquiterpenes, Guaiane / chemistry

Substances

  • Antioxidants
  • NF-E2-Related Factor 2
  • Sesquiterpenes
  • Sesquiterpenes, Guaiane
  • guaiane
  • Nitric Oxide