Sesquiterpene Lactones from Artemisia argyi: Absolute Configuration and Immunosuppressant Activity

J Nat Prod. 2019 Jun 28;82(6):1424-1433. doi: 10.1021/acs.jnatprod.8b00791. Epub 2019 Jun 5.

Abstract

A library of extracts from plants used in Chinese Traditional Medicine was screened for inhibition of T lymphocyte proliferation. An ethyl acetate extract from aerial parts of Artemisia argyi showed promising activity and was submitted to HPLC-based activity profiling to track the active compounds. From the most active time window, three guaianolides (1, 2, and 5) and two seco-tanapartholides (3 and 4) were identified and, in a less active time window, five new sesquiterpene lactones (8-11, 17), along with six known sesquiterpene lactones and two known flavonoids. The absolute configurations of compounds 1, 2, 5-10, 13-15, 17, and 18 were established by comparison of experimental with calculated electronic circular dichroism (ECD) spectra. For seco-tanapartholides B (3) and A (4), ECD yielded ambiguous results, and their absolute configurations were determined by comparing experimental and calculated vibrational circular dichroism (VCD) spectra. Compounds 1-5 showed significant, noncytotoxic inhibition of T lymphocyte proliferation, with IC50 values between 1.0 and 3.7 μM.

MeSH terms

  • Artemisia / chemistry*
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Immunosuppressive Agents / chemistry*
  • Immunosuppressive Agents / pharmacology
  • Lactones / chemistry*
  • Lactones / pharmacology
  • Phytochemicals
  • Plant Leaves / chemistry*
  • Sesquiterpenes / pharmacology

Substances

  • Immunosuppressive Agents
  • Lactones
  • Phytochemicals
  • Sesquiterpenes