Cadinane-Type Sesquiterpenoids with Cytotoxic Activity from the Infected Stems of the Semi-mangrove Hibiscus tiliaceus

J Nat Prod. 2022 Jan 28;85(1):127-135. doi: 10.1021/acs.jnatprod.1c00849. Epub 2022 Jan 18.

Abstract

Eight new cadinane sesquiterpenoids (1-8), along with two known compounds (9 and 10), were isolated from infected stems of the semi-mangrove plant, Hibiscus tiliaceus. The structures of compounds 1-8 were elucidated through the analysis of their 1D and 2D NMR and MS data, and their absolute configurations were determined by comparing their experimental and calculated ECD spectra and by single-crystal X-ray diffraction. The two confused known compounds (9 and 10) were resolved using single-crystal X-ray crystallography. Compounds 1-3 have novel norsesquiterpene carbon skeletons arising from a ring contraction rearrangement. All obtained isolates were evaluated against the HepG2 and Huh7 cell lines, and compounds 1b, 2b, 4, 6, and 8 showed cytotoxic activity toward both cell lines, with IC50 values ranging from 3.5 to 6.8 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Hibiscus / chemistry*
  • Humans
  • Molecular Structure
  • Plant Stems / chemistry*
  • Polycyclic Sesquiterpenes / chemistry
  • Polycyclic Sesquiterpenes / isolation & purification
  • Polycyclic Sesquiterpenes / pharmacology*
  • Spectrum Analysis / methods

Substances

  • Polycyclic Sesquiterpenes
  • cadinane