Structurally diverse limonoids and bio-active evaluation from Trichilia connaroides

Fitoterapia. 2021 Sep:153:105001. doi: 10.1016/j.fitote.2021.105001. Epub 2021 Jul 27.

Abstract

Four new limonoids, named as trichiconlide G (1), 2-hydroxyltrijugin F (2), 23-oxo-21-hydroxyltrijugin F (3), 21-oxo-23-hydroxyltrijugin F (4), along with sixteen known analogues (5-20) were isolated from the leaves and twigs of Trichilia connaroides. Their structures and absolute configurations were determined by spectroscopic analyses, X-ray diffraction analysis, and TD-DFT-ECD calculations. Trichiconlide G (1) is one rare naturally occurring 1,2-seco phragmalin-type limonoid bearing a C-7/28 δ-lactone ring. Additionally, 2-hydroxyltrijugin F (2), 23-oxo-21-hydroxyltrijugin F (3), and 21-oxo-23-hydroxyltrijugin F (4) are three naturally occurring limonoids with a rare C-16/8 δ-lactone ring. All isolates were evaluated for their cytotoxic and anti-inflammatory activities. None of compounds exhibited cytotoxicity against five human cancer cell lines A-549, HepG2, 5-8F, Siha, and SCC-4 at the concentration of 40 μM. Compounds 16 and 17 showed moderate anti-inflammatory activity with IC50 values of 28.45 ± 2.51 and 22.66 ± 2.01 μM, respectively.

Keywords: Anti-inflammatory; Cytotoxicity; Limonoid; Meliaceae; Trichilia connaroides.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Cell Line, Tumor
  • China
  • Humans
  • Limonins / isolation & purification
  • Limonins / pharmacology*
  • Meliaceae / chemistry*
  • Mice
  • Molecular Structure
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Leaves / chemistry
  • RAW 264.7 Cells

Substances

  • Anti-Inflammatory Agents
  • Limonins
  • Phytochemicals
  • phragmalin