Phragmalin-type limonoids with structural diversity at D-ring from the fruit shells of Chukrasia tabularis

Fitoterapia. 2019 Apr:134:188-195. doi: 10.1016/j.fitote.2019.02.032. Epub 2019 Feb 28.

Abstract

Ten undescribed phragmalin-type limonoids (Chuktabularoids A-J, 1-10) and four known compounds (11-14) were isolated from the fruit shells of Chukrasia tabularis A. Juss. Their chemical structures were elucidated through a combination of HRESIMS, NMR, and ECD experiments. Their frameworks differed mainly in D-ring, including C-15-acyl, 16-nor C-15 acyl, C-13/14/18-cyclopropane, and Δ14, 15 types. The majority of the isolated compounds were investigated for multidrug resistance (MDR) reversal activity against doxorubicin-resistant human breast carcinoma (MCF-7/DOX) cells, compounds 11 and 12 exhibited a 5.6-fold and 19.7-fold enhancing effect on doxorubicin susceptibility at 30 μM, respectively.

Keywords: Chukrasia tabularis; Limonoid; Multidrug resistance reversal effect; Phragmalin.

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • China
  • Drug Resistance, Multiple
  • Drug Resistance, Neoplasm
  • Fruit / chemistry*
  • Humans
  • Limonins / isolation & purification
  • Limonins / pharmacology*
  • MCF-7 Cells
  • Meliaceae / chemistry*
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • RAW 264.7 Cells

Substances

  • Antineoplastic Agents, Phytogenic
  • Limonins
  • Phytochemicals
  • phragmalin
  • Nitric Oxide