Cytotoxic aporphine alkaloids from leaves and twigs of Pseuduvaria trimera (Craib)

Molecules. 2014 Jun 25;19(7):8762-72. doi: 10.3390/molecules19078762.

Abstract

From ethyl acetate-methanol extracts of leaves and twigs of Pseuduvaria trimera a new aporphine alkaloid; 8-hydroxy-1,4,5-trimethoxy-7-oxoaporphine or 8-hydroxyartabonatine C (1) was isolated, together with the known 1,2,3-trimethoxy-4,5-dioxo-6a,7-dehydroaporphine (ouregidione, 2). Their structures were elucidated by a combination of spectral methods; mainly 2D NMR; IR and MS. Compounds 1 and 2 exhibited cytotoxic activity with IC50 values of 26.36±5.18 μM and 12.88±2.49 μM, respectively, for human hepatocellular carcinoma HepG2 cells, and 64.75±4.45 and 67.06±3.5 μM, respectively, for human breast cancer MDA-MB231 cells. Both compounds displayed anti-cancer activity but less than that of doxorubicin; a conventional chemotherapeutic drug, the IC50 levels of which were 2.21±1.72 and 1.83±0.09 μM for HepG2 and MDA-MB231 cells, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Annonaceae / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Aporphines / chemistry
  • Aporphines / isolation & purification*
  • Aporphines / pharmacology
  • Crystallography, X-Ray
  • Doxorubicin / pharmacology
  • Drug Screening Assays, Antitumor
  • Hep G2 Cells
  • Humans
  • Inhibitory Concentration 50
  • Molecular Conformation
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*
  • Plant Extracts / pharmacology
  • Plant Leaves / chemistry*
  • Plant Stems / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Aporphines
  • Plant Extracts
  • Doxorubicin