Oxidative burst inhibitory and cytotoxic activity of constituents of the fruits of Odyendyea gabonensis

Planta Med. 2012 Dec;78(18):1949-56. doi: 10.1055/s-0032-1327878. Epub 2012 Nov 7.

Abstract

The methanol extract of dried fruits of Odyendyea gabonensis afforded one new quassinoid [(-)-odyendanol (1)], one new canthin-6-one alkaloid [9-hydroxy-5-methoxycanthin-6-one (4)], and two new steroids [22E, 24R-stigmasta-5,22-diene-3,7-dione (7) and 22E,24R-stigmast-22-ene-3,7-dione (8)] along with fourteen known compounds. The structures of all compounds were established by analyzing the spectroscopic data. The ¹³C-NMR values of (-)-odyendene (2) and (-)-odyendane (3), as well as the single-crystal X-ray structure of 5-methoxycanthin-6-one (6) are also reported.The oxidative burst inhibitory activity of pure compounds 1-12 was determined by the chemoluminescence assay, and cytotoxic activities of compounds 2-6 against the human prostate cancer cell PC-3 line were evaluated. Compounds 1-6 exhibited a clear suppressive effect on the phagocytosis response upon activation with serum-opsonized zymosan in the range of IC₅₀ = 0.9-2.0 µM versus ibuprofen with IC₅₀ = 12.1 µM, while all canthin-6-one alkaloids (4-6) displayed moderate cytotoxic activity against the human prostate cancer cell PC-3 line, with IC₅₀ values ranging from 13.5-15.4 µM versus doxorubicine with IC₅₀ = 1.5 µM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Carbolines / pharmacology
  • Fruit / chemistry
  • Humans
  • Indole Alkaloids / pharmacology
  • Male
  • Molecular Structure
  • Phytosterols / pharmacology
  • Plant Extracts / pharmacology*
  • Plant Stems / chemistry
  • Prostatic Neoplasms / drug therapy*
  • Prostatic Neoplasms / metabolism
  • Quassins / pharmacology
  • Respiratory Burst / drug effects*
  • Simaroubaceae / chemistry*
  • Tumor Cells, Cultured / drug effects

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Carbolines
  • Indole Alkaloids
  • Phytosterols
  • Plant Extracts
  • Quassins
  • canthin-6-one