ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation

Bioorg Med Chem Lett. 2014 Aug 1;24(15):3315-20. doi: 10.1016/j.bmcl.2014.06.005. Epub 2014 Jun 11.

Abstract

This work describes a novel ent-kaurane diterpene, ent-3β-hydroxy-kaur-16-en-19-al along with five known ent-kaurane diterpenes, ent-3β,19-dihydroxy-kaur-16-eno, ent-3β-hydroxy-kaur-16-eno, ent-3β-acetoxy-kaur-16-eno, ent-3β-hydroxy-kaurenoic acid and kaurenoic acid, as well as caryophyllene oxide, humulene epoxide II, β-sitosterol, stigmasterol and campesterol from the stem bark of Annona vepretorum Mart. (Annonaceae). Cytotoxic activities towards tumor B16-F10, HepG2, K562 and HL60 and non-tumor PBMC cell lines were evaluated for ent-kaurane diterpenes. Among them, ent-3β-hydroxy-kaur-16-en-19-al was the most active compound with higher cytotoxic effect over K562 cell line (IC50 of 2.49 μg/mL) and lower over B16-F10 cell line (IC50 of 21.02 μg/mL).

Keywords: Annona vepretorum; Annonaceae; Cytotoxicity; ent-Kaurane diterpenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Annonaceae / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Diterpenes, Kaurane / chemistry
  • Diterpenes, Kaurane / isolation & purification
  • Diterpenes, Kaurane / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Hep G2 Cells
  • Humans
  • K562 Cells
  • Leukocytes, Mononuclear / drug effects*
  • Mice
  • Molecular Structure
  • Plant Bark / chemistry*
  • Plant Stems / chemistry*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes, Kaurane