Ent-Clerodane Diterpenes from the Bark of Croton oligandrus Pierre ex Hutch. and Assessment of Their Cytotoxicity against Human Cancer Cell Lines

Molecules. 2018 Feb 13;23(2):410. doi: 10.3390/molecules23020410.

Abstract

New clerodane diterpenes, 12-epi-megalocarpodolide D (2) and an epimeric mixture of crotonolins A (3) and B (4), were isolated from the bark of Croton oligandrus following a bioassay-guided isolation protocol. Known compounds, megalocarpodolide D (1), 12-epi-crotocorylifuran (5), cluytyl-ferulate (6), hexacosanoyl- ferulate (7), vanillin (8), acetyl-aleuritolic acid (9) and lupeol (10), were also isolated. The structures of the isolated compounds (1-10) were elucidated by spectroscopic means. The cytotoxicity of compounds 1-10 was assessed against A549, MCF7, PC3 and PNT2 cell lines using the MTT assay. Compounds 1 and 2 showed moderate levels of activity against both A549 and MCF7 cells with 1 being the most active with IC50 values of 63.8 ± 13.8 and 136.2 ± 22.7 µM against A549 and MCF7 cells, respectively. The epimeric mixture of 3 and 4 was moderately active against A549 and PC3 cells (IC50 = 128.6 ± 31.0 and 111.2 ± 2.9 µM, respectively).

Keywords: Croton oligandrus; Euphorbiaceae; crotonolin A; crotonolin B; cytotoxicity; ent-clerodanes.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Croton / chemistry*
  • Cytotoxins / chemistry*
  • Cytotoxins / isolation & purification
  • Cytotoxins / pharmacology
  • Diterpenes, Clerodane / chemistry*
  • Diterpenes, Clerodane / isolation & purification
  • Diterpenes, Clerodane / pharmacology
  • Furans / chemistry*
  • Furans / isolation & purification
  • Furans / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • MCF-7 Cells
  • Molecular Structure
  • Pentacyclic Triterpenes / chemistry*
  • Pentacyclic Triterpenes / isolation & purification
  • Pentacyclic Triterpenes / pharmacology
  • Plant Bark / chemistry*
  • Plant Extracts / chemistry

Substances

  • Antineoplastic Agents, Phytogenic
  • Cytotoxins
  • Diterpenes, Clerodane
  • Furans
  • Pentacyclic Triterpenes
  • Plant Extracts