Isolation and cytotoxicity evaluation of taxanes from the barks of Taxus wallichiana var. mairei

Bioorg Med Chem Lett. 2015 Mar 15;25(6):1240-3. doi: 10.1016/j.bmcl.2015.01.056. Epub 2015 Jan 30.

Abstract

Fifteen taxanes (1-15) including a new taxane glucoside, 7β,9α,10β-triacetoxy-13α-hydroxy-5α-O-(β-d-glucopyranosyl)taxa-4(20),11-diene (1), were isolated from the barks of Taxus wallichiana var. mairei. Compounds 1-15 representing three sub-types of 6/8/6-taxane were evaluated in vitro for anti-proliferative activity against a panel of parental and drug-resistant cancer cells. Potent compounds were found while several exhibited selective cytotoxicity. Especially, 3, 8, and 10 showed selective inhibition to breast carcinoma cell line MCF-7, while 13 selectively inhibited taxol resistant human ovarian carcinoma cell line A2780/TAX (IC50=0.19μM), being more potent than the clinical drugs taxol (IC50=4.4μM) and docetaxol (IC50=0.42μM), and less cytotoxic to mouse embryonic fibroblast cell line NIH-3T3, a cell line close to normal cell line. The possible P-glycoprotein evasion mechanism of 13 against A2780/TAX and the preliminary structure-activity relationships (SARs) of this group of compounds were also discussed.

Keywords: Cytotoxicity; Drug resistant; Structure–activity relationships; Taxanes; Taxus wallichiana var. mairei.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism
  • Animals
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Humans
  • MCF-7 Cells
  • Mice
  • Molecular Conformation
  • NIH 3T3 Cells
  • Paclitaxel / pharmacology
  • Plant Bark / chemistry
  • Plant Bark / metabolism
  • Structure-Activity Relationship
  • Taxoids / chemistry*
  • Taxoids / isolation & purification
  • Taxoids / pharmacology
  • Taxus / chemistry*
  • Taxus / metabolism

Substances

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Antineoplastic Agents
  • Taxoids
  • taxacin
  • Paclitaxel