Cytotoxic calanquinone A from Calanthe arisanensis and its first total synthesis

  • Bioorg Med Chem Lett. 2008 Aug 1;18(15):4275-7. doi: 10.1016/j.bmcl.2008.06.099.
Chia-Lin Lee  1 ,  Kyoko Nakagawa-Goto ,  Donglei Yu ,  Yi-Nan Liu ,  Kenneth F Bastow ,  Susan L Morris-Natschke ,  Fang-Rong Chang ,  Yang-Chang Wu ,  Kuo-Hsiung Lee
Affiliations
  • 1. Natural Products Research Laboratories, School of Pharmacy, University of North Carolina at Chapel Hill, 315 Beard Hall, CB# 7360, NC 27599-7360, USA.
PMID: 18640035 DOI: 10.1016/j.bmcl.2008.06.099
Abstract

Calanquinone A (1) was isolated from an EtOAc-soluble extract of Calanthe arisanensis through bioassay-guided fractionation. Its structure was identified by spectroscopic methods. Compound 1 showed potent cytotoxicity (EC(50)<0.5microg/mL) against lung (A549), prostate (PC-3 and DU145), colon (HCT-8), breast (MCF7), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KB-VIN) Cancer cell lines, and interestingly, showed an improved drug resistance profile compared to paclitaxel. The total synthesis of 1 was also achieved and is reported herein.