Cytotoxic phenanthrenequinones and 9,10-dihydrophenanthrenes from Calanthe arisanensis

J Nat Prod. 2009 Feb 27;72(2):210-3. doi: 10.1021/np800622a.

Abstract

Two new phenanthrenequinones, calanquinones B and C (2 and 3) and four new 9,10-dihydrophenanthrenes, calanhydroquinones A-C (4-6) and calanphenanthrene A (7), along with five known compounds (1 and 8-11), were isolated from an EtOAc-soluble extract of Calanthe arisanensis through bioassay-guided fractionation. Their structures were identified from spectroscopic data, and the compounds were tested for in vitro cytotoxic activity against human lung (A549), prostate (PC-3 and DU145), colon (HCT-8), breast (MCF-7), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KBVIN) cancer cell lines. Compound 1 showed the highest potency (EC(50) < 0.5 microg/mL) against all seven cancer cell lines, with the greatest activity against breast cancer MCF-7 cells (EC(50) < 0.02 microg/mL). Generally, except for 7, compounds 2-11 also showed significant cytotoxic activity (EC(50) < 4 microg/mL) against some cell lines (especially PC-3 and MCF-7) in the panel.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Drug Resistance, Neoplasm / drug effects
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Male
  • Molecular Structure
  • Orchidaceae / chemistry*
  • Phenanthrenes / chemistry
  • Phenanthrenes / isolation & purification*
  • Phenanthrenes / pharmacology*
  • Plants, Medicinal / chemistry*
  • Quinones / chemistry
  • Quinones / isolation & purification*
  • Quinones / pharmacology*
  • Vincristine / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Phenanthrenes
  • Quinones
  • Vincristine