Cytotoxic constituents from the fruiting branches of Callicarpa americana collected in southern Florida

J Nat Prod. 2007 Mar;70(3):372-7. doi: 10.1021/np060534z. Epub 2007 Feb 6.

Abstract

Bioassay-guided fractionation of the combined fruits, leaves, and twigs (fruiting branches) of Callicarpa americana, collected from a plot in a forested area in southern Florida, led to the isolation of six new clerodane diterpenes (1-6) and eight known compounds. The structures of 1-6 [12(S),16xi-dihydroxycleroda-3,13-dien-15,16-olide (1), 12(S)-hydroxy-16xi-methoxycleroda-3,13-dien-15,16-olide (2), 12(S)-hydroxycleroda-3,13-dien-15,16-olide (3), 16xi-hydroxycleroda-3,11(E),13-trien-15,16-olide (4), 3beta,12(S)-dihydroxycleroda-4(18),13-dien-15,16-olide (5), and 12(S)-hydroxycleroda-3,13-dien-16,15-olide (6)] were elucidated by interpretation of spectroscopic data and chemical methods. The absolute configuration at C-12 in 1 and 3 was ascertained using the Mosher ester technique. The cytotoxicity of all isolates was tested against a panel of human cancer cell lines, and compounds 1, 4, and 6, and the known compounds genkwanin, 16xi-hydroxycleroda-3,13-dien-15,16-olide, and 2-formyl-16xi-hydroxy-3-A-norcleroda-2,13-dien-15,16-olide were active (ED50 <5 microg/mL). However, 1 was found to be inactive against human cancer cells implanted in mice using a hollow-fiber tumor model.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic* / chemistry
  • Antineoplastic Agents, Phytogenic* / isolation & purification
  • Antineoplastic Agents, Phytogenic* / pharmacology
  • Callicarpa / chemistry*
  • Disease Models, Animal
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / isolation & purification
  • Diterpenes, Clerodane / pharmacology
  • Drug Screening Assays, Antitumor
  • Florida
  • Fruit / chemistry
  • Humans
  • Mice
  • Molecular Structure
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes, Clerodane