Actinoranone, a cytotoxic meroterpenoid of unprecedented structure from a marine adapted Streptomyces sp

Org Lett. 2013 Nov 1;15(21):5400-3. doi: 10.1021/ol402080s. Epub 2013 Oct 23.

Abstract

The isolation and structure elucidation of a new meroterpenoid, actinoranone (1), produced by a marine bacterium closely related to the genus Streptomyces is reported. Actinoranone is composed of an unprecedented dihydronaphthalenone polyketide linked to a bicyclic diterpenoid. The stereochemistry of 1 was defined by application of the advanced Mosher's method and by interpretation of spectroscopic data. Actinoranone (1) is significantly cytotoxic to HCT-116 human colon cancer cells with an LD50 = 2.0 μg/mL.

Publication types

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

MeSH terms

  • Animals
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Diterpenes / toxicity*
  • HCT116 Cells
  • Humans
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Streptomyces / chemistry*
  • Terpenes / chemistry*

Substances

  • Diterpenes
  • Terpenes
  • actinoranone