Naphtoquinones and Sesquiterpene Cyclopentenones from the Sponge Smenospongia cerebriformis with Their Cytotoxic Activity

Chem Pharm Bull (Tokyo). 2017 Jun 1;65(6):589-592. doi: 10.1248/cpb.c17-00123. Epub 2017 Mar 31.

Abstract

Two new naphtoquinones (smenocerones A and B, 1 and 2) and four known sesquiterpene cyclopentenones (dactylospongenones A-D, 3-6) were isolated from sponge Smenospongia cerebriformis living in the Eastern Sea of Vietnam. Their chemical structures were determined by high resolution electrospray ionization (HR-ESI)-MS, NMR spectroscopic analysis, and in comparison with the reported data. The chiroptical properties of compounds 3-6 were examined by experiment and theoretical calculation of circular dichroism (CD) spectra to prove their absolute configurations. Compound 2 significantly exhibited cytotoxic activity towards lung carcinoma (LU-1), hepatocellular carcinoma (HepG-2), promyelocytic leukemia (HL-60), breast carcinoma (MCF-7), and melanoma (SK-Mel-2) human cancer cells with IC50 values of 5.5±0.8, 3.2±0.2, 4.0±0.7, 4.1±0.8, and 5.7±1.1 µg/mL, respectively.

Keywords: Smenospongia cerebriformis; chiroptical property; cytotoxicity; dactylospongenone; smenocerone A; smenocerone B.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Circular Dichroism
  • Cyclopentanes / isolation & purification*
  • Cyclopentanes / pharmacology*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Naphthoquinones / isolation & purification*
  • Naphthoquinones / pharmacology*
  • Porifera / chemistry*

Substances

  • Cyclopentanes
  • Naphthoquinones
  • cyclopentenone