Cytotoxic and anti-inflammatory prenylated benzoylphloroglucinols and xanthones from the twigs of Garcinia esculenta

J Nat Prod. 2014 Jul 25;77(7):1700-7. doi: 10.1021/np5003498. Epub 2014 Jun 24.

Abstract

Five new prenylated benzoylphloroglucinol derivatives, garciesculentones A-E (1-5), a new xanthone, garciesculenxanthone A (6), and 15 known compounds were isolated from the petroleum ether extract and the EtOAc-soluble fraction of a 80% (v/v) EtOH extract of Garcinia esculenta. The structures of the new compounds were elucidated by 1D- and 2D-NMR spectroscopic analysis and mass spectrometry. Experimental and calculated ECD and a convenient modified Mosher's method were used to determine the absolute configurations. The cytotoxicity of these compounds were evaluated by MTT assay against three human cancer cell lines (HepG2, MCF-7, and MDA-MB-231) and against normal hepatic cells (HL-7702). In addition, these isolates were evaluated for their inhibitory effects on interferon-γ plus lipopolysaccharide-induced nitric oxide production in RAW264.7 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents* / chemistry
  • Anti-Inflammatory Agents* / isolation & purification
  • Anti-Inflammatory Agents* / pharmacology
  • Antineoplastic Agents, Phytogenic* / chemistry
  • Antineoplastic Agents, Phytogenic* / isolation & purification
  • Antineoplastic Agents, Phytogenic* / pharmacology
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal* / chemistry
  • Drugs, Chinese Herbal* / isolation & purification
  • Drugs, Chinese Herbal* / pharmacology
  • Female
  • Garcinia / chemistry*
  • Hep G2 Cells
  • Humans
  • Interferon-gamma / drug effects
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Phloroglucinol* / analogs & derivatives
  • Phloroglucinol* / chemistry
  • Phloroglucinol* / isolation & purification
  • Phloroglucinol* / pharmacology
  • Prenylation
  • Xanthones* / chemistry
  • Xanthones* / isolation & purification
  • Xanthones* / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Lipopolysaccharides
  • Xanthones
  • Nitric Oxide
  • Interferon-gamma
  • Phloroglucinol