Bioassay-Guided Isolation of Prenylated Xanthone Derivatives from the Leaves of Garcinia oligantha

J Nat Prod. 2016 Jul 22;79(7):1752-61. doi: 10.1021/acs.jnatprod.6b00137. Epub 2016 Jun 22.

Abstract

Four new dihydroxanthone derivatives (1-4), four new tetrahydroxanthone derivatives (5-8), two new xanthone derivatives (9 and 10), and two known caged tetrahydroxanthones were isolated from extracts of the leaves of Garcinia oligantha by bioassay-guided fractionation. These structures of the new compounds were elucidated by NMR and MS spectroscopic data analysis, and the absolute configurations of compounds 1 and 5-7 were determined by electronic circular dichroism and/or single-crystal X-ray diffraction analysis. Compounds 6-9 were shown to be unusual xanthone derivatives with an isopropyl group, which was confirmed by the X-ray crystallographic structure of compound 8. The inhibitory activities of these isolates against four human tumor cell lines (A549, HepG2, HT-29, and PC-3) were assayed, and compounds 1, 2, 5, 11, and 12 showed inhibitory effects on tumor cell growth, with IC50 values ranging from 2.1 to 8.6 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Garcinia / chemistry*
  • HT29 Cells
  • Hep G2 Cells
  • Humans
  • Molecular Conformation
  • Molecular Structure
  • Phloroglucinol / chemistry
  • Plant Leaves / chemistry
  • Prenylation
  • Xanthones / chemistry
  • Xanthones / isolation & purification*
  • Xanthones / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Xanthones
  • Phloroglucinol