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Bioactive benzophenones from Garcinia xanthochymus fruits.

Abstract
A MeOH extract of Garcinia xanthochymus fruits was subjected to activity-guided fractionation, yielding two new benzophenones, guttiferone H (1) and gambogenone (2). Compound 1 contains a seven-membered ring attached to the bicyclo[3.3.1]nonane system at positions 7 and 8 and displayed cytotoxicity in the SW-480 colon cancer cell line (IC(50) = 12 microM). Compound 2 has a novel benzophenone bicyclo[3.3.2]decane system and displayed cytotoxicity in the SW-480 colon cancer cell line (IC(50) = 188 microM). Both 1 and 2 induced apoptosis in SW-480 colon cancer cells and displayed antioxidant activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay (IC(50) = 64 and 38.7 microM, respectively). The structures of 1 and 2 were established by 1D and 2D NMR data analysis. Eleven known compounds, aristophenone A, alloathyriol, amentoflavone, 3,8' '-biapigenin, cycloxanthochymol, (+/-)-fukugetin, (+/-)-fukugiside, guttiferone E, isoxanthochymol, (+/-)-volkensiflavone, and xanthochymol, were also obtained. The 11 known compounds were also tested against SW-480 colon cancer cells and in the DPPH assay.
AuthorsScott Baggett, Petr Protiva, Eugene P Mazzola, Hui Yang, Elizabeth T Ressler, Margaret J Basile, I Bernard Weinstein, Edward J Kennelly
JournalJournal of natural products (J Nat Prod) Vol. 68 Issue 3 Pg. 354-60 (Mar 2005) ISSN: 0163-3864 [Print] United States
PMID15787435 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Benzophenones
  • Biphenyl Compounds
  • Picrates
  • gambogenone
  • guttiferone H
  • 1,1-diphenyl-2-picrylhydrazyl
Topics
  • Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
  • Antioxidants (chemistry, isolation & purification, pharmacology)
  • Benzophenones (chemistry, isolation & purification, pharmacology)
  • Biphenyl Compounds
  • Drug Screening Assays, Antitumor
  • Florida
  • Fruit (chemistry)
  • Garcinia (chemistry)
  • Humans
  • Molecular Structure
  • Picrates (pharmacology)
  • Plants, Medicinal (chemistry)
  • Tumor Cells, Cultured

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