title: 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.
authors.affiliation: Department of Biological Sciences, Lehman College and The Graduate School and University Center, The City University of New York, 250 Bedford Park Boulevard West, Bronx, New York 10468, USA.
authors.forename: Scott
authors.initials: S
authors.lastname: Baggett
authors.forename: Petr
authors.initials: P
authors.lastname: Protiva
authors.forename: Eugene P
authors.initials: EP
authors.lastname: Mazzola
authors.forename: Hui
authors.initials: H
authors.lastname: Yang
authors.forename: Elizabeth T
authors.initials: ET
authors.lastname: Ressler
authors.forename: Margaret J
authors.initials: MJ
authors.lastname: Basile
authors.forename: I Bernard
authors.initials: IB
authors.lastname: Weinstein
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Kennelly
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001577:Benzophenones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001713:Biphenyl Compounds; D004354:Drug Screening Assays, Antitumor; D005431:Florida; D005638:Fruit / Q000737:chemistry; D029760:Garcinia / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D010851:Picrates / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D001577:Benzophenones; D001713:Biphenyl Compounds; D010851:Picrates; C499938:gambogenone; C499940:guttiferone H; C004931:1,1-diphenyl-2-picrylhydrazyl