Bioactive benzophenones from Garcinia xanthochymus fruits.
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.
Baggett
Scott
S
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.
Protiva
Petr
P
Mazzola
Eugene P
EP
Yang
Hui
H
Ressler
Elizabeth T
ET
Basile
Margaret J
MJ
Weinstein
I Bernard
IB
Kennelly
Edward J
EJ
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
D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D001577:Benzophenones; D001713:Biphenyl Compounds; D010851:Picrates; C499938:gambogenone; C499940:guttiferone H; C004931:1,1-diphenyl-2-picrylhydrazyl