Cytotoxic and Antimicrobial Benzophenones from the Leaves of Tovomita longifolia

• Published in: Journal of natural products (Washington, D.C.) Vol. 69; no. 3; pp. 410 - 413
• Main Authors: Pecchio, Marisín, Solís, Pablo N, López-Pérez, José L, Vásquez, Yelkaira, Rodríguez, Nelson, Olmedo, Dionisio, Correa, Mireya, San Feliciano, Arturo, Gupta, Mahabir P
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-03-2006; Glendale, AZ American Society of Pharmacognosy
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; antibacterial properties; antifungal properties; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; benzophenone; Benzophenones - chemistry; Benzophenones - isolation & purification; Benzophenones - pharmacology; Biological and medical sciences; Clusiaceae; Clusiaceae - chemistry; cultured cells; cytotoxicity; Drug Screening Assays, Antitumor; General pharmacology; Humans; Klebsiella pneumoniae; Klebsiella pneumoniae - drug effects; Medical sciences; Microbial Sensitivity Tests; Molecular Structure; Mycobacterium smegmatis; Mycobacterium smegmatis - drug effects; Panama; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytochemicals; plant extracts; Plant Leaves - chemistry; Plants, Medicinal - chemistry; Pseudomonas aeruginosa; Pseudomonas aeruginosa - drug effects; Salmonella - drug effects; Salmonella gallinarum; Staphylococcus aureus; Staphylococcus aureus - drug effects; Tovomita longifolia; Panama; Central America; America; Pseudomonadales; Salmonella; Benzophenone derivatives; Guttiferae; Lung; Central nervous system; Mycobacterium smegmatis; Cytotoxicity; Antimicrobial agent; Medicinal plant; Chroman derivatives; Xanthene derivatives; Dicotyledones; Angiospermae; Bacteria; Micrococcales; Pseudomonadaceae; Pseudomonas aeruginosa; Micrococcaceae; Mammary gland; Tumor cell; Staphylococcus aureus; Enterobacteriaceae; Non small cell carcinoma; Human; Pharmacognosy; Plant leaf; In vitro; Biological activity; Cell line; Glioma; Mycobacteriales; Plant origin; Mycobacteriaceae; Isolation; Actinomycetes; Spermatophyta; Klebsiella pneumoniae; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050338c

Bioassay-guided fractionation of the chloroform and ethanol extracts of Tovomita longifolia leaves using cytotoxic and antimicrobial assays resulted in the isolation of four new benzophenones, (E)-3-(2-hydroxy-7-methyl-3-methyleneoct-6-enyl)-2,4,6-trihydroxybenzophenone (1), (E)-3-(6-hydroxy-3,7-dimethylocta-2,7-dienyl)-2,4,6-trihydroxybenzophenone (2), 8-benzoyl-2-(4-methylpenten-3-yl)chromane-3,5,7-triol (3), and 5-benzoyl-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-6,8-diol (4), and two known benzophenones, 4-geranyloxy-2,6-dihydroxybenzophenone (5) and 3-geranyl-2,4,6-trihydroxybenzophenone (6). The structures of 1−4 were established by spectroscopic means and by molecular modeling calculations. Compounds 1 and 3−5 demonstrated cytotoxic activities against breast (MCF-7), central nervous system (SF-268), and lung (H-460) human cancer cell lines, while compounds 3−6 showed antimicrobial activity against Klebsiella pneumoniae, Mycobacterium smegmatis, Pseudomonas aeruginosa, Salmonella gallinarum, and Staphylococcus aureus.