Anthrone and Oxanthrone C-Glycosides from Picramnia latifolia Collected in Peru

Cytotoxicity-based, bioassay-guided fractionation of the chloroform-soluble extracts of both the roots and leaves of Picramnia latifolia led to the isolation of two new anthrone C-glycosides, picramniosides G (1) and H (2), two new oxanthrone C-glycosides, mayosides D (3) and E (4), and a new benzan...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2004-03, Vol.67 (3), p.352-356
Main Authors: Diaz, Fredyc, Chai, Hee-Byung, Mi, Qiuwen, Su, Bao-Ning, Vigo, Jose Schunke, Graham, James G, Cabieses, Fernando, Farnsworth, Norman R, Cordell, Geoffrey A, Pezzuto, John M, Swanson, Steven M, Kinghorn, A. Douglas
Format: Article
Language:English
Subjects:
Anthracenes - chemistry
Anthracenes - isolation & purification
Anthracenes - pharmacology
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Biological and medical sciences
Drug Screening Assays, Antitumor
General pharmacology
Glycosides - chemistry
Glycosides - isolation & purification
Glycosides - pharmacology
Humans
Medical sciences
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peru
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Leaves - chemistry
Plants, Medicinal - chemistry
Stereoisomerism
Tumor Cells, Cultured
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Summary:Cytotoxicity-based, bioassay-guided fractionation of the chloroform-soluble extracts of both the roots and leaves of Picramnia latifolia led to the isolation of two new anthrone C-glycosides, picramniosides G (1) and H (2), two new oxanthrone C-glycosides, mayosides D (3) and E (4), and a new benzanthrone natural product, 6,8-dihydroxy-10-methyl-7H-benz[de]anthracen-7-one (5), together with 10 known compounds, 6,8-dihydroxy-4-methyl-7H-benz[de]anthracen-7-one (6), nataloe-emodin (7), chrysophanein, chrysophanol, 1,5-dihydroxy-7-methoxy-3-methylanthraquinone, pulmatin, 7-hydroxycoumarin, 7-hydroxy-6-methoxycoumarin, β-sitosterol, and β-sitosterol glucoside. The structures of 1−5 were established by spectroscopic methods, including 1D and 2D NMR, HRMS, and CD data interpretation. The cytotoxic activity of all isolates was evaluated in a small panel of human cancer cell lines. Compound 7 exhibited significant in vitro cytotoxic activity in the tested cell lines, but no significant activity was observed with an in vivo hollow fiber model at doses of 6.25, 12.5, 25, and 50 mg/kg/injection.
ISSN:0163-3864
1520-6025
DOI:10.1021/np030479j