Abstract
Eight new aryltetralin lignans, cleisindosides A-F (1-6), picroburseranin (7), and 7-hydroxypicropolygamain (8), were isolated from the fruits of Cleistanthus indochinensis (Euphorbiaceae). The structures of the isolates were established on the basis of their one- and two-dimensional NMR spectral data, as well as their mass spectrometric data. Compound 7 was found to have potent cytotoxicity against oral epidermoid carcinoma cells with an IC50 value of 0.062 µM, whereas glycosylation to 3 (IC50 7.5 µM) and stereochemical changes to 8 (IC50 10.8 µM) led to marked decreases in biological activity. Thus, it was determined that the C-7 and C-8' positions are critical for the biological activity of the lignans from this plant.
Georg Thieme Verlag KG Stuttgart · New York.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification*
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Antineoplastic Agents, Phytogenic / pharmacology
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Cell Line, Tumor
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Cell Survival / drug effects
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Chromatography, High Pressure Liquid
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Euphorbiaceae / chemistry*
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Fruit / chemistry
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Glycosides / chemistry
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Glycosides / isolation & purification
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Glycosides / pharmacology
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Humans
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Inhibitory Concentration 50
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Lignans / chemistry
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Lignans / isolation & purification*
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Lignans / pharmacology
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Plant Extracts / chemistry
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Plant Extracts / isolation & purification*
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Plant Extracts / pharmacology
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Tetrahydronaphthalenes / chemistry
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Tetrahydronaphthalenes / isolation & purification*
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Tetrahydronaphthalenes / pharmacology
Substances
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Antineoplastic Agents, Phytogenic
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Glycosides
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Lignans
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Plant Extracts
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Tetrahydronaphthalenes
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tetralin