Abstract
The leaves of Ageratina cylindrica afforded a thymol derivative that was characterized by physical and spectroscopical methods as (8S)-8,9-epoxy-6-hydroxy-l0-benzoyloxy-7-oxothymol isobutyrate (1). The absolute configuration of 1 was established as 8S by vibrational circular dichroism spectroscopy in combination with density functional theory calculations and by evaluation of the Flack and Hooft X-ray parameters. Compound 1 showed weak antiprotozoal activity against Entamoeba histolytica and Giardia lamblia trophozoites and a high inhibitory effect on hyperpropulsive movement of the small intestine in rats.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Ageratina / chemistry*
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Animals
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Antidiarrheals* / chemistry
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Antidiarrheals* / isolation & purification
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Antidiarrheals* / pharmacology
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Antiprotozoal Agents* / chemistry
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Antiprotozoal Agents* / isolation & purification
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Antiprotozoal Agents* / pharmacology
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Circular Dichroism
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Entamoeba histolytica / drug effects
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Giardia lamblia / drug effects
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Intestine, Small / drug effects
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Mexico
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Molecular Structure
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Peristalsis / drug effects
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Plant Leaves / chemistry
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Rats
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Thymol* / analogs & derivatives
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Thymol* / chemistry
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Thymol* / isolation & purification
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Thymol* / pharmacology
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Trophozoites / drug effects
Substances
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(8S)-8,9-epoxy-6-hydroxy-l0-benzoyloxy-7-oxothymol isobutyrate
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Antidiarrheals
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Antiprotozoal Agents
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Thymol