Abstract
Chemical investigation of the leaves from Ageratina glabrata yielded four new thymol derivatives, namely: 10-benzoyloxy-8,9-dehydro-6-hydroxythymol isobutyrate (4), 10-benzoyloxy-8,9-dehydrothymol (5), 10-benzoyloxythymol (6) and 10-benzoyloxy-6,8-dihydroxy-9-isobutyryl-oxythymol (7). In addition, (8S)-10-benzoyloxy-8,9-epoxy-6-hydroxythymol isobutyrate (1), together with other two already known thymol derivatives identified as 10-benzoyloxy-8,9-epoxy-6-methoxythymol isobutyrate (2) and 10-benzoyloxy-8,9-epoxythymol isobutyrate (3) were also obtained. In this paper, we report the structures and complete assignments of the 1H and 13C-NMR data of compounds 1–7, and the absolute configuration for compound 1, unambiguously established by single crystal X-ray diffraction, and evaluation of the Flack parameter. The in vitro antiprotozoal assay showed that compound 1 and its derivative 1a were the most potent antiamoebic and antigiardial compounds. Both compounds showed selectivity and good antiamoebic activity comparable to emetine and metronidazole, respectively, two antiprotozoal drugs used as positive controls. In relation to anti-propulsive effect, compound 1 and 1a showed inhibitory activity, with activities comparable to quercetin and compound 9, two natural antipropulsive compounds used as positive controls. These data suggest that compound 1 may play an important role in antidiarrheal properties of Ageratina glabrata.
Highlights
The antipropulsive aim of this paper is to report onthymol the isolation, structural characterization, thecylindrica antiprotozoal evaluation of the isolation, structural andare the antiprotozoal and antipropulsive evaluation of the derivatives
Detailed investigation of a dichloromethane extract of the leaves of A. glabrata resulted in the isolation seven thymol together with of thethe known pectolinaringenin
The HRDARTMS data were recorded on an AccuTOF JMS-T100LC mass spectrometer (Jeol Ltd., Tokyo, Japan)
Summary
Ageratina glabrata (Kunth) R.M. King & H. Rob., Asteraceaea, is a shrub endemic to Mexico widely distributed throughout the country. The importance of A. glabrata in Mexican traditional medicine is indicated by its use for treating pain and gastrointestinal disorders associated with bacterial infections. Chemical studies of the species are scarce. Previous phytochemical studies of A. glabrata show bacterial
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