Preprint Article Version 1 NOT YET PEER-REVIEWED

Antidiarrheal Thymol Derivatives from Ageratina glabrata. Structure and Absolute Configuration of 10-Benzoyloxy-8,9-epoxy-6-hydroxythymol Isobutyrate

  1. Instituto de Química, Universidad Nacional Autónoma de Mexico, Circuito Exterior, Ciudad Universitaria, Mexico D.F. 04510, Mexico
  2. Unidad de Investigación Médica en Farmacología, 2o Piso CORCE, UMAE Hospital de Especialidades, Centro Médico Nacional Siglo XXI, IMSS, Av. Cuauhtémoc 330, Col. Doctores, Mexico D.F. 06725, Mexico
  3. Unidad de Investigación Médica en Enfermedades Infecciosas y Parasitarias, UMAE Hospital de Pediatría, Centro Médico Nacional Siglo XXI, IMSS, Av. Cuauhtémoc 330, Col. Doctores, Mexico D.F. 06725, Mexico
  4. Unidad de Investigación Médica en Genética Humana, UMAE Hospital de Pediatría. Centro Médico Nacional Siglo XXI, IMSS. Centro Médico Nacional Siglo XXI, IMSS, Av. Cuauhtémoc 330, Col. Doctores, Mexico D.F. 06725, Mexico
Version 1 : Received: 5 August 2016 / Approved: 6 August 2016 / Online: 6 August 2016 (11:26:06 CEST)

How to cite: Bustos-Brito, C.; Vázquez-Heredia, V.; Calzada, F.; Yépez-Mulia, L.; Calderón, J.; Hernández-Ortega, S.; Esquivel, B.; García-Hernández, N.; Quijano, L. Antidiarrheal Thymol Derivatives from Ageratina glabrata. Structure and Absolute Configuration of 10-Benzoyloxy-8,9-epoxy-6-hydroxythymol Isobutyrate. Preprints 2016, 2016080062 (doi: 10.20944/preprints201608.0062.v1). Bustos-Brito, C.; Vázquez-Heredia, V.; Calzada, F.; Yépez-Mulia, L.; Calderón, J.; Hernández-Ortega, S.; Esquivel, B.; García-Hernández, N.; Quijano, L. Antidiarrheal Thymol Derivatives from Ageratina glabrata. Structure and Absolute Configuration of 10-Benzoyloxy-8,9-epoxy-6-hydroxythymol Isobutyrate. Preprints 2016, 2016080062 (doi: 10.20944/preprints201608.0062.v1).

Abstract

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-dehydro thymol (5), 10-benzoyloxythymol (6) and 10-benzoyloxy-6,8-dihydroxy-9-isobutyryloxythymol (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). In this paper, we wish to publish the structures and complete assignments of 1H and 13C NMR data of compounds 17, 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 like emetine and metronidazole, respectively, two antiprotozoal drugs used as positive controls. In relation of anti-propulsive effect, compound 1 and 1a showed moderate inhibitory activity, their activities were comparable to quercetin and compound 9, respectively, 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.

Subject Areas

Ageratina glabrata; thymol derivatives; antiprotozoal and antidiarrheal properties

Readers' Comments and Ratings (0)

Discuss and rate this article
Views 227
Downloads 178
Comments 0
Metrics 0
Discuss and rate this article

×
Alerts
Notify me about updates to this article or when a peer-reviewed version is published.