title: Structure, absolute configuration, and antidiarrheal activity of a thymol derivative from Ageratina cylindrica.
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.
authors: Instituto de Química, Universidad Nacional Autónoma de México , Circuito Exterior, Ciudad Universitaria, D.F., 04510 México.
authors: Celia
authors: C
authors: Bustos-Brito
authors: Mariano
authors: M
authors: Sánchez-Castellanos
authors: Baldomero
authors: B
authors: Esquivel
authors: José S
authors: JS
authors: Calderón
authors: Fernando
authors: F
authors: Calzada
authors: Lilian
authors: L
authors: Yepez-Mulia
authors: Angelina
authors: A
authors: Hernández-Barragán
authors: Pedro
authors: P
authors: Joseph-Nathan
authors: Gabriel
authors: G
authors: Cuevas
authors: Leovigildo
authors: L
authors: Quijano
mesh_terms: D036603:Ageratina / Q000737:chemistry*; D000818:Animals; D000930:Antidiarrheals / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002942:Circular Dichroism; D004748:Entamoeba histolytica / Q000187:drug effects; D016829:Giardia lamblia / Q000187:drug effects; D007421:Intestine, Small / Q000187:drug effects; D008800:Mexico; D015394:Molecular Structure; D010528:Peristalsis / Q000187:drug effects; D018515:Plant Leaves / Q000737:chemistry; D051381:Rats; D013943:Thymol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D053058:Trophozoites / Q000187:drug effects
chemical_list: C000590252:(8S)-8,9-epoxy-6-hydroxy-l0-benzoyloxy-7-oxothymol isobutyrate; D000930:Antidiarrheals; D000981:Antiprotozoal Agents; D013943:Thymol