title: Further Thymol Derivatives from Ageratina cylindrica.
abstract: From the leaves of Ageratina cylindrica, in addition to the described [(2S)-2-{4-formyl-5-hydroxy-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl]methyl benzoate (cylindrinol A, 8), seven new thymol derivatives were isolated and named cylindrinols B - H (1 - 7). The structures of these compounds were established as (2-{4-(hydroxymethyl)-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (1), (2-{4-formyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (2), (2-{4-[(acetyloxy)methyl]-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (3), [2-(2-[(2-methylpropanoyl)oxy]-4-{[(2-methylpropanoyl)oxy]methyl}phenyl)oxiran-2-yl]methyl benzoate (4), [2-(5-hydroxy-2-[(2-methylpropanoyl)oxy]-4-{[(2-methylpropanoyl)oxy]methyl}phenyl)oxiran-2-yl]methyl benzoate (5), 2-{4-(hydroxymethyl)-2-[(2-methylpropanoyl)oxy]phenyl}prop-2-en-1-yl benzoate (6), and 2-hydroxy-2-[2-hydroxy-4-(hydroxymethyl)-phenyl]-3-[(2-methylpropanoyl)oxy]propyl benzoate (7), by spectroscopic means. Compounds 1 showed moderate antiprotozoal activity on both protozoa. Compounds 4 and 5 showed selectivity on Giardia lamblia trophozoites. All isolated compounds were less active than two antiprotozoal drugs, metronidazole and emetine, used as positive controls. Compound 5 exhibited a high inhibitory effect on hyperpropulsive movement of the small intestine in rats; its effect was best than loperamide, antidiarrheal drug used as a positive control.
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F., 04510, México. bustosbritocelia@yahoo.com.mx.
authors.forename: Celia
authors.initials: C
authors.lastname: Bustos-Brito
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F., 04510, México. baldo@unam.mx.
authors.forename: Baldomero
authors.initials: B
authors.lastname: Esquivel
authors.affiliation: Unidad de Investigación Médica en Farmacología, UMAE Hospital de Especialidades, Centro Médico Nacional Siglo XXI, IMSS, 2o Piso CORCE, Av. Cuauhtémoc 330, Col. Doctores, México, D.F., 06725, México.
authors.forename: Fernando
authors.initials: F
authors.lastname: Calzada
authors.affiliation: Unidad de Investigación Médica en Enfermedades Infecciosas y Parasitarias, UMAE Hospital de Pediatría, Centro Médico Nacional Siglo XXI, IMSS, Av. Cuauhtémoc 330, Col. Doctores, México, D.F., 06725, México.
authors.forename: Lilian
authors.initials: L
authors.lastname: Yepez-Mulia
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F., 04510, México.
authors.forename: José S
authors.initials: JS
authors.lastname: Calderón
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F., 04510, México.
authors.forename: Javier
authors.initials: J
authors.lastname: Porras-Ramirez
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F., 04510, México.
authors.forename: Leovigildo
authors.initials: L
authors.lastname: Quijano
mesh_terms: D036603:Ageratina / Q000737:chemistry*; D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D016829:Giardia lamblia / Q000187:drug effects*; D007421:Intestine, Small / Q000187:drug effects* / Q000502:physiology; D021261:Parasitic Sensitivity Tests; D018515:Plant Leaves / Q000737:chemistry; D051381:Rats; D013329:Structure-Activity Relationship; D013943:Thymol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D000981:Antiprotozoal Agents; D013943:Thymol
keywords: 
  Ageratina cylindrica
  ; Antihyperpropulsive activity; Antiprotozoal activity; Cylindrinols B - H; Thymol derivatives