Antidiarrheal Thymol Derivatives from Ageratina glabrata. Structure and Absolute Configuration of 10-Benzoyloxy-8,9-epoxy-6-hydroxythymol Isobutyrate.
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 (13)C-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.
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico. bustosbritocelia@comunidad.unam.mx.
Celia
C
Bustos-Brito
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico. la_campanella@comunidad.unam.mx.
Valeria J
VJ
Vázquez-Heredia
UIM en Farmacología, 2o Piso CORCE, UMAE Hospital de Especialidades, Centro Médico Nacional Siglo XXI, IMSS, Av. Cuauhtémoc 330, Col. Doctores, México, D.F. 06725, Mexico. fercalber10@gmail.com.
Fernando
F
Calzada
UIM en Enfermedades Infecciosas y Parasitarias, UMAE Hospital de Pediatría, Centro Médico Nacional Siglo XXI, IMSS, Av. Cuauhtémoc 330, Col. Doctores, México, D.F. 06725, Mexico. lilianyepez@yahoo.com.
Lilian
L
Yépez-Mulia
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico. uscalder@unam.mx.
José S
JS
Calderón
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico. shernandezortega@gmail.com.
Simón
S
Hernández-Ortega
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico. baldo@unam.mx.
Baldomero
B
Esquivel
UIM en Genética Humana, UMAE Hospital de Pediatría, Centro Médico Nacional Siglo XXI, IMSS, Centro Médico Nacional Siglo XXI, IMSS, Av. Cuauhtémoc 330, Col. Doctores, México, D.F. 06725, Mexico. normandgarcia@gmail.com.
Normand
N
García-Hernández
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico. quijano@unam.mx.
Leovigildo
L
Quijano
D036603:Ageratina / Q000737:chemistry*; D000930:Antidiarrheals / Q000737:chemistry / Q000302:isolation & purification; D006801:Humans; D058610:Isobutyrates / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D018515:Plant Leaves / Q000737:chemistry*; D013943:Thymol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification
D000930:Antidiarrheals; D058610:Isobutyrates; D013943:Thymol
Ageratina glabrata; antiprotozoal and antidiarrheal properties; thymol derivatives