Smooth muscle relaxant action of benzyl benzoates and salicylic acid derivatives from Brickellia veronicaefolia on isolated guinea-pig ileum.
A dichloromethane-MeOH extract prepared from the aerial parts of Brickellia veronicaefolia inhibited the spontaneous contractions (IC50 = 39.22 microg/mL) of the guinea-pig ileum. Bioassay-guided fractionation of the extract led to the isolation of three new benzoic acid derivatives, 1,2-bis-O-(2-methoxybenzoyl)-beta-d-glucopyranoside (1), 3-(beta-glucopyranosyloxy)benzyl 2,6-dimethoxybenzoate (2) and 3-hydroxybenzyl 2,6-dimethoxybenzoate (3), together with the known compounds taraxasteryl acetate (4), 4-allyl-2-methyloxyphenyl-beta-glucopyranoside (5), 2-hydroxy-6-methoxybenzoic acid (6), 2-methoxybenzoic acid (7), chamazulene (8), 2-methoxybenzyl 2-hydroxybenzoate (9), benzyl 2,6-dimethoxybenzoate (10), 3-methoxybenzyl 2-hydroxy-6-methoxybenzoate (11), benzyl 2-hydroxy-6-methoxybenzoate (12), benzyl 2,3,6-trimethoxybenzoate (13), benzyl 2-hydroxy-3,6-dimethoxybenzoate (14) and 3-methoxybenzyl 2,6-dimethoxybenzoate (15). The isolates were characterized by spectral means. Compounds 2 - 6, 8 - 11, 14 and 15 induced a concentration-dependent inhibition of the spontaneous contractions of the guinea-pig ileum with IC50 values ranging from 1.49 to 4.96 microM. Their activity was comparable to that of papaverine (IC50 = 4.23 microM).
Rivero-Cruz
Blanca
B
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México DF, México.
Rojas
María Alejandra
MA
Rodríguez-Sotres
Rogelio
R
Cerda-García-Rojas
Carlos M
CM
Mata
Rachel
R
D000818:Animals; D019659:Asteraceae; D001565:Benzoates / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D004305:Dose-Response Relationship, Drug; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects; D008297:Male; D009126:Muscle Relaxation / Q000187:drug effects*; D009130:Muscle, Smooth / Q000187:drug effects; D010276:Parasympatholytics / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D008517:Phytotherapy; D035261:Plant Components, Aerial; D010936:Plant Extracts / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D020156:Salicylic Acid / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D013329:Structure-Activity Relationship
D001565:Benzoates; D010276:Parasympatholytics; D010936:Plant Extracts; D020156:Salicylic Acid