Alkaloids, amides and antispasmodic activity of Zanthoxylum hyemale.
Two quinoline alkaloids, (-)-R-geilbalansine (1) and hyemaline (2), as well as aromatic amide, N-[2-(3,4-dimethoxyphenyl)-2-methoxyethyl)-2-methoxyethyl]benzamide (O-methylbalsamide) (3), were isolated as new natural products from the stem barks of Zanthoxylum hyemale, together with seven known compounds. Their structures were determined on the basis of spectroscopic data (IR, (1)H- and (13)C-NMR, MS). In addition, the antispasmodic activity of the crude extract of Z. hyemale and three other more abundant isolated compounds (4, 5 and 10) were studied in two different antispasmodic test models on isolated rat ileum and only the crude ethanolic extract presented antispasmodic activity.
de Moura
Neusa F
NF
Departamento de Quimica, Universidade Federal de Santa Maria, RS, Brazil.
Morel
Ademir F
AF
Dessoy
Emilia C
EC
Zanatta
Nilo
N
Bürger
Marilise M
MM
Ahlert
Neusa
N
Porto
Gerusa P
GP
Baldisserotto
Bernardo
B
D000109:Acetylcholine / Q000008:administration & dosage; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000577:Amides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D017609:Barium Compounds / Q000008:administration & dosage; D001549:Benzamides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D053119:Benzophenanthridines; D002712:Chlorides / Q000008:administration & dosage; D004305:Dose-Response Relationship, Drug; D007082:Ileum / Q000187:drug effects / Q000502:physiology; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D015394:Molecular Structure; D009119:Muscle Contraction / Q000187:drug effects; D010276:Parasympatholytics / Q000494:pharmacology; D010617:Phenanthridines / Q000302:isolation & purification; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D011804:Quinolines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D027821:Rutaceae; D019265:Spectroscopy, Near-Infrared
D000470:Alkaloids; D000577:Amides; D017609:Barium Compounds; D001549:Benzamides; D053119:Benzophenanthridines; D002712:Chlorides; C465094:N-(2-(3,4-dimethoxyphenyl)-2-methoxyethyl-2-methoxyethyl)benzamide; C465095:N-(2-(4-methoxyphenyl)-2-methoxyethyl-2-methoxyethyl)benzamide; D010276:Parasympatholytics; D010617:Phenanthridines; D010936:Plant Extracts; D011804:Quinolines; C465093:geilbalansine; C465092:hyemaline; C024986:barium chloride; C035932:skimmianine; C013615:nitidine; D000109:Acetylcholine