Phenylpropanoyl esters from Horseweed (Conyza canadensis) and their inhibitory effects on catecholamine secretion.
Three unique phenylpropanoyl 2,7-anhydro-3-deoxy-2-octulosonic acid derivatives were isolated from Conyza canadensis (horseweed). Their structures were defined as rel-(1S,2R,3R,5S,7R)-methyl 7-caffeoyloxymethyl-2-hydroxy-3-feruloyloxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (1), rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (2), and rel-(1R,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-feruloyloxy-3-hydroxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (3). Compound 1 and a 5:3 mixture of compounds 2 and 3 were demonstrated to inhibit the catecholamine secretion induced by acetylcholine with IC(50) values of 94.65 and 42.35 microM, respectively, and to inhibit the catecholamine secretion induced by veratridine and high [K(+)] at a dose of 100 microM in cultured bovine adrenal medullary cells.
Ding
Yuexu
Y
School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, People's Republic of China.
Su
Yanfang
Y
Guo
Hao
H
Yang
Fan
F
Mao
Haoping
H
Gao
Xiumei
X
Zhu
Zhiqiang
Z
Tu
Guangzhong
G
D000313:Adrenal Medulla / Q000166:cytology / Q000187:drug effects; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002395:Catecholamines / Q000378:metabolism; D002417:Cattle; D035401:Conyza / Q000737:chemistry*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004952:Esters; D020128:Inhibitory Concentration 50; D010666:Phenylpropionates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism; D014701:Veratridine / Q000494:pharmacology
D019086:Bridged Bicyclo Compounds, Heterocyclic; D002395:Catecholamines; D004365:Drugs, Chinese Herbal; D004952:Esters; D010666:Phenylpropionates; C548097:rel-(1R,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-feruloyloxy-3-hydroxy-6,8-dioxabicyclo(3.2.1)octane-5-carboxylate; C548098:rel-(1S,2R,3R,5S,7R)-methyl 7-caffeoyloxymethyl-2-hydroxy-3-feruloyloxy-6,8-dioxabicyclo(3.2.1)octane-5-carboxylate; C548096:rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6,8-dioxabicyclo(3.2.1)octane-5-carboxylate; D014701:Veratridine