Two new acyl flavone glucosides, luteolin-4⿲- O -(6- p -hydroxybenzoyl)-β- d -glucopyranoside (leontopodioside A, 1 ) and luteolin-4⿲- O -[6-(2-methylbutyryl)]-β- d -glucopyranoside (leontopodioside B, 2 ), and a new acyl lignan glucoside, lariciresinol-9-angeloyl-4- O -β- d -glucopyranoside (leontopodioside C, 3 ) were isolated from the whole plants of Leontopodium leontopodioides (Asteraceae). Their structures were determined by spectroscopic and chemical methods. Compounds 1 3 exhibited α-glucosidase inhibitory activity with the half maximal inhibitory concentration (IC 50 ) values of 55.6, 39.7, and 474.9 μM, respectively, in comparison with acarbose (626.3 μM).
Three new glucosides of hydroquinone , monoterpene , and megastigmane, benzyl 2,5-dihydroxybenzoate 5- O -β- d -glucopyranoside (isotrichocarpin, 1 ), (2 S ,3 R )-3,7-dimethyl-6-octene-1,2,3-triol 2- O -β- d -glucopyranoside (leontopodioside D, 4 ), and (6 R ,7 R ,8 R ,9 S )-6,9-epoxy-7,8-dihydroxymegastigman-4-en-3-one 8- O -β- d -glucopyranoside (leontopodioside E, 7 ) were isolated from the whole herbs of Leontopodium leontopodioides (Willd.) Beauv. (Asteraceae), along with nebrodenside A ( 2 ), pungenin ( 3 ), betulalbuside A ( 5 ), geranyl O -β- d -glucopyranoside ( 6 ), and 3β-hydroxy-β-ionone 3- O -β- d -glucopyranoside ( 8 ). Their structure were determined by spectroscopic and chemical methods. All the known compounds were reported from this species for the first time. Compounds 2 – 6 showed potent in vitro pancreatic lipase inhibitory activity, suggesting their participation in the reductive effect of the herbs on triglyceride absorption.