Newα-Glucosidase Inhibitors from the Mongolian Medicinal PlantFerula mongolica

Abstract

The four new and four known sesquiterpenoid derivatives 1 ± 4 and 5 ± 8, respectively, were isolated from the air-dried roots of Ferula mongolica. The structures of these compounds were determined by spectroscopic methods and found to be rel-(4), (4E,8E)-1-(2-hydroxy-4-methoxyphenyl)-5,9,13-trimethyltetradeca-4,8,12-trien-1-one (5), the rel-(2R,3S) diastereoisomer 6 of 2, the rel-(2R,3S) diastereoisomer 7 of 4, and (4E,8E)-1-(2,4-dihydroxyphenyl)-5,9,13trimethyltetradeca-4,8,12-trien-1-one (8). These compounds were tested as inhibitors against the enzyme aglucosidase. The compounds 1 ± 6 and 8 exhibited significant inhibitory activity and, therefore, represent a new class of a-glucosidase inhibitors. HÀC(5') 7.91 (d, J 8.7) 7.94 (d, J 8.5) 7.50 (d, J 8.5) 7.58 (d, J 9.4) 6.49 (dd, J 2.5, 8.5) 7.93 (d, J 8.7) 7.57 (d, J 9.3) 6.49 (dd, J 2.5, 8.5) HÀC(6') 6.88 (dd, J 2.2, 8.7) 6.90 (dd, J 2.0, 8.5) 6.80 (dd, J 2.0, 8.5) 6.96 (dd, J 2.2, 9.4) 7.79 (d, J 8.9) 6.90 (dd, J 2.2, 8.7) 6.95 (dd, J 2.3, 9.4) 7.79 (d, J 8.9) HÀC(8') 6.76 (d, J 2.2) 6.81 (d, J 2.0) 6.73 (d, J 2.0) 6.93 (d, J 2.2) ± 6.81 (d, J 2.2) 6.93 (d, J 2.3) ±

Chloroform Extract of Underground Parts of Ferula heuffelii: Secondary Metabolites and Spasmolytic Activity

“…The obtained spectral data of isolated compounds are in agreement with those previously reported: latifolone (1) [20], elemicin (2) [21], (6E)-1-(2,4-dihydroxyphenyl)-3,7,11-trimethyl-3-vinyldodeca-6,10dien-1-one [22] (3), dshamirone (4) [23], (3S*,4R*,5R*)-3- (6) [24], samarkandin acetate (7) [25], fukanedone B (8) [26] -Structure Elucidation and Quantification of Isolated Compounds.…”

Sesquiterpenoids with Anti‐MDR Staphylococcus aureus Activities from Ferula ferulioides

“…Structures of 21 known sesquiterpenes were identified by comparison of their spectroscopic data with those reported in the literature.T hey were 2,4-dihydroxyacetophenone (1), 2,4-dihydroxybenzoic acid (3), 2,4-dihydroxy-a-oxobenzeneacetic acid (4) [32], 2-hydroxy-4-methoxyacetophenone (2) [33], dshamirone (5) [24], (4E,8E)-1- (2-hydroxy-4-methoxyphenyl)-5,9,13-trimethyltetradeca-4,8,12-trien-1-one (6) [ 34], (4E,8E)-1-(2,4-dihydroxyphenyl)-2-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-one (7), (6E)-1- (2,4-dihydroxyphenyl)-3,7,11-trimethyl-3-vinyldodeca-6,10-dien-1one (8) [ 24], 8,9-dihydroxydshamirone( 9 ), 8,9-oxoisopropanyldshamirone (10), ferulaeolactone A [ 29], 3-(2,4-dihydroxybenzoyl)-4,5-dimethyl-5-[(3E,7E)-4,8-dimethylnona-3,7-dien-1-yl]tetrahydrofuran-2-one (11) [ 22], (2S*,3R*)-2,3-dihydro-7hydroxy-2,3-dimethyl-2-[(3E) -4,8-dimethylnona-3,7-dienyl]furo [3,2-c]coumarin (17), [3,2-c]coumarin (18), (2R*,3R*)-2,3-dihydro-7-methoxy-2,3-dimethyl-2-[(3E) -4,8-dimethylnona-3,7-dienyl]furo [3,2-c]coumarin (20) [ 26], (2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-3-[(3E) -4,8-dimethylnona-3,7-dienyl]furo [3,2-c]coumarin (21), (2S*,3R*)-2,3-dihydro-7-hydroxy-2,3-dimethyl-3-[(3E) -4,8dimethylnona-3,7-dienyl]furo [3,2-c]coumarin (22), (2S*,3R*)-2,3-dihydro-7-methoxy-2,3-dimethyl-3-[(3E) -4,8-dimethylnona-3,7-dienyl]furo [3,2-c]coumarin (23) [ 23], ferulin A ( 27), and ferulin B( 28) [35].…”

Screening of Mongolian Plants for Influence on Amylase Activity in Mouse Plasma and Gastrointestinal Tube

“…4,[10][11][12][13][14][15][16] In particular, from one such plant, the Mongolian medicinal plant Ferula mongolica, sesquiterpenoid derivatives have been isolated as the inhibitory active component. 4) As revealed in Fig. 2, the inhibitory actions of 4 particular plant extracts, showing intense activities greater than 40%, are mostly concentration-dependent.…”