Abstract
Three new coumarins (1-3), a prenylated flavanone (4), and two iridoids (5 and 6), together with 17 known secondary metabolites, were isolated from the aerial parts of Arcytophyllum thymifolium. The structures of the new compounds were elucidated on the basis of their spectroscopic data. The potential hypoglycemic properties of the new and known compounds were evaluated by measuring their α-amylase and α-glucosidase inhibitory effects. The iridoid asperulosidic acid (15) and the flavonoid rhamnetin (13) showed the highest activities versus α-amylase (IC50 = 69.4 ± 3.1 and 73.9 ± 5.9 μM, respectively). In turn, the new eriodictyol derivative 4 exhibited the most potent effect as an α-glucosidase inhibitor, with an IC50 value of 28.1 ± 2.6 μM, and was more active than acarbose, used as a positive control. Modeling studies were also performed to suggest the interaction mode of compound 4 in the α-glucosidase enzyme active site.
MeSH terms
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Acarbose / pharmacology
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Algorithms
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Coumarins / chemistry
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Coumarins / isolation & purification*
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Coumarins / pharmacology*
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Ecuador
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Enzyme Inhibitors / chemistry
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Flavanones
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Flavonoids / isolation & purification*
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Flavonoids / pharmacology*
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Glycoside Hydrolase Inhibitors / chemistry
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Glycoside Hydrolase Inhibitors / isolation & purification*
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Glycoside Hydrolase Inhibitors / pharmacology*
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Hypoglycemic Agents / chemistry
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Hypoglycemic Agents / isolation & purification*
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Hypoglycemic Agents / pharmacology*
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Iridoids / chemistry
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Iridoids / isolation & purification*
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Iridoids / pharmacology*
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Quercetin / analogs & derivatives
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Quercetin / pharmacology
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Rubiaceae / chemistry*
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alpha-Amylases / antagonists & inhibitors*
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alpha-Glucosidases / metabolism*
Substances
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(2'R)-7-hydroxy-8-(2',3'-dihydroxyisopentyl)-6-methoxycoumarin
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(2S)-7-prenyloxyeriodictyol
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5'-hydroxy-3'-dehydrotoddanin
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6-demethyl-5'-hydroxy-3'-dehydrotoddanin
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Coumarins
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Enzyme Inhibitors
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Flavanones
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Flavonoids
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Glycoside Hydrolase Inhibitors
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Hypoglycemic Agents
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Iridoids
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rhamnetin
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Quercetin
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alpha-Amylases
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alpha-Glucosidases
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Acarbose