Abstract
The first total synthesis of both broussonetine I and J2 together with their enantiomers have been accomplished via the same synthetic route through 18 and 16 steps in excellent overall yields (18% and 19%, respectively), starting from R-glyceraldehyde. Broussonetine I was found to be a potent inhibitor of β-glucosidase (IC50 = 2.9 μM), while ent-broussonetine I and ent-broussonetine J2 were found to be potent inhibitors of α-glucosidase (IC50 = 0.33 and 0.53 μM, respectively).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Aspergillus niger / enzymology
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Cattle
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Dose-Response Relationship, Drug
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Glycoside Hydrolases / antagonists & inhibitors*
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Glycoside Hydrolases / metabolism
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Helix, Snails / enzymology
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Imino Sugars / chemical synthesis
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Imino Sugars / chemistry
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Imino Sugars / pharmacology*
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Molecular Conformation
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Plants / enzymology
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Rats
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Saccharomyces cerevisiae / enzymology
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Enzyme Inhibitors
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Imino Sugars
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broussonetine I
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broussonetine J
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Glycoside Hydrolases