Abstract
(-)-β-Caryophyllene was decorated with a privileged β-lactam motif and subsequently converted into highly diverse scaffolds via remodeling of the ring system. The structures were defined by spectroscopic data, X-ray diffraction analysis, and experimental and calculated ECD data. Compound 19 displayed the most potent activity against the rice blast fungus, while 6 had a more potent α-glucosidase inhibition than the drug acarbose. These findings demonstrate a concise protocol to exploit natural product-driven diversity.
MeSH terms
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Antifungal Agents / chemical synthesis
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Antifungal Agents / chemistry
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Antifungal Agents / pharmacology*
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Biological Products / chemical synthesis
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Biological Products / chemistry
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Biological Products / pharmacology*
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Dose-Response Relationship, Drug
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Glycoside Hydrolase Inhibitors / chemical synthesis
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Glycoside Hydrolase Inhibitors / chemistry
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Glycoside Hydrolase Inhibitors / pharmacology*
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Humans
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Magnaporthe / drug effects*
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Models, Molecular
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Molecular Conformation
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Oryza / microbiology
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Polycyclic Sesquiterpenes
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Quantum Theory
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Sesquiterpenes / chemistry
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Sesquiterpenes / pharmacology*
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Structure-Activity Relationship
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alpha-Glucosidases / metabolism
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beta-Lactams / chemistry
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beta-Lactams / pharmacology*
Substances
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Antifungal Agents
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Biological Products
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Glycoside Hydrolase Inhibitors
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Polycyclic Sesquiterpenes
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Sesquiterpenes
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beta-Lactams
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caryophyllene
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alpha-Glucosidases