Abstract
Hyperforin is a polyprenylated acylphloroglucinol derivative from Hypericum perforatum (St. John's wort). It exhibits antidepressant activity by a novel mechanism of action, antibiotic activity against gram-positive bacteria, and antitumoral activity in vivo. However, it also produces drug-drug interactions by activation of the pregnan X receptor. No total synthesis has been described. Some natural and semisynthetic analogues are available to study structure-activity relationships. Enzymatically, the skeleton of hyperforin is formed by isobutyrophenone synthase from isobutyryl-CoA and three molecules of malonyl-CoA. The first prenylation step is catalyzed by a soluble and ion-dependent dimethylallyltransferase. Hyperforin mainly accumulates in pistils and fruits where it probably serves as defensive compound.
MeSH terms
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Anti-Bacterial Agents / chemistry*
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Anti-Bacterial Agents / metabolism
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Anti-Bacterial Agents / pharmacology
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Antineoplastic Agents, Phytogenic / chemistry*
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Antineoplastic Agents, Phytogenic / metabolism
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Antineoplastic Agents, Phytogenic / pharmacology
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Bridged Bicyclo Compounds / chemistry
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Bridged Bicyclo Compounds / metabolism
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Bridged Bicyclo Compounds / pharmacology
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Hypericum / anatomy & histology
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Hypericum / chemistry*
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Hypericum / metabolism
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Neurotransmitter Uptake Inhibitors / chemistry*
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Neurotransmitter Uptake Inhibitors / metabolism
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Neurotransmitter Uptake Inhibitors / pharmacology
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Nuclear Magnetic Resonance, Biomolecular
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Phloroglucinol / analogs & derivatives*
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Phloroglucinol / chemistry
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Phloroglucinol / metabolism
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Phloroglucinol / pharmacology
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Terpenes / chemistry*
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Terpenes / metabolism
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Terpenes / pharmacology
Substances
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Anti-Bacterial Agents
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Antineoplastic Agents, Phytogenic
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Bridged Bicyclo Compounds
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Neurotransmitter Uptake Inhibitors
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Terpenes
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Phloroglucinol
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hyperforin