Pyrrolizidine alkaloids (lycopsamine, intermedine)

Strong

Pyrrolizidine alkaloid (1,2-unsaturated necine type)

Mechanism of Action

Unsaturated PAs are bioactivated in the liver by CYP3A4 to form reactive pyrrolic metabolites (dehydropyrrolizidine alkaloids) that cross-link DNA and proteins, causing hepatocyte necrosis (sinusoidal obstruction syndrome/veno-occlusive disease), hepatic fibrosis, and potentially hepatocellular carcinoma with chronic exposure. The reactive metabolites alkylate cellular macromolecules and disrupt hepatic sinusoidal endothelium.

Research Notes

BorageWestern

The European Medicines Agency established a maximum daily intake of 0.007 µg/kg body weight for unsaturated PAs from herbal products (2014 assessment). Borage leaf contains measurable levels of lycopsamine and intermedine, necessitating PA-free certification for any internal use product. Borage seed oil typically contains less than 0.5 µg/mL total PAs and is generally considered safe. The German BfR (Federal Institute for Risk Assessment) specifically warns against internal use of borage leaf preparations that have not been tested for PA content.

Found In 1 Herb

Borage

Western

3D Molecular Structure

Pyrrolizidine alkaloid (1,2-unsaturated necine type)

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Pyrrolizidine alkaloids (lycopsamine, intermedine)

Pyrrolizidine alkaloid (1,2-unsaturated necine type)Nitrogen-containing compounds with potent pharmacological effects

Representative pattern: C₉H₇N₂O

Atoms

Nitrogen

Carbon

Hydrogen

Oxygen

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