Polyacetylenes from water hemlock, Cicuta virosa

Area of Science:

• Phytochemistry
• Natural Product Chemistry
• Botany

Background:

• Water hemlock (Cicuta virosa L.) is a plant known to contain various bioactive compounds.
• Polyacetylenes are a class of organic compounds with diverse biological activities.
• Previous research has identified some polyacetylenes in Cicuta virosa, but a comprehensive analysis is lacking.

Purpose of the Study:

• To isolate and characterize polyacetylenes from different parts of Cicuta virosa.
• To identify novel polyacetylenes and their isomers within the plant.
• To investigate the quantitative and qualitative variations in polyacetylene composition.

Main Methods:

• Extraction of polyacetylenes from aerial and subterranean parts of Cicuta virosa.
• High-Performance Liquid Chromatography (HPLC) for profiling lipophilic extracts.
• Chemical characterization of isolated compounds.

Main Results:

• Eleven C17-polyacetylenes were isolated, including known compounds like cicutoxin and cicutol, novel isomers, and a new polyacetylene (1,8 E/ Z,10 E,12 E)-heptadecatetraene-4,6-diyn-3-ol.
• Configurational isomers of cicutoxin and cicutol, along with two incompletely characterized isomers, were identified.
• HPLC analysis revealed quantitative, but not qualitative, variations in polyacetylene profiles across different organs, individuals, provenances, and seasons.

Conclusions:

• The study expands the known repertoire of polyacetylenes in Cicuta virosa, identifying several novel compounds and isomers.
• Polyacetylene composition in water hemlock exhibits quantitative variability influenced by environmental and developmental factors, but not fundamental qualitative differences.
• The findings contribute to a deeper understanding of the chemical diversity within the Apiaceae family.