ichthyothereol

Other names: (2S,3R)-2-[(1E)-Non-1-ene-3,5,7-triyn-1-yl]oxan-3-ol, cunaniol

C₁₄H₁₄O₂

41/50 uncommon

Ichthyothereol is a remarkable polyacetylenic natural product with an extraordinarily linear molecular structure. Isolated from the Ichthyothere genus of flowering plants native to South and Central America, this compound features an unusual arrangement of seven consecutive carbon atoms in a straight line, comprising a rare natural polyyne system. Ichthyothereol derives its name from its potent ichthyotoxicity (fish-poisoning properties), with concentrations as low as 1 part per million proving lethal to certain fish species. Indigenous tribes throughout the Amazon basin have long utilized piscicidic plants like ichthyothere for traditional fishing techniques such as "barbasco" or "timbo". By crushing plant material containing ichthyothereol and introducing it to streams or ponds, fish are temporarily stunned or killed, allowing for efficient harvesting. Notably, the compound's toxicity is highly selective, primarily affecting gill-breathing organisms while posing minimal risk to humans consuming the fish. This molecule exemplifies how complex natural products with unusual chemical architectures can be leveraged as sophisticated ecological tools in traditional knowledge systems.