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As a candidate for bioherbicide, 4,8-dihydroxy-1-tetralone (4,8-DHT) was isolated from  Caryospora callicarpa  epicarp and its two enantiomers,  S -(+)-isosclerone and  R -(−)-regiolone, were separated by chiral high-performance liquid chromatography (HPLC) on a Chiralcel OD column with chiral stationary phase (CSP)-coated cellulose-tris(3,5-dimethylphenylcarbamate). Then, the phytotoxicity of 4,8-DHT and its enantiomers toward the seeds germination and seedling growth of the five tested plant species, including lettuce ( Latuca sativa ), radish ( Raphanus sativus ), cucumber ( Cucumis sativus ), onion ( Allium cepa ), and wheat ( Triticum aestivum ), were investigated and the results indicated a hormesis at low concentration of 4,8-DHT and its enantiomers, but a retardant effect at high concentration. Between the two enantiomers of 4,8-DHT, the  S- (+)-isosclerone was more toxic to seeds germination and seedling growth of the five tested plant species than the  R -(−)-regiolone, and also the phytotoxicity of  S -(+)-isosclerone varied with different plants. For example,  S -(+)-isosclerone was the most active to seedling growth of lettuce, indicating that  S -(+)-isosclerone had specific effects on different organisms. Thus, all of the chirality and concentration of 4,8-DHT, as well as the affected plant species, need to be taken into consideration in the development and utilization of 4,8-DHT.

Enantioselective Separation of 4,8-DHT and Phytotoxicity of the Enantiomers on Various Plant Species