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Molecules 2016, 21(4), 528; doi:10.3390/molecules21040528

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

1
Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China
2
College of Life Sciences, Zhejiang University, Hangzhou 310058, China
3
College of Forestry and Horticulture, Xinjiang Agricultural University, Urumqi 830052, China
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 23 March 2016 / Revised: 18 April 2016 / Accepted: 19 April 2016 / Published: 22 April 2016
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Abstract

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. View Full-Text
Keywords: 4,8-dihydroxy-1-tetralone (4,8-DHT); chiral-selective separation; enantiomers; phytotoxicity 4,8-dihydroxy-1-tetralone (4,8-DHT); chiral-selective separation; enantiomers; phytotoxicity
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Yang, L.; Ma, X.-Y.; Ruan, X.; Jiang, D.-A.; Pan, C.-D.; Wang, Q. Enantioselective Separation of 4,8-DHT and Phytotoxicity of the Enantiomers on Various Plant Species. Molecules 2016, 21, 528.

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