Enantioselective Separation of 4,8-DHT and Phytotoxicity of the Enantiomers on Various Plant Species.
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.
Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China. yangli0817@yeah.net.|College of Life Sciences, Zhejiang University, Hangzhou 310058, China. yangli0817@yeah.net.
Li
L
Yang
Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China. 15676230509@yeah.net.|College of Forestry and Horticulture, Xinjiang Agricultural University, Urumqi 830052, China. 15676230509@yeah.net.
Xiao-Yan
XY
Ma
Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China. ruanxiao@nit.net.cn.
Xiao
X
Ruan
College of Life Sciences, Zhejiang University, Hangzhou 310058, China. dajiang@zju.edu.cn.
De-An
DA
Jiang
College of Forestry and Horticulture, Xinjiang Agricultural University, Urumqi 830052, China. pancunde@163.com.
Cun-De
CD
Pan
Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China. wangqiangsky@263.net.
Qiang
Q
Wang
D003044:Coccidia / Q000737:chemistry*; D018556:Crops, Agricultural / Q000187:drug effects* / Q000254:growth & development*; D018553:Cucumis sativus / Q000187:drug effects / Q000254:growth & development; D018525:Germination / Q000187:drug effects; D006540:Herbicides / Q000302:isolation & purification / Q000633:toxicity*; D018545:Lactuca / Q000187:drug effects / Q000254:growth & development; D019697:Onions / Q000187:drug effects / Q000254:growth & development; D031224:Raphanus / Q000187:drug effects / Q000254:growth & development; D036226:Seedlings / Q000187:drug effects; D013237:Stereoisomerism; D044024:Tetralones / Q000302:isolation & purification / Q000633:toxicity*; D014908:Triticum / Q000187:drug effects / Q000254:growth & development
D006540:Herbicides; D044024:Tetralones
4,8-dihydroxy-1-tetralone (4,8-DHT); chiral-selective separation; enantiomers; phytotoxicity