Yan, Zhiqiang, Guo, Hongru, Yang, Jiayue, Liu, Quan, Jin, Hui, Xu, Rui, Cui, Haiyan, and Qin, Bo
Allelopathy, the negative effect on plants of chemicals released to the surroundings by a neighboring plant, is an important factor which contributes to the spread of some weeds in plant communities. In this field, Stellera chamaejasme L . (Thymelaeaceae) is one of the most toxic and ecologically-threatening weeds in some of the grasslands of north and west China. Bioassay-guided fractionation of root extracts of this plant led to the isolation of eight flavonoids 1 – 8 , whose structures were elucidated by spectroscopic analysis. All compounds obtained, except 7-methoxylneochaejasmin A ( 4 ) and (+)-epiafzelechin ( 5 ), showed strong phytotoxic activity against Arabidopsis thaliana seedlings. Seedling growth was reduced by neochamaejasmin B ( 1 ), mesoneochamaejasmin A ( 2 ), chamaejasmenin C ( 3 ), genkwanol A ( 6 ), daphnodorin B ( 7 ) and dihydrodaphnodorin B ( 8 ) with IC 50 values of 6.9, 12.1, 43.2, 74.8, 7.1 and 27.3 μg/mL, respectively, and all of these compounds disrupted root development. Endogenous auxin levels at the root tips of the A. thaliana DR5::GUS transgenic line were largely reduced by compounds 1 , 2 and 6 – 8 , and were increased by compound 4 . Moreover, the inhibition rate of A. thaliana auxin transport mutants pin2 and aux1 – 7 by compounds 1 – 8 were all lower than the wild type (Col-0). The influence of these compounds on endogenous auxin distribution is thus proposed as a critical factor for the phytotoxic effect. Compounds 1 , 2 , 4 and 8 were found in soils associated with S. chamaejasme , and these flavonoids also showed phytotoxicity to Clinelymus nutans L., an associated weed of S. chamaejasme . These results indicated that some phytotoxic compounds from roots of S. chamaejasme may be involved in the potential allelopathic behavior of this widespread weed. [ABSTRACT FROM AUTHOR]