Derivatives of (+)(-) limonene. Effect of chain length in n-alkyl quaternary ammonium derivatives on plant growth retardant activity

1968 ◽  
Vol 16 (3) ◽  
pp. 523-524 ◽  
Author(s):  
A. P. Pieringer ◽  
W. F. Newhall











2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Takashi Ishida ◽  
Haruna Yoshimura ◽  
Masatsugu Takekawa ◽  
Takumi Higaki ◽  
Takashi Ideue ◽  
...  

AbstractThe discovery and useful application of natural products can help improve human life. Chemicals that inhibit plant growth are broadly utilized as herbicides to control weeds. As various types of herbicides are required, the identification of compounds with novel modes of action is desirable. In the present study, we discovered a novelN-alkoxypyrrole compound, kumamonamide fromStreptomyces werraensisMK493-CF1 and established a total synthesis procedure. Resulted in the bioactivity assays, we found that kumamonamic acid, a synthetic intermediate of kumamonamide, is a potential plant growth inhibitor. Further, we developed various derivatives of kumamonamic acid, including a kumamonamic acid nonyloxy derivative (KAND), which displayed high herbicidal activity without adverse effects on HeLa cell growth. We also detected that kumamonamic acid derivatives disturb plant microtubules; and additionally, that KAND affected actin filaments and induced cell death. These multifaceted effects differ from those of known microtubule inhibitors, suggesting a novel mode of action of kumamonamic acid, which represents an important lead for the development of new herbicides.



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