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Molecules 2015, 20(9), 16741-16756; doi:10.3390/molecules200916741

Insecticidal and Nematicidal Activities of Novel Mimosine Derivatives

1
Department of Bioscience and Biotechnology, The United Graduate School of Agricultural Sciences, Kagoshima University, Korimoto 1-21-24, Kagoshima 890-8580, Japan
2
Department of Agronomy, Faculty of Agriculture, Kasetsart University, Kamphaeng Saen Campus, Nakhon Pathom 73140, Thailand
3
Department of Bioscience and Biotechnology, Faculty of Agriculture, University of the Ryukyus, Senbaru 1, Nishihara-Cho, Okinawa 903-0213, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: D. Hadjipavlou-Litina
Received: 11 August 2015 / Revised: 4 September 2015 / Accepted: 10 September 2015 / Published: 14 September 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [787 KB, uploaded 14 September 2015]   |  

Abstract

Mimosine, a non-protein amino acid, is found in several tropical and subtropical plants, which has high value for medicine and agricultural chemicals. Here, in continuation of works aimed to development of natural product-based pesticidal agents, we present the first significant findings for insecticidal and nematicidal activities of novel mimosine derivatives. Interestingly, mimosinol and deuterated mimosinol (D-mimosinol) from mimosine had strong insecticidal activity which could be a result of tyrosinase inhibition (IC50 = 31.4 and 46.1 μM, respectively). Of synthesized phosphoramidothionate derivatives from two these amino alcohols, two compounds (1a and 1b) showed high insecticidal activity (LD50 = 0.5 and 0.7 μg/insect, respectively) with 50%–60% mortality at 50 μg/mL which may be attributed to acetylcholinesterase inhibition. Compounds 1a and 1b also had strong nematicidal activity with IC50 = 31.8 and 50.2 μM, respectively. Our results suggest that the length of the alkyl chain and the functional group at the C5-position of phosphoramidothionates derived from mimosinol and d-mimosinol are essential for the insecticidal and nematicidal activities. These results reveal an unexplored scaffold as new insecticide and nematicide. View Full-Text
Keywords: mimosine; mimosinol; insecticidal; nematicidal; tyrosinase; acetylcholinesterase mimosine; mimosinol; insecticidal; nematicidal; tyrosinase; acetylcholinesterase
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Nguyen, B.C.Q.; Chompoo, J.; Tawata, S. Insecticidal and Nematicidal Activities of Novel Mimosine Derivatives. Molecules 2015, 20, 16741-16756.

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