title: Insecticidal and Nematicidal Activities of Novel Mimosine Derivatives.
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.
authors.affiliation: Department of Bioscience and Biotechnology, The United Graduate School of Agricultural Sciences, Kagoshima University, Korimoto 1-21-24, Kagoshima 890-8580, Japan. ncqbinh@gmail.com.
authors.forename: Binh Cao Quan
authors.initials: BC
authors.lastname: Nguyen
authors.affiliation: Department of Agronomy, Faculty of Agriculture, Kasetsart University, Kamphaeng Saen Campus, Nakhon Pathom 73140, Thailand. mcmine56@yahoo.com.
authors.forename: Jamnian
authors.initials: J
authors.lastname: Chompoo
authors.affiliation: Department of Bioscience and Biotechnology, Faculty of Agriculture, University of the Ryukyus, Senbaru 1, Nishihara-Cho, Okinawa 903-0213, Japan. b986097@agr.u-ryukyu.ac.jp.
authors.forename: Shinkichi
authors.initials: S
authors.lastname: Tawata
mesh_terms: D000110:Acetylcholinesterase / Q000737:chemistry; D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry / Q000494:pharmacology*; D017173:Caenorhabditis elegans / Q000187:drug effects*; D007887:Fabaceae / Q000737:chemistry; D007306:Insecticides / Q000737:chemistry / Q000494:pharmacology*; D008898:Mimosine / Q000737:chemistry / Q000494:pharmacology*; D010575:Pesticides / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry
chemical_list: D000969:Antinematodal Agents; D007306:Insecticides; D010575:Pesticides; D010936:Plant Extracts; D008898:Mimosine; D000110:Acetylcholinesterase
keywords: acetylcholinesterase; insecticidal; mimosine; mimosinol; nematicidal; tyrosinase