Sasithorn Buppatano. Design, synthesis and insecticidal activity against spodoptera spp of monoterpenoid derivatives and their enzyme inhibitory activity. Master's Degree(Chemistry). Kasetsart University. Office of the University Library. : Kasetsart University, 2022.
Design, synthesis and insecticidal activity against spodoptera spp of monoterpenoid derivatives and their enzyme inhibitory activity
Abstract:
Monoterpenoids are a class of terpenes that consist of two isoprene units and display biological abilities such as antibacterial, anti-inflammatory, antioxidant and insecticidal activities. The structural modification of monoterpenoids into monoterpenoid derivatives is a potential approach for the development of novel active compounds. Therefore, this work aims to design and synthesize monoterpenoid derivatives from natural monoterpenoid and carboxylic acid via esterification using reagent PPh3/CBr4/Et3N/rt that the desired products were obtained in 4-66% yields. All monoterpenoid derivatives were examined their insecticidal activity against the second instars of Spodoptera spp. representing three insect pest species; S. exigua, S. litura and S. frugiperda using topical application at a concentration of 10,000 ppm (10 μg/larva). Carvacryl benzoate (CBZ) exhibited the highest toxicity to S. exigua with %mortality values of 16.67% ± 0.49 and 20.00% ± 0.37 after 24 and 48 hours posttreatment, respectively. (-)-Bornyl benzoate (BBZ) exhibited the most toxicity to S. litura with %mortality values of 15.00 ± 0.34 and 16.67 ± 0.33 after 24 and 48 hours posttreatment, respectively and (-)-menthyl benzoate (MBZ) exhibited the highest toxicity to S. frugiperda with %mortality values of 18.33 ± 0.31 and 25.00 ± 0.22 after 24 and 48 hours posttreatment, respectively. The synthesized monoterpenoid derivatives were further examined for their biological activities assay (in vitro experiment) such as α-glucosidase, acetylcholinesterase and tyrosinase inhibitory activities. The results found cinnamate (TM) exhibited the highest inhibition against α-glucosidase with IC50 values of 0.93 ± 0.51 µM (acarbose, IC50 = 389.2 ± 14.2 µM). Whereas hinokitiol cinnamate (HT) exhibited the highest inhibition against tyrosinase with IC50 values of 1.58 ± 0.09 µM (kojic acid, IC50 = 14.06 ± 0.91 µM). However, the synthesized monoterpenoid derivatives were not active against acetylcholinesterase to exhibit satisfactory inhibition and monoterpenoid derivatives have no antioxidant activity.
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