The increasingly serious resistance of Tetranychus cinnabarinus Boisduval to a wide range of insecticides/acaricides poses a major challenge to their control. The citrus processing industry generates a huge quantity of various wastes that contain many limonoids. To effectively utilize these byproducts and discover more potent green acaricidal molecules as sustainable alternatives for traditional resistant pesticides, various limonoid-type derivatives (halogenated/seven-membered lactam derivatives of obacunone and halogenated/oxime esters/oxime ethers/seven-membered lactam derivatives of limonin) were synthesized based on a diversity-oriented synthetic strategy. The key steric configurations of 10 derivatives were further confirmed by X-ray crystallography. Compound 9m, which displayed greater than 9.7-fold potent acaricidal activity of limonin, was of preeminence. In addition, some interesting structure−activity relationships were observed. Moreover, a biocompatible O/W nanoemulsion delivery system was used to prepare the limonin-based agronanoacaricide, which exhibited pronounced control efficiency against T. cinnabarinus Boisduval in the greenhouse. This systematic investigation will provide valuable information and guidance for future value-added applications of novel eco-friendly natural product-based nanopesticides.
Background:
Human immunodeficiency virus (HIV) infection and acquired immunodeficiency syndrome (AIDS) have resulted in a global health threat. Meanwhile, due to the emergence of drug-resistant HIV-1 strains, the discovery of potent compounds for antiretroviral therapy success is highly desirable.
Objective:
This study aimed to develop anti-HIV-1 candidates which can be effectively applied for the treatment of HIV infection.
Method:
Based upon our previous results, a series of E isomers of C15-imines of matrine (3a-l) were semi-synthesized from a natural quinolizidine alkaloid matrine. Their anti-HIV-1 activities were evaluated against HIV-1ⅢB replication in acutely infected C8166 cells in vitro.
Results:
Derivatives 3c, 3h and 3j showed good anti-HIV-1 activities with EC50 and therapeutic index (TI) values of 0.0089/0.012/0.0091 mM, and 23.71/32.49/27.43, respectively.
Conclusion:
The substituents and their corresponding positions on the phenyl ring of C15-imine derivatives of matrine were vital for anti-HIV-1 activities. Compounds 3c, 3h and 3j can be used as leads for further structural modification as HIV-1 inhibitors.
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