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Synthesis and Biological Evaluation of 3,5‐Dimethoxystilbene Analogs
Author(s) -
Weng JianQuan,
Ali Abbas,
Estep Alden,
Becnel James,
Meyer Susan L. F.,
Wedge David E.,
Jacob Melissa,
Rimando Agnes M.
Publication year - 2016
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201500516
Subject(s) - meloidogyne incognita , aedes aegypti , antimicrobial , chemistry , staphylococcus aureus , biological activity , cryptococcus neoformans , microbiology and biotechnology , terra incognita , bacteria , pesticide , larva , fungus , nematode , pest analysis , antibacterial activity , biology , horticulture , botany , biochemistry , in vitro , ecology , genetics
In our continuing effort to discover natural product‐based pest management agents, derivatives of 3,5‐dimethoxystilbene were synthesized yielding 27 new and six known compounds. Compounds 11 and 12 showed strong Aedes aegypti larvicidal activity ( LC 50 45.31 and 49.93 μ m , respectively). Furthermore, 11 and 12 exhibited high effectiveness against larvae of pesticide‐susceptible and pyrethroid‐resistant strains of Ae . aegypti ; activity against the adult mosquitoes was low. Compounds 6f , 6g , and 6i at either 83.3 or 166.7 μg/ml reduced the mobility of second‐stage juveniles (J2) of the root‐knot nematode ( Meloidogyne incognita ) that hatched from eggs immersed in the test compounds for 7 days. However, there was little or no effect on J2 placed directly into these compounds, and none of the analogs suppressed M . incognita egg hatch. The compounds were tested for inhibition of some agriculturally important fungi; 6a , 7a , and 7e demonstrated strong inhibition of Colletotrichum species. Activity of the stilbenes against some human pathogens was also explored; 11 , 12 , and 16 showed moderate inhibitory activity against Cryptococcus neoformans , Staphylococcus aureus , methicillin‐resistant S . aureus , and Mycobacterium intracellulare . Except for 11 and 12 , which were active against mosquito larvae and some human pathogens, no single analog demonstrated activity in all the tests, indicating specific activities. Synthesis of the analogs and structure–activity relationships are discussed.