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Schistosomicidal Activity of Dihydrobenzofuran Neolignans
Author(s) -
Dias Herbert J.,
Patrocínio Andressa B.,
Pagotti Mariana C.,
Fukui Murilo J.,
Rodrigues Vanderlei,
Magalhães Lizandra G.,
Crotti Antônio E. M.
Publication year - 2018
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.201800134
Subject(s) - schistosoma mansoni , chemistry , praziquantel , stereochemistry , in vitro , double bond , biochemistry , schistosomiasis , organic chemistry , biology , immunology , helminths
We have evaluated the antischistosomal activity of synthetic dihydrobenzofuran neolignans (DBNs) derived from (±)‐ trans ‐dehydrodicoumaric acid dimethyl ester ( 1 ) and (±)‐ trans ‐dehydrodiferulic acid dimethyl ester ( 2 ) against adult Schistosoma mansoni worms in vitro . Compound 4 ((±)‐ trans ‐4‐ O ‐acetyldehydrodiferulic acid dimethyl ester) displayed the most promising activity; at 200 μ m , it kills 100 ± 0% of worms after 24 h, which resembles the result achieved with praziquantel (positive control) at 1.56 μ m . The hydrogenation of the double bond between C7′ and C8′, the introduction of an additional methyl group at C3′, and a double bond between C7 and C8 decreased the schistosomicidal activity of DBNs. On the other hand, the presence of the acetoxy group at C4 played an interesting role in this activity. These results demonstrated the interesting schistosomicidal potential of DBNs, which could be further exploited.