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Antileishmanial Carbasugars from Geosmithia langdonii

مؤلف البحث
Lourin G. Malak, Mohamed Ali Ibrahim, Ahmed M. Moharram, Pankaj Pandey, Babu Tekwani, Robert J. Doerksen, Daneel Ferreira, Samir A. Ross
قسم البحث
مجلة البحث
J. Nat. Prod., DOI: 10.1021/acs.jnatprod.8b00473
الناشر
NULL
تصنيف البحث
1
عدد البحث
Vol. 81, No. 10
موقع البحث
NULL
سنة البحث
2018
المشارك في البحث
ملخص البحث

Two new carbasugar-type metabolites, (1S,2R,3R,4R,5R)-2,3,4-trihydroxy-5-methylcyclohexyl-2',5'-dihydroxybenzoate (1) and (1S,2S,3S,4R,5R)-4-[(2',5'-dihydroxybenzyl)oxy]-5-methylcyclohexane-1,2,3-triol (2), were isolated from the filamentous fungus Geosmithia langdonii isolated from cotton textiles from Assiut, Egypt. The structures of 1 and 2 were elucidated based on comprehensive 1D and 2D NMR and MS data. Compounds 1 and 2 showed antileishmanial activity against Leishmania donovani with IC50 values of 100 and 57 μM, respectively. The (1S,2R,3R,4R,5R) absolute configuration of carbasugar 1 was assigned via 2D NMR and experimental and calculated electronic circular dichroism (ECD) data. Similarly, the tentative structure of compound 2 was shown to possess a (1S,2S,3S,4R,5R) absolute configuration via comparing its experimental ECD data and the specific rotation with 1 as well as examining the energy-minimized 3D computational models of compounds 1 and 2.