Abstract
Six novel neomacrophorin and four novel premacrophorin congeners were isolated from the fungus Trichoderma sp. 1212-03. Their planar structures and relative configurations were determined by conventional NMR and mass spectrometry techniques. The electronic circular dichroism (ECD) spectral comparisons with known neomacrophorins were effective for elucidating the structures of congeners carrying 2,3-epoxybenzoquinone (1, 2) and 2,3-epoxybenzosemiquinol substructures (3, 4, 5, 7, 8, and 9). The configuration of the 6-hydroxy-2-cyclohexene-1,4-dione moiety in 5′-deoxyneomacrophorin IV (6) was elucidated by NMR spectral comparison with those of known purpurogemutantidin (16) and mancrophorin F (17). This also resulted in the configurational revision of 16. The relative configuration of the 5,6-epoxy-2-cyclohexen-1,4-diol in premacrophorintriol-II (10) was determined by 13C chemical shift analysis using density functional theory calculations at the ωB97X-D/6-31G* level of theory. Compounds 1 and 6 exhibited potent cytotoxicity against human Caucasian colon adenocarcinoma cell line COLO 201.
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