AbstractTrilobacin (1) is the only previously reported Annonaceous acetogenin with the erythro relative configuration between the adjacent bis-tetrahydrofuran (THF) rings. The relative configuration in the adjacent bis-THF moiety of 1 was corrected to threo/trans/erythro/cis/threo from C-15 to C-24,...
AbstractTrilobacin (1) is the only previously reported Annonaceous acetogenin with the erythro relative configuration between the adjacent bis-tetrahydrofuran (THF) rings. The relative configuration in the adjacent bis-THF moiety of 1 was corrected to threo/trans/erythro/cis/threo from C-15 to C-24, and the absolute configuration was determined as 4R, 15R, 16R, 19R, 20S, 23R, 24R and 36S by advanced Mosher ester methodology and the COSY and NOESY spectral analyses of its 4,24-diacetate (1a). Further investigation of the EtOH extract of the stem bark of the paw paw tree, Asimina triloba, monitoring for bioactivity by brine shrimp lethality, led to a novel acetogenin, trilobin (2). Spectral and chemical methods identified 2 as a 4-deoxy-10-hydroxy isomer of 1. The absolute configuration of 2 was determined as 10R, 15R, 16R, 19R, 20S, 23R, 24R, and 36S by analyses of its Mosher ester derivatives. 2 was selectively cytotoxic among three human solid tumor cell lines with over a billion times the potency of adriamycin. The stereochemistries of trilobacin (1) and trilobin (2), a novel acetogenin, were determined by the MTPA (Mosher) ester method and their 2D-NMR spectral analyses. 2 is selectively cytotoxic with over a billion times the potencies of adriamycin.
AbstractTrilobacin (1) is the only previously reported Annonaceous acetogenin with the erythro relative configuration between the adjacent bis-tetrahydrofuran (THF) rings. The relative configuration in the adjacent bis-THF moiety of 1 was corrected to threo/trans/erythro/cis/threo from C-15 to C-24, and the absolute configuration was determined as 4R, 15R, 16R, 19R, 20S, 23R, 24R and 36S by advanced Mosher ester methodology and the COSY and NOESY spectral analyses of its 4,24-diacetate (1a). Further investigation of the EtOH extract of the stem bark of the paw paw tree, Asimina triloba, monitoring for bioactivity by brine shrimp lethality, led to a novel acetogenin, trilobin (2). Spectral and chemical methods identified 2 as a 4-deoxy-10-hydroxy isomer of 1. The absolute configuration of 2 was determined as 10R, 15R, 16R, 19R, 20S, 23R, 24R, and 36S by analyses of its Mosher ester derivatives. 2 was selectively cytotoxic among three human solid tumor cell lines with over a billion times the potency of adriamycin. The stereochemistries of trilobacin (1) and trilobin (2), a novel acetogenin, were determined by the MTPA (Mosher) ester method and their 2D-NMR spectral analyses. 2 is selectively cytotoxic with over a billion times the potencies of adriamycin.
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