Structure Elucidation and Confirmation of Phloroglucinols from the Roots of Garcinia dauphinensis by Comparison of Experimental and Calculated ECD Spectra and Specific Rotations

Eight phloroglucinols from Garcinia dauphinensis were recently reported to have good to moderate antiplasmodial and anticancer activities, consistent with other phloroglucinol derivatives isolated from natural sources. Chiroptical properties were previously calculated and compared to experimental data for compound 2 as a means to deduce its absolute configuration. Tentative assignments for the remaining compounds were also reported based on these data. In order to arrive at stereochemical assignments for phloroglucinols 1 and 3-8, ECD spectra and specific rotations were computed for all stereoisomers of each compound. Molecular orbital analyses were also carried out for the most energetically favorable conformers of each compound. Absolute configurations are reported for all eight phloroglucinols for the first time.

Automated summary

Eight phloroglucinols isolated from Garcinia dauphinensis showed good to moderate antiplasmodial and anticancer activities, with their absolute configurations deduced through chiroptical properties calculation and comparison with experimental data. ECD spectra and specific rotations were computed for all stereoisomers of each compound to arrive at stereochemical assignments, with molecular orbital analyses conducted for the most energetically favorable conformers. Absolute configurations of all eight phloroglucinols were reported for the first time.