Targeting Trimeric and Tetrameric Proanthocyanidins of Cinnamomum verum Bark as Bioactives for Dental Therapies
American Chemical Society
Journal of Natural Products
Original Item ID
The present study elucidated the structures of three A-type tri- and tetrameric proanthocyanidins (PACs) isolated from Cinnamomum verum bark to the level of absolute configuration and determined their dental bioactivity using two therapeutically relevant bioassays. After selecting a PAC oligomer fraction via a biologically diverse bioassay-guided process, in tandem with centrifugal partition chromatography, phytochemical studies led to the isolation of PAC oligomers that represent the main bioactive principles of C. verum: two A-type tetrameric PACs, epicatechin-(2β→O→7,4β→8)-epicatechin-(4β→6)-epicatechin-(2β→O→7,4β→8)-catechin (1) and parameritannin A1 (2), together with a trimer, cinnamtannin B1 (3). Structure determination of the underivatized proanthocyanidins utilized a combination of HRESIMS, ECD, 1D/2D NMR, and 1H iterative full spin analysis data and led to NMR-based evidence for the deduction of absolute configuration in constituent catechin and epicatechin monomeric units.
Nam, Joo-Won; Phansalkar, Rasika S.; Lankin, David C.; McAlpine, James; Leme-Kraus, Ariene A.; Bedran-Russo, Ana K.; Chen, Shao-Nong; and Pauli, Guido F., "Targeting Trimeric and Tetrameric Proanthocyanidins of Cinnamomum verum Bark as Bioactives for Dental Therapies" (2020). School of Dentistry Faculty Research and Publications. 387.
Accepted version. Journal of Natural Products, Vol. 83, No. 11 (November 25, 2020): 3287-3297. DOI. © 2020 American Chemical Society and American Society of Pharmacognosy. Used with permission.