Document Type

Article

Publication Date

11-25-2020

Publisher

American Chemical Society

Source Publication

Journal of Natural Products

Source ISSN

1520-6025

Original Item ID

10.1021/acs.jnatprod.0c00570

Abstract

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.

Comments

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.

Available for download on Monday, January 03, 2022

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