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Proanthocyanidin Tetramers and Pentamers from Cinnamomum verum Bark and Their Dentin Biomodification Bioactivities.


ABSTRACT: To enable the further exploration of structure-activity relationships (SARs) of proanthocyanidins (PACs) with dentin biomodification abilities, Cinnamomum verum was selected for scaled-up purification of mixed A-/B-type, medium-size PAC oligomers. Sequential purification by centrifugal partition chromatography (CPC), Sephadex LH-20, and semiprep HPLC chromatography yielded four underivatized tetrameric (5-8) and two pentameric (9-10) PACs. Their unambiguous structural characterization involved extensive spectral and chemical degradation approaches to show that epicatechin units are connected by plant-specific combinations of doubly linked A- and singly linked B-type interflavanyl bonds. The biomechanical properties (via dynamic mechanical analysis) and physicochemical structure (via infrared spectroscopy) were assessed to evaluate the biomodification potency of PAC-treated collagen in a preclinical dentin model. This study revealed that (4→8) versus (4→6) bonds in PAC interflavan linkages have limited influence on biomechanical outcomes of dentin. By exhibiting a 25-fold increase in the complex modulus of treated dentin compared to control, aesculitannin E (5) was found to be the most potent PAC known to date for enhancing the mechanical properties of dentin in this preclinical model.

SUBMITTER: Jing SX 

PROVIDER: S-EPMC8881394 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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Proanthocyanidin Tetramers and Pentamers from <i>Cinnamomum verum</i> Bark and Their Dentin Biomodification Bioactivities.

Jing Shu-Xi SX   Alania Yvette Y   Reis Mariana M   McAlpine James B JB   Chen Shao-Nong SN   Bedran-Russo Ana K AK   Pauli Guido F GF  

Journal of natural products 20220202 2


To enable the further exploration of structure-activity relationships (SARs) of proanthocyanidins (PACs) with dentin biomodification abilities, <i>Cinnamomum verum</i> was selected for scaled-up purification of mixed A-/B-type, medium-size PAC oligomers. Sequential purification by centrifugal partition chromatography (CPC), Sephadex LH-20, and semiprep HPLC chromatography yielded four underivatized tetrameric (<b>5</b>-<b>8</b>) and two pentameric (<b>9</b>-<b>10</b>) PACs. Their unambiguous str  ...[more]

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