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B-type Proanthocyanidins with Dentin Biomodification Activity from Cocoa (Theobroma cacao).


ABSTRACT: To enable translational studies, a scalable preparative isolation scheme was developed for underivatized cocoa (Theobroma cacao) proanthocyanidins (PACs), affording six all-B-type oligomeric PACs, including a new tetramer 4. Their structures, including absolute configuration, were unambiguously established by comprehensive spectroscopic and chemical methods. Evaluation of the PACs' dentin biomodification properties employed dynamic mechanical and infrared spectroscopic analyses in dentin bioassay models. PAC treatment enhanced the biomechanical strength of dentin by 5- to 15-fold compared to untreated dentin. Among the PAC agents, the pentamer, cinnamtannin A3 (6), led to the highest complex modulus value of 131 MPa, whereas the "branched" tetramer, 4, showed the lowest, yet still significant bioactivity. This study of specifically singly linked medium-length oligomeric PACs indicates that the linkage site is paramount in determining the potency of these PACs as dentin biomodifiers.

SUBMITTER: Jing SX 

PROVIDER: S-EPMC9547875 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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B-type Proanthocyanidins with Dentin Biomodification Activity from Cocoa (<i>Theobroma cacao</i>).

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

Journal of agricultural and food chemistry 20220922 39


To enable translational studies, a scalable preparative isolation scheme was developed for underivatized cocoa (<i>Theobroma cacao</i>) proanthocyanidins (PACs), affording six all-B-type oligomeric PACs, including a new tetramer <b>4</b>. Their structures, including absolute configuration, were unambiguously established by comprehensive spectroscopic and chemical methods. Evaluation of the PACs' dentin biomodification properties employed dynamic mechanical and infrared spectroscopic analyses in  ...[more]

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