Proanthocyanidin Dimers and Trimers from Vitis vinifera Provide Diverse Structural Motifs for the Evaluation of Dentin Biomodification

Rasika S Phansalkar; Joo-Won Nam; Ariene A Leme-Kraus; Li-She Gan; Bin Zhou; James B McAlpine; Shao-Nong Chen; Ana K Bedran-Russo; Guido F Pauli

doi:10.1021/acs.jnatprod.8b00953

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Proanthocyanidin Dimers and Trimers from Vitis vinifera Provide Diverse Structural Motifs for the Evaluation of Dentin Biomodification

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Proanthocyanidin Dimers and Trimers from Vitis vinifera Provide Diverse Structural Motifs for the Evaluation of Dentin Biomodification

Rasika S Phansalkar, Joo-Won Nam, Ariene A Leme-Kraus, Li-She Gan, Bin Zhou, James B McAlpine, Shao-Nong Chen, Ana K Bedran-Russo and Guido F Pauli

Journal of natural products (Washington, D.C.), Vol.82(9), pp.2387-2399

09/27/2019

DOI: 10.1021/acs.jnatprod.8b00953

PMCID: PMC6899061

PMID: 31433178

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https://www.ncbi.nlm.nih.gov/pmc/articles/6899061View

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Abstract

Aimed at exploring the dentin biomodification potential of proanthocyanidins (PACs) for the development of dental biomaterials, this study reports the phytochemical and dental evaluation of nine B-type PACs from grape seed extract (GSE). Out of seven isolated dimers (1–7), four new compounds (2, 3, 5, and 6) involved relatively rare ent-catechin or ent-epicatechin monomeric flavan-3-ol units. Low-temperature NMR analyses conducted along with phloroglucinolysis and electronic circular dichroism enabled unequivocal structural characterization and stereochemical assignment. Additionally, one known (8) and one new (9) B-type trimer were characterized. Differential 13C NMR chemical shifts (Δδ) were used to determine the absolute configuration of 9, relative to the dimers 1 and 2 as the possible constituent subunits. Compared to the dimers, the trimers showed superior dentin biomodification properties. The dimers, 1–7, exhibited pronounced differences in their collagenase inhibitory activity, while enhancing dentin stiffness comparably. This suggests that PAC structural features such as the degree of polymerization, relative and absolute configuration have a differential influence on enhancement of dentin biomechanical and biostability. As mechanical enhancement to dentin and resistance to proteolytic biodegradation are both essential properties functional and stable dentin substrate, the structurally closely related PACs suggest a new metric, the dentin biomodification potential (DBMP) that may rationalize both properties.

Details

Title: Subtitle: Proanthocyanidin Dimers and Trimers from Vitis vinifera Provide Diverse Structural Motifs for the Evaluation of Dentin Biomodification
Creators: Rasika S Phansalkar - University of Illinois Chicago
Joo-Won Nam - Yeungnam University
Ariene A Leme-Kraus - University of Illinois Chicago
Li-She Gan - Zhejiang University
Bin Zhou - University of Illinois Chicago
James B McAlpine - University of Illinois Chicago
Shao-Nong Chen - University of Illinois Chicago
Ana K Bedran-Russo - University of Illinois Chicago
Guido F Pauli - University of Illinois Chicago
Resource Type: Journal article
Publication Details: Journal of natural products (Washington, D.C.), Vol.82(9), pp.2387-2399
DOI: 10.1021/acs.jnatprod.8b00953
PMID: 31433178
PMCID: PMC6899061
NLM abbreviation: J Nat Prod
ISSN: 0163-3864
eISSN: 1520-6025
Publisher: American Chemical Society and American Society of Pharmacognosy
Grant note: DOI: 10.13039/100000072, name: National Institute of Dental and Craniofacial Research, award: R01 DE021040, R56 DE021040, R01 DE028194
Language: English
Date published: 09/27/2019
Academic Unit: Operative Dentistry
Record Identifier: 9984367647402771

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