A galloylated dimeric proanthocyanidin from grape seed exhibits dentin biomodification potential

Rasika S Phansalkar; Joo-Won Nam; Shao-Nong Chen; James B McAlpine; José G Napolitano; Ariene Leme; Cristina M.P Vidal; Thaiane Aguiar; Ana K Bedran-Russo; Guido F Pauli

doi:10.1016/j.fitote.2014.12.006

Journal article

A galloylated dimeric proanthocyanidin from grape seed exhibits dentin biomodification potential

Rasika S Phansalkar, Joo-Won Nam, Shao-Nong Chen, James B McAlpine, José G Napolitano, Ariene Leme, Cristina M.P Vidal, Thaiane Aguiar, Ana K Bedran-Russo and Guido F Pauli

Fitoterapia, Vol.101, pp.169-178

03/2015

DOI: 10.1016/j.fitote.2014.12.006

PMCID: PMC4346468

PMID: 25542682

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https://www.ncbi.nlm.nih.gov/pmc/articles/4346468View

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Abstract

Grape seeds are a rich source of polyphenols, especially proanthocyanidins (PACs), and are also known for the presence of galloylated oligomeric PACs (OPACs). The present study focuses on the phytochemical methodology for grape seed (O)PACs and their potential role as dentin biomodifiers to be used in restorative and reparative dentistry. A new method using centrifugal partition chromatography (CPC) was developed for the preparative separation of the grape seed (O)PACs. Orthogonal phytochemical profiling of the resulting CPC fractions was performed using C18 and diol HPLC, normal phase HPTLC, and IT-TOF MS analysis. A galloylated procyanidin dimer (1) was isolated from a CPC fraction in order to evaluate its potential to enhance dentin bio-mechanical properties. Moreover, it helped to evaluate the impact of the galloyl moiety on the observed bioactivity. Structure elucidation was performed using ESI-MS, 1D and 2D NMR analyses. For the first time, 1H iterative full spin analysis (HiFSA) was performed on this type of molecule, enabling a detailed proton chemical shift and coupling constant assignment. The CPC fractions as well as 1 showed promising results in the dentin stiffness bioassay and indicate that they may be used as dental intervention biomaterial.\n[Display omitted]

Galloylation

HiFSA

Centrifugal partition and countercurrent chromatography (CPC/CCC)

Oligomeric proanthocyanidins (OPACs)

Countercurrent separation (CS)

Dentin stiffness and biomodification

Details

Title: Subtitle: A galloylated dimeric proanthocyanidin from grape seed exhibits dentin biomodification potential
Creators: Rasika S Phansalkar - Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
Joo-Won Nam - Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
Shao-Nong Chen - Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
James B McAlpine - Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
José G Napolitano - Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
Ariene Leme - Department of Restorative Dentistry, College of Dentistry, University of Illinois at Chicago, Chicago, IL, USA
Cristina M.P Vidal - Department of Restorative Dentistry, College of Dentistry, University of Illinois at Chicago, Chicago, IL, USA
Thaiane Aguiar - Department of Restorative Dentistry, College of Dentistry, University of Illinois at Chicago, Chicago, IL, USA
Ana K Bedran-Russo - Department of Restorative Dentistry, College of Dentistry, University of Illinois at Chicago, Chicago, IL, USA
Guido F Pauli - Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
Resource Type: Journal article
Publication Details: Fitoterapia, Vol.101, pp.169-178
DOI: 10.1016/j.fitote.2014.12.006
PMID: 25542682
PMCID: PMC4346468
NLM abbreviation: Fitoterapia
ISSN: 0367-326X
eISSN: 1873-6971
Publisher: Elsevier B.V
Grant note: name: NIDCR/NIH, award: R01 DE021040
Language: English
Date published: 03/2015
Academic Unit: Operative Dentistry
Record Identifier: 9984066094302771

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