Targeting Trimeric and Tetrameric Proanthocyanidins of Cinnamomum verum Bark as Bioactives for Dental Therapies

Joo-Won Nam; Rasika S Phansalkar; David C Lankin; James B McAlpine; Ariene A Leme-Kraus; Ana K Bedran-Russo; Shao-Nong Chen; Guido F Pauli

doi:10.1021/acs.jnatprod.0c00570

Back

Targeting Trimeric and Tetrameric Proanthocyanidins of Cinnamomum verum Bark as Bioactives for Dental Therapies

Journal article

Open access

Peer reviewed

Targeting Trimeric and Tetrameric Proanthocyanidins of Cinnamomum verum Bark as Bioactives for Dental Therapies

Joo-Won Nam, Rasika S Phansalkar, David C Lankin, James B McAlpine, Ariene A Leme-Kraus, Ana K Bedran-Russo, Shao-Nong Chen and Guido F Pauli

Journal of natural products (Washington, D.C.), Vol.83(11), pp.3287-3297

11/25/2020

DOI: 10.1021/acs.jnatprod.0c00570

PMCID: PMC8041212

PMID: 33151073

Files and links (1)

url

https://www.ncbi.nlm.nih.gov/pmc/articles/8041212View

Open Access

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.

Details

Title: Subtitle: Targeting Trimeric and Tetrameric Proanthocyanidins of Cinnamomum verum Bark as Bioactives for Dental Therapies
Creators: Joo-Won Nam - Yeungnam University
Rasika S Phansalkar
David C Lankin
James B McAlpine
Ariene A Leme-Kraus - University of Illinois Chicago
Ana K Bedran-Russo - Marquette University
Shao-Nong Chen
Guido F Pauli
Resource Type: Journal article
Publication Details: Journal of natural products (Washington, D.C.), Vol.83(11), pp.3287-3297
DOI: 10.1021/acs.jnatprod.0c00570
PMID: 33151073
PMCID: PMC8041212
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: R01DE021040, R01DE028194, R56DE021040; DOI: 10.13039/100000057, name: National Institute of General Medical Sciences, award: P41 GM068944
Language: English
Date published: 11/25/2020
Academic Unit: Operative Dentistry
Record Identifier: 9984367620702771

Metrics

8 Record Views

8 Times Cited - Web of Science