ArticleThe Journal of organic chemistry2015
Subtle Chemical Shifts Explain the NMR Fingerprints of Oligomeric Proanthocyanidins with High Dentin Biomodification Potency.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
41 citing papers in PubMed, 62 citations in OpenAlex.
- Proanthocyanidins: structure, biosynthesis, regulation, and structure-activity relationships.aBIOTECH · 2026Review
- Procyanidins: Structural Properties, Production Methods, and Modern Applications.Molecules (Basel, Switzerland) · 2026Review
- A Bioinspired Approach to Mechanically Reinforce Collagen-Rich Tissues Using Modularly Defined Stilbenoids.Biopolymers · 2026Article
- A nuclear chemical descriptor based on NMR databases for molecular information: characterization of π-conjugated oligomers.Journal of molecular modeling · 2025Article
- From Desert Greening to Human Health: A Systematic Review of the Extraction, Unique Structure, and Bioactivity of Sea Buckthorn Proanthocyanidins.Foods (Basel, Switzerland) · 2025Review
- Optimization of dental adhesive interfaces using tissue biomodulation with DESIGNER biopolymers.Dental materials : official publication of the Academy of Dental Materials · 2025Article
- Polymerization of proanthocyanidins under the catalysis of miR397a-regulated laccases in Salvia miltiorrhiza and Populus trichocarpa.Nature communications · 2025Article
- Preparation, Modification, Quantitation, and Dentin Biomodification Activity of Selectively Enriched Proanthocyanidins.Journal of natural products · 2025Article
- Potential Use of Selected Natural Compounds with Anti-Biofilm Activity.International journal of molecular sciences · 2025Review
- Chemical Transformation of B- to A-type Proanthocyanidins and 3D Structural Implications.Journal of natural products · 2024Article
- Unprecedented Benzoquinone Motifs Reveal Post-Oligomerizational Modification of Proanthocyanidins.The Journal of organic chemistry · 2023Article
- Review
- B-type Proanthocyanidins with Dentin Biomodification Activity from Cocoa (Journal of agricultural and food chemistry · 2022Article
- Evidence of improved bond strength of resin-based sealer with the use of natural antioxidants on hypochlorite treated dentin: anMedicine and pharmacy reports · 2022Article
- Structural Elucidation of an Atropisomeric Entcassiflavan-(4β→8)-Epicatechin Isolated fromMolecules (Basel, Switzerland) · 2022Article
- Proanthocyanidin Tetramers and Pentamers fromJournal of natural products · 2022Article
- Unveiling structure-activity relationships of proanthocyanidins with dentin collagen.Dental materials : official publication of the Academy of Dental Materials · 2021Article
- H/D Exchange Processes in Flavonoids: Kinetics and Mechanistic Investigations.Molecules (Basel, Switzerland) · 2021Article
- Quantum mechanical NMR full spin analysis in pharmaceutical identity testing and quality control.Journal of pharmaceutical and biomedical analysis · 2021Review
- Proanthocyanidins as a Potential Novel Way for the Treatment of Hemangioma.BioMed research international · 2021Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
12 authors at 3 institutions in 3 countries.
Funding
Abstract
The ability of certain oligomeric proanthocyanidins (OPACs) to enhance the biomechanical properties of dentin involves collagen cross-linking of the 1.3-4.5 nm wide space via protein-polyphenol interactions. A systematic interdisciplinary search for the bioactive principles of pine bark has yielded the trimeric PAC, ent-epicatechin-(4β→8)-epicatechin-(2β→O→7,4β→8)-catechin (3), representing the hitherto most potent single chemical entity capable of enhancing dentin stiffness. Building the case from two congeneric PAC dimers, a detailed structural analysis decoded the stereochemistry, spatial arrangement, and chemical properties of three dentin biomodifiers. Quantum-mechanics-driven (1)H iterative full spin analysis (QM-HiFSA) of NMR spectra distinguished previously unrecognized details such as higher order J coupling and provided valuable information about 3D structure. Detection and quantification of H/D-exchange effects by QM-HiFSA identified C-8 and C-6 as (re)active sites, explain preferences in biosynthetic linkage, and suggest their involvement in dentin cross-linking activity. Mapping of these molecular properties underscored the significance of high δ precision in both (1)H and (13)C NMR spectroscopy. Occurring at low- to subppb levels, these newly characterized chemical shift differences in ppb are small but diagnostic measures of dynamic processes inherent to the OPAC pharmacophores and can help augment our understanding of nanometer-scale intermolecular interactions in biomodified dentin macromolecules.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.