Unveiling structure–activity relationships of proanthocyanidins with dentin collagen

Reis, Mariana; Zhou, Bin; Alania, Yvette; Leme-Kraus, Ariene A.; Jing, Shu-Xi; McAlpine, James B.; Chen, Shao-Nong; Pauli, Guido F.; Bedran-Russo, Ana K.

doi:10.1016/j.dental.2021.08.013

Cited by 21 publications

(51 citation statements)

References 49 publications

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“…Significant differences were observed when comparing dentin matrices treated with trimer 2 and tetramer 4 versus the untreated matrix (control) ( p = 0.007), where a decrease in amide III/CH 2 was evident. In previous studies, the 4 → 8 versus 4 → 6 IFLs in complex, mixed A/B-type PACs were found to have a limited effect on the biomechanical properties of dentin matrices, and the most potent PACs, in terms of DP, were the trimers and tetramers. , …”

Section: Resultsmentioning

confidence: 88%

“…Mainly, they provide the new insights that branching (i.e, an additional 4 → 6 IFL in a middle unit) of B-type PACs may limit the mechanical enhancement of the dentin matrix despite showing similar structural changes on the collagen compared to their unbranched 4 → 8 IFL analogues. Another new conclusion is that the DP has little or no influence on biomechanical properties among B-type trimers and pentamers as both showed similar E * values, most likely because they are already in the range of DP with optimum biomechanical performance . Some biological studies have reported that A-type PAC fractions were more effective and stable than B-type PAC fractions. , Trimeric PACs from red wine (Vitis vinifera) with 4 → 8 linkages showed stronger skin-whitening effects than 4 → 6 linkages by the PAC in vitro assay .…”

Section: Resultsmentioning

confidence: 99%

“…Fourier-transform infrared (FTIR) spectroscopy has been established for the characterization of the structure of collagens and collagen-based materials. , Figure S47 shows the FTIR spectra of PAC-treated versus unmodified (control) collagen of dentin extracellular matrix (ECM). New peaks, shifts, and changes of absorbance intensity of bands were observed between 1150–1000 cm –1 in the fingerprint region of the spectra of PAC-treated dentin, which indicated the structural modification of dentin collagen.…”

Section: Resultsmentioning

confidence: 99%

“…Fourier-transform infrared (FTIR) spectroscopy (Nicolet 6700, Thermo Fisher Scientific) was applied for the biochemical characterization of the functional groups of the dentin extracellular matrix (ECM), as previously described. , Briefly, spectra were collected with an attenuated total reflectance (ATR) apparatus from 4,500 to 600 cm –1 . An accumulation of 128 scans per sample ( n = 3) was collected at a resolution of 4 cm –1 and analyzed with OMNIC software (Thermo Fisher Scientific).…”

Section: Methodsmentioning

confidence: 99%

“…Our dental natural products research has identified a series of plant-derived PACs as potential dentin biomodifiers. Promising agents include PACs isolated from pine (Pinus massoniana) and cinnamon (Cinnamomum verum) barks, ranging from dimers to hexamers featuring mixed A- and B-type IFLs, as well as B-type dimers and trimers from grape seed extract (GSE), all with potent activities in enhancing the mechanical properties of dentin. − The recent implementation of graphical structural descriptors, termed PAC Block ARrays (PACBAR), has facilitated these interdisciplinary studies, particularly with regard to the exploration of structure–activity relationships (SARs) of PACs with complex A- and B-type linkage patterns and their impact on dentin biomodification activities …”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

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

Jing

Reis

Alania

et al. 2022

J. Agric. Food Chem.

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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.

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Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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

Jing

Reis

Alania

et al. 2022

J. Agric. Food Chem.

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From medical strategy to foodborne prophylactic strategy: Stabilizing dental collagen with aloin

Jia,

Li,

Yang

et al. 2023

Food Science & Nutrition

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Infectious oral diseases are longstanding global public health concerns. However, traditional medical approaches to address these diseases are costly, traumatic, and prone to relapse. Here, we propose a foodborne prophylactic strategy using aloin to safeguard dental collagen. The effect of aloin on the stability of dental collagen was evaluated by treating dentin with a solution containing aloin (0.1 mg/mL) for 2 min. This concentration is comparable to the natural aloin content of edible aloe. Furthermore, we investigated the mechanisms underlying the interactions between aloin and dentin collagen. Our findings, obtained through fluorescence spectroscopy, attenuated total reflection Fourier transform infrared spectroscopy, Gaussian peak fitting, circular dichroism spectroscopy, and X‐ray diffraction, revealed that aloin interacts with dental collagen through noncovalent bonding, specifically hydrogen bonding in situ. This interaction leads to a reduction in the distance between molecules and an increase in the proportion of stable α‐helical chains in the dental collagen. The ultimate tensile strength and thermogravimetric analysis demonstrated that dental collagen treated with aloin exhibited improved mechanical strength and thermostability. Additionally, the release of hydroxyproline, cross‐linked carboxy‐terminal telopeptide of type I collagen, and C‐terminal cross‐linked telopeptide of type I collagen, along with weight loss, indicated an enhancement in the enzymatic stability of dental collagen. These findings suggest that aloin administration could be a daily, nondestructive, and cost‐effective strategy for managing infectious oral diseases.

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Modulatory role of terminal monomeric flavan‐3‐ol units in the viscoelasticity of dentin

Reis‐Havlat,

Alania,

Zhou

et al. 2023

J Biomed Mater Res

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Flavan‐3‐ol monomers are the building blocks of proanthocyanidins (PACs), natural compounds from plants shown to mediate specific biologic activities on dentin. While the stereochemistry of the terminal flavan‐3‐ols, catechin (C) versus epicatechin (EC), impacts the biomechanical properties of the dentin matrix treated with oligomeric PACs, structure–activity relationships driving this bioactivity remain elusive. To gain insights into the modulatory role of the terminal monomers, two highly congruent trimeric PACs from Pinus massoniana only differing in the stereochemistry of the terminal unit (Trimer‐C vs. Trimer‐EC) were prepared to evaluate their chemical characteristics as well as their effects on the viscoelasticity and biostability of biomodified dentin matrices via infrared spectroscopy and multi‐scale dynamic mechanical analyses. The subtle alteration of C versus EC as terminal monomers lead to distinct immediate PAC‐trimer biomodulation of the dentin matrix. Nano‐ and micro‐dynamic mechanical analyses revealed that Trimer‐EC increased the complex moduli (0.51 GPa) of dentin matrix more strongly than Trimer‐C (0.26 GPa) at the nanoscale length (p < 0.001), whereas the reverse was found at the microscale length (p < .001). The damping capacity (tan δ) of dentin matrix decreased by 70% after PAC treatment at the nano‐length scale, while increased values were found at the micro‐length scale (~0.24) compared to the control (0.18 ; p < .001). An increase in amide band intensities and a decrease of complex moduli was observed after storage in simulated body fluid for both Trimer‐C and Trimer‐EC modified dentin. The stereochemical configuration of the terminal monomeric units, C and EC, did not impact the chemo‐mechanical stability of dentin matrix.

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Unveiling structure–activity relationships of proanthocyanidins with dentin collagen

Cited by 21 publications

References 49 publications

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

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

From medical strategy to foodborne prophylactic strategy: Stabilizing dental collagen with aloin

Modulatory role of terminal monomeric flavan‐3‐ol units in the viscoelasticity of dentin

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