Vanillic acid and syringic acid: Exceptionally robust aromatic moieties for inhibiting in vitro self-assembly of type I collagen

Rasheeda, K.; Bharathy, H.; Fathima, Nishter Nishad

doi:10.1016/j.ijbiomac.2018.03.015

Cited by 39 publications

(21 citation statements)

References 26 publications

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“…And the Rpn value decreased to 0.098 when the dosage of proyanidin increased to 40%. It has been reported that the micro unfolding of the collagen triple helical structure rather than denaturing was observed under the effect of phenolic compound and the corresponding Rpn values decreased (27,(33)(34). Therefore, the decreasing of Rpn values here was probably attributed to the conformational change of collagen molecule, which agreed well with the investigation of AFM (globular aggregates shown in Figure 1e and f).…”

Section: Circular Dichroism (Cd) Studiessupporting

confidence: 88%

“…Compared with native collagen, the peaks at 222nm of collagen treated by different amount of procyanidin had little change, while the peak intensities at 197nm decreased slightly as the increase of procyanidin concentration. It is confirmed that a red shift in 222nm signal would occur when the collagen denatured or its triple helical structure unfolded (27). However, there was no red shift was observed on the spectrum of collagen treated by procyanidin.…”

Section: Circular Dichroism (Cd) Studiesmentioning

confidence: 69%

“…The CD spectra of type I collagen treated by different concentration of procyanidin were shown in Figure 2. For the case of natural type I collagen, specific peaks in far ultraviolet (UV) region at 222nm and 197nm can be observed on CD spectrum, which were due to n to π* transition of polyproline II ring and π to π* transition, respectively (27,(30)(31)(32). Shown as Figure 2, the absorption bands on CD spectrum (curve a) were typical peaks of collagen type I, which indicated that the secondary structure of collagen kept well.…”

Section: Circular Dichroism (Cd) Studiesmentioning

confidence: 92%

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A Reconsideration of the Effect of Procyanidin on the Assembly of Collagen Type I

Wang

Jin

2018

Preprint

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In order to elucidating the exact effect mechanism of polyphenols on the assembly of collagen, the assembled architectures of collagen treated with different amounts of procyanidin (PA) were investigated in details. The assembled morphologies of collagen were greatly influenced by the content of PA according to atomic force microcopy (AFM) images.When the content of PA was more than 20% (w/w), the fibrillar morphologies were substituted by globular aggregates, which were driven by the intense hydrogen bonding action originating from PA. While the formation of the non-fibrous aggregates was due to the coiling and entangling of flexible collagen molecules rather than their gelatinization based on the appearance of typical adsorption peaks at 222nm and 197nm on circular dichroism (CD) spectra. After being crosslinked by glutaraldehyde (GA), not only the diameters but also the lengths of fibrils increased. Unfortunately, the fibrillogenesis was still inhibited when the collagen suffered from 20% PA firstly and then 4% GA. Conversely, the fibrous morphologies of the fibrils stabilized by 4% GA and then underwent 20% PA maintained well, in spite of accompanying with grievous intertwining. This difference was derived from the change of flexibilities of collagen before and after being crosslinked by GA. Additionally, the differential scanning calorimeter (DSC) analysis confirmed the PA had no positive effect on the improvement of thermal stability of hydrous collagen, whereas the denaturation temperature of hydrated collagen stabilized by 4% GA increased from 40 °C to 80 °C.

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Section: Circular Dichroism (Cd) Studiessupporting

confidence: 88%

Section: Circular Dichroism (Cd) Studiesmentioning

confidence: 69%

Section: Circular Dichroism (Cd) Studiesmentioning

confidence: 92%

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A Reconsideration of the Effect of Procyanidin on the Assembly of Collagen Type I

Wang

Jin

2018

Preprint

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“…Recent studies have suggested that C3G potentially exerts functions primarily through C3G metabolites (C3G-Ms) [7], and more than 20 kinds of C3G-Ms have been identified in serum by a pharmacokinetics study in humans [8]. Although the function and mechanism of C3G-Ms are still not clear, protocatechuic acid (PCA) [9][10][11][12], phloroglucinaldehyde (PGA) [1], vanillic acid (VA) [13][14][15], ferulic acid (FA) [16][17][18][19], and their derivates represent the main bioactive metabolites of C3G due to their antioxidant and anti-inflammatory properties. Figure 1.…”

Section: Introductionmentioning

confidence: 99%

The Effects and Mechanisms of Cyanidin-3-Glucoside and Its Phenolic Metabolites in Maintaining Intestinal Integrity

et al. 2019

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Cyanidin-3-glucoside (C3G) is a well-known natural anthocyanin and possesses antioxidant and anti-inflammatory properties. The catabolism of C3G in the gastrointestinal tract could produce bioactive phenolic metabolites, such as protocatechuic acid, phloroglucinaldehyde, vanillic acid, and ferulic acid, which enhance C3G bioavailability and contribute to both mucosal barrier and microbiota. To get an overview of the function and mechanisms of C3G and its phenolic metabolites, we review the accumulated data of the absorption and catabolism of C3G in the gastrointestine, and attempt to give crosstalk between the phenolic metabolites, gut microbiota, and mucosal innate immune signaling pathways.

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“…Syringic acid (4-Hydroxy-3,5-dimethoxybenzoic acid) is a naturally occurring phenolic compound mainly found in fruits of edible plants and mushrooms (Itoh et al, 2009;Pacheco-Palencia, Mertens-Talcott, & Talcott, 2008). It has wide range of pharmaceutical applications including antioxidant (Gao et al, 2018;Wang et al, 2016;Zhou et al, 2017), anti-diabetic (Muthukumaran, Srinivasan, Venkatesan, Ramachandran, & Muruganantham, 2013), hepatoprotective (Itoh et al, 2009;Itoh et al, 2010;Yan, Wang, Yen, Lee, & Yin, 2016), antihyperlipidemic (Ramachandran, 2010), cardioprotective (Ding et al, 2017;Rasheeda, Bharathy, & NishadFathima, 2018), neuroprotective (Rasheeda et al, 2018;Tokmak et al, 2017), and anti-inflammatory properties (Ham et al, 2016;Lee et al, 2012). Syringic acid extracted from Herba dendrobii has potential inhibiting activity on aldose reductase and its gene expression and thereby suppresses the diabetic cataract in eye lenses of rat model (Wei et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Effect of Syringic acid on antioxidant biomarkers and associated inflammatory markers in mice model of asthma

Zhang

Wang

et al. 2018

Drug Development Research

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Asthma is termed as the induction of chronic inflammation in the airway lumen of lungs due to accumulation of inflammatory cells which affects normal breathing process. Prolonged accumulation of inflammatory cells leads to oxidative stress and suppression of antioxidant activities. Therefore, in our present investigation, a potential phenolic compound, Syringic acid was tested for the suppression of inflammatory markers toward an antiasthmatic activity in ovalbumin (OVA)‐induced asthmatic mice model. As a result, the Syringic acid treatment was found to suppress the inflammatory cells; eosinophil, neutrophil, macrophage, lymphocyte, and other inflammatory markers including IL‐4, IL‐5, IL‐13, and TNF‐α in the BALF of OVA‐induced asthmatic mice. Similarly, IgE levels were significantly reduced in the blood serum of Syringic acid treated mice groups. In this context, the IFN‐γ levels were found enhanced in the BALF of Syringic acid treated asthmatic mice groups, expressing an anti‐inflammatory response. Enzymatic and nonenzymatic antioxidants such as SOD, CAT, and GSH levels were found high in the Syringic acid treatment than the asthmatic control group, which depicts the antioxidant response of Syringic acid on asthmatic groups. Intriguingly, the ROS, NO2, NO3, and MDA levels were inhibited in the BALF of Syringic acid treated mice groups. The airway hyper‐reactivity (AHR) was comparatively normal in the Syringic acid treatment as it was severe in the case of asthmatic control group. Consequently, the effect of Syringic acid is prominent in the treatment of asthma by controlling the accumulation of inflammatory cells, other inflammatory markers along with enhancement of antioxidant markers, suppression of ROS and controlling airway hyperreactivity. Hence, Syringic acid may be recommended for clinical trials in the treatment of asthma.

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Vanillic acid and syringic acid: Exceptionally robust aromatic moieties for inhibiting in vitro self-assembly of type I collagen

Cited by 39 publications

References 26 publications

A Reconsideration of the Effect of Procyanidin on the Assembly of Collagen Type I

A Reconsideration of the Effect of Procyanidin on the Assembly of Collagen Type I

The Effects and Mechanisms of Cyanidin-3-Glucoside and Its Phenolic Metabolites in Maintaining Intestinal Integrity

Effect of Syringic acid on antioxidant biomarkers and associated inflammatory markers in mice model of asthma

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