Comparative analysis of oxidative mechanisms of phloroglucinol and dieckol by electrochemical, spectroscopic, cellular and computational methods

Zhang, Di; Wang, Chengtao; Shen, Lingqin; Shin, Hyeon‐Cheol; Lee, Kyung Bok; Ji, Baoping

doi:10.1039/c7ra10875c

Cited by 25 publications

(17 citation statements)

References 25 publications

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“…The biofabrication of marine biomolecule-functionalized silver nanoparticles was accomplished using a spontaneous oxidation-reduction (donor-acceptor electron) reaction process 38 . Frequently, the O-H and N-H functional groups for upholding strong affinity towards metal ions consequently during oxidation, the enormous amount of electron donor amine and hydroxyl functional groups in chitosan and algae-derived polyphenolic compounds such as phlorotannins, dieckol, phloroglucinol, and eckol 39,45 function as potential reducing and capping agents 46 through transferring electrons to silver ions as www.nature.com/scientificreports/ an electron acceptor in the synthesis reaction. As the reaction progresses, electron-rich organic biomolecules increasingly lose their outer electrons while Ag + cations gain the electrons and could be reduced to metallic atoms.…”

Section: Mechanism Of Agnps Biosynthesismentioning

confidence: 99%

Synergistic effects of combinatorial chitosan and polyphenol biomolecules on enhanced antibacterial activity of biofunctionalized silver nanoparticles

Rezazadeh

Buazar

Matroodi

2020

Sci Rep

146

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The present study reports the synergistic antibacterial activity of biosynthesized silver nanoparticles (AgNPs) with the aid of a combination of chitosan and seaweed-derived polyphenols as a green synthetic route. Under optimum synthesis conditions, the rapid color change from yellowish to dark brown and UV–visible absorption peak at 425 confirmed the initial formation of AgNPs. DLS, TEM, XRD, and EDX analyses revealed the spherical shape of pure biogenic AgNPs with a mean diameter size of 12 nm ± 1.5 nm, and a face-centered cubic crystal structure, respectively. FTIR and TGA results indicated the significant contribution of chitosan and polyphenol components into silver ions bioreduction and thermal stability of freshly formed AgNPs. Long-term colloidal stability of AgNPs was obtained after 6-month storage at room temperature. The bio-prepared AgNPs possessed a negative surface charge with a zeta potential value of − 27 mV. In contrast to naked chemical silver nanoparticles, the green Ag nanosamples demonstrated the distinct synergistic antibacterial in vitro toward all selected human pathogens presumably due to the presence of high content of biomolecules on their surface. The results show that synergy between chitosan and polyphenol results in the enhancement of bactericidal properties of biogenic AgNPs. We also highlighted the underlying mechanism involved in AgNPs formation based on nucleophile–electrophile interaction.

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Section: Mechanism Of Agnps Biosynthesismentioning

confidence: 99%

Synergistic effects of combinatorial chitosan and polyphenol biomolecules on enhanced antibacterial activity of biofunctionalized silver nanoparticles

Rezazadeh

Buazar

Matroodi

2020

Sci Rep

146

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“…Although has being a technique used to analyze crude extracts or fractions, in order to confirm the reliability of spectrophotometric analysis (as discussed above), NMR has been also used in the identification (or confirmation) of isolated phenolic compounds [21,27,156,176], as well as of isolated phlorotannins [32,33,43,45,46,60,62,73,101,115,116,153,154,[177][178][179]184,189,207,[215][216][217]. In fact, NMR analysis has allowed to identify different groups of isolated phlorotannins, in particular, phlorethols, fuhalols, fucols, fucophlorethols, and eckols [32,33,40,43,45,46,60,62,73,153,154,[177][178][179]184,207,[215][216][217].…”

Section: Nmr Analysis Of Isolated Phenolic Compounds From Macroalgae mentioning

confidence: 99%

The Quest for Phenolic Compounds from Macroalgae: A Review of Extraction and Identification Methodologies

et al. 2019

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The current interest of the scientific community for the exploitation of high-value compounds from macroalgae is related to the increasing knowledge of their biological activities and health benefits. Macroalgae phenolic compounds, particularly phlorotannins, have gained particular attention due to their specific bioactivities, including antioxidant, antiproliferative, or antidiabetic. Notwithstanding, the characterization of macroalgae phenolic compounds is a multi-step task, with high challenges associated with their isolation and characterization, due to the highly complex and polysaccharide-rich matrix of macroalgae. Therefore, this fraction is far from being fully explored. In fact, a critical revision of the extraction and characterization methodologies already used in the analysis of phenolic compounds from macroalgae is lacking in the literature, and it is of uttermost importance to compile validated methodologies and discourage misleading practices. The aim of this review is to discuss the state-of-the-art of phenolic compounds already identified in green, red, and brown macroalgae, reviewing their structural classification, as well as critically discussing extraction methodologies, chromatographic separation techniques, and the analytical strategies for their characterization, including information about structural identification techniques and key spectroscopic profiles. For the first time, mass spectrometry data of phlorotannins, a chemical family quite exclusive of macroalgae, is compiled and discussed.

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“…Recently, some researchers discovered that mango ( M. indica ) peel is a rich source of phenolic compounds, with amounts up to 0.55~1.1 g·kg −1 dry mango peel (DMP) [ 2 , 3 ]. Although many studies had been carried out on extraction and purification of mango phenols [ 4 , 5 , 6 , 7 , 8 , 9 ], few have reported on the compositional analysis, antioxidant and cytotoxic effects of mango peel phenols (MPPs). The present work is the first to describe an evaluation of the in vitro antioxidant activities of mango ( M. indica L.) peel extract (MPE) and its MPPs, including DPPH•, ABTS•+ and FRAP scavenging, as well as their cytotoxic effect on the A549 human lung carcinoma cell line.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Antioxidant Activities of Phenols and Oleanolic Acid from Mango Peel and Their Cytotoxic Effect on A549 Cell Line

Lai

Zhou

et al. 2018

Molecules

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Mango peel, the main by-product of juice processing, possesses appreciable quantities of bioactive phenolic compounds and is worthy of further utilization. The present work reports for the first time the HPLC analysis and in vitro antioxidant evaluation of mango peel phenols (MPPs) and their cytotoxic effect on the A549 lung cancer cell line. These results indicated that mango peel has the total phenolic content of 723.2 ± 0.93 mg·kg−1 dry mango peel (DMP), which consisted mainly of vanillic aldehyde, caffeic acid, chlorogenic acid, gallic acid, procyanidin B2 and oleanolic acid. Antioxidant assays showed that MPPs had strong antioxidant activities, with 92 ± 4.2% of DPPH radical scavenging rate, 79 ± 2.5% of ABTS radical inhibition rate and 4.7 ± 0.5 μM Trolox equivalents per kg−1 DMP of ferric reducing power. Gallic acid possess a stronger antioxidant capacity than other phenols. In vitro cytotoxic tests suggested that mango peel extract (MPE) had an IC50 value of 15 mg·mL−1 and MPPs had a stronger inhibitory effect on the A549 cell line. Oleanolic acid exhibited the strongest cytotoxicity, with an IC50 value of 4.7 μM, which was similar with that of the positive control 5-fluorouracil.

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Comparative analysis of oxidative mechanisms of phloroglucinol and dieckol by electrochemical, spectroscopic, cellular and computational methods

Abstract: The pH-dependent oxidative mechanism of two phlorotannin compounds.

Cited by 25 publications

References 25 publications

Synergistic effects of combinatorial chitosan and polyphenol biomolecules on enhanced antibacterial activity of biofunctionalized silver nanoparticles

Synergistic effects of combinatorial chitosan and polyphenol biomolecules on enhanced antibacterial activity of biofunctionalized silver nanoparticles

The Quest for Phenolic Compounds from Macroalgae: A Review of Extraction and Identification Methodologies

In Vitro Antioxidant Activities of Phenols and Oleanolic Acid from Mango Peel and Their Cytotoxic Effect on A549 Cell Line

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