Oxidation mechanism of flavanone taxifolin. Electrochemical and spectroelectrochemical investigation

Kocábová, Jana; Fiedler, Jan; Degano, Ilaria; Sokolová, Romana

doi:10.1016/j.electacta.2015.11.077

Cited by 27 publications

(19 citation statements)

References 30 publications

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“…Component III shows prominent IR bands at 1637, 1658, and 1728 cm -1 in the ray, tracheid lumen, and S3 layer. The band around 1637 cm -1 was assigned to the ketone bond in taxifolin (Ruddick and Xie, 1994;Miklečić et al, 2012;Kocábová et al, 2016;Liu et al, 2018), one of the most abundant phenolic compounds in larch wood (Giwa and Swan, 1975;Babkin et al, 2001;Ivanova et al, 2012;Zule et al, 2017) (see reference spectrum of taxifolin in Figure S4 for comparison). The other peaks seen in the taxifolin spectrum are not seen due to overlap with the spectra of the structural wood cell wall biopolymers.…”

Section: Discussionmentioning

confidence: 99%

“…Besides, bands are observed around 1600, 1637, and 1660 cm -1 ; the same ones as found in components IV and V, but weaker. Candidates for para substituted ketones are flavonoids such as taxifolin and dihydrokaempferol (Ruddick and Xie, 1994;Kocábová et al, 2016), known to be abundant in larch (Nisula, 2018). This component is represented in all the images in the ray, as well as tracheid lumina and S3 layer.…”

Section: Resolution Of Image Multiset Structures Mcr-als On Completementioning

confidence: 99%

“…Imaging of the ray and the cell wall in contact mode was particularly difficult because of their different material properties. This is why the image is blurry and Schwanninger et al, 2004;b Fackler et al, 2010;c Ghosh et al, 2015;d Popescu et al, 2010;e Popescu et al, 2007;f Zu et al, 2012;g Faix, 1991;h Traoré et al, 2018;i Lawther et al, 1996;j Kocábová et al, 2016;k Bock and Gierlinger, 2019. it appears as if the ray is smeared over the cell wall ( Figure 6). Such topography and relationship between the ray and the cell wall are unrealistic and simply an artefact of imaging in contact mode.…”

Section: Afm-ir Spectra Analysismentioning

confidence: 99%

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Understanding the Formation of Heartwood in Larch Using Synchrotron Infrared Imaging Combined With Multivariate Analysis and Atomic Force Microscope Infrared Spectroscopy

et al. 2020

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Formation of extractive-rich heartwood is a process in live trees that make them and the wood obtained from them more resistant to fungal degradation. Despite the importance of this natural mechanism, little is known about the deposition pathways and cellular level distribution of extractives. Here we follow heartwood formation in Larix gmelinii var. Japonica by use of synchrotron infrared images analyzed by the unmixing method Multivariate Curve Resolution-Alternating Least Squares (MCR-ALS). A subset of the specimens was also analyzed using atomic force microscopy infrared spectroscopy. The main spectral changes observed in the transition zone when going from sapwood to heartwood was a decrease in the intensity of a peak at approximately 1660 cm-1 and an increase in a peak at approximately 1640 cm-1. There are several possible interpretations of this observation. One possibility that is supported by the MCR-ALS unmixing is that heartwood formation in larch is a type II or Juglans-type of heartwood formation, where phenolic precursors to extractives accumulate in the sapwood rays. They are then oxidized and/or condensed in the transition zone and spread to the neighboring cells in the heartwood.

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Section: Discussionmentioning

confidence: 99%

Section: Resolution Of Image Multiset Structures Mcr-als On Completementioning

confidence: 99%

Section: Afm-ir Spectra Analysismentioning

confidence: 99%

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Understanding the Formation of Heartwood in Larch Using Synchrotron Infrared Imaging Combined With Multivariate Analysis and Atomic Force Microscope Infrared Spectroscopy

et al. 2020

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“…Therefore, in the reaction mixture, a complex equilibrium between ROS formation and their scavenging may have developed. Furthermore, this equilibrium is additionally affected by the reaction products of the flavans with • OH which oxidize the phenols to semiquinones and quinones, but also form hydroxyl derivatives as well as flavan oligomers [28,46,47]. These flavan reaction products between flavans and • OH may also show pro- or antioxidant properties.…”

Section: Discussionmentioning

confidence: 99%

“…The flavanol (±)-catechin was compared with two structurally-related flavanones, (+)-eriodictyol and (+)-taxifolin, both with different oxygen functions on ring C, the first one with a keto group on C4 and the second one with an additional hydroxyl group on C3 (Figure 1). All three substances lack a 2,3-double bond on ring C; the ring A and B systems are not conjugated [28]. …”

Section: Introductionmentioning

confidence: 99%

Pro- and Antioxidant Activity of Three Selected Flavan Type Flavonoids: Catechin, Eriodictyol and Taxifolin

Chobot

Hadaček

Bachmann

et al. 2016

IJMS

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The flavanol (±)-catechin shows an OH group but no 4-keto group on ring C (C3), and no conjugation between ring A and B. The related flavanone (+)-eriodictyol has a keto group on C4 but no 3-OH group on ring C. (+)-Taxifolin, another flavanone, has an OH on C3 and a keto group on C4 of the C ring. Deoxyribose degradation assay systems, with hydrogen peroxide and ascorbic acid either added or omitted, were performed in variants in which Fe(III) was added in a complex with ethylenediaminetetraacetic acid (EDTA). In combination with differential pulse voltammetry (DVP), the specific redox-chemical contributions of the ring A m-dihydroxyl groups could be explored more specifically in addition to those of the traditionally investigated o-dihydroxyl groups of ring B.

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Long‐Lasting Reactive Oxygen Species Generation by Porous Redox Mediator‐Potentiated Nanoreactor for Effective Tumor Therapy

Ding

Wang

Xia

et al. 2021

Adv Funct Materials

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The therapeutic efficiency of reactive oxygen species (ROS)‐based nanotherapeutics is restrained by the rigorous production conditions of relatively sufficient and kinetically matching supply of intracellular substrates. The cumulative disruption of redox homeostasis and consequent pathology (e.g., Parkinson's disease) with low levels of substrates in living organisms may provide a promising model for ROS‐based therapy. Herein, a catechol chemistry‐mediated ternary nanostructure is prepared for long‐lasting generation of oxidative •OH in weakly acidic, low H2O2 homeostasis conditions of tumor. This platform employs mesoporous polydopamine (MPDA) as the porous redox mediator, while PDA‐induced sequential precipitation and biomineralization lead to hydroxy iron oxide (FeOOH) as the “iron reservoir,” and calcium phosphate (CaP) as the pH‐sensitive sheddable shell. In weakly acidic conditions, the CaP layer can be degraded to expose the catalytic surface of Fe‐dopamine interplay, where FeOOH dissolution, Fe(III) chelation, Fe(III) reduction, Fe(II) release take place sequentially and continuously for Fe(II) recycling and Fenton catalysis. Both in vitro and in vivo studies verify the significant inhibition of cancer cells and tumor regression, which can also be strengthened by the local photothermal heating. This work establishes the first paradigm of pathologically inspired nanohybrids of ROS generators with long‐lasting efficacy for cancer therapy.

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Oxidation mechanism of flavanone taxifolin. Electrochemical and spectroelectrochemical investigation

Cited by 27 publications

References 30 publications

Understanding the Formation of Heartwood in Larch Using Synchrotron Infrared Imaging Combined With Multivariate Analysis and Atomic Force Microscope Infrared Spectroscopy

Understanding the Formation of Heartwood in Larch Using Synchrotron Infrared Imaging Combined With Multivariate Analysis and Atomic Force Microscope Infrared Spectroscopy

Pro- and Antioxidant Activity of Three Selected Flavan Type Flavonoids: Catechin, Eriodictyol and Taxifolin

Long‐Lasting Reactive Oxygen Species Generation by Porous Redox Mediator‐Potentiated Nanoreactor for Effective Tumor Therapy

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