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Natural Antioxidants, Dyes and Their Synthetic Analogs
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Natural Antioxidants, Dyes and Their Synthetic Analogs

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 May 2024) | Viewed by 9958

Special Issue Editor

Dr. Veronika Nagy

E-Mail Website
Guest Editor
Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Szigeti u. 12, H-7624 Pécs, Hungary
Interests: carotenoids; carbohydrates; organic synthesis; supramolecular organization; antioxidant activity

Special Issue Information

Dear Colleagues,

Beneficial properties of natural compounds can be improved by covalent or noncovalent chemical modifications. The modified derivatives may find useful applications in medical and material sciences. Antioxidant compounds, especially with an extended conjugated electron system, such as carotenoids or polyphenols, are proven radical scavengers and efficient agents against oxidative stress-related conditions. Nevertheless, these compounds are also promising candidates to create novel structures being organic conductive materials, molecular wires, or dyes with specific light-absorption properties, as well as amphipatic molecules with self-organization.

The aim of this Special Issue, “Natural Antioxidants, Dyes and Their Synthetic Analogs” is to collect the recent discoveries about the native or modified structures, including isolation, structure elucidation, chemical modification, (semi)synthesis, antioxidant studies, structure-activity relationship, synergic effects, delivery, supramolecular organization, electrochemical and spectroscopic properties, in silico calculations, and other related findings. Both original full research articles and reviews on these topics are welcome.

We look forward to your valuable contribution.

Dr. Veronika Nagy
Guest Editor

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Keywords

  • carotenoids
  • terpenoids
  • (poly)phenols
  • porphyrins
  • polyenes
  • antioxidants

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Published Papers (5 papers)

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Research

18 pages, 9888 KiB  
Article
Cosmetic Products with Potential Photoprotective Effects Based on Natural Compounds Extracted from Waste of the Winemaking Industry
by Ana-Maria Draghici-Popa, Diana-Ioana Buliga, Ioana Popa, Stefan Theodor Tomas, Raluca Stan and Aurelian Cristian Boscornea
Molecules 2024, 29(12), 2775; https://doi.org/10.3390/molecules29122775 - 11 Jun 2024
Cited by 1 | Viewed by 993
Abstract
Grape marc is a by-product resulting from the winemaking industry that still contains beneficial compounds that can be valorized. Thus, we report here the possibility of using polyphenolic extracts of grape marc origin to obtain sun protection creams. The extractions were performed in [...] Read more.
Grape marc is a by-product resulting from the winemaking industry that still contains beneficial compounds that can be valorized. Thus, we report here the possibility of using polyphenolic extracts of grape marc origin to obtain sun protection creams. The extractions were performed in ethanol and acetone solutions using pomace from different grape varieties (Merlot, Bläufrankisch, Fetească Neagră, Isabella) as a raw material. The obtained extracts were analyzed in order to determine the total phenolic content, the antioxidant activity, and the sun protection factor (SPF) via Mansur spectrophotometric assay. The best results were achieved using 70% ethanol in water as a solvent. The extracts with the highest potential photoprotective effects are from the Merlot variety (SPFspectrophotometric = 7.83 ± 0.76). The sunscreens were prepared using the 70% ethanolic extract of the Merlot variety evaporated to dryness, redissolved in either distilled water or ethanol. The SPF estimated in vitro via the COLIPA method showed values of 14.07 ± 1.50 and 11.46 ± 1.32 for the aqueous and ethanolic extracts, respectively, when working with a cream to polyphenolic extract a ratio of 1/1 (w/w). At the same time, the use of aqueous polyphenolic extracts ensures the better stability of creams compared with the ethanolic ones. Full article
(This article belongs to the Special Issue Natural Antioxidants, Dyes and Their Synthetic Analogs)
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15 pages, 1509 KiB  
Article
Theoretical Insight into Psittacofulvins and Their Derivatives
by Marcin Molski
Molecules 2024, 29(12), 2760; https://doi.org/10.3390/molecules29122760 - 10 Jun 2024
Cited by 1 | Viewed by 880
Abstract
Psittacofulvins are polyenal dyes responsible for coloring parrot feathers and protecting them against photo-oxidation, harmful radicals, and bacterial degradation. To explain the unusual properties of these compounds, the thermodynamic and global chemical activity descriptors characterizing four natural and three synthetic psittacofulvins, as well [...] Read more.
Psittacofulvins are polyenal dyes responsible for coloring parrot feathers and protecting them against photo-oxidation, harmful radicals, and bacterial degradation. To explain the unusual properties of these compounds, the thermodynamic and global chemical activity descriptors characterizing four natural and three synthetic psittacofulvins, as well as their hydroxyl, carboxyl and dialdehyde derivatives, were determined. To this aim, the DFT method at the B3LYP/QZVP theory level and the C-PCM solvation model were used. The calculations enabled the selection of the projected compounds for the greatest bioactivity and potential applicability as multifunctional ingredients in medicines, cosmetics, supplements, and food, in which they may play a triple role as preservative, radical scavenger, and coloring agent. The results obtained provide arguments for the identification of a fifth psittacofulvin within the parrot feather pigment, characterized by ten conjugated double bonds (docosadecaenal). Full article
(This article belongs to the Special Issue Natural Antioxidants, Dyes and Their Synthetic Analogs)
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17 pages, 5083 KiB  
Article
Reaction with ROO• and HOO• Radicals of Honokiol-Related Neolignan Antioxidants
by Nunzio Cardullo, Filippo Monti, Vera Muccilli, Riccardo Amorati and Andrea Baschieri
Molecules 2023, 28(2), 735; https://doi.org/10.3390/molecules28020735 - 11 Jan 2023
Cited by 9 | Viewed by 1792
Abstract
Honokiol is a natural bisphenol neolignan present in the bark of Magnolia officinalis, whose extracts have been employed in oriental medicine to treat several disorders, showing a variety of biological properties, including antitumor activity, potentially related to radical scavenging. Six bisphenol neolignans [...] Read more.
Honokiol is a natural bisphenol neolignan present in the bark of Magnolia officinalis, whose extracts have been employed in oriental medicine to treat several disorders, showing a variety of biological properties, including antitumor activity, potentially related to radical scavenging. Six bisphenol neolignans with structural motifs related to the natural bioactive honokiol were synthesized. Their chain-breaking antioxidant activity was evaluated in the presence of peroxyl (ROO•) and hydroperoxyl (HOO•) radicals by both experimental and computational methods. Depending on the number and position of the hydroxyl and alkyl groups present on the molecules, these derivatives are more or less effective than the reference natural compound. The rate constant of the reaction with ROO• radicals for compound 7 is two orders of magnitude greater than that of honokiol. Moreover, for compounds displaying quinonic oxidized forms, we demonstrate that the addition of 1,4 cyclohexadiene, able to generate HOO• radicals, restores their antioxidant activity, because of the reducing capability of the HOO• radicals. The antioxidant activity of the oxidized compounds in combination with 1,4-cyclohexadiene is, in some cases, greater than that found for the starting compounds towards the peroxyl radicals. This synergy can be applied to maximize the performances of these new bisphenol neolignans. Full article
(This article belongs to the Special Issue Natural Antioxidants, Dyes and Their Synthetic Analogs)
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12 pages, 1388 KiB  
Article
Quantitative Determination of Polyphenols and Flavonoids in Cistus × incanus on the Basis of IR, NIR and Raman Spectra
by Sonia Pielorz, Izabela Fecka, Karolina Bernacka and Sylwester Mazurek
Molecules 2023, 28(1), 161; https://doi.org/10.3390/molecules28010161 - 25 Dec 2022
Cited by 4 | Viewed by 2340
Abstract
Cistus is a plant that has been used in natural medicine for hundreds of years; it works primarily as an antioxidant and cleansing agent. Cistus × incanus leaves or herb can be an attractive source of polyphenols and flavonoids. The official protocols of [...] Read more.
Cistus is a plant that has been used in natural medicine for hundreds of years; it works primarily as an antioxidant and cleansing agent. Cistus × incanus leaves or herb can be an attractive source of polyphenols and flavonoids. The official protocols of active compound analysis relies on the extraction of compounds of interest from plant matter, which makes their determination long and costly. An analysis of plant material in its native state can be performed using vibrational spectroscopy. This paper presents a comparison of Raman spectroscopy, attenuated total reflection in mid-infrared and diffuse reflectance technique in the near-infrared region for the simultaneous quantification of total polyphenols (TPC) and flavonoids (TF) content, as well as the determination of FRAP antioxidant activity of C. incanus material. Utilizing vibrational spectra and using partial least squares algorithm, TPC and TF were quantified with the RSEPVAL errors in the 2.7–5.4% range, while FRAP antioxidant activity for validation sets was determined with relative errors ranged from 5.2 to 9.3%. For the analyzed parameters, the lowest errors of predictions were computed for models constructed using Raman data. The developed models allow for fast and precise quantification of the studied active compounds in C. incanus material without any chemical sample treatment. Full article
(This article belongs to the Special Issue Natural Antioxidants, Dyes and Their Synthetic Analogs)
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19 pages, 3947 KiB  
Article
The Influence of Lactic Acid Fermentation on Selected Properties of Pickled Red, Yellow, and Green Bell Peppers
by Emilia Janiszewska-Turak, Dorota Witrowa-Rajchert, Katarzyna Rybak, Joanna Rolof, Katarzyna Pobiega, Łukasz Woźniak and Anna Gramza-Michałowska
Molecules 2022, 27(23), 8637; https://doi.org/10.3390/molecules27238637 - 6 Dec 2022
Cited by 10 | Viewed by 2736
Abstract
Red, yellow, and green peppers are vegetables rich in natural pigments. However, they belong to seasonal vegetables and need to be treated to prolong their shelf life. One new approach to processing vegetables is to pickle them using lactic acid bacteria. The use [...] Read more.
Red, yellow, and green peppers are vegetables rich in natural pigments. However, they belong to seasonal vegetables and need to be treated to prolong their shelf life. One new approach to processing vegetables is to pickle them using lactic acid bacteria. The use of such a process creates a new product with high health value, thanks to the active ingredients and lactic acid bacteria. Therefore, this study aimed to evaluate the effect of the applied strain of lactic acid bacteria (LAB) on the chemical properties, including the content of active compounds (pigments) and the physical properties of the peppers. Levilactobacillus brevis, Limosilactobacillus fermentum, and Lactoplantibacillus plantarum were used for fermentation and spontaneous fermentation. The pigments, polyphenols content, and antioxidant properties were determined in the pickled peppers, as well as sugar content, color, dry matter, texture properties, and the count of lactic acid bacteria. In all samples, similar growth of LAB was observed. Significant degradation of chlorophylls into pheophytins was observed after the fermentation process. No significant differences were observed in the parameters tested, depending on the addition of dedicated LAB strains. After the fermentation process, the vitamin C and total polyphenols content is what influenced the antioxidant activity of the samples. It can be stated that the fermentation process changed the red bell pepper samples in the smallest way and the green ones in the highest way. Full article
(This article belongs to the Special Issue Natural Antioxidants, Dyes and Their Synthetic Analogs)
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