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Bioactive Flavonoids and Xanthones: From Bench to Industry. Pharmaceutical, Cosmetic and Industrial Applications

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

Deadline for manuscript submissions: closed (28 February 2023) | Viewed by 13149

Special Issue Editors


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Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua Jorge Viterbo Ferreira n° 228, 4050-313 Porto, Portugal
Interests: medicinal chemistry; organic synthesis; drug discovery; anticancer activity; antimicrobial activity; chiral drugs; natural products
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Guest Editor
1. Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências, Químicas, Faculdade de Farmácia, Universidade do Porto, Rua Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal
2. CIIMAR | Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Novo Edifício do Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos, s/n, 4450-208 Matosinhos, Portugal
Interests: medicinal chemistry; synthesis of sulfated and glycosylated small-molecule mimetics of heparin; discovery of biological activities for persulfated versus partially sulfated small molecules; antifouling studies of partially sulfated small molecules; antithrombotic studies of persulfated small molecules; structure–activity and structure–property relationship studies of bioactive small molecules
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
UCIBIO/REQUIMTE, MedTech-Laboratory of Pharmaceutical Technology, Department of Drug Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira nº 228, 4050-313 Porto, Portugal
Interests: antioxidants; natural products; sunscreens and anti-aging cosmetics; phototoxicity; photostability and photoprotection; mechanical and sensory characterization of topical formulations; patient centric design of topical products; health literacy in cosmetology
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Flavonoids and xanthones are versatile scaffolds commonly found in nature, which have long been recognized for their wide range of biological and pharmacological activities, such as antimicrobial, anti-inflammatory, antitumor, antioxidant, antiaging, anti-browning and antifouling activities, which has led to their great interest as candidates for drug discovery, as well as other industrial applications. In the form of extracts and as pure compounds, flavonoids and xanthones have long been used in dermatological and cosmetic products. Considering the well-known biological potential of these classes of natural products, several studies have proposed their use as food additives due to their ability to preserve foods, to provide colour and flavour and to make dietary supplements, among other important industrial applications. This Special Issue aims to provide both updates and new perspectives on natural flavonoids and xanthones and their synthetic analogues for drug discovery, as well as candidates for other industrial applications. Original articles and short communications, as well as reviews of studies on this topic, are welcome.

Dr. Honorina Cidade
Prof. Dr. Marta Correia-da-Silva
Prof. Dr. Isabel Martins de Almeida
Guest Editors

Manuscript Submission Information

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Keywords

  • Flavonoids
  • Xanthones
  • Biological activity
  • Natural Products
  • Synthesis
  • Industrial applications
  • Cosmetic applications
  • Food industry applications

Published Papers (6 papers)

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Research

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12 pages, 1731 KiB  
Article
Synthesis and Characterization of Curcumin-Chitosan Loaded Gold Nanoparticles by Oryctes rhinoceros’ Chitin for Cosmeceutical Application
by Nurul Alyani Zainol Abidin, Faridah Kormin, Nurul Akhma Zainol Abidin, Mohd Fadzelly Abu Bakar and Iqbal Ahmed Moujdin
Molecules 2023, 28(4), 1799; https://doi.org/10.3390/molecules28041799 - 14 Feb 2023
Cited by 2 | Viewed by 1987
Abstract
A breakthrough in cosmeceuticals by utilizing insects as major ingredients in cosmetic products is gaining popularity. Therefore, the interest in rare sources of ingredients, for instance, from the Oryctes rhinoceros beetle, can bring huge benefits in terms of turning pests into wealth. In [...] Read more.
A breakthrough in cosmeceuticals by utilizing insects as major ingredients in cosmetic products is gaining popularity. Therefore, the interest in rare sources of ingredients, for instance, from the Oryctes rhinoceros beetle, can bring huge benefits in terms of turning pests into wealth. In this study, curcumin was chosen as the active ingredient loaded into chitosan-gold nanoparticles (CCG-NP). Curcumin is unstable and has poor absorption, a high rate of metabolism, and high sensitivity to light. These are all factors that contribute to the low bioavailability of any substance to reach the target cells. Therefore, chitosan extracted from O. rhinoceros could be used as a drug carrier to overcome these limitations. In order to overcome these limitations, CCG-NPs were synthesized and characterized. Chitosan was isolated from O. rhinoceros and CCG-NPs were successfully synthesized at 70 °C for 60 min under optimal conditions of a reactant ratio of 2:0.5 (0.5 mM HAuCl4: 0.1% curcumin). Characterizations of CCG-NP involved FTIR analysis, zeta potential, morphological properties determination by FE-SEM, particle size analysis, crystallinity study by XRD, and elemental analysis by EDX. The shape of the CCG-NP was round, its size was 128.27 d.nm, and the value of the zeta potential was 20.2 ± 3.81 mV. The IC50 value for cell viability is 58%, indicating a mild toxicity trait. To conclude, CCG-NP is a stable, spherical, nano-sized, non-toxic, and homogeneous solution. Full article
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13 pages, 1997 KiB  
Article
Spectrum-Effect Relationship-Based Strategy Combined with Molecular Docking to Explore Bioactive Flavonoids from Sceptridium ternatum
by Junfeng Zhu, Haiying Ding, Like Zhong, Wenxiu Xin, Xiaojiao Yi and Luo Fang
Molecules 2022, 27(17), 5698; https://doi.org/10.3390/molecules27175698 - 4 Sep 2022
Cited by 3 | Viewed by 1463
Abstract
Sceptridium ternatum is a herbaceous plant with significant potential for pharmaceutical and cosmetic applications. In this study, we established a spectrum-effect relationship-based strategy to investigate the bioactive basis and tissue distribution in S. ternatum. First, a phytochemical analysis on the ethanol extracts [...] Read more.
Sceptridium ternatum is a herbaceous plant with significant potential for pharmaceutical and cosmetic applications. In this study, we established a spectrum-effect relationship-based strategy to investigate the bioactive basis and tissue distribution in S. ternatum. First, a phytochemical analysis on the ethanol extracts from roots, stems, and leaves of S. ternatum was performed using the colorimetric method, high-performance liquid chromatography–ultraviolet (HPLC–UV), and high-performance liquid chromatography–electrospray ionization quadrupole time-of-flight mass spectrometry (HPLC–ESI-Q-TOF-MS/MS). Then, radical scavenging assays and the lipopolysaccharide-stimulated RAW 264.7 cell model were used to estimate the antioxidant and anti-inflammatory activities, respectively. Spectrum-effect relationship analysis and molecular docking were further employed to evaluate the correlation between the phytochemical profile and anti-inflammatory activity. Our results demonstrate that S. ternatum leaves contained the most abundant flavonoids and exerted the best biological activities. Their IC50 values for scavenging 2,2ʹ-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) and 1,1-diphenyl-2-picrylhydrazyl radicals were 2.43 ± 0.13 and 5.36 ± 0.54 mg/mL, respectively. In lipopolysaccharide-stimulated RAW 264.7 cells, the leaf extract caused the greatest reduction in nitric oxide production (38.15%) and interleukin-6 release (110.86%). Spectrum-effect relationship analysis and molecular docking indicated that quercetin 3-O-rhamnoside-7-O-glucoside possessed high anti-inflammatory activity by binding with interleukin-6. In conclusion, S. ternatum is a rich source of bioactive flavonoids with potential for exploitation in the prevention and treatment of oxidative stress and inflammation-related pathologies. Full article
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11 pages, 1315 KiB  
Article
Impact of Tralopyril and Triazolyl Glycosylated Chalcone in Human Retinal Cells’ Lipidome
by Cátia Vilas-Boas, Logan Running, Daniela Pereira, Honorina Cidade, Marta Correia-da-Silva, Gunes Ekin Atilla-Gokcumen and Diana S. Aga
Molecules 2022, 27(16), 5247; https://doi.org/10.3390/molecules27165247 - 17 Aug 2022
Cited by 4 | Viewed by 1960
Abstract
Antifouling (AF) coatings containing booster biocides are used worldwide as one of the most cost-effective ways to prevent the attachment of marine organisms to submerged structures. Nevertheless, many of the commercial biocides, such as Econea® (tralopyril), are toxic in marine environments. For [...] Read more.
Antifouling (AF) coatings containing booster biocides are used worldwide as one of the most cost-effective ways to prevent the attachment of marine organisms to submerged structures. Nevertheless, many of the commercial biocides, such as Econea® (tralopyril), are toxic in marine environments. For that reason, it is of extreme importance that new efficient AF compounds that do not cause any harm to non-target organisms and humans are designed. In this study, we measured the half-maximal inhibitory concentration (IC50) of a promising nature-inspired AF compound, a triazolyl glycosylated chalcone (compound 1), in an immortalized human retinal pigment epithelial cell line (hTERT-RPE-1) and compared the results with the commercial biocide Econea®. We also investigated the effects of these biocides on the cellular lipidome following an acute (24 h) exposure using liquid chromatography quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS). Our results showed that compound 1 did not affect viability in hTERT-RPE-1 cells at low concentrations (1 μM), in contrast to Econea®, which caused a 40% reduction in cell viability. In total, 71 lipids were found to be regulated upon exposure to 10 µM of both compounds. Interestingly, both compounds induced changes in lipids involved in cell death, membrane modeling, lipid storage, and oxidative stress, but often in opposing directions. In general, Econea® exposure was associated with an increase in lipid concentrations, while compound 1 exposure resulted in lipid depletion. Our study showed that exposure to human cells at sublethal Econea® concentrations results in the modulation of several lipids that are linked to cell death and survival. Full article
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13 pages, 3277 KiB  
Communication
Mechanistic Insights into the Ameliorating Effect of Melanogenesis of Psoralen Derivatives in B16F10 Melanoma Cells
by Yeji Lee and Chang-Gu Hyun
Molecules 2022, 27(9), 2613; https://doi.org/10.3390/molecules27092613 - 19 Apr 2022
Cited by 11 | Viewed by 2099
Abstract
The objectives of this study were to investigate the melanogenetic potential of the psoralen derivatives 5-hydroxypsoralen, 5-methoxypsoralen, 8-hydroxypsoralen, 8-methoxypsoralen, and 5,8-dimethoxypsoralen in B16F10 melanoma cells. The results indicated that melanin production is significantly stimulated in B16F10 melanoma cells with 5-methoxypsoralen, 8-methoxypsoralen, and 5,8-dimethoxypsoralen, [...] Read more.
The objectives of this study were to investigate the melanogenetic potential of the psoralen derivatives 5-hydroxypsoralen, 5-methoxypsoralen, 8-hydroxypsoralen, 8-methoxypsoralen, and 5,8-dimethoxypsoralen in B16F10 melanoma cells. The results indicated that melanin production is significantly stimulated in B16F10 melanoma cells with 5-methoxypsoralen, 8-methoxypsoralen, and 5,8-dimethoxypsoralen, especially for 5-methoxypsoralen (bergapten), as reported previously. In addition, Western blot results showed that the protein levels of microphthalmia-associated transcription factor (MITF), tyrosinase, tyrosinase-related protein-1 (TRP-1), and tyrosinase-related protein-2 (TRP-2) increase after bergapten treatment for the first time. The results also showed that bergapten promotes the phosphorylation of Akt at Ser 473 and glycogen synthase kinase-3β at Ser 9. Moreover, bergapten increased the content of β-catenin in the cell cytoplasm and nucleus by reducing the phosphorylated β-catenin (p-β-catenin) content. The results also indicated that bergapten regulates melanogenesis by upregulating the phosphorylation of p38 and JNK-mitogen-activated protein kinase. Taken together, these findings suggest that the regulation of melanogenesis by bergapten may be mediated by the β-catenin and MAPK signaling pathways and that bergapten might provide new insights into the pathogenesis of pigmented diseases. Full article
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12 pages, 3644 KiB  
Article
Chlorogenic Acid-Loaded Mesoporous Silica Nanoparticles Modified with Hexa-Histidine Peptides Reduce Skin Allergies by Capturing Nickel
by Tianyu Wang, Liying Yin, Zheng Ma and Yanrong Zhang
Molecules 2022, 27(4), 1430; https://doi.org/10.3390/molecules27041430 - 21 Feb 2022
Cited by 6 | Viewed by 2303
Abstract
Nickel-induced contact dermatitis is a severe allergic reaction to objects or environments that contain nickel. Many nanomaterials have been developed to reduce skin allergies by capturing nickel, but few agents are effective and safe. In this work, mesoporous silica nanoparticles (MSN) were synthesized [...] Read more.
Nickel-induced contact dermatitis is a severe allergic reaction to objects or environments that contain nickel. Many nanomaterials have been developed to reduce skin allergies by capturing nickel, but few agents are effective and safe. In this work, mesoporous silica nanoparticles (MSN) were synthesized and decorated with hexa-histidine peptides (denoted as MSN-His6), making it a strong nickel chelator. Subsequently, a dietary polyphenol, chlorogenic acid, was loaded into the mesopores of MSN (denoted as MSN-His6@CGA), realizing the potential of its anti-inflammatory properties. In vitro and in vivo experiments revealed that the synthesized MSN-His6@CGA nanoparticles exhibited more stable and stronger chelation, better biocompatibility, and ideal allergy-relieving ability, whether for environmental metal contamination or for allergic contact dermatitis caused by prolonged nickel exposure. Thus, the application of mesoporous silica-based nanoparticles may represent an ideal approach to alleviate skin allergies by capturing nickel, which would benefit people who suffer from metal-induced contact dermatitis. Full article
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Review

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28 pages, 10358 KiB  
Review
Some Nanocarrier’s Properties and Chemical Interaction Mechanisms with Flavones
by Cecilia Espíndola
Molecules 2023, 28(6), 2864; https://doi.org/10.3390/molecules28062864 - 22 Mar 2023
Cited by 3 | Viewed by 1606
Abstract
Flavones such as 7,8-dihydroxyflavone (tropoflavin), 5,6,7-trihydroxyflavone (baicalein), 3′,4′,5,6-tetrahydroxyflavone (luteolin), 3,3′,4′,5,5′,7-hexahydroxyflavone (myricetin), 4′,5,7-trihydroxyflavone (apigenin), and 5,7-dihydroxyflavone (chrysin) are important both for their presence in natural products and for their pharmacological applications. However, due to their chemical characteristics and their metabolic processes, they have [...] Read more.
Flavones such as 7,8-dihydroxyflavone (tropoflavin), 5,6,7-trihydroxyflavone (baicalein), 3′,4′,5,6-tetrahydroxyflavone (luteolin), 3,3′,4′,5,5′,7-hexahydroxyflavone (myricetin), 4′,5,7-trihydroxyflavone (apigenin), and 5,7-dihydroxyflavone (chrysin) are important both for their presence in natural products and for their pharmacological applications. However, due to their chemical characteristics and their metabolic processes, they have low solubility and low bioavailability. Knowledge about the physicochemical properties of nanocarriers and the possible mechanisms of covalent and non-covalent interaction between nanoparticles (NPs) and drugs is essential for the design of nanocarriers to improve the bioavailability of molecules with pharmacological potential, such as tropoflavin, baicalein, luteolin, myricetin, apigenin, and chrysin. The parameters of characterization of some NPs of these flavones, such as size, polydispersity index (PDI), zeta potential, encapsulation efficiency (EE), and % release/time, utilized in biomedical applications and the covalent and non-covalent interactions existing between the polymeric NPs and the drug were analyzed. Similarly, the presence of functional groups in the functionalized carbon nanotubes (CNTs), as well as the effect of pH on the % adsorption of flavonoids on functionalized multi-walled carbon nanotubes (MWCNT-COOH), were analyzed. Non-covalent interaction mechanisms between polymeric NPs and flavones, and covalent interaction mechanisms that could exist between the NPs and the amino and hydroxyl functional groups, are proposed. Full article
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