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Natural and Synthetic Compounds with Antioxidant Properties in Biological Systems
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Natural and Synthetic Compounds with Antioxidant Properties in Biological Systems

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 2021) | Viewed by 38615

Special Issue Editors

Prof. Dr. Elena Grasselli

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Guest Editor
DISTAV, Dipartimento di Scienze della Terra, dell'Ambiente e della Vita, Università di Genova, Genova, Italy
Interests: NAFLD; thyroid hormones; lipid metabolism; dietary polyphenols; antioxidant molecules
Prof. Dr. Chiara Lambruschini

E-Mail Website
Guest Editor
DCCI, Dipartimento di Chimica e Chimica Industriale, Università di Genova, Genova, Italy
Interests: organic synthesis; multicomponent reactions; polyphenols; medicinal chemistry
Prof. Dr. Lisa Moni

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Guest Editor
Department of Chemistry and Industrial Chemistry, Universita degli Studi di Genova, Genoa, Italy
Interests: diversity oriented synthesis; heterogeneous catalyst; photooxidation; bio-based resources
Prof. Dr. Ilaria Demori

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Guest Editor
DISTAV, Dipartimento di Scienze della Terra, dell'Ambiente e della Vita, Università di Genova, Genova, Italy
Interests: nutrition and metabolism; nutrition and stress; physiology of stress; Psychoneuroendocrineimmunology (PNEI)
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

We are living in a oxidative atmosphere, thus promoting oxidation of organic and inorganic compounds. Some key biological reactions are based on oxidative processes catalyzed by metalloproteins such as iron-containing cytochromes of the mitochondrial respiratory chain. In living organisms, oxidative stress occurs from the imbalance between reactive oxygen and nitrogen species and the activity/amount of antioxidant defenses.

Several natural molecules are able to counteract and/or prevent this tendency to oxidation, thus increasing the antioxidant arsenal. The consumption of some food categories such as fruits and vegetables is widely recognized as beneficial for human health.

Oxidative stress is not to be underestimated since it constitutes the common denominator of a variety of pathologies encompassing metabolic disorders, cardiovascular and neurodegenerative diseases, cellular aging, inflammatory conditions and cancer.  

Synthetic compounds, obtained by modification of natural products, are generally prepared for ameliorating pharmacokinetic properties and biological activities and overcoming poor drug-likeness. On the other hand, a powerful strategy for improving the efficiency, is the synthesis of de novo natural-based compounds. Following this approach, short and smart synthetic sequences can be designed, generating molecular complexity, providing new molecular entities inspired by natural products with different scaffolds.

Therefore, the aim of this issue is to provide new insights into the biological effects of natural or synthetic antioxidant molecules. Research papers describing the extraction or synthesis of new antioxidant compounds, their structural characterization and demonstration of beneficial effects in biological systems, either in vitro or in vivo, are welcome. Similarly, narrative or systematic reviews on biological activities of selected antioxidant molecules are appreciated.

Prof. Dr. Chiara Lambruschini
Prof. Dr. Lisa Moni
Prof. Dr. Elena Grasselli
Prof. Dr. Ilaria Demori
Guest Editors

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Keywords

  • Antioxidant compounds
  • Metabolic disorders
  • Cardiovascular diseases
  • Neurodegenerative diseases
  • Inflammation
  • Aging
  • Natural compounds
  • Synthetic compounds
  • Polyphenols
  • Vitamins
  • Organic synthesis
  • Structure–activity relationship (SAR)

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Published Papers (6 papers)

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Research

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9 pages, 1277 KiB  
Article
Comparison of Antioxidant and Anticancer Properties of Soft Coral-Derived Sinularin and Dihydrosinularin
by Sheng-Chieh Wang, Ruei-Nian Li, Li-Ching Lin, Jen-Yang Tang, Jui-Hsin Su, Jyh-Horng Sheu and Hsueh-Wei Chang
Molecules 2021, 26(13), 3853; https://doi.org/10.3390/molecules26133853 - 24 Jun 2021
Cited by 9 | Viewed by 2211
Abstract
Marine natural products are abundant resources for antioxidants, but the antioxidant property of the soft corals-derived sinularin and dihydrosinularin were unknown. This study aimed to assess antioxidant potential and antiproliferation effects of above compounds on cancer cells, and to investigate the possible relationships [...] Read more.
Marine natural products are abundant resources for antioxidants, but the antioxidant property of the soft corals-derived sinularin and dihydrosinularin were unknown. This study aimed to assess antioxidant potential and antiproliferation effects of above compounds on cancer cells, and to investigate the possible relationships between them. Results show that sinularin and dihydrosinularin promptly reacted with 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS), and hydroxyl (•OH), demonstrating a general radical scavenger activity. Sinularin and dihydrosinularin also show an induction for Fe+3-reduction and Fe+2-chelating capacity which both strengthen their antioxidant activities. Importantly, sinularin shows higher antioxidant properties than dihydrosinularin. Moreover, 24 h ATP assays show that sinularin leads to higher antiproliferation of breast, lung, and liver cancer cells than dihydrosinularin. Therefore, the differential antioxidant properties of sinularin and dihydrosinularin may contribute to their differential anti-proliferation of different cancer cells. Full article
(This article belongs to the Special Issue Natural and Synthetic Compounds with Antioxidant Properties in Biological Systems)
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13 pages, 821 KiB  
Article
Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5-O-Acyl Derivatives of Quercetin
by Stephen Lo, Euphemia Leung, Bruno Fedrizzi and David Barker
Molecules 2021, 26(6), 1608; https://doi.org/10.3390/molecules26061608 - 14 Mar 2021
Cited by 9 | Viewed by 2330
Abstract
Quercetin is a flavonoid that is found in many plant materials, including commonly eaten fruits and vegetables. The compound is well known for its wide range of biological activities. In this study, 5-O-acyl derivatives of quercetin were synthesised and assessed for [...] Read more.
Quercetin is a flavonoid that is found in many plant materials, including commonly eaten fruits and vegetables. The compound is well known for its wide range of biological activities. In this study, 5-O-acyl derivatives of quercetin were synthesised and assessed for their antiproliferative activity against the HCT116 colon cancer and MDA-MB-231 breast cancer cell lines; and their radical scavenging activity against the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical species. Four derivatives were found to have improved the antiproliferative activity compared to quercetin whilst retaining radical scavenging activity. Full article
(This article belongs to the Special Issue Natural and Synthetic Compounds with Antioxidant Properties in Biological Systems)
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34 pages, 6416 KiB  
Article
Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities
by Adesola A. Adeleke, Sizwe J. Zamisa, Md. Shahidul Islam, Kolawole Olofinsan, Veronica F. Salau, Chunderika Mocktar and Bernard Omondi
Molecules 2021, 26(5), 1205; https://doi.org/10.3390/molecules26051205 - 24 Feb 2021
Cited by 37 | Viewed by 3972
Abstract
A series of fifteen silver (I) quinoline complexes Q1–Q15 have been synthesized and studied for their biological activities. Q1–Q15 were synthesized from the reactions of quinolinyl Schiff base derivatives L1–L5 (obtained by condensing 2-quinolinecarboxaldehyde with various aniline [...] Read more.
A series of fifteen silver (I) quinoline complexes Q1–Q15 have been synthesized and studied for their biological activities. Q1–Q15 were synthesized from the reactions of quinolinyl Schiff base derivatives L1–L5 (obtained by condensing 2-quinolinecarboxaldehyde with various aniline derivatives) with AgNO3, AgClO4 and AgCF3SO3. Q1–Q15 were characterized by various spectroscopic techniques and the structures of [Ag(L1)2]NO3Q1, [Ag(L1)2]ClO4Q6, [Ag(L2)2]ClO4Q7, [Ag(L2)2]CF3SO3Q12 and [Ag(L4)2]CF3SO3Q14 were unequivocally determined by single crystal X-ray diffraction analysis. In vitro antimicrobial tests against Gram-positive and Gram-negative bacteria revealed the influence of structure and anion on the complexes′ moderate to excellent antibacterial activity. In vitro antioxidant activities of the complexes showed their good radical scavenging activity in ferric reducing antioxidant power (FRAP). Complexes with the fluorine substituent or the thiophene or benzothiazole moieties are more potent with IC50 between 0.95 and 2.22 mg/mL than the standard used, ascorbic acid (2.68 mg/mL). The compounds showed a strong binding affinity with calf thymus-DNA via an intercalation mode and protein through a static quenching mechanism. Cytotoxicity activity was examined against three carcinoma cell lines (HELA, MDA-MB231, and SHSY5Y). [Ag(L2)2]ClO4Q7 with a benzothiazole moiety and [Ag(L4)2]ClO4Q9 with a methyl substituent had excellent cytotoxicity against HELA cells. Full article
(This article belongs to the Special Issue Natural and Synthetic Compounds with Antioxidant Properties in Biological Systems)
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14 pages, 1421 KiB  
Article
Antioxidant and Antisteatotic Activities of a New Fucoidan Extracted from Ferula hermonis Roots Harvested on Lebanese Mountains
by Zeinab El Rashed, Giulio Lupidi, Hussein Kanaan, Elena Grasselli, Laura Canesi, Hala Khalifeh and Ilaria Demori
Molecules 2021, 26(4), 1161; https://doi.org/10.3390/molecules26041161 - 22 Feb 2021
Cited by 10 | Viewed by 2904
Abstract
Fucoidan is a fucose-rich sulfated polysaccharide with attractive therapeutic potential due to a variety of biological activities, including antioxidant action. Fucoidan is typically found in the cell wall of marine brown algae, but extra-algal sources have also been discovered. In the present work, [...] Read more.
Fucoidan is a fucose-rich sulfated polysaccharide with attractive therapeutic potential due to a variety of biological activities, including antioxidant action. Fucoidan is typically found in the cell wall of marine brown algae, but extra-algal sources have also been discovered. In the present work, for the first time we extracted a water soluble fucoidan fraction from the roots of the terrestrial shrub Ferula hermonis. This fucoidan fraction was termed FUFe, and contained fucose, glucose, sulfate, smaller amounts of monosaccharides such as galactose and mannose, and a minor quantity of proteins. FUFe structural features were investigated by FTIR, 1H NMR and 13C NMR spectroscopy. The antioxidant property of FUFe was measured by DPPH, ABTS and FRAP assays, which revealed a high radical scavenging capacity that was confirmed in in vitro cellular models. In hepatic and endothelial cells, 50 μg/mL FUFe could reduce ROS production induced by intracellular lipid accumulation. Moreover, in hepatic cells FUFe exhibited a significant antisteatotic action, being able to reduce intracellular triglyceride content and to regulate the expression of key genes of hepatic lipid metabolism. Altogether, our results candidate FUFe as a possible bioactive compound against fatty liver disease and related vascular damage. Full article
(This article belongs to the Special Issue Natural and Synthetic Compounds with Antioxidant Properties in Biological Systems)
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15 pages, 4450 KiB  
Article
Synthesis, Photoisomerization, Antioxidant Activity, and Lipid-Lowering Effect of Ferulic Acid and Feruloyl Amides
by Chiara Lambruschini, Ilaria Demori, Zeinab El Rashed, Leila Rovegno, Elena Canessa, Katia Cortese, Elena Grasselli and Lisa Moni
Molecules 2021, 26(1), 89; https://doi.org/10.3390/molecules26010089 - 28 Dec 2020
Cited by 17 | Viewed by 2982
Abstract
The Ugi four-component reaction employing naturally occurred ferulic acid (FA) is proposed as a convenient method to synthesize feruloyl tertiary amides. Applying this strategy, a peptoid-like derivative of ferulic acid (FEF77) containing 2 additional hydroxy-substituted aryl groups, has been synthesized. The influence of [...] Read more.
The Ugi four-component reaction employing naturally occurred ferulic acid (FA) is proposed as a convenient method to synthesize feruloyl tertiary amides. Applying this strategy, a peptoid-like derivative of ferulic acid (FEF77) containing 2 additional hydroxy-substituted aryl groups, has been synthesized. The influence of the configuration of the double bond of ferulic acid and feruloyl amide on the antioxidant activity has been investigated thanks to light-mediated isomerization studies. At the cellular level, both FA, trans and cis isomers of FEF77 were able to protect human endothelial cord vein (HECV) cells from the oxidative damage induced by exposure to hydrogen peroxide, as measured by cell viability and ROS production assays. Moreover, in steatotic FaO rat hepatoma cells, an in vitro model resembling non-alcoholic fatty liver disease (NAFLD), the molecules exhibited a lipid-lowering effect, which, along with the antioxidant properties, points to consider feruloyl amides for further investigations in a therapeutic perspective. Full article
(This article belongs to the Special Issue Natural and Synthetic Compounds with Antioxidant Properties in Biological Systems)
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Review

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21 pages, 1496 KiB  
Review
The Role of Taurine in Mitochondria Health: More Than Just an Antioxidant
by Chian Ju Jong, Priyanka Sandal and Stephen W. Schaffer
Molecules 2021, 26(16), 4913; https://doi.org/10.3390/molecules26164913 - 13 Aug 2021
Cited by 73 | Viewed by 22966
Abstract
Taurine is a naturally occurring sulfur-containing amino acid that is found abundantly in excitatory tissues, such as the heart, brain, retina and skeletal muscles. Taurine was first isolated in the 1800s, but not much was known about this molecule until the 1990s. In [...] Read more.
Taurine is a naturally occurring sulfur-containing amino acid that is found abundantly in excitatory tissues, such as the heart, brain, retina and skeletal muscles. Taurine was first isolated in the 1800s, but not much was known about this molecule until the 1990s. In 1985, taurine was first approved as the treatment among heart failure patients in Japan. Accumulating studies have shown that taurine supplementation also protects against pathologies associated with mitochondrial defects, such as aging, mitochondrial diseases, metabolic syndrome, cancer, cardiovascular diseases and neurological disorders. In this review, we will provide a general overview on the mitochondria biology and the consequence of mitochondrial defects in pathologies. Then, we will discuss the antioxidant action of taurine, particularly in relation to the maintenance of mitochondria function. We will also describe several reported studies on the current use of taurine supplementation in several mitochondria-associated pathologies in humans. Full article
(This article belongs to the Special Issue Natural and Synthetic Compounds with Antioxidant Properties in Biological Systems)
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