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Cinnamic Acids and Analogs: Food and Health Applications
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Cinnamic Acids and Analogs: Food and Health Applications

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

Deadline for manuscript submissions: closed (31 December 2019) | Viewed by 17979

Special Issue Editors

Prof. Dr. Fernanda Borges

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Guest Editor
Centro de Investigação em Química da Universidade do Porto (CIQUP), Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre s/n, 4169–007 Porto, Portugal
Interests: drug discovery; nanomedicine; ADME-Tox; neurodegenerative; infectious diseases; antioxidants
Special Issues, Collections and Topics in MDPI journals
Dr. Jorge Garrido

E-Mail Website
Guest Editor
CIQUP, Department of Chemical Engineering, School of Engineering (ISEP), Polytechnic of Porto, 4200-072 Porto, Portugal
Interests: analytical methods; electroanalysis; nanotechnology; bioactive compounds
Special Issues, Collections and Topics in MDPI journals
Dr. Tiago Barros Silva

E-Mail Website
Guest Editor
CNC/Center for Neurosciences and Cell Biology, UCBiotech, Coimbra, Portugal
Interests: COMT; Heterocycle catechol mimics; Neuroprotection; Dual-target drugs

Special Issue Information

Dear Colleagues,

Cinnamic acids (CAs) are a remarkable class of secondary metabolites ubiquitously distributed across multiple sources in nature. The chemical scaffold of CAs can be found in a vast number of naturally-occurring and synthetic bioactive molecules, which makes it a privileged structure for food applications and drug discovery. The academic community has become increasingly interested in studying the effects of Cas, discovering promising bioactivities that go beyond their established role as antioxidants. In this context, CAs may provide a versatile chemical building block to develop safe and low-cost functional foods, nutraceuticals, additives, and drug candidates for therapy. This Special Issue aims to provide a multidisciplinary platform for scientists to publish reviews or original research concerning CAs and derivatives thereof. From the study and analysis of natural sources to the development of drug-like synthetic derivatives, we encourage contributions on all aspects of the chemistry and bioactivity of CAs that make substantial advances within this field.

Prof. Fernanda Borges
Prof. Jorge Garrido
Dr. Tiago Barros Silva
Guest Editors

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Keywords

  • Cinnamic acids
  • Bioactivity
  • Analysis
  • Natural products
  • Phytochemicals
  • Functional food
  • Nutraceuticals
  • Additives
  • Drug discovery
  • Food applications
  • Health applications

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Published Papers (5 papers)

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Research

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14 pages, 3130 KiB  
Article
Hydroxycinnamoyl Amino Acids Conjugates: A Chiral Pool to Distinguish Commercially Exploited Coffea spp.
by Federico Berti, Luciano Navarini, Silvia Colomban and Cristina Forzato
Molecules 2020, 25(7), 1704; https://doi.org/10.3390/molecules25071704 - 8 Apr 2020
Cited by 15 | Viewed by 2749
Abstract
The synthesis of five hydroxycinnamoyl amides (HCAs) was accomplished and their identification and quantification in the green coffee bean samples of Coffea arabica, Coffea canephora, and Coffea liberica was performed. The HCAs p-coumaroyl-N-tyrosine 1b, caffeoyl-N-phenylalanine [...] Read more.
The synthesis of five hydroxycinnamoyl amides (HCAs) was accomplished and their identification and quantification in the green coffee bean samples of Coffea arabica, Coffea canephora, and Coffea liberica was performed. The HCAs p-coumaroyl-N-tyrosine 1b, caffeoyl-N-phenylalanine 2b, caffeoyl-N-tyrosine 3b, and p-coumaroyl-N-tryptophan 4b were characteristic of the C. canephora species while caffeoyl-N-tryptophan 5b was present in both C. canephora and C. arabica, but with higher content in C. canephora. The HCAs presence was also analyzed in C. liberica for the first time and none of the targeted compounds was found, indicating that this species is very similar to C. arabica species. Between C. canephora samples from various origins, significant differences were observed regarding the presence of all the HCAs, with C. canephora from Tanzania containing all five derivatives. Full article
(This article belongs to the Special Issue Cinnamic Acids and Analogs: Food and Health Applications)
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21 pages, 2622 KiB  
Article
Synthesis and Antibacterial Activity of Difluoromethyl Cinnamoyl Amides
by Mario David Martínez, Diego Ariel Riva, Cybele Garcia, Fernando Javier Durán and Gerardo Burton
Molecules 2020, 25(4), 789; https://doi.org/10.3390/molecules25040789 - 12 Feb 2020
Cited by 4 | Viewed by 3198
Abstract
Series of novel amides of isoferulic acid, where the phenolic hydroxyl was replaced by a difluoromethyl group, were synthesized and their in vitro antibacterial activities assayed against fourteen bacterial strains (six Gram-positive and eight Gram-negative). A one-pot methodology was developed to obtain the [...] Read more.
Series of novel amides of isoferulic acid, where the phenolic hydroxyl was replaced by a difluoromethyl group, were synthesized and their in vitro antibacterial activities assayed against fourteen bacterial strains (six Gram-positive and eight Gram-negative). A one-pot methodology was developed to obtain the 3′-(difluoromethyl)-4′-methoxycinnamoyl amides using Deoxofluor® as a fluorinating agent. The N-isopropyl, N-isopentyl, and N-(2-phenylethyl) amides 11b, 11d and 11g were the most active and selective against Mycobacterium smegmatis (MIC = 8 µg/mL) with 11b and 11g displaying negligible or no cytotoxicity against HepG2 and A549 cells. Thirteen analogs of N-isopropylamide 11b were also synthesized and their antibacterial activity assayed. Results show that the difluoromethyl moiety enhanced antibacterial activity and selectivity towards M. smegmatis, changing the microorganism inhibition profile of the parent compound. The selectivity exhibited by some of the compounds towards M. smegmatis makes them potential leads in the search for new narrow spectrum antibiotics against M. tuberculosis. Full article
(This article belongs to the Special Issue Cinnamic Acids and Analogs: Food and Health Applications)
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11 pages, 2706 KiB  
Article
Cinnamic Derivatives as Antitubercular Agents: Characterization by Quantitative Structure–Activity Relationship Studies
by Cátia Teixeira, Cristina Ventura, José R. B. Gomes, Paula Gomes and Filomena Martins
Molecules 2020, 25(3), 456; https://doi.org/10.3390/molecules25030456 - 21 Jan 2020
Cited by 10 | Viewed by 3262
Abstract
Tuberculosis, caused by Mycobacterium tuberculosis (Mtb), remains one of the top ten causes of death worldwide and the main cause of mortality from a single infectious agent. The upsurge of multi- and extensively-drug resistant tuberculosis cases calls for an urgent need [...] Read more.
Tuberculosis, caused by Mycobacterium tuberculosis (Mtb), remains one of the top ten causes of death worldwide and the main cause of mortality from a single infectious agent. The upsurge of multi- and extensively-drug resistant tuberculosis cases calls for an urgent need to develop new and more effective antitubercular drugs. As the cinnamoyl scaffold is a privileged and important pharmacophore in medicinal chemistry, some studies were conducted to find novel cinnamic acid derivatives (CAD) potentially active against tuberculosis. In this context, we have engaged in the setting up of a quantitative structure–activity relationships (QSAR) strategy to: (i) derive through multiple linear regression analysis a statistically significant model to describe the antitubercular activity of CAD towards wild-type Mtb; and (ii) identify the most relevant properties with an impact on the antitubercular behavior of those derivatives. The best-found model involved only geometrical and electronic CAD related properties and was successfully challenged through strict internal and external validation procedures. The physicochemical information encoded by the identified descriptors can be used to propose specific structural modifications to design better CAD antitubercular compounds. Full article
(This article belongs to the Special Issue Cinnamic Acids and Analogs: Food and Health Applications)
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16 pages, 2930 KiB  
Article
Insights into the Discovery of Novel Neuroprotective Agents: A Comparative Study between Sulfanylcinnamic Acid Derivatives and Related Phenolic Analogues
by Daniel Chavarria, Carlos Fernandes, Brandon Aguiar, Tiago Silva, Jorge Garrido, Fernando Remião, Paulo J. Oliveira, Eugenio Uriarte and Fernanda Borges
Molecules 2019, 24(23), 4405; https://doi.org/10.3390/molecules24234405 - 2 Dec 2019
Cited by 11 | Viewed by 3628
Abstract
Exogenous antioxidants may be beneficial therapeutic tools to tackle the oxidative damage in neurodegenerative diseases by regulation of the redox state that is critical for cell viability and organ function. Inspired by natural plant polyphenols, a series of cinnamic acid-based thiophenolic and phenolic [...] Read more.
Exogenous antioxidants may be beneficial therapeutic tools to tackle the oxidative damage in neurodegenerative diseases by regulation of the redox state that is critical for cell viability and organ function. Inspired by natural plant polyphenols, a series of cinnamic acid-based thiophenolic and phenolic compounds were synthesized and their antioxidant and neuroprotective properties were studied. In general, our results showed that the replacement of the hydroxyl group (OH) by a sulfhydryl group (SH) increased the radical scavenging activity and enhanced the reaction rate with 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•) and galvinoxyl radical (GO•). These results correlated well with the lower oxidation potential (Ep) values of thiophenols. However, a lower peroxyl radical (ROO•) scavenging activity was observed for thiophenols in oxygen radical absorbance capacity (ORAC-FL) assay. Furthermore, the introduction of 5-methoxy and 5-phenyl groups in the aromatic ring of 4-thioferulic acid (TFA) 2 and ferulic acid (FA) 1 did not significantly improve their antioxidant activity, despite the slight decrease of Ep observed for compounds 5, 6, and 9. Concerning cinnamic acid amides, the antioxidant profile was similar to the parent compounds. None of the compounds under study presented significant cytotoxic effects in human differentiated neuroblastoma cells. Thiophenolic amide 3 stands out as the most promising thiophenol-based antioxidant, showing cellular neuroprotective effects against oxidative stress inducers (hydrogen peroxide and iron). Full article
(This article belongs to the Special Issue Cinnamic Acids and Analogs: Food and Health Applications)
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Review

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15 pages, 2218 KiB  
Review
Cinnamic Acid Conjugates in the Rescuing and Repurposing of Classical Antimalarial Drugs
by Ana Teresa Silva, Clara M. Bento, Ana C. Pena, Luísa M. Figueiredo, Cristina Prudêncio, Luísa Aguiar, Tânia Silva, Ricardo Ferraz, Maria Salomé Gomes, Cátia Teixeira and Paula Gomes
Molecules 2020, 25(1), 66; https://doi.org/10.3390/molecules25010066 - 24 Dec 2019
Cited by 25 | Viewed by 4442
Abstract
Cinnamic acids are compounds of natural origin that can be found in many different parts of a wide panoply of plants, where they play the most diverse biological roles, often in a conjugated form. For a long time, this has been driving Medicinal [...] Read more.
Cinnamic acids are compounds of natural origin that can be found in many different parts of a wide panoply of plants, where they play the most diverse biological roles, often in a conjugated form. For a long time, this has been driving Medicinal Chemists towards the investigation of the therapeutic potential of natural, semi-synthetic, or fully synthetic cinnamic acid conjugates. These efforts have been steadily disclosing promising drug leads, but a wide chemical space remains that deserves to be further explored. Amongst different reported approaches, the combination or conjugation of cinnamic acids with known drugs has been addressed in an attempt to produce either synergistic or multi-target action. In this connection, the present review will focus on efforts of the past decade regarding conjugation with cinnamic acids as a tool for the rescuing or the repurposing of classical antimalarial drugs, and also on future perspectives in this particular field of research. Full article
(This article belongs to the Special Issue Cinnamic Acids and Analogs: Food and Health Applications)
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