GC- and UHPLC-MS Profiles as a Tool to Valorize the Red Alga Asparagopsis armata

Asparagopsis armata Harvey is a red alga native from the southern hemisphere and then introduced in the Mediterranean Sea and the Atlantic Ocean, including the Azores Archipelago, where it is considered an invasive alga. Some studies show that the extracts exhibit antimicrobial and antifouling activities, and it is incorporated in some commercialized cosmetic products. (e.g., Ysaline®). However, knowledge of this species chemical composition is scarce. The GC-MS and UHPLC-MS profiles of both the nonpolar and polar extracts were established to contribute to this problem solution. According to the results, A. armata is rich in a great structural variety of halogenated lipophilic and aromatic compounds, some of them identified here for the first time. In the lipophilic extract, 25 compounds are identified, being the halogenated compounds and fatty acids, the two major compound families, corresponding to 54.8% and 35.7% of identified compounds (224 and 147 mg/100 g of dry algae, respectively). The 1,4-dibromobuten-1-ol and the palmitic acid are the two most abundant identified compounds (155 and 83.4 mg/100 g of dry algae, respectively). The polar extract demonstrated the richness of this species in brominated phenolics, from which the cinnamic acid derivatives are predominant. The results obtained herein open new perspectives for valuing the A. armata as a source of halogenated compounds and fatty acids, consequently improving its biotechnological and economic potential. Promoting this seaweed and the consequent increase in its demand will contribute to biodiversity conservation and ecosystem sustainability.

Ethnotherapeutic Uses and Phytochemical Composition of Physalis peruviana L.: An Overview

Background. Plant-derived medicines are widespread and continue to increase in traditional and modern medicine, especially in developing countries. Physalis peruviana L. is among the most used plants in conventional medication worldwide. This review aimed to highlight the ethnotherapeutic uses and phytochemical status of identified compounds in P. peruviana. Methods. Data were collected from Google Scholar, PubMed/Medline, SciFinder, Science Direct, Scopus, the Wiley Online Library, Web of Science, and any other helpful search engine using Physalis peruviana as the primary keyword. Results. Some countries, worldwide, use P. peruviana in their traditional medicine system to manage diverse ailments, mainly diseases and gastrointestinal tract disorders (25.33%). Leaf was the mostly used part (49.28%), prepared by decoction (31.58%) and overall administrated orally (53.57%) as the main route of admission. Around 502 phytoconstituents were identified in different plant parts, especially fruit (38.19%) ethanol/ethyl acetate extract. In most cases (36.17%), the solvent of the extract was not specified. Several phytochemical classes were found in the plant, especially terpenes (26.09%) and phenolic compounds (14.94%). Esters were also abundant (11.55%). In the terpenes category, carotenoids were the most abundant (11.15% followed by monoterpenes (8.76%) and diterpenes (3.18%). However, flavonoids (5.17%) followed by cinnamic acid derivatives (3.99%), monophenolic compounds (1.79%), and phenolic acids (1.33 M) are the most reported phenolic compounds. Hexadecanoic acid (palmitic acid) was the most cited (five times). Conclusion. P. peruviana plays an essential role in managing diseases in some countries and is rich in chemical compounds, which need to be isolated and investigated pharmacologically before clinical trials.

Comparative Analysis of Phenolic Composition of Six Commercially Available Chamomile (Matricaria chamomilla L.) Extracts: Potential Biological Implications

Several phytochemical-containing herbal extracts are increasingly marketed as health-promoting products. In particular, chamomile (Matricaria recutita L.) is well known for its anti-inflammatory, analgesic, and antitumor properties. Here, we evaluated differences in chemical composition among six commercially available products and their potential impact on biological activity in human immortalized colonocytes. Our investigation encompassed: (i) preparation of dry extracts and yield evaluation; (ii) qualitative and quantitative analysis of phenol content; (iii) modulation of redox state; and (iv) bioavailability of main bioactive compounds. We demonstrated that apparently identical products showed huge heterogeneity, in terms of yield extraction, chemical composition, and antioxidant effects. All samples contained high amounts of flavonoids and cinnamic acid derivatives, but differentially concentrated in the six extracts. Depending on polyphenol content, chamomile samples possessed variable antioxidant potential, in terms of decreased radical generation and increased reduced glutathione levels. The observed effects might be ascribed to flavones (apigenin, luteolin, and their glycones) highly represented in the six extracts. Nonetheless, chamomile extracts exerted cytotoxic effects at high concentrations, suggesting that a herbal medicine is not always safe. In conclusion, due to the complexity and variability of plant matrices, studies evaluating effectiveness of chamomile should always be accompanied by preliminary characterization of phytochemical composition.

Chemo-Enzymatic Cascade for the Generation of Fragrance Aldehydes

In this study, we present the synthesis of chiral fragrance aldehydes, which was tackled by a combination of chemo-catalysis and a multi-enzymatic in vivo cascade reaction and the development of a highly versatile high-throughput assay for the enzymatic reduction of carboxylic acids. We investigated a biocompatible metal-catalyzed synthesis for the preparation of α or β substituted cinnamic acid derivatives which were fed directly into the biocatalytic system. Subsequently, the target molecules were synthesized by an enzymatic cascade consisting of a carboxylate reduction, followed by the selective C-C double bond reduction catalyzed by appropriate enoate reductases. We investigated a biocompatible oxidative Heck protocol and combined it with cells expressing a carboxylic acid reductase from Neurospora crassa (NcCAR) and an ene reductase from Saccharomyces pastorianus for the production fragrance aldehydes.

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

Background: New drugs must be designed and synthesized for combating resistant pathogens. In this study, antibacterial and antifungal activities of 4 new derivatives of 1,3,4-oxadiazole were assessed against 8 bacterial and 2 fungal pathogens. Methods: To this end, the cinnamic acid derivatives were dissolved in acetonitrile solvent and N-iso-ciano-imino-triphenyl-phosphorane was added to the above-mentioned solution, followed by applying Petroleum ether and Ethyl acetate as solvent and base. Then, antimicrobial susceptibility tests were used to determine inhibition zone diameter, minimum inhibitory concentration, the minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC) values. Results: The chemical structure of all compounds was characterized with infrared spectra, 1H-NMR, and 13C-NMR. A variety of inhibitory effects were observed by the synthesized compounds. Methoxyphenyl derivative (3c) affected bacterial strains, especially Streptococcus mutans. Other compounds also had antibacterial properties. Additionally, compound 3c showed the greatest effect on fungal samples, especially Aspergillus flavus. Conclusions: In general, our new derivatives of 1,3,4-oxadiazole are able to destroy Gram-positive bacteria. In addition, developing new derivatives of 1,3,4-oxadiazole in future research can improve therapeutic properties. It seems that with the addition of other functional groups and increasing the destructive power of compounds, inhibitory effects on fungal samples can also be observed.

Synthesis, applications and Structure-Activity Relationship (SAR) of cinnamic acid derivatives: a review

The article aims to analyze the progress of the evolution of cinnamic acid derivatives through a bibliographic review, describing the main synthetic routes in obtaining this class, as well as remarkable biological applications and application of the structure-activity relationship (SAR) as a strategy for design pharmacologically active molecules. The methodology used consists of reading and analyzing articles, whose approach is descriptive, with data being collected regarding the therapeutic potential of derivatives of cinnamic acid and its relationship with structural scaffolding, as well as the most widely used synthetic approaches. As a result, it was observed that cinnamic acid and its derivatives from natural sources can be synthesized in appreciable quantities with varied synthetic routes, as well as being candidates for therapeutic agents, since they have several therapeutic applications against diabetes, infectious and degenerative diseases, among others, in addition to presenting activity such as pest control, which has attracted the attention of academic and industrial researchers. These compounds are highly versatile since their activity is intrinsically associated with the mode of interaction between the structure and its molecular target. However, in nature they are obtained in small quantities, therefore, the development of new approaches of synthetic methodologies to obtain such compounds in substantial quantities and linked to medicinal chemistry can contribute to the development of very effective bioactive molecules in comparison with their precursors.