Centro de Química Estrutural

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First Chemical Profile Analysis of Acacia Pods

Publication . Pedro, Soraia; Fernandes, Tiago A.; Luís, Ângelo; Antunes, A M M; Gonçalves, J. C.; Gominho, Jorge; Gallardo, Eugenia; Anjos, Ofélia

This study intended to evaluate the potential industrial applications of various Acacia species (Acacia melanoxylon, Acacia longifolia, Acacia cyclops, Acacia retinodes, Acacia pycnantha, Acacia mearnsii, and Acacia dealbata) by examining their chemical composition, antioxidant, and antimicrobial properties. Using high-resolution mass spectrometry, a comprehensive analysis successfully identified targeted compounds, including flavonoids (flavonols/flavones) and phenolic acids, such as 4-hydroxybenzoic acid, p-coumaric acid, and ellagic acid. Additionally, p-coumaric acid was specifically identified and quantified within the hydroxycinnamic aldehydes. This comprehensive characterization provides valuable insights into the chemical profiles of the studied species. Among the studied species, A. pycnantha exhibited a higher concentration of total phenolic compounds, including catechin, myricetin, quercetin, and coniferaldehyde. Furthermore, A. pycnantha displayed notable antibacterial activity against K. pneumoniae, E. coli, S. Typhimurium, and B. cereus. The identified compounds in Acacia pods and their shown antibacterial activities exhibit promising potential for future applications. Moreover, vibrational spectroscopy was a reliable method for distinguishing between species. These significant findings enhance our understanding of Acacia species and their potential for various industrial applications.

2023Journal article

Open access

Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes

Publication . Gomes, Filipa Ramilo; Addis, Yemataw; Tekamo, Israel; Cavaco, Isabel; Campos, Débora L.; Pavan, Fernando R.; Gomes, Clara S.B.; Brito, Vanessa; Santos, Adriana O.; Domingues, F.C.; Luís, Ângelo; Marques, M. Matilde; Pessoa, João Costa; Ferreira, Susana; Silvestre, Samuel; Correia, Isabel

Schiff bases (SB) obtained from S-methyl dithiocarbazate and aromatic aldehydes: salicylaldehyde (H2L1), o-vanillin (H2L2), pyridoxal (H2L3) and 2,6-diformyl-4-methylphenol (H3L4), and their corresponding Zn(II)-complexes (1-4), are synthesized. All compounds are characterized by elemental analyses, infrared, UV-Vis, nuclear magnetic resonance spectroscopy and mass spectrometry. The structures of H2L2 and [Zn2(L1)2(H2O)(DMF)] (1a) (DMF = dimethylformamide) are solved by single crystal X-ray diffraction. The SB coordinates the metal center through the Ophenolate, Nimine and Sthiolate atoms. The radical scavenging activity is tested using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, with all ligand precursors showing IC50 values ~40 μM. Cytotoxicity studies with several tumor cell lines (PC-3, MCF-7 and Caco-2) as well as a non-tumoral cell line (NHDF) are reported. Interestingly, 1 has relevant and selective antiproliferative effect against Caco-2 cells (IC50 = 9.1 μM). Their antimicrobial activity is evaluated in five bacterial strains (Klebsiella pneumoniae, Acinetobacter baumannii, Listeria monocytogenes, Pseudomonas aeruginosa and Staphylococcus aureus) and two yeast strains (Candida albicans and Candida tropicalis) with some compounds showing bacteriostatic and fungicidal activity. The minimal inhibitory concentration (MIC90) of HnL against Mycobacterium tuberculosis is also reported, with H2L2 and H3L4 showing very high activity (MIC90 < 0.6 μg/mL). The ability of the compounds to bind bovine serum albumin (BSA) and DNA is evaluated for H3L4 and [Zn2(L4)(CH3COO)] (4), both showing high binding constants to BSA (ca. 106 M-1) and ability to bind DNA. Overall, the reported compounds show relevant antitumor and antimicrobial properties, our data indicating they may be promising compounds in several fields of medicinal chemistry.

2021Journal article

Restricted access