Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis

Rodrigues, Débora Munhoz; Portapilla, Gisele Bulhões; Silva, Guilherme Martins; Duarte, Ana Maria Ribeiro de Castro; Rotta, Cristiana Gonçalez; Silva, Carlos Henrique Tomich de Paula da; Albuquerque, Sérgio de; Bastos, Jairo Kenupp; Campo, Vanessa Leiria

doi:10.1016/j.bmc.2021.116372

Cited by 14 publications

(6 citation statements)

References 42 publications

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“…Interestingly, other molecular components extracted from propolis (such as combinations of biochanin A, formononetin, and liquiritigenin [ 171 ]) or isolated prenylated components, which are further modified to obtain specific molecules ( e.g. , artepillin C and baccharin modified with amino acids) have shown anti-proliferative effects against breast cancer cells in vitro [ 172 ]. Finally, propolis components/extracts were suggested to be beneficial in combating other diseases such as diabetes [ 173 ] and obesity [ 174 , 175 ].…”

Section: Chemistry Of Biological Adhesives and Their Biomedical Applicationsmentioning

confidence: 99%

Bio-based and bio-inspired adhesives from animals and plants for biomedical applications

Lutz

Kımna

Casini

et al. 2022

Materials Today Bio

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With the “many-headed” slime mold Physarum polycelphalum having been voted the unicellular organism of the year 2021 by the German Society of Protozoology, we are reminded that a large part of nature's huge variety of life forms is easily overlooked – both by the general public and researchers alike. Indeed, whereas several animals such as mussels or spiders have already inspired many scientists to create novel materials with glue-like properties, there is much more to discover in the flora and fauna. Here, we provide an overview of naturally occurring slimy substances with adhesive properties and categorize them in terms of the main chemical motifs that convey their stickiness, i.e. , carbohydrate-, protein-, and glycoprotein-based biological glues. Furthermore, we highlight selected recent developments in the area of material design and functionalization that aim at making use of such biological compounds for novel applications in medicine – either by conjugating adhesive motifs found in nature to biological or synthetic macromolecules or by synthetically creating (multi-)functional materials, which combine adhesive properties with additional, problem-specific (and sometimes tunable) features.

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Section: Chemistry Of Biological Adhesives and Their Biomedical Applicationsmentioning

confidence: 99%

Bio-based and bio-inspired adhesives from animals and plants for biomedical applications

Lutz

Kımna

Casini

et al. 2022

Materials Today Bio

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“…These phenolic acids are commonly detected and identified in Brazilian green propolis [23,[29][30][31]. In the literature, many studies have reported the biological and pharmacological activities of artepillin C [23,29,32,33] and drupanin [30,31,34]. However, data on the antibacterial activity of these prenylated compounds against cariogenic bacteria are still scarce [35] In this study, we investigated the antibacterial activity of a series of synthetic prenylated phenylpropanoids, including the naturally occurring compounds artepillin C and drupanin and their derivatives against a representative panel of cariogenic bacteria.…”

Section: Introductionmentioning

confidence: 99%

In vitro and in silico studies of prenylated phenylpropanoids of green propolis and their derivatives against cariogenic bacteria

Vieira,

Santos,

Souza

et al. 2024

Preprint

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Artepillin C, drupanin, and plicatin B are prenylated phenylpanoids naturally occurring in Brazilian green propolis. In this study, these compounds and eleven derivatives were synthesized and evaluated for their in vitro antimicrobial activity against a representative panel of cariogenic bacteria in terms of their minimum inhibitory concentration (MIC) values. Plicatin B (2) and its hydrogenated derivative 8 (2’,3’,7,8-tetrahydro-plicatin B) were the most active compounds. Plicatin B (2) displayed strong activity against all bacteria tested (MIC = 31.2 μg/mL). On the other hand, compound 8 (2’,3’,7,8-tetrahydro-plicatin A) displayed strong activity against Streptococcus mutans, S. salivarius, S. sobrinus, Lactobacillus paracasei (MIC = 62.5 μg/mL) and S. mitis (MIC = 31.2 μg/mL) as well as a moderate activity against Enterococcus faecalis and S. sanguinis (MIC = 125 μg/mL). In silico studies showed that the complexes formed compound 2 and 8 has energy score values close to those of the native ligands of S. mitis, S. sanguinis, and S. mutans due to the formation of strong hydrogen bonds with the active sites of those bacteria. Moreover, all the estimated physicochemical parameters satisfy the drug-likeness criteria without violating the Lipinski, Veber, and Egan rules, so these compounds are not expected to cause problems with oral bioavailability and pharmacokinetic parameters. Compounds 2 and 8 also have suitable ADME-T parameters, as the online server pkCSM calculates. These results make compounds 2 and 8 good candidates as anticariogenic compounds.

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“…Propolis and its pure bioactive compounds are reported to be effective and safe medicines as alternative therapies for chronic diseases [8]. In silico studies of Brazilian and Sulawesi propolis constituents with molecular docking promised propolis and its constituents as future drug candidates [9,10].…”

Section: Introductionmentioning

confidence: 99%

Propolis and Their Active Constituents for Chronic Diseases

et al. 2023

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Propolis is a mass of chemically diverse phytoconstituents with gummy textures that are naturally produced by honeybees upon collection of plant resins for utilization in various life processes in beehives. Since ancient times, propolis has been a unique traditional remedy globally utilized for several purposes, and it has secured value in pharmaceutical and nutraceutical areas in recent years. The chemical composition of propolis comprises diverse constituents and deviations in the precise composition of the honeybee species, plant source used for propolis production by bees, climate conditions and harvesting season. Over 300 molecular structures have been discovered from propolis, and important classes include phenolic acids, flavonoids, terpenoids, benzofurans, benzopyrene and chalcones. Propolis has also been reported to have diverse pharmacological activities, such as antidiabetic, anti-inflammatory, antioxidant, anticancer, immunomodulatory, antibacterial, antiviral, antifungal, and anticaries. As chronic diseases have risen as a global health threat, abundant research has been conducted to track propolis and its constituents as alternative therapies for chronic diseases. Several clinical trials have also revealed the potency of propolis and its constituents for preventing and curing some chronic diseases. This review explores the beneficial effect of propolis and its active constituents with credible mechanisms and computational studies on chronic diseases.

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Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis

Cited by 14 publications

References 42 publications

Bio-based and bio-inspired adhesives from animals and plants for biomedical applications

Bio-based and bio-inspired adhesives from animals and plants for biomedical applications

In vitro and in silico studies of prenylated phenylpropanoids of green propolis and their derivatives against cariogenic bacteria

Propolis and Their Active Constituents for Chronic Diseases

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