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Antimicrobial and cytotoxic effects of the Copaifera reticulata oleoresin and its main diterpene acids
Open accessAbstract
Ethnopharmacological relevance The oleoresin of Brazilian Copaifera reticulata is a traditional remedy used for the treatment of skin and urinary tract infections, respiratory diseases, rheumatism, ulcer and tumours; thus, playing an important role in the primary health care of the indigenous population.Aim As most previous pharmacological tests used the crude oleoresin and only a few studies so far dealt with enriched fractions or pure chemically defined compounds, the aim of this study was to systematically evaluate the antimicrobial and cytotoxic properties of the Copaifera reticulata oleoresin and to assign traditional uses to specific secondary metabolites.Materials and methods The oleoresin, as well as its neutral and acidic fractions were tested for their activity against six cancer cell lines, two clinically relevant bacterial strains, and two dermatophytes. Both fractions were analysed by GC-MS and UHPLC-ELSD, respectively. The antibacterial acidic phase was further fractionated by preparative chromatography to purify and characterize the compounds responsible for the observed pharmacological effect.Results Whereas no cytotoxic activity was detected, the crude oleoresin and its acidic fraction showed antibacterial activity against gram-positive bacteria Enterococcus faecium (IC 50 values 4.2 and 4.8 µg/mL, respectively) and methicillin-resistant Staphylococcus aureus (MRSA, IC 50 values 5.3 and 7.2 µg/mL, respectively). Purification of the acidic fraction of the C. reticulata oleoresin yielded two dicarboxylic diterpene acids and the four main diterpene acids, comprising three different diterpene scaffolds. Interestingly, the activity was not restricted to a particular diterpene-type but rather depended on the compounds' lipophilicity, with the most active constituent showing IC 50 values of 1.6 (E. faecium) and 2.5 µg/mL (MRSA), respectively. Furthermore, ent-polyalthic acid, the major diterpenoid, was significantly active against dermatophytes with IC 50 values of 6.8 µg/mL (Trichophyton rubrum) and 4.3 µg/mL against (T. mentagrophytes).Conclusion The present study proved the antimicrobial effects of the C. reticulata oleoresin and its diterpenoid constituents, confirming its wide use in folk medicine for the treatment of skin and urinary tract infections. The inhibitory activity of copaiba diterpenoids against dermatophytic fungi as well as the gram-positive bacteria E. faecium and MRSA is being reported for the first time, providing potential lead structures for the treatment of these clinically relevant bacterial strains.
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“It has demonstrated antimicrobial, anticarcinogenic, anti-inflammatory, antioxidant, anxiolytic-like, and local anesthetic effects and anticancer properties, including against prostate, breast, pancreatic, skin, leukemia, lymphatic, and cervical cancer [11,14,21,37,38,39,40,41].”
From Clove essential oil (Syzygium aromaticum L. Myrtaceae): Extraction, chemical composition, food applications, and essential bioactivity for human health (2021) · cites this paper as [39]
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Sorted by citations
Haro-González, J. N., Castillo-Herrera, G. A., Martínez-Velázquez, M., & Espinosa-Andrews, H. (2021) · Molecules · doi:10.3390/molecules26216387 · Cited by 463
Metadata
- Authors
- Pfeifer Barbosa, A. L., Wenzel-Storjohann, A., Barbosa, J. D., Zidorn, C., Peifer, C., Tasdemir, D., & Çiçek, S. S.
- Affiliations
- Universidade Federal do Pará (BR)
- Christian-Albrechts-Universität zu Kiel (DE)
- Corresponding author
- Çiçek, Serhat Sezai
- Venue
- Journal of Ethnopharmacology
- Publisher
- Elsevier BV
- Published
- 2019-04
- Volume
- 233
- Pages
- 94-100
- ISSN
- 0378-8741 (ISSN-L)
- OpenAlex
- W2901705460
- Cited by
- 57
- References
- 44
- Citations by year
- 2026: 2 · 2025: 6 · 2024: 5 · 2023: 9 · 2022: 13 · 2021: 12 · 2020: 8 · 2019: 2
- FWCI
- 1.96
- Type
- journal article
- Language
- en
- Open access
- green
- oceanrep.geomar.de
- Licence
- Locations
- Journal of Ethnopharmacology (publishedVersion)
- PubMed (publishedVersion)
- Helmholtz Centre for Ocean Research Kiel (GEOMAR) (acceptedVersion, other-oa)
- Helmholtz Centre for Ocean Research Kiel (GEOMAR) (acceptedVersion)
- MACAU: Open Access Repository of Kiel University (University Library Kiel) (submittedVersion, cc-by-nc-nd)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Bioactive Natural Diterpenoids Research
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry Medicinal Plant Applications
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Plant-Derived Bioactive Compounds
- Keywords
- Copaifera reticulata, oleoresin, antimicrobial activity, antibacterial activity, cytotoxicity, Enterococcus faecium, methicillin-resistant Staphylococcus aureus, dermatophytes, Trichophyton rubrum, Trichophyton mentagrophytes, diterpene acids, lipophilicity
- MeSH terms
- Anti-Infective Agents, Bacteria, Cell Line, Cell Survival, Diterpenes, Humans, Fabaceae, Plant Extracts, Trichophyton
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