Isolation, antioxidant and antimicrobial activities of ecdysteroids from Serratula cichoracea
Abstract
Background: Several Serratula species are used in folk medicine and showed interesting biological activities. The objective of this work was to continue the investigation of the chemical composition of the ethyl acetate extract of the flowers of Serratula cichoracea which in our previous study showed a significant antioxidant activity in 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•) essay compared to quercetin used as control molecule and to evaluate the isolated compounds for their antioxidant and antimicrobial activities. Methods: Ethyl acetate extract (15 g) was fractionated by column chromatography on silica gel. After purification on preparative plates, the isolated compounds were identified by spectral analyses mainly high resolution electrospray ionisation mass spectrometry (HR-ESIMS) and one- and two-dimensionnal nuclear magnetic resonance spectroscopy experiments, and were evaluated in vitro for antioxidant activity using 1,1-diphenyl-2-picrylhydrazyl radical and for antimicrobial properties. Results: A new phytoecdysteroid named 22-epi-ajugasterone C (1) together with ajugasterone C (2), were isolated. Compounds 1 and 2 had weak scavenging effect compared with myricetin used as positive control, whereas the two compounds showed antimicrobial properties against multiresistant strains like Staphylococcus aureus, Escherichia coli, Serratia sp., Klebsiella pneumoniae and Candida albicans. Conclusion: The new isolated phytoecdysteroid and its epimer ajugasterone C, responded to their effectiveness against different various antibiotic-resistant bacteria. Keywords: Serratula cichoracea, Asteraceae, phytoecdysteroids, antimicrobial, antioxidant activities, chromatography.
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22-epi-Ajugasterone C showed weak DPPH radical-scavenging and antimicrobial activity against multi-resistant Gram-positive bacteria, Gram-negative bacteria, and yeasts.
“Weak DPPH radical-scavenging and antimicrobial activity against multi resistant strains Gram positive bacteria (Staphylococcus aureus 118), Gram negative bacteria such as (Escherichia coli 113, Klebsiella pneumoniae 112, Proteus mirabilis 23, Serratia sp. 2028, Pseudomonas aurogenosa43) and yeasts (Candida albicans).”
From The Phytochemical, Biological, and Medicinal Attributes of Phytoecdysteroids: An Updated Review (2021) · cites this paper as [68]
22-epi-Ajugasterone C showed in vitro antioxidant activity by DPPH radical scavenging assay.
“PE 22-epi-ajugasterone C (62) also showed in vitro antioxidant activity by DPPH radical scanging assay68.”
From The Phytochemical, Biological, and Medicinal Attributes of Phytoecdysteroids: An Updated Review (2021) · cites this paper as [68]
PEs display antimicrobial properties against multi-resistant strains such as Escherichia coli, Staphylococcus aureus, Candida albicans, and Klebsiella pneumoniae.
“PEs display antimicrobial properties against multi-resistant strains such as Escherichia coli, Staphylococcus aureus, Candida albicans, and Klebsiella pneumoniae [60].”
From Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones (2022) · cites this paper as [60]
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“Serratula cichoracea 22-epi-ajugasterone C [60]”
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“The compounds exhibited antimicrobial properties against multiple resistant strains such as Staphylococcus aureus, Escherichia coli, Serratia sp., Klebsiella pneumoniae, and Candida albicans (Aliouche et al., 2018).”
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- Authors
- Aliouche, L., Larguet, H., Amrani, A., Leon, F., Brouard, I., Benayache, S., Zama, D., Meraihi, Z., & Benayache, F.
- Affiliations
- University Frères Mentouri Constantine 1 (DZ)
- Instituto de ProductosNaturales y Agrobiologia-C.S.I.C., Av. Astrofisico Francisco Sanchez 3, 38206 La Laguna, Tenerife, Spain
- Instituto de Productos Naturales y Agrobiología (ES)
- Laboratoire de Genie Microbiologique et Applications, Faculte des Sciences de la Nature et de la Vie, Departement de Biochimie et Biologie Cellulaire & Moleculaire, Universite Freres Mentouri Constantine 1, Route d`Ain El Bey 25017, Algeria
- Corresponding author
- Benayache, Fadila
- Venue
- Current Bioactive Compounds
- Publisher
- Bentham Science Publishers Ltd.
- Published
- 2018-04-30
- Volume
- 14
- Issue
- 1
- Pages
- 60-66
- ISSN
- 1573-4072 (ISSN-L)
- OpenAlex
- W2774433130
- Cited by
- 21
- References
- 0
- Citations by year
- 2026: 4 · 2025: 1 · 2023: 3 · 2022: 5 · 2020: 4 · 2019: 2 · 2018: 2
- FWCI
- 0.89
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Current Bioactive Compounds (publishedVersion)
- DIGITAL.CSIC (Spanish National Research Council (CSIC)) (submittedVersion)
- Funders
- Direction Générale de la Recherche Scientifique et du Développement Technologique
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive Natural Diterpenoids Research
- Keywords
- phytoecdysteroids, ecdysteroids, antioxidant activity, antimicrobial activity, antibiotic-resistant bacteria, Staphylococcus aureus, Escherichia coli, Serratia, Klebsiella pneumoniae, Candida albicans, DPPH radical scavenging, ethyl acetate extract, flower constituents, natural product isolation
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