Comparative analysis of the antibacterial and drug-modulatory effect of d-limonene alone and complexed with β-cyclodextrin

Costa, Maria do Socorro; Rocha, Janaína Esmeraldo; Campina, Fábia F.; Silva, Ana Raquel Pereira da; Cruz, Rafael Pereira da; Pereira, Raimundo Luiz Silva; Quintans‐Júnior, Lucindo José; Menezes, Irwin Rose Alencar de; Araújo, Adriano Antunes de Souza; Freitas, Thiago Sampaio de; Teixeira, Alexandre Magno Rodrigues; Coutinho, Henrique Douglas Melo

doi:10.1016/j.ejps.2018.11.036

Cited by 47 publications

(32 citation statements)

References 18 publications

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“…Not much convergence between our results and those previously reported is noted, which could be owing to the differences in the EO compositions. The studied species was rich in 1,8-cineole rather than limonene (case of Lawal), which was previously reported to be less active [ 27 , 28 , 29 ].…”

Section: Resultsmentioning

confidence: 99%

“…The biological activity of H. foetidum was studied by Samie [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ] and reported in the review of Maroyi [ 32 ]. Although the authors did not investigate the EO composition, they described its antifungal and antibacterial activities (MIC value on S. aureus >7.5mg/mL).…”

Section: Resultsmentioning

confidence: 99%

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Volatilome Analyses and In Vitro Antimicrobial Activity of the Essential Oils from Five South African Helichrysum Species

et al. 2020

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Helichrysum genus was used in folk South African medicine to treat various human disorders. As a part of our on-going research addressing the exploitation of South African plants belonging to this genus, five species were investigated for their volatile and antimicrobial activities. The volatile organic compounds (VOCs) and the essential oils (EOs) were analysed by gas chromatography mass spectrometry (GC-MS). Microdilution was the method used for assessing both antimycotic and antibacterial activities, which was also tested by Kirby-Bauer agar disc diffusion. Total monoterpenes (TMs) dominated the VOCs of four species (H. trilineatum (70.6%), H. edwardsii (79.3%), H. cooperi (84.5%), and H. pandurifolium (57.0%)). H. cooperi and H. edwardsii EOs showed the predominance of TMs (68.2% and 84.5%, respectively), while H. pandurifolium and H. trilineatum EOs were characterized by the prevalence of TSs (86.5% and 43.6%, respectively). H. odoratissimum EO evidenced a similar amount of both TMs (49.5%) and TSs (46.4%). Microsporum canis was more sensitive to these EOs. The lowest minimum inhibitory concentration (MIC) was observed with H. pandurifolium and H. edwardsii EOs (0.25%). H. pandurifolium and H. trilineatum had a good effect on Staphylococcus aureus (MIC 5%). These findings open new perspectives for the exploitation of these natural compounds for application in cosmetics and pharmaceutics.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Volatilome Analyses and In Vitro Antimicrobial Activity of the Essential Oils from Five South African Helichrysum Species

et al. 2020

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“…d-limonene ((4R)-1-methyl-4-isopropenylcyclohex-1-ene) ( Figure 6) is one of nature's most common terpenes, an important constituent in various citrus oils (orange, lemon, mandarin, lime and grapefruit). It can decrease oxidative stress and inflammation [73], has potentially beneficial effects on colon cancer [74], antibacterial activity [75], and neuroprotective properties [76] described in the literature. [77].…”

Section: D-limonenementioning

confidence: 99%

Intestinal Anti-Inflammatory Activity of Terpenes in Experimental Models (2010–2020): A Review

et al. 2020

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Inflammatory bowel diseases (IBDs) refer to a group of disorders characterized by inflammation in the mucosa of the gastrointestinal tract, which mainly comprises Crohn’s disease (CD) and ulcerative colitis (UC). IBDs are characterized by inflammation of the intestinal mucosa, are highly debilitating, and are without a definitive cure. Their pathogenesis has not yet been fully elucidated; however, it is assumed that genetic, immunological, and environmental factors are involved. People affected by IBDs have relapses, and therapeutic regimens are not always able to keep symptoms in remission over the long term. Natural products emerge as an alternative for the development of new drugs; bioactive compounds are promising in the treatment of several disorders, among them those that affect the gastrointestinal tract, due to their wide structural diversity and biological activities. This review compiles 12 terpenes with intestinal anti-inflammatory activity evaluated in animal models and in vitro studies. The therapeutic approach to IBDs using terpenes acts basically to prevent oxidative stress, combat dysbiosis, restore intestinal permeability, and improve the inflammation process in different signaling pathways.

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“…The results of modulatory activity against E. coli ( Figure 7A) evidenced a decrease in the MIC of AMP from 256 to 128 µg/mL when this antibiotic was used in combination with EOO, EOO-β-CD prepared by either method and EOO-HP-β-CD prepared by slurry, highlighting a synergistic effect, while EOO-HP-β-CD prepared by kneading did not influence its activity. Such a synergistic effect was unexpected since the cell wall of Gram-negative bacteria is more complex than the one of Gram-positive bacteria, which has a greater number of peptidoglycan layers directly linked to penicillin-binding proteins [50,51]. Similar synergism was reported for the combination of Croton limae essential oil and neomycin against another strain of the same bacterial species [51].…”

Section: Drug Modulating Activitymentioning

confidence: 77%

“…Such a synergistic effect was unexpected since the cell wall of Gram-negative bacteria is more complex than the one of Gram-positive bacteria, which has a greater number of peptidoglycan layers directly linked to penicillin-binding proteins [50,51]. Similar synergism was reported for the combination of Croton limae essential oil and neomycin against another strain of the same bacterial species [51]. The addition of EOO to PIP + TAZ increased the MIC from 2.0 to 4.0 µg/mL ( Figure 7B), suggesting antagonistic activity, possibly related to oil solubility.…”

Section: Drug Modulating Activitymentioning

confidence: 99%

Development and Evaluation of Antimicrobial and Modulatory Activity of Inclusion Complex of Euterpe oleracea Mart Oil and β-Cyclodextrin or HP-β-Cyclodextrin

Magalhães

Macedo

Pacheco

et al. 2020

IJMS

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The development of inclusion complexes is used to encapsulate nonpolar compounds and improve their physicochemical characteristics. This study aims to develop complexes made up of Euterpe oleracea Mart oil (EOO) and β-cyclodextrin (β-CD) or hydroxypropyl-β-cyclodextrin (HP-β-CD) by either kneading (KND) or slurry (SL). Complexes were analyzed by molecular modeling, Fourier-transform infrared spectroscopy, scanning electron microscopy, powder X-ray diffraction, thermogravimetry analysis and differential scanning calorimetry. The antibacterial activity was expressed as Minimum Inhibitory Concentration (MIC), and the antibiotic resistance modulatory activity as subinhibitory concentration (MIC/8) against Escherichia coli, Streptomyces aureus, Pseudomonas aeruginosa and Enterococcus faecalis. Inclusion complexes with β-CD and HP-β-CD were confirmed, and efficiency was proven by an interaction energy between oleic acid and β-CD of −41.28 ± 0.57 kJ/mol. MIC values revealed higher antibacterial activity of complexes compared to the isolated oil. The modulatory response of EOO and EOO-β-CD prepared by KND as well as of EOO-β-CD and EOO-HP-β-CD prepared by SL showed a synergistic effect with ampicillin against E. coli, whereas it was not significant with the other drugs tested, maintaining the biological response of antibiotics. The antimicrobial response exhibited by the complexes is of great significance because it subsidizes studies for the development of new pharmaceutical forms.

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Comparative analysis of the antibacterial and drug-modulatory effect of d-limonene alone and complexed with β-cyclodextrin

Cited by 47 publications

References 18 publications

Volatilome Analyses and In Vitro Antimicrobial Activity of the Essential Oils from Five South African Helichrysum Species

Volatilome Analyses and In Vitro Antimicrobial Activity of the Essential Oils from Five South African Helichrysum Species

Intestinal Anti-Inflammatory Activity of Terpenes in Experimental Models (2010–2020): A Review

Development and Evaluation of Antimicrobial and Modulatory Activity of Inclusion Complex of Euterpe oleracea Mart Oil and β-Cyclodextrin or HP-β-Cyclodextrin

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