Antimycobacterial activity generated by the amide coupling of (−)-fenchone derived aminoalcohol with cinnamic acids and analogues

Slavchev, Ivaylo; Dobrikov, Georgi M.; Valcheva, Violeta; Ugrinova, Iva; Pasheva, Evdokia; Dimitrov, Vladimir

doi:10.1016/j.bmcl.2014.09.021

Cited by 11 publications

(4 citation statements)

References 25 publications

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“…Thirty-one fenchol hybrids were prepared with different substitutions on the cinnamic ring, and four hybrids 169 – 172 resulted with potent activity against M. tuberculosis H 37 Rv [165]. The fenchol hybrids 169 and 170 having respectively a 3,4-methylenedioxy and a 2-nitro substituents ( 170 ) on the aryl ring of the cinnamic moiety, displayed an MIC value of 6.7 µM (Table 5).…”

Section: Synthetic Cinnamic Hybridsmentioning

confidence: 99%

“…The fenchol hybrids 169 and 170 having respectively a 3,4-methylenedioxy and a 2-nitro substituents ( 170 ) on the aryl ring of the cinnamic moiety, displayed an MIC value of 6.7 µM (Table 5). The fenchol hybrid 171 with 3,4,5-trimethoxy substitution on the cinnamic acid showed higher potency (MIC = 2.4 µM), while the hybrid 172 having 4-dimethylamine substitution was the most active (MIC = 540 nM) against the H 37 Rv pathogenic strain [165].…”

Section: Synthetic Cinnamic Hybridsmentioning

confidence: 99%

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Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

2014

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Antimicrobial natural preparations involving cinnamon, storax and propolis have been long used topically for treating infections. Cinnamic acids and related molecules are partly responsible for the therapeutic effects observed in these preparations. Most of the cinnamic acids, their esters, amides, aldehydes and alcohols, show significant growth inhibition against one or several bacterial and fungal species. Of particular interest is the potent antitubercular activity observed for some of these cinnamic derivatives, which may be amenable as future drugs for treating tuberculosis. This review intends to summarize the literature data on the antimicrobial activity of the natural cinnamic acids and related derivatives. In addition, selected hybrids between cinnamic acids and biologically active scaffolds with antimicrobial activity were also included. A comprehensive literature search was performed collating the minimum inhibitory concentration (MIC) of each cinnamic acid or derivative against the reported microorganisms. The MIC data allows the relative comparison between series of molecules and the derivation of structure-activity relationships.

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Section: Synthetic Cinnamic Hybridsmentioning

confidence: 99%

Section: Synthetic Cinnamic Hybridsmentioning

confidence: 99%

Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

2014

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“…Fenchone exists as a bicyclic monoterpene and is present in the essential oil of various fragrant plants, including Foeniculum vulgare and Peumus boldus ( Kim, Song, Cho, and Lee, 2020 ). Previous pharmacological research has confirmed the anti-inflammatory, antioxidant, wound-healing, antidiarrheal, antifungal, antinociceptive, and bronchodilator activities of fenchone ( Him, Ozbek, Turel, and Oner, 2008 ; Slavchev et al, 2014 ; Keskin et al, 2017 ; de Souza Pessoa et al, 2020 ; Rehman, Ansari, Samad, and Ahmad, 2022 ). The therapeutic efficacy of the fruits of Foeniculum vulgare is generally accredited to its essential oils.…”

Section: Introductionmentioning

confidence: 90%

Fenchone, a monoterpene: Toxicity and diuretic profiling in rats

et al. 2023

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Fenchone is a monoterpene present in the essential oils of various plants, including Foeniculum vulgare and Peumus boldus. Previous studies confirmed the anti-inflammatory, antioxidant, wound-healing, antidiarrheal, antifungal, antinociceptive, and bronchodilator activities of fenchone. Owing to various pharmacological activities of Fenchone, the current research was designed to evaluate its diuretic activity along with toxicity profiling. For evaluating acute toxicity, OECD guideline 425 was followed in which a single dose of 2000 mg/kg was orally administered to rats. For evaluating the diuretic potential in rats, three doses of Fenchone (100, 200, and 400 mg/kg) were assayed in comparison to furosemide (15 mg/kg) as the standard drug, followed by measurements of urinary volume, urinary electrolytes, uric acid, and urinary creatinine in saline-loaded rats for 8 h. The acute toxicity study showed a significant increase in hemoglobin (Hb), red blood cells (RBCs), alkaline phosphatase (ALP), and alkaline transaminase (ALT) along with a significant decrease in serum triglycerides, cholesterol, and uric acid levels when compared with the control group. The oxidative stress parameter, superoxide dismutase (SOD), was increased in the heart and spleen. Nitrite (NO) and glutathione were significantly increased in the kidney. The acute diuretic effect of Fenchone (400 mg/kg) significantly increased the urinary output, electrolytes (Na+, K+, and Ca++), urinary creatinine, and urinary uric acid in a dose-dependent manner. The Na+/K+ ratio was remarkably higher in the treatment group than that of the control group. The diuretic index, saluretic index, and Lipschitz value were also calculated from electrolyte concentration and urinary volume measurements, and the values were significantly increased in rats administered with fenchone at 400 mg/kg dose. The current study concluded that fenchone is safe and has remarkable diuretic action.

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“…Fenchone is found in the essential oil of multiple fragrant plants, including Foeniculum vulgare and Peumus boldus. Pharmacological studies have confirmed that fenchone possessed the antiinflammatory, antioxidant, antidiarrheal, bronchodilator, wound healing, analgesic, and antifungal activities (Keskin et al, 2017;Pessoa et al, 2020;Slavchev et al, 2014). Foeniculum vulgare is largely used in Brazil for the treatment of constipation because of its laxative effect (Picon et al, 2010).…”

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confidence: 99%

Combination of fenchone and sodium hyaluronate ameliorated constipation‐predominant irritable bowel syndrome and underlying mechanisms

Cui,

Hua,

Zou

et al. 2023

Chem Biol Drug Des

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We sought to explore the protective effect of the combination of fenchone (FE) and sodium hyaluronate (SH) on ice water‐induced IBS‐C rats and the potential mechanism. The neurotransmitter levels, including substance P (SP), motilin (MTL), 5‐hydroxytryptamine (5‐HT), and vasoactive intestinal peptide (VIP), were determined by ELISA methods. The stem cell factors (SCF)/c‐Kit signaling pathway‐related protein and mRNA levels were determined by western blot and reverse transcription quantitative polymerase chain reaction (RT‐qPCR) analyses, respectively. The expressions of tight ZO‐1, Occludin, and Claudin‐1 were also measured by western blot assay and immunofluorescence staining. The 16S rRNA gene sequence was used to measure the composition of gut microbiota. The co‐administration of FE and SH improved the body weight, number of fecal pellets, fecal moisture, abdominal with drawal reflex score, and gastrointestinal transit rate in IBS‐C rats. The unique efficacy of combination depended on the regulation of balance between excitatory and inhibitory neurotransmitters, enhancement of intestinal barrier function, and activation of SCF/c‐Kit pathway. The gut microbiota structure was also restored. The ability of FE combined with SH to regulate SCF/c‐Kit signaling pathway, enhance intestinal barrier function, and modulate gut microbiota contributes to their efficacy in managing IBS‐C in rats.

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Antimycobacterial activity generated by the amide coupling of (−)-fenchone derived aminoalcohol with cinnamic acids and analogues

Cited by 11 publications

References 25 publications

Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

Fenchone, a monoterpene: Toxicity and diuretic profiling in rats

Combination of fenchone and sodium hyaluronate ameliorated constipation‐predominant irritable bowel syndrome and underlying mechanisms

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