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Considering the COVID-19 pandemic, this research aims to investigate some herbs as probable therapies for this disease. Achillea millefolium (Yarrow), Alkanet, Rumex patientia (Patience dock), Dill, Tarragon, and sweet fennel, including some principal chemical compounds of achillin, alkannin, cuminaldehyde, dillapiole, estragole, and fenchone have been selected. The possible roles of these medicinal plants in COVID-19 treatment have been investigated through quantum sensing methods. The formation of hydrogen bonding between the principal substances selected in anti-COVID natural drugs and Tyr-Met-His (the database amino acids fragment), as the active area of the COVID protein, has been evaluated. The physical and chemical attributes of nuclear magnetic resonance, vibrational frequency, the highest occupied molecular orbital energy and the lowest unoccupied molecular orbital energy, partial charges, and spin density have been investigated using the DFT/TD-DFT method and 6-311+G (2d,p) basis set by the Gaussian 16 revision C.01 program toward the industry of drug design. This research has exhibited that there is relative agreement among the results that these medicinal plants could be efficient against COVID-19 symptoms. [ABSTRACT FROM AUTHOR]

Conjugates of isatin and hydrazones based on (+)-camphor and (–)-fenchone were synthesized for the first time. The physicochemical properties of the synthesized compounds have been studied, and for the hydrazone product of fenchone and isatin X-ray diffraction data have been obtained. Molecular modeling of the possible interaction of new compounds with the active site of the basic protease 3CLpro of the SARS-CoV-2 virus was carried out, and the properties of isatin-terpene compounds as inhibitors of the 3CLpro protease were studied. It was found that the new conjugates do not exhibit inhibitory properties against 3CLpro, which makes it possible to clarify the direction of further chemical modifications of monoterpenoid derivatives in order to obtain molecules with antiviral properties. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

The soluble epoxide hydrolase (sEH) is a potential target to treat cardiovascular, renal and neuronal diseases. A series of sEH inhibitors containing naturally occurring lipophilic groups (originating from camphor and fenchone) were developed. Inhibitory potency ranging from 0.7 nM to 6.47 μM was obtained. It was discovered that ureas derived from L-camphor were more active against sEH (2.3-fold average) than the corresponding analogues derived from D-camphor indicating enantiomeric preference of sEH. Ureas derived from fenchone possess lower activity against sEH (ca. 80-fold on average) than their camphor-derived analogs due to the specific structure of the lipophilic fragment and show less enantiomeric preference (1.75-fold on average). Moreover, fenchone-derived ureas show no consistency in enantiomeric preference. Endo/exo-form of compound L-3a derived from L-camphor is 4-fold more potent than the corresponding analogue prepared from D-camphor (IC50 = 0.7 nM vs. 2.8 nM) making it the most promising sEH inhibitor among the tested series.

Fenchone (a bicyclic monoterpene) is present in the essential oils of plant species like Foeniculum vulgare and Peumus boldus and is used to treat GIT disorders. Research reports have indicated its strong anti-inflammatory, antioxidant, and anti-nociceptive properties. The present study was designed to investigate fenchone's anti-arthritic effects in a rat model of chronic joint inflammation (Complete Freud's Adjuvant-mediated inflammation [CFA]). Molecular docking analysis revealed a high binding interaction of fenchone with inducible nitric oxide synthase (iNOS), Interleukin-17, Prostaglandin E Receptor EP4, and Cycloxygenase-2 (COX-2), indicating its anti-inflammatory efficacy using computational tests. Fenchone treatment at 100 mg/kg, 200 mg/kg, and 400 mg/kg significantly enhanced the tail-flick latency when compared with the solvent-treated group. Correspondingly, the raised mRNA values of iNOS, IL-17, IL-1β, IL-6, TNF-α, and COX-2 in solvent-treated group were significantly reduced following treatment with fenchone. Moreover, fenchone significantly lowered spleen and thymus indices, Nitric oxide (NO) and PGE2 values as compared to solvent-treated group. Hence, the results of the present study indicated that fenchone has a potent anti-inflammatory effect by inhibiting pro-inflammatory markers and thus may have therapeutic potential for chronic joint inflammation as well as chronic inflammatory disorders. [ABSTRACT FROM AUTHOR]

Fenchone is a monoterpene present in the essential oils of various plants, including Foeniculum vulgare and Peumus boldus. Previous studies confirmed the antiinflammatory, 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. [ABSTRACT FROM AUTHOR]

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.

This study was conducted to evaluate the allelopathic effect of essential oil (EO) extracted from five Foeniculum vulgare Mill. cultivars against two weed species, Portulaca oleracea L. and Amaranthus retroflexus L. Various EO concentrations (0, 100, 200, 400, 600, and 800 mgL−1) were used to determine their effects on germination and seedling growth of P. oleracea and A. retroflexus. Radicle length, plumule length, radicle wet weight, plumule wet weight, plumule dry weight, and germination percentage of the target plants were measured. GC-MS analysis revealed the presence of different compounds in studied F. vulgare cultivars. Cultivars containing α-pinene possessed strong inhibitory potential towards weeds growth. On the contrary, cultivars containing fenchone showed poor inhibitory potential on both weeds. Moreover, the results indicate that with increasing EO concentration of F. vulgare, radicle length, plumule length, radicle wet weight, plumule wet weight, plumule dry weight, and germination percentage of both weed species decreased. The highest inhibitory effects were observed at 600 and 800 mg L−1 concentrations. Boushehr F. vulgare cultivar showed the highest inhibitory effect, while Esfahan and Yazd cultivars were identified as least inhibitory against the two weeds. Both P. oleracea and A. retroflexus showed similar sensitivities to F. vulgare EO. [ABSTRACT FROM AUTHOR]

Abstract Tetradenia riparia (Hochst.) Codd (Lamiaceae) is a species native to the African continent and used as an insect repellent. The objective of the study was to evaluate the larvicidal potential of essential oils (EOs) from the leaves, flower buds, and stem of T. riparia, collected in winter against Aedes aegypti larvae. The EOs were extracted by hydrodistillation (3 h) and identified by GC/MS. The EOs were tested against larvae of A. aegypti at concentrations ranging from 12500 to 1.5 µg/mL for 24 h. The insecticide activity was evaluated by probit analysis, and the anticholinesterase activity was determined by bioautographic method. The results of the class projection indicated sesquiterpenes as the majority class, corresponding to 60.66% (leaves), 64.70% (flower buds) and 83.99% (stem), and the bioassays on A. aegypti larvae indicated LC50 of 1590, 675 and 665 µg/mL, respectively. The anticholinesterase activity indicated that the EO of the leaves inhibited the enzyme at a concentration of 780 µg/mL, and those from the flower buds and stem inhibited up to 1560 µg/mL. The results indicated weak activity of essential oils against A. aegypti larvae.

The aim of the present study is to investigate the effective antimicrobial and antibiofilm properties of fenchone, a biologically active bicyclic monoterpene, against infections caused by bacteria and Candida spp. The interactions between fenchone and three distinct proteins from Escherichia coli (β-ketoacyl acyl carrier protein synthase), Candida albicans (1, 3-β–D-glucan synthase), and Pseudomonas aeruginosa (Anthranilate-CoA ligase) were predicted using molecular docking and in silico/ADMET methods. Further, to validate the in-silico prediction, the antibacterial and antifungal potential of fenchone was evaluated against E. coli, P. aeruginosa, and C. albicans by determining minimum inhibitory concentration (MIC), minimum bacterial concentration (MBC), and minimum fungicidal concentration (MFC). The lowest MIC/MBC values of fenchone against E. coli and P. aeruginosa obtained was 8.3 ± 3.6/25 ± 0.0 and 266.6 ± 115.4/533.3 ± 230.9 mg/mL, respectively, whereas the MIC/MFC value for C. albicans was found to be 41.6 ± 14.4/83.3 ± 28.8 mg/mL. It was observed that fenchone has a significant effect on antimicrobial activity (p < 0.05). Our findings demonstrated that fenchone at 1 mg/mL significantly reduced the production of biofilm (p < 0.001) in E. coli, P. aeruginosa, and C. albicans by 70.03, 64.72, and 61.71%, respectively, in a dose-dependent manner when compared to control. Based on these results, it has been suggested that the essential oil from plants can be a great source of pharmaceutical ingredients for developing new antimicrobial drugs. [ABSTRACT FROM AUTHOR]

The gas chromatography–mass spectrometry (GC-MS) approach is established for the simultaneous determination of fenchone (FCO) and trans-anethole (TOH) in the essential oils and methanolic extracts of fennel (Foeniculum vulgare Mill.) fruits obtained from India (IND), Pakistan (PAK), and Saudi Arabia (SA). The simultaneous determination of FCO and TOH was performed via Agilent 190914S HP–5MS fused-silica capillary column (30 m × 250 µm ID, 0.25 µm film thickness). The proposed GC-MS approach was linear in the range of 0.10–50 µg/g for FCO and TOH. FCO's detection (LOD) and quantification (LOQ) limits were calculated to be 0.04 and 0.12 µg/g, respectively. The LOD and LOQ values for TOH, on the other hand, were calculated to be 0.05 and 0.15 µg/g, respectively. In addition, the proposed GC-MS approach was accurate and precise for the simultaneous determination of FCO and TOH. The amount of FCO in essential oils of F. vulgare was computed as 0.021, 0.034, and 0.029 mg/g in the samples obtained from IND, PAK, and SA, respectively. The amount of TOH in the essential oils of F. vulgare was computed as 7.40, 14.8, and 10.2 mg/g in the samples obtained from IND, PAK, and SA, respectively. However, the amount of FCO in the methanolic extract of F. vulgare was estimated as 0.031, 0.021, and 0.057 mg/g in the samples obtained from IND, PAK, and SA, respectively. On the other hand, the amount of TOH in the methanolic extract of F. vulgare was estimated as 0.440, 0.498, and 1.74 mg/g in the samples obtained from IND, PAK, and SA, respectively. These findings suggested that the proposed GC-MS approach might be used to simultaneously determine the FCO and TOH in a variety of essential oils and plant extracts. [ABSTRACT FROM AUTHOR]

The soluble epoxide hydrolase (sEH) is a potential target to treat cardiovascular, renal and neuronal diseases. A series of sEH inhibitors containing naturally occurring lipophilic groups (originating from camphor and fenchone) were developed. Inhibitory potency ranging from 0.7 nM to 6.47 μM was obtained. It was discovered that ureas derived from l-camphor were more active against sEH (2.3-fold average) than the corresponding analogues derived from d-camphor indicating enantiomeric preference of sEH. Ureas derived from fenchone possess lower activity against sEH (ca. 80-fold on average) than their camphor-derived analogs due to the specific structure of the lipophilic fragment and show less enantiomeric preference (1.75-fold on average). Moreover, fenchone-derived ureas show no consistency in enantiomeric preference. Endo/exo-form of compound L-3a derived from l-camphor is 4-fold more potent than the corresponding analogue prepared from d-camphor (IC50 = 0.7 nM vs 2.8 nM) making it the most promising sEH inhibitor among the tested series.

Selective synthesis of polycarbonyl conjugates of (+)-fenchone and (+)-camphor was carried out (44-91 % yields) via the ring-opening transformation of 5-acyl-4-pyrones with hydrazones of the corresponding monoterpenoids. A strong influence of the hydrazone fragment on the observed tautomeric equilibrium of the tricarbonyl system was shown. Although the major tautomer of the conjugates is the acyclic polycarbonyl form, the camphor-based conjugates undergo new type of ring-chain tautomerism, diketoenaminone-dihydropyridone equilibrium, and predominantly exist in the cyclic dihydropyridone form in DMSO-d 6 . The polyketones can undergo intramolecular cyclization to form N-amino-4-pyridones in high selectivity. In vitro screening for activity against the influenza virus H1 N1 and vaccinia virus was estimated for the obtained conjugates. The (+)-fenchone derivatives demonstrated the higher activity against vaccinia virus than camphor derivatives. The conjugate, which was prepared from diethyl isochelidonate and hydrazone (+)-fenchone, showed the highest activity against vaccinia virus (SI=17)., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

N,N′-Disubstituted ureas and thioureas containing a lipophilic optically active bicyclic fragment of natural origin were synthesized by reaction of (R)- and (S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-amine (prepared from the natural terpenoid fenchone) with aromatic isocyanates and isothiocyanates in up to 88 and 87% yield, respectively, with the goal of assessing the enantiomeric specificity of human soluble epoxide hydrolase (hsEH). The synthesized compounds were found to be promising as inhibitors of RNA virus replication and hsEH. [ABSTRACT FROM AUTHOR]

The present study was designed to evaluate the insecticidal activity of different concentrations of Foeniculum vulgare and two of its components, trans‐anethole and fenchone, against the different stages of Musca domestica. The tested concentrations were applied through a residual film method and topical application on larvae and pupae respectively. Trans‐anethole achieved the best results against larvae when compared with those of the fennel or fenchone with LC50 values of 0.58%, 1.57%, and 17.22%, respectively. Moreover, tans‐anethole killed 100% of larvae at concentration of 2.5% and fennel achieved the same effect at concentration of 10%, meanwhile fenchone did not reach such an effect at any of the tested concentrations. At the concentration of 10%, fennel oil and trans‐anethole induced morphological deformation in the dead larvae such as shrunk bodies with dark colored integument. Regarding the pupicidal activity, fennel oil showed percentage inhibition rate (PIR) of 100% at the concentration of 10% while the same effect was achieved by trans‐anethole at concentration of 5%. On the contrary, fenchone did not show any pupicidal activity. Treatment of the third instar house fly larvae with LC5o of fennel oil, trans‐anethole, and fenchone significantly inhibited the acetylcholinestrase (AchE) when compared with the control untreated larvae. Additionally, the glutathione‐s‐transferase (GST) and malondialdehyde (MDA) production significantly increased in the larvae treated with trans‐anethole. The results of the present study indicate that the insecticidal activity of fennel oil was mainly attributed to the presence of trans‐anethole as a major constituent. [ABSTRACT FROM AUTHOR]

The aim of the present study is to investigate the effective antimicrobial and antibiofilm properties of fenchone, a biologically active bicyclic monoterpene, against infections caused by bacteria and Candida spp. The interactions between fenchone and three distinct proteins from Escherichia coli (β-ketoacyl acyl carrier protein synthase), Candida albicans (1, 3-β–D-glucan synthase), and Pseudomonas aeruginosa (Anthranilate-CoA ligase) were predicted using molecular docking and in silico/ADMET methods. Further, to validate the in-silico prediction, the antibacterial and antifungal potential of fenchone was evaluated against E. coli, P. aeruginosa, and C. albicans by determining minimum inhibitory concentration (MIC), minimum bacterial concentration (MBC), and minimum fungicidal concentration (MFC). The lowest MIC/MBC values of fenchone against E. coli and P. aeruginosa obtained was 8.3 ± 3.6/25 ± 0.0 and 266.6 ± 115.4/533.3 ± 230.9 mg/mL, respectively, whereas the MIC/MFC value for C. albicans was found to be 41.6 ± 14.4/83.3 ± 28.8 mg/mL. It was observed that fenchone has a significant effect on antimicrobial activity (p < 0.05). Our findings demonstrated that fenchone at 1 mg/mL significantly reduced the production of biofilm (p < 0.001) in E. coli, P. aeruginosa, and C. albicans by 70.03, 64.72, and 61.71%, respectively, in a dose-dependent manner when compared to control. Based on these results, it has been suggested that the essential oil from plants can be a great source of pharmaceutical ingredients for developing new antimicrobial drugs.

Alkylation of the primary amino group of hydrazones of (+)-camphor and (–)-fenchone with dihaloalkanes leading to the production of novel nitrogen-containing heterocyclic derivatives was investigated. It was shown that the reaction of hydrazones with 1,2-ethanedithiol in the presence of formaldehyde with the addition of 5% Sm(NO3)3·6H2O leads to the formation of compounds containing the 1,5,3-dithiazepane fragment. The method developed by us offers the advantage of the use of commercially available reagents and good yields in the synthesis of hydrazone heterocyclic derivatives. Studies of antiviral activity have shown that camphor-based N-heterocyclic compounds can be considered promising agents with activity against influenza A. [ABSTRACT FROM AUTHOR]

The gas chromatography–mass spectrometry (GC-MS) approach is established for the simultaneous determination of fenchone (FCO) and trans-anethole (TOH) in the essential oils and methanolic extracts of fennel (Foeniculum vulgare Mill.) fruits obtained from India (IND), Pakistan (PAK), and Saudi Arabia (SA). The simultaneous determination of FCO and TOH was performed via Agilent 190914S HP–5MS fused-silica capillary column (30 m × 250 µm ID, 0.25 µm film thickness). The proposed GC-MS approach was linear in the range of 0.10–50 µg/g for FCO and TOH. FCO’s detection (LOD) and quantification (LOQ) limits were calculated to be 0.04 and 0.12 µg/g, respectively. The LOD and LOQ values for TOH, on the other hand, were calculated to be 0.05 and 0.15 µg/g, respectively. In addition, the proposed GC-MS approach was accurate and precise for the simultaneous determination of FCO and TOH. The amount of FCO in essential oils of F. vulgare was computed as 0.021, 0.034, and 0.029 mg/g in the samples obtained from IND, PAK, and SA, respectively. The amount of TOH in the essential oils of F. vulgare was computed as 7.40, 14.8, and 10.2 mg/g in the samples obtained from IND, PAK, and SA, respectively. However, the amount of FCO in the methanolic extract of F. vulgare was estimated as 0.031, 0.021, and 0.057 mg/g in the samples obtained from IND, PAK, and SA, respectively. On the other hand, the amount of TOH in the methanolic extract of F. vulgare was estimated as 0.440, 0.498, and 1.74 mg/g in the samples obtained from IND, PAK, and SA, respectively. These findings suggested that the proposed GC-MS approach might be used to simultaneously determine the FCO and TOH in a variety of essential oils and plant extracts.

Fenchone is a bicyclic monoterpene found in a variety of aromatic plants, including Foeniculum vulgare and Peumus boldus, and is used in the management of airways disorders. This study aimed to explore the bronchodilator effect of fenchone using guinea pig tracheal muscles as an ex vivo model and in silico studies. A concentration-mediated tracheal relaxant effect of fenchone was evaluated using isolated guinea pig trachea mounted in an organ bath provided with physiological conditions. Sustained contractions were achieved using low K+ (25 mM), high K+ (80 mM), and carbamylcholine (CCh; 1 µM), and fenchone inhibitory concentration–response curves (CRCs) were obtained against these contractions. Fenchone selectively inhibited with higher potency contractions evoked by low K+ compared to high K+ with resultant EC50 values of 0.62 mg/mL (0.58–0.72; n = 5) and 6.44 mg/mL (5.86–7.32; n = 5), respectively. Verapamil (VRP) inhibited both low and high K+ contractions at similar concentrations. Pre-incubation of the tracheal tissues with K+ channel blockers such as glibenclamide (Gb), 4-aminopyridine (4-AP), and tetraethylammonium (TEA) significantly shifted the inhibitory CRCs of fenchone to the right towards higher doses. Fenchone also inhibited CCh-mediated contractions at comparable potency to its effect against high K+ [6.28 mg/mL (5.88–6.42, n = 4); CCh] and [6.44 mg/mL (5.86–7.32; n = 5); high K+]. A similar pattern was obtained with papaverine (PPV), a phosphodiesterase (PDE), and Ca2+ inhibitor which inhibited both CCh and high K+ at similar concentrations [10.46 µM (9.82–11.22, n = 4); CCh] and [10.28 µM (9.18–11.36; n = 5); high K+]. However, verapamil, a standard Ca2+ channel blocker, showed selectively higher potency against high K+ compared to CCh-mediated contractions with respective EC50 values of 0.84 mg/mL (0.82–0.96; n = 5) 14.46 mg/mL (12.24–16.38, n = 4). The PDE-inhibitory action of fenchone was further confirmed when its pre-incubation at 3 and 5 mg/mL potentiated and shifted the isoprenaline inhibitory CRCs towards the left, similar to papaverine, whereas the Ca2+ inhibitory-like action of fenchone pretreated tracheal tissues were authenticated by the rightward shift of Ca2+ CRCs with suppression of maximum response, similar to verapamil, a standard Ca2+ channel blocker. Fenchone showed a spasmolytic effect in isolated trachea mediated predominantly by K+ channel activation followed by dual inhibition of PDE and Ca2+ channels. Further in silico molecular docking studies provided the insight for binding of fenchone with Ca2+ channel (−5.3 kcal/mol) and K+ channel (−5.7), which also endorsed the idea of dual inhibition.

A series of novel cannabinoid-type derivatives were synthesized by the coupling of (1S,4R)-(+) and (1R,4S)-(−)-fenchones with various resorcinols/phenols. The fenchone-resorcinol derivatives were fluorinated using Selectfluor and demethylated using sodium ethanethiolate in dimethylformamide (DMF). The absolute configurations of four compounds were determined by X-ray single crystal diffraction. The fenchone-resorcinol analogs possessed high affinity and selectivity for the CB2 cannabinoid receptor. One of the analogues synthesized, 2-(2′,6′-dimethoxy-4′-(2″-methyloctan-2″-yl)phenyl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (1d), had a high affinity (Ki = 3.51 nM) and selectivity for the human CB2 receptor (hCB2). In the [35S]GTPγS binding assay, our lead compound was found to be a highly potent and efficacious hCB2 receptor agonist (EC50 = 2.59 nM, E(max) = 89.6%). Two of the fenchone derivatives were found to possess anti-inflammatory and analgesic properties. Molecular-modeling studies elucidated the binding interactions of 1d within the CB2 binding site.

The method of direct reductive amination of camphor and fenchone was proposed. The most effective reducing agent is iron carbonyl. No ligands or solvents are needed. The stereochemistry of the corresponding products was determined by HMBC, HSQC, and NOESY spectra. The limitations of the method were shown. The reaction of camphor with primary amines led to exclusively exo product, while the reaction of fenchone led to exclusively endo product. The reaction of camphor with cyclic secondary amines led to the mixture of endo and exo isomers. [ABSTRACT FROM AUTHOR]

In this work, the photoionization of chiral molecules by an elliptically polarized, high repetition rate, femtosecond laser is probed. The resulting 3D photoelectron angular distribution shows a strong forward–backward asymmetry, which is highly dependent not only on the molecular structure but also on the ellipticity of the laser pulse. By continuously varying the laser ellipticity, we can observe molecular and enantiomer changes in real time at a previously unseen speed and precision. The technique allows enantiomeric excess of a pure compound to be measured with a 5% precision within 3 s, and a 10‐min acquisition yields a precision of 0.4%. The isomers camphor and fenchone can be easily distinguished, unlike with conventional mass spectrometry. Preliminary results for the pharmaceutically interesting ibuprofen are also given, showing the capability of photoionization as a means of distinguishing larger molecular systems. [ABSTRACT FROM AUTHOR]

The importance of the electric‐dipole—electric‐quadrupole polarizability contribution to the vibrational Raman optical activity (VROA) and dimensionless circular intensity difference spectra of (1S)‐camphor is examined. The spectra are simulated with and without this tensor contribution using density functional theory calculations, and similarity is evaluated for each against the experimental spectra. Careful examination of the comparison between experimental and calculated spectra reveals multiple vibrational bands, in the ~1,130–950 cm−1 region, originating from −C–H bending vibrations that are dominated by the electric‐dipole—electric‐quadrupole polarizability contributions. The similarity overlap analysis also reveals that the similarity overlap between experimental and predicted spectra in the measured spectral range increases, by up to 12%, when electric‐dipole—electric‐quadrupole polarizability contributions are included. The negative VROA band at 1,125 cm−1 in the experimental spectrum of (1S)‐(‐)‐camphor can only be reproduced in the predicted spectra when electric‐dipole—electric‐quadrupole polarizability contribution is included. Investigations on additional molecules indicated that (a) two experimental VROA bands of (1S,4R)‐(+)‐fenchone at ~1,740 and 220 cm−1 originate from dominating electric‐dipole—electric‐quadrupole polarizability contribution and (b) the symmetric and antisymmetric ring deformation modes of dimethyloxirane have dominating electric‐dipole—electric‐quadrupole polarizability contribution. These observations establish the importance of electric‐dipole—electric‐quadrupole polarizability contribution to VROA for the first time. [ABSTRACT FROM AUTHOR]

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We study here how soil bacterial communities of different ecosystems respond to disturbances caused by enrichments with monoterpenes that are common essential oil constituents. We used fenchone, 1,8-cineol and α-pinene, and soils from phrygana, a typical Mediterranean-type ecosystem where aromatic plants abound, and from another five ecosystem types, focusing on culturable bacteria. Patterns of response were common to all ecosystems, but responses themselves were not always as pronounced in phrygana as in the other ecosystems, suggesting that these enrichments are less of a disturbance there. More specifically, soil respiration and abundance of the bacterial communities increased, becoming from below two up to 16 times as high as in control soils (for both attributes) and remained at high levels as long as these compounds were present. Bacteria that can utilize these three compounds as substrates of growth became dominant members of the bacterial communities in the enriched soils. All changes were readily reversible once monoterpene addition stopped. Bacteria with the ability to utilize these monoterpenes as carbon sources were found in soils from all ecosystems, 15 strains in total, suggesting a rather universal presence; of these, six could also utilize the organic pollutants toluene or p-xylene. These results suggest also potential novel applications of monoterpenes in combating soil pollution.

Abstract Background The essential oil from Mesosphaerum sidifolium (L’Hérit.) Harley & J.F.B.Pastore (syn. Hyptis umbrosa), Lamiaceae (EOM), and its major component, have been tested for toxicity and antitumor activity. Methods EOM was obtained from aerial parts of M. sidifolium subjected to hydro distillation, and gas chromatography-mass spectrometry was used to characterize the EOM chemical composition. The toxicity was evaluated using haemolysis assay, and acute toxicity and micronucleus tests. Ehrlich ascites carcinoma model was used to evaluate the in vivo antitumor activity and toxicity of EOM (50, 100 and 150 mg/kg), and fenchone (30 and 60 mg/kg) after 9 d of treatment. Results The EOM major components were fenchone (24.8%), cubebol (6.9%), limonene (5.4%), spathulenol (4.5%), β-caryophyllene (4.6%) and α-cadinol (4.7%). The HC50 (concentration producing 50% haemolysis) was 494.9 μg/mL for EOM and higher than 3000 μg/mL for fenchone. The LD50 for EOM was approximately 500 mg/kg in mice. The essential oil induced increase of micronucleated erythrocytes only at 300 mg/kg, suggesting moderate genotoxicity. EOM (100 or 150 mg/kg) and fenchone (60 mg/kg) reduced all analyzed parameters (tumor volume and mass, and total viable cancer cells). Survival also increased for the treated animals with EOM and fenchone. For EOM 150 mg/kg and 5-FU treatment, most cells were arrested in the G0/G1 phase, whereas for fenchone, cells arrested in the S phase, which represents a blockage in cell cycle progression. Regarding the toxicological evaluation, EOM induced weight loss, but did not induce hematological, biochemical or histological (liver and kidneys) toxicity. Fenchone induced decrease of AST and ALT, suggesting liver damage. Conclusions The data showed EOM caused in vivo cell growth inhibition on Ehrlich ascites carcinoma model by inducing cell cycle arrest, without major changes in the toxicity parameters evaluated. In addition, this activity was associated with the presence of fenchone, its major component.

In this study we sought to elucidate the therapeutic effects of fenchone on constipation-predominant irritable bowel syndrome (IBS-C) and the underlying mechanisms. An IBS-C model was established in rats by administration of ice water by gavage for 14 days. Fenchone increased the reduced body weight, number of fecal pellets, fecal moisture, and intestinal transit rate, and decreased the enhanced visceral hypersensitivity in the rat model of IBS-C. In addition, fenchone increased the serum content of excitatory neurotransmitters and decreased the serum content of inhibitory neurotransmitters in the IBS-C rat model. Meanwhile, western blot and immunofluorescence experiments indicated that fenchone increased the expressions of SCF and c-Kit. Furthermore, compared with the IBS-C model group, fenchone increased the relative abundance of Lactobacillus , Blautia , Allobaculum , Subdoligranulum , and Ruminococcaceae&#95;UCG-008 , and reduced the relative abundance of Bacteroides , Enterococcus , Alistipes , and Escherichia-Shigella on the genus level. Overall, fenchone ameliorates IBS-C via modulation of the SCF/c-Kit pathway and gut microbiota, and could therefore serve as a novel drug candidate against IBS-C.

Copyright of Phytothérapie is the property of John Libbey Eurotext Ltd. and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

In the present study, various phytoconstituents of methanolic extract of Foeniculum vulgare were identified using gas-chromatography mass spectrometry (GC–MS) method. GC–MS method was also applied for the analysis of biomarker fenchone in extract and eight different commercial formulations. The mass of prepared extract and formulations A–D and H (commercial herbal mixtures and commercial extract) used for the analysis of fenchone was 10 g. However, the mass of formulations E–G (soft gelatin capsules) was 100 mg. Fifty seven different phytoconstituents were identified in the methanolic extract of F. vulgare using GC–MS technique. The main compounds identified were trans-anethole (31.49%), 2-pentanone (25.01%), fenchone (11.68%) and benzaldehyde-4-methoxy (8.01%). Several other compounds were also identified in higher amounts and some compounds were identified in trace amounts. Many compounds have been reported for the first time in the methanolic extract of F. vulgare. The amount of fenchone was found to be maximum in plant extract (9.789 mg/g) in comparison with other commercial formulations by the proposed GC–MS technique. In three different commercial formulations (F, G and H), the amount of fenchone was obtained as more than 1.0 mg/g. However, in five different commercial formulations (A, B, C, D and E), the amount of fenchone was recorded as less than 0.1 mg/g. This method could be utilized for the analysis of fenchone contents in the commercial formulations containing fenchone as an active ingredient. The results obtained in this work could be useful in standardization of commercial formulations containing fenchone. [ABSTRACT FROM AUTHOR]

The present experiment has been conducted as factorial to investigate the effect of biofertilizers on seed yield and chemical composition of essential oil from fennel (Foeniculum vulgare L.). The experiment is based on randomized complete block design with three replications and twelve treatments at the Research Farm of the Faculty of Agriculture, University of Urmia, Iran during growing season of 2015-2016. The first factor includes three Landraces of Urmia, Hamdan, and Germany; while the second factor is composed of four biofertilizers, namely bacterial biofertilizers (which supply nitrogen, phosphorus, potassium, and sulfur), mycorrhizal fungi (Rhizophagus irregularis), combination of the two, and the control. Results indicate that application of biofertilizers have enhanced seed yield, colonization percentage, nutrients absorption, essential oil content, essential oil yield, and essential oil composition. Among the treatments, usage of biofertilizers shows a substantial increase in the studied traits than individual consumption. Also there has been a significant difference between the landrace for all quantitative and qualitative traits, with the exception of seed nitrogen. The application of bacterial bio-fertilizers and mycorrhizal fungi has raised seed yield by 21.52%, in comparison to the control. Seed yield of German landrace is 11.38% and 10.15%, higher than Hamedan and Urmia landrace. The main components of the essential oils fennel are Anethol, Fenchone, Limonene, and p-Allylanisole, with the highest amount of the former being found in Urmia landrace when inoculated with mycorrhiza and bacterial biofertilizers. In general, results show that the use of biofertilizers have had a significant effect on improving the quality and quantity of fennel traits. [ABSTRACT FROM AUTHOR]

[Display omitted] • Fenchone oxidation in a JSR at 10 atm and φ = 0.5, 1, and 2. • Development of a detailed kinetic mechanism. • Carbon #1 and #2 are not a favorable sites for H-abstraction reactions. • Benzene formation pathways need further investigation. Increasing fuel energy density constitutes a potential way to reduce engine exhaust carbon emission. Fenchone, a strained ring molecule, could be an interesting candidate. The present study investigates the oxidation of fenchone in a jet-stirred reactor at high pressure (10 atm) between 700 and 1180 K at constant fuel mole fraction and constant residence time of 0.1% and 0.7 s, respectively. Mole fraction profiles were obtained through sonic probe sampling, and analyzed by gas chromatography and Fourier transform infrared spectrometry. More than 30 species were identified and most of them were quantified. Also, a kinetic mechanism is developed in this study and tested against the present conditions showing good agreement. The present mechanism allows to illuminate the major reaction pathways involved in the decomposition routes of the fuel and its primary radicals as well as the formation pathways of the quantified intermediate species. During fenchone oxidation, the carbonyl group is mostly found in CO, CO 2 and formaldehyde while heavier carbonyl species were identified at much lower quantities, indicating decarbonylation occurs early during the oxidation process. Aromatic compounds such as benzene and toluene are formed especially in rich conditions while some potential oxygenated pollutants like methacrolein and acetaldehyde were quantified as well. [ABSTRACT FROM AUTHOR]

Fennel seeds contain a good amount of dietary fiber that is essential for the body. The fiber content helps improve digestion in the body, by facilitating timely breaking down of food molecules that make energy reactions possible. The carcinogenic diseases should be treated at the right stage so that their effect can be curbed or eliminated in the future. This is made possible by the anti-oxidant capabilities of the fennel seeds. Another effect of prevention of free radical reactions by fennel seeds - Neurological diseases are helpfully kept at bay. Cholesterol absorption in the arteries is prevented by the action of the fiber binding to the bile salts. Fiber present in fennel seeds decreases reabsorption of cholesterol, thereby preventing any heart-related diseases. A number of volatile oil compounds like myrcene, fenchone, chavicol, cineole are present in these seeds that assist in digestive, carminative, and antioxidant reactions in the body. Production of Red Blood Cells is enhanced by the consumption of Fennel Seeds. Copper, which is required by the body for the production of red blood cells, is present in these seeds. The growth and development of the body are geared up. Zinc, found in the fennel seeds, promotes regular growth and development. These days, when people face tensions in their day to day lives, it is very important to maintain the blood pressure and keep the heart rate balanced. Fennel Seeds help a lot in this process. The potassium content helps in maintaining the blood pressure and hence the heart rate is also maintained. [ABSTRACT FROM AUTHOR]

The chemical composition and seasonal variation of the essential oil from the aerial parts ofPlectranthus hadiensisgrown during the rainy and summer seasons in the Western Ghats of India was analysed by GC–MS technique. The analysis of rainy season oil led to the identification of 31 compounds, representing 96.4% of the essential oil and the winter season oil led to 25 compounds, representing 95.1% of the oil. Most of the compounds were sesquiterpenes and oxygenated monoterpenes. The major components of the rainy season oil were L-fenchone (30.42%), β-farnesene (11.87%), copaene(11.10%), 2,3-dimethyl hydroquinone (10.78%), α-caryophyllene(8.41%) and piperitone oxide (3.94%) and of the summer season oil are L-fenchone (31.55%), copaene(11.93%), β-farnesene (10.45%), 1,8-naphthalenedione, 8a-ethylperhydro (10.06%), α-caryophyllene(6.36%), piperitone oxide (5.79%) and limonene(4.63%). Antibacterial activity of the essential oil ofP. hadiensis wastested using zone of inhibition and minimum inhibition concentration methods. Both the oils inhibited the organisms and showed the zone of inhibition in the range of 20–35 mm with MIC values between 32 and 64 mg/dL. [ABSTRACT FROM PUBLISHER]

This paper investigated effects of grinding time (GT) and mass of raw material in mill (m s ) on both global SFE yield from Fennel and its main volatile oil content namely Anethol and Fenchone. For this purpose, extractor of SFE equipment was filled with milled Fennel obtained at various values of m s , from 15 g to 35 g, and GT, from 15 s to 20 min. Extractor was subjected to pressure of 200 bar, temperature of 313 K, and supercritical CO 2 flow rate of 1.67 × 10 −4 kg/s for 10 min. Then, extract composition was evaluated by Gas Chromatography (GC) analysis. Moreover, for better understanding how GT and m s affect SFE yield and extract composition, their effects were initially investigated on temperature raising and diameter of Fennel seeds during grinding process. It was found that m s and GT have considerable effects on Anethole and Fenchone content of Fennel extract. [ABSTRACT FROM AUTHOR]

Background: The essential oil from Mesosphaerum sidifolium (L'Hérit.) Harley & J.F.B.Pastore (syn. Hyptis umbrosa), Lamiaceae (EOM), and its major component, have been tested for toxicity and antitumor activity. Methods: EOM was obtained from aerial parts of M. sidifolium subjected to hydro distillation, and gas chromatography- mass spectrometry was used to characterize the EOM chemical composition. The toxicity was evaluated using haemolysis assay, and acute toxicity and micronucleus tests. Ehrlich ascites carcinoma model was used to evaluate the in vivo antitumor activity and toxicity of EOM (50, 100 and 150 mg/kg), and fenchone (30 and 60 mg/kg) after 9 d of treatment. Results: The EOM major components were fenchone (24.8%), cubebol (6.9%), limonene (5.4%), spathulenol (4.5%), β-caryophyllene (4.6%) and α-cadinol (4.7%). The HC50 (concentration producing 50% haemolysis) was 494.9 μg/mL for EOM and higher than 3000 μg/mL for fenchone. The LD50 for EOM was approximately 500 mg/kg in mice. The essential oil induced increase of micronucleated erythrocytes only at 300 mg/kg, suggesting moderate genotoxicity. EOM (100 or 150 mg/kg) and fenchone (60 mg/kg) reduced all analyzed parameters (tumor volume and mass, and total viable cancer cells). Survival also increased for the treated animals with EOM and fenchone. For EOM 150 mg/kg and 5-FU treatment, most cells were arrested in the G0/G1 phase, whereas for fenchone, cells arrested in the S phase, which represents a blockage in cell cycle progression. Regarding the toxicological evaluation, EOM induced weight loss, but did not induce hematological, biochemical or histological (liver and kidneys) toxicity. Fenchone induceddecreaseofASTandALT,suggestingliverdamage. Conclusions: The data showed EOM caused in vivo cell growth inhibition on Ehrlich ascites carcinoma model by inducing cell cycle arrest, without major changes in the toxicity parameters evaluated. In addition, this activity was associated with the presence of fenchone, its major component. [ABSTRACT FROM AUTHOR]

We investigated the wound healing efficacy of theFoeniculum vulgarecompounds, fenchone and limonene, using an excisional cutaneous wound model in rats. An excision wound was made on the back of the rat and fenchone and limonene were applied topically to the wounds once daily, separately or together, for 10 days. Tissue sections from the wounds were evaluated for histopathology. The healing potential was assessed by comparison to an untreated control group and an olive oil treated sham group. We scored wound healing based on epidermal regeneration, granulation tissue thickness and angiogenesis. After day 6, wound contraction with limonene was significantly better than for the control group. Ten days after treatment, a significant increase was observed in wound contraction and re-epithelialization in both fenchone and limonene oil treated groups compared to the sham group. Groups treated with fenchone and with fenchone + limonene scored significantly higher than the control group, but the difference was not statistically significant compared to the olive oil treated group. Our findings support the beneficial effects of fenchone and limonene for augmenting wound healing. The anti-inflammatory and antimicrobial activities of fenchone and limonene oil increased collagen synthesis and decreased the number of inflammatory cells during wound healing and may be useful for treating skin wounds. [ABSTRACT FROM AUTHOR]