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[Objective] This study aimed to improve the added value of the industry of Illicium verum Hook. f. [Methods] The anise oil in I. verum was separated by steam distillation, and the high-purity shikimic acid was obtained from the crude by ion exchange. During the distillation process, parameters such as particle size of I. verum powder, material liquid ratio, and number of steam distillation times were determined. In the separation and purification process of shikimic acid, single factor experiments and response surface methodology were used to optimize the pH of the sample solution, elution flow rate, and volume fraction of HCl of the elution solution. The steam distillation method was compared with the thermal reflux method. [Results] The yield of anise oil reached 13.55% with the particle size of I. verum powder (100 mesh), the material liquid ratio 1:15 (g/mL), and steam distillation twice; In the ion exchange purification process, when the pH of the sample solution was 4.0, the elution flow rate was 27 mL/h, and the volume fraction of HCl of the eluent was 4.40%, the yield and purity of shikimic acid reached 11.05% and 98.50%, respectively; The steam distillation method had more industrial value. [Conclusion] This method achieved the goal of high-yield rate comprehensive extraction of two active ingredients. [ABSTRACT FROM AUTHOR]

Scientific relevance. The State Pharmacopoeia of the Russian Federation, edition XIV, requires the identification of aniseed and fennel fruits by the same thin-layer chromatography (TLC) procedure using Sudan III and menthol. These markers are neither specific nor related to the therapeutic effects of these herbal drug products. The visual interpretation of chromatograms is complicated because of the low intensity of adsorption zones. Moreover, the corresponding compendial monographs do not characterise the adsorption zones specific to each of the plants. The most abundant component in aniseed and fennel essential oils, trans-anethole, would make a better reference standard from a methodological point of view.Aim. This study aimed to optimise the TLC procedure for essential oil determination in herbal drugs and herbal medicinal products of aniseed and fennel fruits and subsequently recommend it for inclusion in the relevant compendial monographs.Materials and methods. The study examined samples from several batches of herbal drugs, including aniseed and common fennel fruits, sourced from Russian manufacturers. The reference standards comprised commercial reagents, including trans-anethole, anise oil, and linalool, as well as fresh essential oils that had been steam distilled from the test samples in a Clevenger apparatus. The study was conducted by TLC. Sample preparation involved using Merck aluminium TLC plates, an IKA KS-501 digital orbital shaker, and a CAMAG Linomat 5 semi-automatic sample application system. The authors heated the plates in either a Binder ED53 drying oven or a CAMAG TLC plate heater. For visualisation, the authors selected a CAMAG TLC VISUALIZER 2 UV imaging and documentation system.Results. The informational and experimental research showed the feasibility of using trans-anethole as an identification reference standard for common anise and fennel fruits. The authors selected the optimal solvent for extracting active substances from the test products (hexane) and a detection reagent for improving visual evaluation of the chromatograms (1% sulfovanillin). The authors established characteristic adsorption zones for differentiating between aniseed and fennel fruits.Conclusions. The optimised procedure identifies the main components in the essential oils of aniseed and fennel fruits with a specific reference standard. This procedure may be recommended for inclusion in draft monographs for the corresponding herbal medicinal products.

The purpose of this study was to compare the antioxidant activity of litsea cubeba oil (LCO), cinnamon oil (CO), anise oil (AO), and eucalyptus oil (EUC) in vitro. The chemical compositions of the essential oils (EOs) were analyzed using gas chromatography-mass spectrometry (GC-MS). The antioxidant activity of the four EOs was evaluated through scavenging DPPH free radicals, chelating Fe2+, scavenging hydroxyl free radicals, and inhibiting yolk lipid peroxidation. The results showed that the major compounds found in LCO, CO, AO, and EUC are citral (64.29%), cinnamaldehyde (84.25%), anethole (78.51%), and 1,8-cineole (81.78%), respectively. The four EOs all had certain antioxidant activity. The ability to scavenge DPPH radical was ranked in the order of LCO > CO > AO > EUC. The hydroxyl radical scavenging ability was ranked in the order of EUC > CO > LCO > AO. The chelating Fe2+ capacity was ranked in the order of EUC > AO > CO > LCO. The yolk lipid peroxidation inhibition ability was ranked in the order of CO > AO > EUC > LCO. In different antioxidant activity assays, the antioxidant activity of the EOs was different. It was speculated that the total antioxidant activity of an EO may be the result of the joint action of different antioxidant capacities. [ABSTRACT FROM AUTHOR]

Following a request from the European Commission, EFSA was asked to deliver a scientific opinion on the safety and efficacy of anise oil and anise tincture obtained from the fruit of Pimpinella anisum L., when used as sensory additives. The use of the anise oil at the proposed use level in complete feed of 1.9 mg/kg for laying hens and 5 mg/kg for horses was considered of low concern. The EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) had no safety concern when anise oil is used at the proposed use levels of 1.5 mg/kg for chickens for fattening and at 1.7 mg/kg for turkeys for fattening. The use of anise tincture at the proposed conditions of use was considered of low concern in dogs, cats, horses and laying hens, and of no concern in chickens for fattening. The use of the additives up to the highest level in feed which was considered of low or no concern for target animals was also expected to be of no concern for consumers. The additives under assessment should be considered as irritants to skin and eyes, and as dermal and respiratory sensitisers. Due to the high concentration of estragole (≥ 1%), anise oil is classified as suspected of causing genetic defects and of causing cancer and should be handled accordingly. When handling anise tincture, exposure of unprotected users to estragole may occur. Therefore, to reduce the risk, the exposure of the users should be minimised. The use of these additives in animal feed was not expected to pose a risk to the environment. Since the fruit of P. anisum and its preparations are recognised to flavour food and their function in feed would be the same, no further demonstration of efficacy was considered necessary. [ABSTRACT FROM AUTHOR]

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Nine essential oils from fennel (seeds and herbs) and anise (seeds) from different origins were analysed for density, refractive index and for a complete composition through GC-MS and 1H-NMR-spectroscopy. Anethole was the main compound identified in fennel and anise essential oils. Anethole content varied between 30 – 90% in fennel oils and between 80 – 99% in anise oils; anethole is often used as flavouring substance in foods with a good antimicrobial activity also. A positive correlation was found between anethole content determined by GC-MS and 1H-NMR (r = 0.8567 for fennel oils and r = 0.6986 for anise oils). The results showed different levels of anethole in oils (values ranged between 30.66 % and 99.24 %). Electronic nose was a very good and rapid method for discrimination of essential oils based on PCA (Principal Component Analysis) with discrimination index above 90 for both essential oils.

The two-spotted spider mite, Tetranychus urticae, also known as the red spider, is one of the most harmful pests in agriculture and causes large losses of many crops. These mites have rapidly developed a resistance to many chemical pesticides in recent years. In this study, the essential oil of seeds of the anise plant (Pimpinella anisum) was extracted by hydrodistillation, and the chemical composition of the oil was analyzed. The antioxidant activity of the volatile oil was determined by the DPPH radical scavenging assay. The acaricidal activity of the anise oil, a natural acaricide, was evaluated for its ability to protect green bean plants from mite injury. The two-spotted spiders were spread on green bean seedlings for 1 week; then, different plants were sprayed with different concentrations of anise oil (10, 20, 30, or 40 µL/L). Our results revealed that anethole was the major component of anise oil, at 53.23%. The acaricidal effect of the various concentrations on T. urticae was recorded after 24, 48, and 72 h of treatment. Our findings suggest that anise oil showed significant acaricidal activity against T. urticae in a dose- and time-dependent manner. Anise oil at a concentration of 40 µL/L killed 96.0% of the red spiders after 72 h. Also, all concentrations of anise oil inhibited acetylcholinesterase, and the spiders’ protease activity declined when the plants were treated with 30 or 40 µL/L of anise oil. The concentrations of 10 and 20 µL/L did not significantly affect the protease activity of T. urticae mites. We can conclude that anise oil exhibited acaricidal activity against T. urticae and that this was highly correlated with the inhibition of acetylcholinesterase and protease activities in the mites.

Anesthetics have been important in ornamental fishes for transport and restriction of behaviors as well as for surgical applications and studies in science. Also, more economical and appropriate anesthetics can be common choice for these stiuations. In the study, a total of two hundred and fifty two zebrafish (forty two females and forty two males in each group) divided in three groups were studied as group A (Anise oil); group T (Thyme oil); group M (Mint oil). Anesthesia intake and lethal dose values were determined by following the anesthetic entry and recovery times. There was no anesthetic effect in group A, while anesthetic effects occured in groups T and M in concentrations 1, 5, 10, 20 and 30 mg/l. Similarity was found in groups T and M in terms of anesthesia entry and recovery times (P>0.05). Nevertheless, no mortality occured in group M. However, 5mg/l tyme oil anesthesia was determined to cause 50% mortality in male fishes (group T). It was also observed that mint oil has an anesthetic effect on zebrafish with increasing doses determined by anesthesia entry and recorvery times (group M, P<0.05). Thereby, mint oil may be an alternative herbal anesthetic agent for zebrafish. However, further studies are neccessary to show the herbal anesthetics effect on ornamental fishes. [ABSTRACT FROM AUTHOR]

Plants are often simultaneously exposed to diverse environmental stresses, and can tune suitable responses to them through hormones. Salicylic acid (SA) and jasmonic acid (JA) signaling pathways are known to enhance resistance against heat stress and tomato yellow leaf curl Thailand virus (TYLCTHV) infection. However, there is limited information regarding alternative natural priming agents against heat stress and viruses. In this study, two plant-derived priming agents, eugenol and anise oil, were tested for their roles in conferring thermotolerance and virus resistance in tomato plants. Under heat stress, the survival rates and average fresh weight were higher in plants treated with eugenol or anise oil than in control plants. These two priming agents were further tested for antiviral activities. After TYLCTHV infection, the disease incidence and relative abundance of TYLCTHV were lower in anise oil- and eugenol-treated plants than in control plants. Further analyses revealed that a few SA, JA, and RNA silencing genes were enhanced in the former. Moreover, SA, JA, and H2O2 contents increased considerably after eugenol and anise oil treatments. Our findings imply that anise oil and eugenol initiated SA- and JA-mediated defenses to promote thermotolerance and antiviral responses of tomato plants.

Plants are often simultaneously exposed to diverse environmental stresses, and can tune suitable responses to them through hormones. Salicylic acid (SA) and jasmonic acid (JA) signaling pathways are known to enhance resistance against heat stress and tomato yellow leaf curl Thailand virus (TYLCTHV) infection. However, there is limited information regarding alternative natural priming agents against heat stress and viruses. In this study, two plant-derived priming agents, eugenol and anise oil, were tested for their roles in conferring thermotolerance and virus resistance in tomato plants. Under heat stress, the survival rates and average fresh weight were higher in plants treated with eugenol or anise oil than in control plants. These two priming agents were further tested for antiviral activities. After TYLCTHV infection, the disease incidence and relative abundance of TYLCTHV were lower in anise oil- and eugenol-treated plants than in control plants. Further analyses revealed that a few SA, JA, and RNA silencing genes were enhanced in the former. Moreover, SA, JA, and H2O2 contents increased considerably after eugenol and anise oil treatments. Our findings imply that anise oil and eugenol initiated SA- and JA-mediated defenses to promote thermotolerance and antiviral responses of tomato plants. [ABSTRACT FROM AUTHOR]

The effect of various thermal treatments (electric oven, microwave) and g-irradiation at three doses (6, 8 and 10 KGy) on the composition of volatile and non-volatile of anise essential oil and also their antioxidant properties were considered. The hydrodistilled oil (HD) of control and treated samples were subjected to gas chromatography–mass spectrometry (GC/MS) analysis. The volatile profile of raw HD oil of anise consisted mainly of transe-anethole (79.68%) followed by hexahydrofarnesyl acetone (6.95%), para-anisaldehyde (5.49%); g-himachalene (2.53%) and estragole (0.76%). Although the effect of roasting didn’t cause significant changes in the total yield of major compounds of HD anise oil which are phenylpropanoid derivative (transe anethole , para-anisaldehyde, cis-anethole and estragole (=methylchavicol), it is found that gamma irradiation revealed the same behavior at the 10 KGy irradiated sample but decrease the total yield of these compounds in 6.8 KGy irradiated sample compared to control one. also the thermal and g- irradiation caused drastic increase in the total yield of sesquiterpenes whereas decreased oxygenated compounds in all samples under investigation compared to control one. Such changes affected the antioxidant activity of the treated samples 1.1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging as well as β-carotene bleaching test against butylated hydroxy toluene (BHT). The strongest effect of reduction of DPPH radical as well as the highest inhibiting effect of the oxidation of linoleic acid and the subsequent bleaching of β-carotene was by 8 KGy irradiated sample which comprised (84.57%±1.43); (85.21% ± 0.12) respectively, in comparison to BHT (98% ± 0.0) at the same concentration 30 µg/mL besides all samples under investigation revealed high antioxidant activities due to their high content of phenylpropanoid and oxygenated compounds. These confirmed by total phenolic content. High performance liquid chromatography (HPLC) method was used for the analysis of phenolic compounds in the selected sample. Polyphenolic compounds were analysed on C18 Reversed Phase (RP) HPLC. A total of 9 phenolic compounds were identified, the obtained results showed that the predominant compound was P-qumaric acid (43.36%) followed by ferulic acid (21.06%).

The objective of this study was to evaluate antimethanogenic activity of eucalyptus oil (EUC) and anise oil (ANI) in vitro and in vivo using sheep as a model. In vitro study was conducted using batch culture technique, each of EUC and ANI were added at 0, 50, 100, 200, or 400 mg/L of fermentation media with substrate containing 60% corn-based concentrate and 40% hay (DM basis). Total gas production (GP) linearly (P < 0.01) decreased with increasing ANI, whereas the GP was not affected with EUC addition. Supplementation of ANI and EUC linearly (P < 0.01) decreased total methane production and methane proportion in total gas. Total VFA and ammonia-nitrogen (NH3- N) concentration linearly (P < 0.01) decreased with increasing ANI supplementation. For the in vivo study, a replicated 3 × 3 Latin square design was carried out using six ruminal cannulated Du Han hybrid sheep (BW, 64.5 ± 8.56 kg) with 22 d of periods. Three treatments were control diet (consisted of 60% corn-based concentrate and 40% Chinese wildrye hay), EUC (control diet supplemented with 0.5 g EUC/d per head), and ANI (control diet supplemented with 0.5 g ANI/d per head). Each period consisted of 14 d for adaption and 8 d for sampling and data collection. Supplementation of EUC and ANI had no effects on feed intake and apparent nutrient digestibility. Ruminal NH3-N concentration was greater with EUC (P < 0.01) and ANI (P = 0.03) than control. Urinal allantoin output was less (P < 0.05) in sheep fed EUC and ANI than control animals. Methane emission was less (P = 0.03) in sheep fed ANI than sheep fed EUC, and a tendency of decrease for an eduction in this parameter was found for sheep fed with ANI (P = 0.08) compared to control. The in vitro results indicated a reduction of methane production with both EUC and ANI but in a dose-dependant manner. Supplementation of ANI tended to reduce ruminal methane production without adversely affecting rumen fermentation characteristics, nutrient intake, and digestibility, suggesting potential inhibition of ruminal methane emission in sheep supplemented with ANI. [ABSTRACT FROM AUTHOR]

Anise oil (AO) is a phytochemical with antibiotic properties and it reduces the growth of Clostridium perfringens in vitro, which is the main causal agent of necrotic enteritis. A series of battery experiments was conducted to determine an AO dosage to feed to broilers and its effect during 2 C. perfringens challenges, and a floor pen experiment to determine its effect in performance. Anise oil linearly reduced (P < 0.05) ADFI and ADG, but feeding broilers 500 to 2,000 mg/kg of AO resulted in similar performance with positive control (PC) fed broilers. Broilers were challenged on d 10 (Experiment 2) or on d 10 and 13 (Experiment 3). Broilers fed AO had lower (P < 0.05) ADFI and ADG compared with broilers fed PC from zero to 18 d (Experiment 2). Growth performance of broilers fed AO was not affected (P > 0.05) during Experiment 3. In both challenges, the jejunum of broilers fed AO had fewer and milder (P < 0.05) lesions compared with broilers fed PC or negative control (NC) diets. In a floor pen trial, 1,000 mg/kg of AO was fed to broilers from zero to 42 days. Broilers fed AO or PC had similar (P > 0.10) growth performance for the entire trial. Broilers fed PC or AO had greater ADG (P < 0.05) and tended (P = 0.07) to be heavier than broilers fed NC at the end of the trial. Breast yield percentage was similar (P > 0.10) among broilers fed any of the dietary treatments. Residues of AO were not present at detectable levels in breast meat. [ABSTRACT FROM AUTHOR]

The effect of various thermal treatments (electric oven, microwave) and -irradiation at three doses (6, 8 and 10 KGy) on the composition of volatile and non-volatile of anise essential oil and also their antioxidant properties were considered. The hydrodistilled oil (HD) of control and treated samples were subjected to gas chromatography– mass spectrometry (GC/MS) analysis. The volatile profile of raw HD oil of anise consisted mainly of transe-anethole (79.68%) followed by hexahydrofarnesyl acetone (6.95%), paraanisaldehyde (5.49%); -himachalene (2.53%) and estragole (0.76%). Although the effect of roasting didn’t cause significant changes in the total yield of major compounds of HD anise oil which are phenylpropanoid derivative (transe anethole , paraanisaldehyde, cis-anethole and estragole (=methylchavicol), it is found that gamma irradiation revealed the same behavior at the 10 KGy irradiated sample but decrease the total yield of these compounds in 6.8 KGy irradiated sample compared to control one. also the thermal and - irradiation caused drastic increase in the total yield of sesquiterpenes whereas decreased oxygenated compounds in all samples under investigation compared to control one. Such changes affected the antioxidant activity of the treated samples 1.1-diphenyl-2- picrylhydrazyl (DPPH) free radical scavenging as well as β-carotene bleaching test against butylated hydroxy toluene (BHT). The strongest effect of reduction of DPPH radical as well as the highest inhibiting effect of the oxidation of linoleic acid and the subsequent bleaching of β-carotene was by 8 KGy irradiated sample which comprised (84.57%±1.43); (85.21% ± 0.12) respectively, in comparison to BHT (98% ± 0.0) at the same concentration 30 μg/mL besides all samples under investigation revealed high antioxidant activities due to their high content of phenylpropanoid and oxygenated compounds. These confirmed by total phenolic content. High performance liquid chromatography (HPLC) method was used for the analysis of phenolic compounds in the selected sample. Polyphenolic compounds were analysed on C18 Reversed Phase (RP) HPLC. A total of 9 phenolic compounds were identified, the obtained results showed that the predominant compound was Pqumaric acid (43.36%) followed by ferulic acid (21.06%). [ABSTRACT FROM AUTHOR]

Abstract: The effect of heat curing (30–100 °C) on the antifungal activity of rubberwood impregnated with anise oil and garlic oil (10–100 μl ml−1) against Aspergillus niger was examined. Essential oil constituents left within the rubberwood after the heat curing and after incubation were analyzed by GC–MS. Response surface methodology (RSM) with a central composite face-centered (CCF) design was employed to evaluate the time needed for initiation of mold growth. The mathematical models containing only significant parameters (p ≤ 0.05) as functions of treatment temperature and essential oil concentration were obtained. Heat curing adversely and positively influenced the antifungal activities of anise oil and garlic oil, respectively. Such thermal effect was more pronounced at a higher concentration of essential oil. Decomposition of trans-anethole and estragole in anise oil and formation of diallyl disulfide in garlic oil by heat was proposed as the agent responsible for temperature dependencies of the essential oil antifungal activities observed. [Copyright &y& Elsevier]

Abstract: The antifungal activities of cinnamon oil, clove oil, anise oil, and peppermint oil, and their main components (cinnamaldehyde, eugenol, trans-anethole, and menthol, respectively) against molds identified from areca palm leaf sheath (Mucor dimorphosporus, Penicillium sp., Aspergillus niger, and Rhizopus sp.) were investigated. An agar dilution method was employed to determine the minimum inhibitory concentration (MIC) of essential oils and their main components. Zone inhibition tests and the inhibitory effect of the leaf sheath dip-treated with essential oils against those molds were examined. Major components of essential oils on the leaf sheath during storage were quantified by gas chromatography analysis. The MIC values of essential oils on agar and on the leaf sheath were identical. With an MIC of 50μgml−1, cinnamon oil had the strongest inhibitory effect. At their MICs the oils were capable of providing protection against mold growth on the leaf sheath for at least 12 weeks during storage at 25°C and 100% RH. Scanning electron microscope examination showed that essential oils prevented spore germination. Except for menthol in peppermint oil, the main components of the essential oils, which were fairly stable over the storage period, largely contributed to the antifungal activity. [ABSTRACT FROM AUTHOR]

The two-spotted spider mite, Tetranychus urticae, also known as the red spider, is one of the most harmful pests in agriculture and causes large losses of many crops. These mites have rapidly developed a resistance to many chemical pesticides in recent years. In this study, the essential oil of seeds of the anise plant (Pimpinella anisum) was extracted by hydrodistillation, and the chemical composition of the oil was analyzed. The antioxidant activity of the volatile oil was determined by the DPPH radical scavenging assay. The acaricidal activity of the anise oil, a natural acaricide, was evaluated for its ability to protect green bean plants from mite injury. The two-spotted spiders were spread on green bean seedlings for 1 week; then, different plants were sprayed with different concentrations of anise oil (10, 20, 30, or 40 µL/L). Our results revealed that anethole was the major component of anise oil, at 53.23%. The acaricidal effect of the various concentrations on T. urticae was recorded after 24, 48, and 72 h of treatment. Our findings suggest that anise oil showed significant acaricidal activity against T. urticae in a dose- and time-dependent manner. Anise oil at a concentration of 40 µL/L killed 96.0% of the red spiders after 72 h. Also, all concentrations of anise oil inhibited acetylcholinesterase, and the spiders' protease activity declined when the plants were treated with 30 or 40 µL/L of anise oil. The concentrations of 10 and 20 µL/L did not significantly affect the protease activity of T. urticae mites. We can conclude that anise oil exhibited acaricidal activity against T. urticae and that this was highly correlated with the inhibition of acetylcholinesterase and protease activities in the mites. [ABSTRACT FROM AUTHOR]

Abstract: The antifungal activities of anise oil, lime oil, and tangerine oil against molds identified from rubberwood surfaces (Aspergillus niger, Penicillium chrysogenum, and Penicillium sp.) were investigated. The broth dilution method was employed to determine the minimal inhibitory concentration (MIC) and minimal fungicidal concentration (MFC) using the concentration of essential oils between 20 and 200μlml−1. Inhibitory effects of the essential oils against those molds on rubberwood were also examined by means of the dip treatment and vacuum impregnation treatment. It was found that the MIC and MFC values for each treatment on agar were identical for all conditions examined. Anise oil was the strongest inhibitor with the MIC and MFC of 40μlml−1 against Penicillium sp. and A. niger, and 60μlml−1 against P. chrysogenum. Lime oil and tangerine oil were also effective against those molds at higher concentrations of 100–180μlml−1. All essential oils at the MIC and MFC provided a protection from mold growth on rubberwood for at least 12 weeks at storage conditions of 30°C with 100% RH. [Copyright &y& Elsevier]

Abstract: Essential oils from anise, hyssop, thyme, ginger, camomile and sandalwood were screened for their inhibitory effect against herpes simplex virus type 2 (HSV-2) in vitro on RC-37 cells using a plaque reduction assay. Genital herpes is a chronic, persistent infection spreading efficiently and silently as sexually transmitted disease through the population. Antiviral agents currently applied for the treatment of herpesvirus infections include acyclovir and its derivatives. The inhibitory concentrations (IC50) were determined at 0.016%, 0.0075%, 0.007%, 0.004%, 0.003% and 0.0015% for anise oil, hyssop oil, thyme oil, ginger oil, camomile oil and sandalwood oil, respectively. A clearly dose-dependent virucidal activity against HSV-2 could be demonstrated for all essential oils tested. In order to determine the mode of the inhibitory effect, essential oils were added at different stages during the viral infection cycle. At maximum noncytotoxic concentrations of the essential oils, plaque formation was significantly reduced by more than 90% when HSV-2 was preincubated with hyssop oil, thyme oil or ginger oil. However, no inhibitory effect could be observed when the essential oils were added to the cells prior to infection with HSV-2 or after the adsorption period. These results indicate that essential oils affected HSV-2 mainly before adsorption probably by interacting with the viral envelope. Camomile oil exhibited a high selectivity index and seems to be a promising candidate for topical therapeutic application as virucidal agents for treatment of herpes genitalis. [Copyright &y& Elsevier]

The neolignan-type substance 2,4-dimethyl-3,5-bis(4’-methoxyphenyl) tetrahydrofuran is presented as a new forensic marker compound for the peracid oxidation of anethole. It is hypothesized that the formation of a stable intermediary carbocation in the hydrolysis reaction of anethole epoxide is not only responsible for the presence of 1,2-diols (and its esters) and 4-methoxyphenyl-2-propanone (PMP2P) but can also be the cause for the creation of this neolignan impurity due to interaction with anethole itself. Moreover, the applicability of this new forensic marker is demonstrated by its retrieval in clandestinely manufactured 4-methoxyamphetamine (PMA) preparations. [Copyright &y& Elsevier]

These days, MDMA is one of the most popular drugs of abuse. Due to its illegality, MDMA and its chemical precursors are watched by governmental organizations in many countries. To avoid conflicts with legal instances, underground chemists have tried to market several new unregulated amphetamine analogues, such as 4-MTA. Para-methoxyamphetamine (PMA), on the other hand, is regulated by law but its precursors are easily obtained since they are cheap and unwatched. This article presents such a case, namely the large scale synthesis of PMA using anethole, a main constituent of anise oil, as precursor. Anethole has been converted to its phenyl acetone analogue via peracid oxidation, while PMA itself has been synthesized using this ketone as precursor in the Leuckart synthesis. The synthesis of PMA using anethole as starting product has been investigated applying GC/MS and GC-HSPME/MS techniques, hereby discovering new specific (4-methoxyphenol) and already identified synthesis impurities (4-methyl-5-(4-methoxyphenyl)pyrimidine, N-(β-4-methoxyphenylisopropyl)-4-methoxybenzyl methyl ketimine, 1-(4-methoxyphenyl)-N-(2-(4-methoxyphenyl)-1-methylethyl-2-propanamine, 1-(4-methoxyphenyl)-N-methyl-N-(2-(4-methoxyphenyl)-1-methylethyl-2-propanamine, N-(β-4-methoxyphenylisopropyl)-4-methoxybenzaldimine). The new impurity 4-methoxyphenol is specific for the application of a peracid oxidation method where anethole is used as precursor. [Copyright &y& Elsevier]

Anise oil was prepared in its nanoemulsion form to facilitate the penetration of microbial walls, causing microbe mortality. The penetration occurred easily owing to the reduction in its size (nm). Nanoemulsions with different concentrations of anise oil were prepared using lecithin as an emulsifying agent with the aid of an ultra-sonification process. Their morphological and chemical properties were then characterized. The promising constituents were l-Menthone (11.22%), Gurjunene (6.78%), Geranyl acetate (4.03%), Elemene (3.93%), Geranyl tiglate (3.53%), geraniol (3.48%), linalool (0.17%) as well as camphene (0.12%). Different concentrations of prepared anise oil in micro and nanoemulsions were tested as antimicrobial agents against Gram-positive bacteria (Staphylococcus aureus), Gram-negative bacteria (Escherichia coli), yeast (Candida albicans) and fungi (Asperigillus niger). The findings illustrated that the anise oil-based nanoemulsion exhibited better results. Different biochemical and biological evaluations of anise oil nanoemulsions were conducted, including determining killing times, antioxidant activities (using three different methods), and total phenolics. A trial to estimate the mode of action of anise oil-based nanoemulsion as an antimicrobial agent against S. aureus and C. albicans was performed via studying the release of reducing sugars and protein and conducting scanning electron microscopy. [ABSTRACT FROM AUTHOR]

• Supplementation of anise, clove and thyme essential oils (EO) improved digestibility with no effect on intake and milk yield. • Supplementation of EO improved rumen fermentation. • Supplementation of EO increased milk fat yield, fat content and concentrations of C18:3 n-3, C18:4 n-3 and n-3 fatty acids (FA) compared with control diet. • Supplementation of EO decreased the concentrations of C18:3 n-6, C20:4 n-6 and n-6 FA in the milk compared with control diet. • The clove and thyme group tended to increase polyunsaturated FA (PUFA) compared with anise group. The present study evaluated the effects of essential oil (EO) from anise (AO), clove (CO) and thyme (TO) on the performance of lactating Shame goats. Eight lactating Shame goats with average body weight 34.90 ± 0.9 kg and 3 years old were randomly assigned to four treatments in a duplicated 4 × 4 Latin square design, with four periods of 22 days. In each period, the goats were adapted to the treatments for 15 days and the remaining 7 days was used for sample collection. Goats were fed a basal diet without supplementation (control) or supplemented with anise (AO), thyme (TO) or clove (CO) at a daily dose of 2 mL/head/d. Feed intake was not affected by EO supplementations. Digestibility of organic matter, ether extract and acid detergent fibre was higher (P < 0.05) with EO supplementations when compared with the control. Supplementations of EO had no effect on milk (g/d) yield, protein and lactose, as well as the composition (g/kg) of protein and lactose. Fat yield (g/d) and fat content (g/kg) were greater (P < 0.05) in EO supplemented goats versus those on the control diet. Compared with control, ruminal ammonia-N was not affected whereas, ruminal pH was increased (P = 0.02) with EO supplementations. Rumen total volatile fatty acid concentration and molar proportion of acetate (C2) were higher (P < 0.05) in goats fed CO and TO compared to control, whereas propionate (C3) and butyrate (C4) and C2:C3 proportions were unchanged with EO inclusion. With the exception of a decrease (P = 0.05) in blood urea nitrogen (BUN) with EO supplementations, other blood parameters were not affected. Milk C8 and C12 fatty acids (FA) were lower (P < 0.05) with EO supplementations compared with control. Composition of unsaturated and monounsaturated FA was higher (P < 0.05) and polyunsaturated FA was decreased (P < 0.05) with EO supplementations compared with control. Proportions of C18:1 n-9 C18:3 n-3 and n-3 FA were increased (P < 0.05) and proportions of C18:3 n-6 C20:4 n-6 and n-6 FA were decreased (P < 0.05) in goats fed EO compared to the control group. Overall, all three EOs tested in this study had beneficial effects on digestion, rumen fermentation parameters and milk composition including milk FA profile. Supplementation of CO and TO tended to increase PUFA concentration in the milk which supports their recommendation in the diet of lactating ruminants. [ABSTRACT FROM AUTHOR]

• Different doses of a mixture of anise and capsicum oils were tested in vitro and in vivo. • Doses above 200 mg/d decreased the acetate to propionate ratio and increased the butyrate proportion. • Doses above 375 mg/d increased dry matter intake. • Effects of the two oils were additive. Three doses (5, 15 and 30 mg/l in experiment 1; and 100, 250 and 500 mg/d in experiment 2) and three proportions of anise oil (A) and capsicum oleoresin (C; 1A:3C, 2A:2C and 3A:1C) were used to evaluate their effects on rumen microbial fermentation. In experiment 1, a completely randomized block in vitro batch fermentations were conducted in triplicate and in two periods. A 100 ml of a 1:9 ruminal fluid-to-buffer solution were introduced into polypropylene tubes supplied with 0.8 g of DM of a 1:9 forage:concentrate diet (160 g/kg CP, 220 g/kg aNDFom) and incubated for 48 h at 39 °C. Samples were collected to determine fermentation fluid pH and the concentration of volatile fatty acids (VFA) and ammonia N (NH 3 N). In experiment 2, twelve Holstein heifers (229 ± 24 kg body weight) fitted with ruminal trocars were used in three 4 × 4 Latin squares design. Heifers were fed the same diet as in Experiment 1. Each Latin square was assigned to one of the three doses and animals within square to the different mixes of A and C. Each period consisted of 15 d for adaptation and 9 d for sampling. On d 16–21, dry matter intake was measured. On d 22–24 ruminal content was sampled at 0, 4, 8 and 12 h after feeding to determine ruminal pH and the concentrations of VFA, large peptide (LPep), small peptides plus amino acid (SPep + AA) and NH 3 N. Statistical differences were declared at P < 0.05. In Experiment 1 at 15 and 30 mg/l, 3A:1C increased ruminal pH. At 15 mg/l, 3A:1C, and at 30 mg/l 2A:2C and 3A:1C reduced the acetate (Ac) proportion, the acetate to propionate (Ac:P) ratio, and the concentration of branch chained VFA (BCVFA) and NH 3 N; and increased the propionate (P) and butyrate (B) proportions. In Experiment 2 at 250 mg/d and 500 mg/d, 3A:1C reduced the A proportion, the Ac:P ratio, and the concentration of BCVFA and NH 3 N; and increased the P proportion and the SPep + AA N concentration. At 500 mg/d, 1A:3C increased concentrate DM intake and SPep + AA N concentration; and reduced the BCVFA and NH 3 N concentrations. At 500 mg/d, 2A:2C reduced the concentration of total VFA, BCVFA and NH 3 N, and the Ac proportion; and increased the proportion of P and the SPep + AA N concentration. Analysis of results suggests that the changes in rumen fermentation profile are attributed to anise at doses above 187.5 mg/d, and the increase in DM intake is attributed to capsicum oleoresin at doses above 375 mg/d. [ABSTRACT FROM AUTHOR]