SciCombinator

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Concept: Anethole

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Anethole [1-methoxy-4-(1-propenyl)benzene] occurs naturally as a major component of the essential oil of star anise (Illicium verum Hook.f., family Illiciaceae), comprising more than 90 % of its volatile components. Studies showed that this substance has antioxidant, antibacterial, antifungal, and anesthetic properties. In this study, the anti-inflammatory properties of anethole in animal models of nonimmune acute inflammation such as croton oil-induced ear edema and carrageenan-induced pleurisy were investigated. The investigated parameters were edema formation, leukocyte migration, and inflammatory mediators involved. Oral administration of anethole at a dose of 250 and 500 mg/kg reduced both the volume of pleural exudates and the number of migrated leukocytes. Levels of nitric oxide (NO) and prostaglandins (PGE(2)) in the inflammatory exudate were reduced by treatment with anethole, but levels of tumor necrosis factor-α and interleukin-1β were not significantly altered. In ear edema, the oral treatment with anethole inhibited the formation of exudate and the activity of myeloperoxidase, but not after topical administration. These results suggest that the anethole may be effective in controlling some nonimmune acute inflammation-related disease, probably by an inhibitory action on production and/or release of PGE(2) and NO.

Concepts: Immune system, Inflammation, Anti-inflammatory, Anise, Star anise, Anethole, Illicium, Austrobaileyales

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A new, practical, rapid, and high-yielding process for the pressurized hot water extraction (PHWE) of multigram quantities of shikimic acid from star anise (Illicium verum) using an unmodified household espresso machine has been developed. This operationally simple and inexpensive method enables the efficient and straightforward isolation of shikimic acid and the facile preparation of a range of its synthetic derivatives.

Concepts: Absinthe, Anise, Japanese star anise, Star anise, Anethole, Illicium, Austrobaileyales, Shikimic acid

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Aphids are an important agricultural pest that not only damage plants by suction, but can also transmit a number of economically important plant viruses. Protection against aphids is based on the use of synthetic insecticides. However, these products can be dangerous for non-target organisms. Therefore, it is important to develop new, environmentally safe plant protection methods.In this study, we have tested an essential oil (EO) obtained from Foeniculum vulgare for the mortality of Myzus persicae, an important polyphagous pest, its natural predator Harmonia axyridis, and Eisenia fetida as a representative of soil organisms. The EO, with its major compounds trans-anethole (67.9%) and fenchone (25.5%), was found to provide excellent efficacy against M. persicae (LC50 = 0.6 and LC90 = 2.4 mL L-1) while not causing any significant mortality of the tested non-target organisms. On the contrary, application of an insecticide based on the active substance alpha-cypermethrin not only caused mortality in the aphids, but also had a fatal negative effect on both the non-target organisms we tested, resulting in their high mortality.Our results indicate very high prospects for using the essential oil from F. vulgare in the development of environmentally safe botanical insecticides designed for plant protection against aphids.

Concepts: Virus, Plant, Hemiptera, Essential oil, Oil, Aphididae, Anise, Anethole

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In this study, biological properties of the essential oil isolated from seeds of Foeniculum vulgare (F. vulgare) were evaluated. GC-MS analysis revealed Trans-Anethole (80.63%), L-Fenchone (11.57%), Estragole (3.67%) and Limonene (2.68%) were the major compounds of the essential oil. Antibacterial activity of the essential oil against nine Gram-positive and Gram-negative strains was studied using disc diffusion and micro-well dilution assays. Essential oil exhibited the antibacterial activity against three Gram-negative strains of Pseudomonas aeruginosa, Escherichia coli, and Shigella dysenteriae. The preliminary study on toxicity of seed oil was performed using Brine Shrimp lethality test (BSLT). Results indicated the high toxicity effect of essential oil (LC50 = 10 μg/mL). In vitro anticancer activity of seed oil was investigated against human breast cancer (MDA-Mb) and cervical epithelioid carcinoma (Hela) cell lines by MTT assay. Results showed the seed oil behave as a very potent anticancer agent with IC50 of lower than 10 μg/mL in both cases.

Concepts: Cancer, Bacteria, Microbiology, Escherichia coli, Gram negative bacteria, Anise, Fennel, Anethole

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The essential oil of fennel (Foeniculum vulgare) is rich in lipophilic secondary metabolites, which can easily cross cell membranes by free diffusion. Several constituents of the oil carry reactive carbonyl groups in their ring structures. Carbonyl groups can react with amino groups of amino acid residues in proteins or in nucleotides of DNA to form Schiff’s bases. Fennel essential oil is rich in anise aldehyde, which should interfere with molecular targets in cells. The aim of the present study was to investigate the chemical composition of the essential oil of fennel growing in Tajikistan. Gas chromatographic-mass spectrometric analysis revealed that the main components of F. vulgare oil were trans-anethole (36.8%); α-ethyl-p-methoxy-benzyl alcohol (9.1%); p-anisaldehyde (7.7%); carvone (4.9%); 1-phenyl-penta-2,4-diyne (4.8%) and fenchyl butanoate (4.2%). The oil exhibited moderate antioxidant activities. The potential cytotoxic activity was studied against HeLa (human cervical cancer), Caco-2 (human colorectal adenocarcinoma), MCF-7 (human breast adenocarcinoma), CCRF-CEM (human T lymphoblast leukaemia) and CEM/ADR5000 (adriamycin resistant leukaemia) cancer cell lines; IC50 values were between 30-210 mg L(-1) and thus exhibited low cytotoxicity as compared to cytotoxic reference compounds.

Concepts: Cell, Cancer, Amino acid, Metabolism, Apiaceae, Anise, Fennel, Anethole

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A new water soluble zinc-aminolevulinic acid nano complex (n[Zn(ALA)2 ]), which characterized by TEM, IR and EDX spectra, has been prepared via sonochemical method under green conditions in water. In the current study, the effectiveness of foliar Zn amendment using synthetic Zn-ALA nano complex, as a new introduced Zn-fertilizer here, was evaluated. As the model plant, Pimpinella anisum, the most valuable spice and medicinal plant grown in warm regions, was used. By using zinc nano complex, further twenty compounds were obtained in the essential oil of anise plants. Application of 0.2% (w/v) Zn-ALA nano complex increased the levels of E-Anethole, β-Bisabolene, Germacrene D, Methyl chavicol and α-Zingiberene in the essential oil. Nano Zn complex at the rate of 0.2% induced considerable high phenolic compounds and zinc content of shoots and seeds. Chlorogenic acid (CGA) had the highest level between four detected phenolic compounds. The maximum antioxidant activity was monitored through the application of Zn nano complex. According to the results, nanoscale nutrients can be provided with further decreased doses for medicinal plants. Using Zn-ALA nano complex is a new and efficient method to improve the pharmaceutical and food properties of anise plants. This article is protected by copyright. All rights reserved.

Concepts: Plant, Water, Apiaceae, Medicinal plants, Essential oil, Anise, Star anise, Anethole

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A comprehensive study on essential oil samples of Foeniculum vulgare Miller from Tarquinia (Italy) is reported. A 24-h systematic steam distillation was performed on different harvested samples applying different extraction times. The GC-MS analysis of the residue outcome showed o-cymene, α-phellandrene, α-pinene and estragole as the major constituents. The predominance and continued presence of o-cymene makes this fennel oil a rather unique chemotype. An evident correlation between the antifungal activity and phenological stage is demonstrated. The most active fractions were particularly rich in estragole, as well as a significant amount of fenchone that possibly exerts some additive effect in the expression of overall antifungal potency. Pre-fruiting material produced oil particularly rich in o-cymene. With reference to the duration of the extraction, the maximum amount of oil was released within the first 3 h, whereas the reproductive phase material needed at least 6 h for the extraction.

Concepts: Apiaceae, Distillation, Essential oil, Absinthe, Anise, Fennel, Anethole, Foeniculum

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Phenylpropenes such as eugenol, chavicol, estragole and anethole contribute to the flavor and aroma of a number of important herbs and spices. They have been shown to function as floral attractants for pollinators, and to have antifungal, and antimicrobial activity. Phenylpropenes are also detected as free volatiles and sequestered glycosides in a range of economically important fresh fruit species including apple, strawberry, tomato and grape. Although they contribute a relatively small percentage of total volatiles compared with esters, aldehydes and alcohols, phenylpropenes have been shown to contribute spicy, anise- and clove-like notes to fruit. Phenylpropenes are typically found in fruit throughout development and to reach maximum concentrations in ripe fruit. Genes involved in the biosynthesis of phenylpropenes have been characterized and manipulated in strawberry and apple which has validated the importance of these compounds to fruit aroma and may help elucidate other functions for phenylpropenes in fruit.

Concepts: Carboxylic acid, Fruit, Tomato, Pollination, Ethylene, Apple, Spice, Anethole

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The present study aimed to prepare liposomes loaded with cyclodextrin/drug inclusion complexes at a pilot scale based on the ethanol injection technique. Anethole (ANE), a major component of anise and fennel essential oils, was used as a model of a volatile and highly hydrophobic drug. Membrane contactor (600mL) and a pilot plant (3L) were used for liposome production. The liposome preparations obtained were characterized for size, polydispersity index, zeta potential, morphology, stability and ANE release rate. All experimental set-ups were shown to be appropriate for the preparation of small, multilamellar vesicles with narrow size distribution and good stability at 4°C. The drug release study showed that only a small amount of ANE was released from liposome formulations after 21days of storage at 4°C. The loading rate of ANE was higher when ethanol was evaporated directly on the pilot plant compared to a rotary evaporation.

Concepts: Water, Liquid, Membrane biology, Distillation, Essential oil, Anise, Fennel, Anethole

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Natural products, known for their medicinal properties since antiquity, are continuously being studied for their biological properties. In the present study, we analyzed the composition of the volatile preparations of essential oils of the Greek plants Ocimum basilicum (sweet basil), Mentha spicata (spearmint), Pimpinella anisum (anise) and Fortunella margarita (kumquat). GC/MS analyses revealed that the major components in the essential oil fractions, were carvone (85.4%) in spearmint, methyl chavicol (74.9%) in sweet basil, trans-anethole (88.1%) in anise, and limonene (93.8%) in kumquat. We further explored their biological potential by studying their antimicrobial, antioxidant and antiproliferative activities. Only the essential oils from spearmint and sweet basil demonstrated cytotoxicity against common foodborne bacteria, while all preparations were active against the fungi Saccharomyces cerevisiae and Aspergillus niger. Antioxidant evaluation by DPPH and ABTS radical scavenging activity assays revealed a variable degree of antioxidant potency. Finally, their antiproliferative potential was tested against a panel of human cancer cell lines and evaluated by using the sulforhodamine B (SRB) assay. All essential oil preparations exhibited a variable degree of antiproliferative activity, depending on the cancer model used, with the most potent one being sweet basil against an in vitro model of human colon carcinoma.

Concepts: Cancer, Fungus, Citrus, Basil, Ocimum basilicum, Essential oil, Anise, Anethole