• Natural Product Sciences
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• v.22 no.1
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• pp.30-34
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• 2016

A simple and rapid method based on proton nuclear magnetic resonance spectroscopy was developed for determination of trans-anethole content in fennel essential oil. Spectra of pure trans-anethole, of the pure essential oil of fennel, and of the pure oil of fennel with thymol internal standard were recorded. The signal of $H-1^/$ was used for quantification of trans-anethole. This proton signal is well separated in the proton magnetic resonance spectrum of the compound. No reference compound is needed and cheap internal standard was used. The results obtained from spectroscopic analysis were compared with those obtained by gas chromatography. Additionally, the developed method was used for determination of the type of vegetable oil used as a carrier in commercial products, which cannot be quantified as such by gas chromatography. This study demonstrates the application of proton nuclear magnetic resonance spectroscopy as a quality control method for estimation of essential oil components.

• Biomolecules & Therapeutics
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• v.20 no.1
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• pp.113-117
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• 2012

The fruits of Foeniculum vulgare (Foeniculi Fructus) have been widely used in Chinese medicine as an antiemetic, ameliorating stomach ailments and as an analgesic. In order to establish its potential for antiallergic use, inhibitory actions of the fruit on 5-lipoxgenase (5-LOX) and ${\beta}$-hexosaminidase release were evaluated. The 70% ethanol extract of this plant material (FR) considerably inhibited 5-LOX-catalyzed leukotriene production from A23187-induced rat basophilic leukemia (RBL)-1 cells. The $IC_{50}$ was $3.2{\mu}g/ml$. From this extract, 12 major compounds including sabinene, fenchone, ${\gamma}$-terpinene, ${\alpha}$-pinene, limonene, p-anisylacetone, panisylaldehyde, estragole (4-allylanisole), trans-anethole, scopoletin, bergapten and umbelliferone were isolated. And it was found that several terpene derivatives including ${\gamma}$-terpinene and fenchone as well as phenylpropanoid, trans-anethole, showed considerable inhibitory action of 5-LOX. In particular, the $IC_{50}$ of trans-anethole was $51.6{\mu}M$. In contrast, FR and the isolated compounds did not show considerable inhibitory activity on the degranulation reaction of ${\beta}$-hexosaminidase release from antigen-treated RBL-2H3 cells. Against arachidonic acid-induced ear edema in mice, FR and trans-anethole showed significant inhibition by oral administration at doses of 100-400 mg/kg. In conclusion, FR and several major constituents are 5-LOX inhibitors and they may have potential for treating 5-LOX-related disorders.

• Korean Journal of Medicinal Crop Science
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• v.11 no.4
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• pp.274-278
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• 2003

The various plant organs of fennel (Foeniculum vulgare Mill.) were investigated to identify their volatile components using Dynamic Headspace (purge & trap). They showed slight differences concerning the volatile components both qualitatively and quantitatively. Results revealed that trans-anethole (12.65%) was the major compound in the leaf. The highest compound was ${\alpha}-pinene$ (28.78%), and trans-anethole (7.90%) was highly detected in the stem. The maximum values were 5.64, 4.59, 1.58, 1.51, and 1.04% for ${\alpha}-pinene,\;{\gamma}-terpinene,\;{\beta}-pinene$, 1,8-cineol and fenchone, respectively in the flower. However, very little trans-anethole was detected (0.27%) in the flower. From these results, it was suggested that the major components were different depending on the plant organs. However it was demonstrated that the related plant organs like flower-fruit and leaf-stem contained the similar components.

• Biomedical Science Letters
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• v.29 no.3
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• pp.190-200
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• 2023

Skeletal muscle, essential for metabolism, thermoregulation, and immunity, undergoes myogenic differentiation that results in myotube formation. Trans-anethole (TA), the major constituent in essential oil produced by anise, star anise, and fennel, whose function in skeletal muscle has not yet been elucidated. Therefore, we investigated whether TA influenced muscle differentiation in mouse C2C12 myoblasts. Cells were induced to differentiate using a differentiation medium with or without TA (50 or 200 mg/mL) daily for 5 days. We measured myotube length and diameter after differentiation days 1, 3, and 5 and analyzed the expression of myogenic markers (myoblast determination protein 1, myogenin, myocyte enhancer factor 2, muscle creatine kinase, and myosin heavy chain) and atrophy-related genes (atrogin-1 and muscle ring finger-1 [MuRF-1]) using quantitative real-time PCR. Additionally, we observed the expression of total protein kinase B (Akt) and phosphorylated Akt (p-Akt) using western blotting. Our data showed that TA significantly induced the formation of smaller and thinner myotubes and reduced the myogenic factor expression. Furthermore, the atrogin-1 and MuRF-1 expression markedly increased by TA. Consistent with these findings, TA significantly decreased the expression of total Akt and p-Akt. Taken together, these results indicate that TA inhibits myogenic differentiation of C2C12 cells via reduction of both total Akt and p-Akt. Our findings may provide valuable insights into the impact of PAA on individuals at risk of muscle atrophy.

• Analytical Science and Technology
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• v.14 no.2
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• pp.109-114
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• 2001

The flavor-related compounds contained in tobacco were analyzed by selected ion monitoring (SIM) method using headspace SPME gas chromatography-mass spectrometry(GC-MS). Flavor-related compounds were estragole pulegone, trans-anethole, safrole, piperonal, eugenol, methyleugenol, coumarin, trans-isoeugenol, trans-methyleugenol and myristicin. More than on of the flavor-related compounds were detected in the range $0.001-1.3{\mu}g/g$ from all brands of tobacco studied. The recovery was ranged from 89.1 to 102.9% and relative standard deviation was ranged from 2.6 to 25.2%.

• Bulletin of the Korean Chemical Society
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• v.28 no.12
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• pp.2389-2395
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• 2007

Headspace solid phase trapping solvent extraction (HS-SPTE) and GC-MS was applied for the characterization of volatile flavors from fennel, anise seed, star-anise, dill seed, fennel bean, and Ricard aperitif liquor. Tenax was used for HS-SPTE adsorption material. Recoveries, precision, linear dynamic ranges, and the limit of detection in the analytical method were validated. There were some similarities and distinct differences between fennel-like samples. The Korean and the Chinese fennels contained trans-anethole, (+)-limonene, anisealdehyde, methyl chavicol as major components. The volatile aroma components from star anise were characterised by rich trans-anethole, (+)-limonene, methyl chavicol, and anisaldehyde. Additionally, principal component analysis (PCA) has been used for characterizing or classifying eight different fennel-like samples according to origin or other features. A quite different pattern of dill seed was found due to the presence of apiol (dill).

• Entomological Research
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• v.48 no.5
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• pp.354-361
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• 2018

Plant essential oils (EOs) exhibit an array of biological activities against insect pests. However, their negative influences on the pheromonal activity of azuki bean beetle (ABB), Callosobruchus chinensis L. have not received research attentions. ABB is a field-to-storage pest of legumes, and its female produces the sex pheromone known as homofarnesal with two isomeric components: 2E- and 2Z-homofarnesal, (2E,6E)-7-ethyl-3,11-dimethyl-2,6,10-dodecatrienals and (2Z,6E)-7-ethyl-3,11-dimethyl-2,6,10-dodecatrienals. We evaluated the effects of three EOs and their two major components on the attractiveness of male ABBs to synthetic homofarnesal (2E-:2Z-homofarnesal = 6:4) using Y-tube olfactometry in laboratory and rocket traps in the semi-open polyhouse. Y-tube olfactometry showed the significant negative effect of EOs of Illicium verum, Croton anisatum at 10 and 100 ng, and Gaultheria fragrantissima at 100 ng against homofarnesal (100 ng) in attracting male ABBs. Similarly trans-anethole (at 10 and 100 ng) and methyl salicylate (at 100 ng) also ascertained significant negative effect against homofarnesal (100 ng) in Y-tube olfactometry. When 10 mg of each of trans-anethole and methyl salicylate was released at the downstream of 30 mg homofarnesal lure in rocket traps, highly significant effect was achieved against attractiveness of homofarnesal to ABB males. This study ascertained significant level of negative effect of the tested EOs and their major components to homofarnesal, tracing out a new opportunity of integrating them in ABB management programs both in field and storage.

• Journal of Microbiology and Biotechnology
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• v.17 no.9
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• pp.1568-1572
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• 2007

To develop a natural fungicide against Botrytis cinerea and Colletotrichum gloeosporioides, a total of 25 essential oils were tested for their fumigant activity against post-harvest pathogens. The vaporous phases of oils were treated to each fungus on potato dextrose agar medium in half-plate separated Petri plates at $10\;{\mu}g$ per plate. The essential oil of Illicium verum strongly inhibited the mycelial growth of both B. cinerea and C. gloeosporioides by over 90%. On the other hand, the essential oil of Schizonepeta tenuifolia showed inhibitory activity against mycelial growth of only B. cinerea by over 90%. Gas chromatography-mass spectrometry and bioassay indicated trans-anethole in I. verum and menthone in S. tenuifolia as a major antifungal constituent. The essential oils of I. verum and S. tenuifolia and their major constituents could be used to manage post-harvest diseases caused by B. cinerea and C. gloeosporioides.

• Journal of Life Science
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• v.18 no.12
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• pp.1644-1650
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• 2008

The essential oil of tea tree (Melaleuca alternifolia) is widely used in traditional Australian medicine for skin lesions and infected injuries. In the present study, we investigated the chemical composition, cytotoxicity and its biological activities. The composition of the oil was analyzed by GC-MS. ${\beta}$-Terpinene (20.87%), ${\alpha}$-pinene (17.60%), p-cymene (11.23%), 3-carene (10.40%), trans-anethole (8.47%) and limonene (4.65%) were the major components in the oil. The results tested by MTT assay indicated that the oil showed no cytotoxic effect, at concentrations up to 5%, for less than 3h. The antiradical capacity was evaluated by measuring the scavenging activity of the essential oil on the 2,20-diphenylpicrylhydrazyl (DPPH) and 2,2'-azino-bis 3-ethyl benzothiazoline-6-sulfonic acid (ABTS) radicals. The oil was able to reduce the both radicals dose-dependently, and the concentration required for 50% reduction ($RC_{50}$) against ABTS radicals ($1.6{\pm}0.02%$) was slightly lower than DPPH radicals ($2.6{\pm}0.29%$). The direct contact and vapor-phase antibacterial activity of the oil were also evaluated using disc diffusion method against Staphylococcus aureus, Streptococcus mutans, Listeria monocytogenes, Acinetobacter baumannii, Escherichia coli, and Vibrio parahaemolyticus. All the Gram-negative bacterial strains tested showed more sensibility to the oil than the Gram-positive strains when compare to the effect of gentamycin. On the other hand, the vapor phase of the essential oil against S. aureus exhibited strongest inhibitory effect.

• Bulletin of the Korean Chemical Society
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• v.30 no.1
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• pp.35-42
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• 2009

Headspace micro solid phase extraction using mulberry paper bag (HS-MPB-$\mu$-SPE) has been developed and validated for the analysis of volatile flavor compounds from five spice by gas chromatography-mass spectrometry (GC/MS). HS-MPB-$\mu$-SPE was performed with adsorbent particles enclosed inside a mulberry paper bag. Four different kinds of adsorbents such as Tenax TA, Porapack Q, dimethylpolysiloxane and polyethylene glycol were tested. The extraction solvents compared were petroleum ether, methylene chloride, and chloroform. Better results were obtained when Tenax TA and petroleum ether were used. The limit of detection (LOD) and the limit of quantitation (LOQ) were in the range of 1.3 ng/mL and 4.3 ng/mL, respectively, for o-cymene as a model compound of monoterpene. Proposed method showed good reproducibility (3.3%, RSD) and good recoveries (94.0%). The HS-MPB- μ-SPE is very simple to use, inexpensive, rapid, requires small sample amounts and solvent consumption. Because the solvent for extraction is reduced to only a very small volume (0.6 mL), there is minimal waste or exposure to toxic organic solvent and no further concentration step. This method allows successful characterization of the headspace in contact with the five spice sample. Strong trans-anethole from star anise or fennel is a characteristic flavor of five spice powders. HS-MPB-$\mu$-SPE combined with GC/MS can be a promising technique for the broad spectrum measurement of volatile aroma compounds from solid spices.