Star Anise Oil Research Articles

Antihypernociceptive activity of anethole in experimental inflammatory pain

Anethole has been reported to have antioxidant, antibacterial, antifungal, antiinflammatory, and anesthetic properties. In the present study, we evaluated the effects of anethole in two pain models of inflammatory origin: acute inflammation induced by carrageenan and persistent inflammation induced by Complete Freund's adjuvant. We evaluated the effects of anethole (125, 250, and 500 mg/kg) on the development of paw oedema and mechanical hypernociception. The liver was collected for histological analysis. Paw skin was collected to determine the levels of the cytokines tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), interleukin-17 (IL-17), and myeloperoxidase activity. Blood was collected to assess alanine transaminase (ALT) and aspartate transaminase (AST). The chemical composition of star anise oil was determined by gas chromatography/mass spectrometry (GC/MS), showing a presence of anethole of 98.1%. Oral pretreatment with anethole in mice inhibited paw oedema, mechanical pernociception, myelopewroxidase activity, TNF-α, IL-1β and IL-17 levels in acute and persistent inflammation models. Additionally, anethole treatment did not alter prostaglandin E2-induced mechanical hypernociception. Possible side effects were also examined. Seven-day anethole treatment did not alter plasma AST and ALT levels, and the histological profile of liver tissue was normal. The present study provides evidence of the antiinflammatory and analgesic activities of anethole in acute and persistent inflammation models.

Synthesis of Some Series of 1,3‐Thiazolidin‐4‐ones and Indoles Incorporating Furoxan Moiety Starting with Anethole Isolated from Star Anise Oil

Some series of 1,3‐thiazolidin‐4‐ones and indoles incorporating furoxan moiety were synthesized from anethole, a main component of star anise oil. The structure of these compounds and the intermediates was examined by elemental and spectral data. Ten compounds were screened against some bacteria and fungi.

Synergistic Antimicrobial Activities of Natural Essential Oils with Chitosan Films

The synergistic antimicrobial activities of three natural essential oils (i.e., clove bud oil, cinnamon oil, and star anise oil) with chitosan films were investigated. Cinnamon oil had the best antimicrobial activity among three oils against Escherichia coli , Staphylococcus aureus , Aspergillus oryzae , and Penicillium digitatum . The chitosan solution exhibited good inhibitory effects on the above bacteria except the fungi, whereas chitosan film had no remarkable antimicrobial activity. The cinnamon oil-chitosan film exhibited a synergetic effect by enhancing the antimicrobial activities of the oil, which might be related to the constant release of the oil. The cinnamon oil-chitosan film had also better antimicrobial activity than the clove bud oil-chitosan film. The results also showed that the compatibility of cinnamon oil with chitosan in film formation was better than that of the clove bud oil with chitosan. However, the incorporated oils modified the mechanical strengths, water vapor transmission rate, moisture content, and solubility of the chitosan film. Furthermore, chemical reaction took place between cinnamon oil and chitosan, whereas phase separation occurred between clove bud oil and chitosan.

Screening for Antiviral Activities of Isolated Compounds from Essential Oils

Essential oil of star anise as well as phenylpropanoids and sesquiterpenes, for example, trans-anethole, eugenol, β-eudesmol, farnesol, β-caryophyllene and β-caryophyllene oxide, which are present in many essential oils, were examined for their antiviral activity against herpes simplex virus type 1 (HSV-1) in vitro. Antiviral activity was analyzed by plaque reduction assays and mode of antiviral action was determined by addition of the drugs to uninfected cells, to the virus prior to infection or to herpesvirus-infected cells. Star anise oil reduced viral infectivity by >99%, phenylpropanoids inhibited HSV infectivity by about 60–80% and sesquiterpenes suppressed herpes virus infection by 40–98%. Both, star anise essential oil and all isolated compounds exhibited anti-HSV-1 activity by direct inactivation of free virus particles in viral suspension assays. All tested drugs interacted in a dose-dependent manner with herpesvirus particles, thereby inactivating viral infectivity. Star anise oil, rich in trans-anethole, revealed a high selectivity index of 160 against HSV, whereas among the isolated compounds only β-caryophyllene displayed a high selectivity index of 140. The presence of β-caryophyllene in many essential oils might contribute strongly to their antiviral ability. These results indicate that phenylpropanoids and sesquiterpenes present in essential oils contribute to their antiviral activity against HSV.

Antifungal Activity of the Essential Oil of Illicium verum Fruit and Its Main Component trans-Anethole

In order to identify natural products for plant disease control, the essential oil of star anise (Illicium verum Hook. f.) fruit was investigated for its antifungal activity on plant pathogenic fungi. The fruit essential oil obtained by hydro-distillation was analyzed for its chemical composition by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). trans-Anethole (89.5%), 2-(1-cyclopentenyl)-furan (0.9%) and cis-anethole (0.7%) were found to be the main components among 22 identified compounds, which accounted for 94.6% of the total oil. The antifungal activity of the oil and its main component trans-anethole against plant pathogenic fungi were determined. Both the essential oil and trans-anethole exhibited strong inhibitory effect against all test fungi indicating that most of the observed antifungal properties was due to the presence of trans-anethole in the oil, which could be developed as natural fungicides for plant disease control in fruit and vegetable preservation.

Chemical constituents, antimicrobial investigations and antioxidative potential of volatile oil and acetone extract of star anise fruits

AbstractGC and GC‐MS analysis of fruit volatile oil of star anise (Illicium verum Hook) showed the presence of 25 components which account for the 99.9% of the total amount. The major components were trans‐anethole (94.37%), methyl chevicol (1.82%) and cis‐anethole (1.59%). 15 Components were identified from its acetone extract accounting for 80.27% of the total amount. trans‐Anethole (51.81%) was found as a major component along with linoleic acid (11.6%), 1‐(4‐methoxyphenyl)‐prop‐2‐one (6.71%), foeniculin (5.29%) and palmitic acid (1.47%). Using an inverted petriplate method, the volatile oil completely inhibited the growth of Fusarium moniliforme at 6 µl dose. In case of extract, 50% mycelial zone inhibition was obtained for Penicillium citrinum and Penicillium viridicatum. Moreover, using food poison technique, the volatile oil was found to be effective for controlling the growth of F. moniliforme and Aspergillus niger whereas the extract has been found to be highly effective for Aspergillus flavus. In antibacterial investigations, using agar well diffusion method, the extract has shown better activity for Staphylococcus aureus and Bacillus cereus in comparison with volatile oil and commercial bactericide, ie Ampicillin. However, volatile oil has shown better activity for Salmonella aeruginosa and Bacillus subtilis. Moreover, the extract has shown excellent activity for the inhibition of primary and secondary oxidation products in rapeseed oil which were evaluated using peroxide, thiobarbituric acid, p‐anisidine and carbonyl values. The activity of extract was further confirmed using other antioxidant properties such as ferric thiocyanate method in linoleic acid system, reducing power and scavenging effect (%) on 1,1‐diphenyl‐2‐picrylhydrazyl radical (DPPH) radical. Hence, the extract could be considered as natural antioxidant which may be used for chemoprevention of diseases occurring due to oxidative deterioration. Copyright © 2005 Society of Chemical Industry

GC/MS Analysis of Star Anise Oil

ABSTRACT The oil of star anise was examined by a combination of GC/MS and retention times. Quantitative data for twenty-seven of the thirty-six compounds identified is presented.

ChemInform Abstract: THERMAL REARRANGEMENT OF 1‐(3‐METHYLBUT‐2‐ENYLOXY)‐4‐PROP‐1‐ENYLBENZENE (FENICULIN): A NEW SYNTHESIS OF ANISOXIDE AND RE‐INVESTIGATION OF THE CONSTITUENTS OF STAR ANISE OIL

Chemischer InformationsdienstVolume 12, Issue 23 Heterocyclic Compounds ChemInform Abstract: THERMAL REARRANGEMENT OF 1-(3-METHYLBUT-2-ENYLOXY)-4-PROP-1-ENYLBENZENE (FENICULIN): A NEW SYNTHESIS OF ANISOXIDE AND RE-INVESTIGATION OF THE CONSTITUENTS OF STAR ANISE OIL H. M. OKELY, H. M. OKELYSearch for more papers by this authorM. F. GRUNDON, M. F. GRUNDONSearch for more papers by this author H. M. OKELY, H. M. OKELYSearch for more papers by this authorM. F. GRUNDON, M. F. GRUNDONSearch for more papers by this author First published: June 9, 1981 https://doi.org/10.1002/chin.198123215Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume12, Issue23June 9, 1981 RelatedInformation

Thermal rearrangement of 1-(3-methylbut-2-enyloxy)-4-prop-1-enylbenzene (feniculin): a new synthesis of anisoxide and re-investigation of the constituents of star anise oil

At 153 °C feniculin (1) undergoes Claisen rearrangement to the 1,1-dimethylallylphenol (3), which is slowly converted into the 1,2-dimethylallylphenol (4); the products of abnormal Claisen rearrangement, phenol (4) and anisoxide (2), are formed at 185 °C. Anisoxide was shown by g.l.c. analysis to be absent in star anise oil and in the seeds of Illicium verum and Foeniculum vulgare, and is believed to have been obtained previously as a result of prolonged distillation of anise oil.

Sensitizing and irritating properties of star anise oil.

Star anise oil in 2 and 1% concentrations produced active sensitization in 5% of test subjects, and positive patch tests in 36 and 34%, respectively, of consecutive patients with dermatitis. A comparison of the results of tests with balsams and other essential oils showed that star anise oil does not give cross-reactions and pseudo cross-sensitivity. Patients positive to this oil are frequently positive to anethole and to other constituents of this oil: alpha-pinene, limonene and safrole. In tests with star anise oil it is noteworthy that a 1% concentration is strongly irritant, and 0.5% reveals sensitivity in only one fifth of the actively sensitized subjects. It is possible that the cause of false negative patch tests might be similar in the case of some other allergens.

Anisoxide: an artefact from star anise oil formed by Claisen rearrangement

The 1,2-dimethylallyl derivative, anisoxide, is not present in star anise oil or in the seeds of Illicium verum; its synthesis from a 3,3-dimethylallyl ether present in the oil suggests that it was obtained earlier as a result of the isolation procedure.

THE ESSENTIAL OIL OF ILLICIUM ANISATUM LINN.

The oil of the Japanese star anise tree, Illiciumanisatum Linn., was analyzed by gas–liquid chromatography. The major constituents were found to be cineole (18.1%), linalool (10.1%), methyleugenol (9.8%), α-terpenyl acetate (6.8%), safrole (6.6%), and a sesquiterpene hydrocarbon of unknown constitution (7.2%). The composition of this oil differs widely from that of the commercially used star anise oil obtained from Illiciumverum Hooker. The most striking difference between the two oils is found in the anethole content, which constitutes 88% of the commercial oil but only 1.2% of the oil here investigated.