Anti-inflammation activities of essential oil and its constituents from indigenous cinnamon (Cinnamomum osmophloeum) twigs

In this study, chemical compositions of hydrodistilled essential oil and anti-inflammatory activities from the twigs of Cinnamomum osmophloeum Kaneh. were investigated for the first time. The chemical constituents of the twig essential oil were further analyzed by GC-MS and they were found to be L-bornyl acetate (15.89%), caryophyllene oxide (12.98%), gamma-eudesmol (8.03%), beta-caryophyllene (6.60%), T-cadinol (5.49%), delta-cadinene (4.79%), trans-beta-elemenone (4.25%), cadalene (4.19%), and trans-cinnamaldehyde (4.07%). The effects of essential oil on nitric oxide (NO) and prostaglandin E2 (PGE2) production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages were also examined. Results of nitric oxide tests indicated that twig essential oil and its major constituents such as trans-cinnamaldehyde, caryophyllene oxide, L-borneol, L-bornyl acetate, eugenol, beta-caryophyllene, E-nerolidol, and cinnamyl acetate have excellent activities. These findings demonstrated that essential oil of C. osmophloeum twigs have excellent anti-inflammatory activities and thus have great potential to be used as a source for natural health products.     

Chemical polymorphism and antifungal activity of essential oils from leaves of different provenances of indigenous cinnamon (Cinnamomum osmophloeum)

The essential oils isolated from nine geographical provenances of indigenous cinnamon (Cinnamomum osmophloeum Kaneh.) leaves were examined by GC-MS and their chemical constituents were compared. According to GC-MS and cluster analyses the leaf essential oils of the nine provenances and their relative contents were classified into six chemotypes-cinnamaldehyde type, cinnamaldehyde/cinnamyl acetate type, cinnamyl acetate type, linalool type, camphor type and mixed type. In addition, the antifungal activities of leaf essential oils and their constituents from six chemotypes of indigenous cinnamon were investigated in this study. Results from the antifungal tests demonstrated that the leaf essential oils of cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type had an excellent inhibitory effect against white-rot fungi, Trametes versicolor and Lenzites betulina and brown-rot fungus Laetiporus sulphureus. The antifungal indices of leaf essential oils from these two chemotypes at the level of 200 micro/ml against T. versicolor, L. betulina and L. sulphureus were all 100%. Among them, the IC(50) (50% of inhibitory concentrations) value of the essential oil of cinnamaldehyde type leaf against L. sulphureus was 52-59microg/ml. Cinnamaldehyde possessed the strongest antifungal activities in comparison with other constituents of the essential oils from cinnamaldehyde type leaf, at the level of 100microg/ml its antifungal indices against T. versicolor, L. betulina and L. sulphureus were 100%. The IC50 values of cinnamaldehyde against T. versicolor, L. betulina and L. sulphureus were 73, 74 and 73microg/ml, respectively.     

Insecticidal activities of leaf essential oils from Cinnamomum osmophloeum against three mosquito species

The larvicidal activities of leaf essential oils and their constituents from six chemotypes of indigenous cinnamon (Cinnamomum osmophloeum Kaneh.) trees were evaluated against three mosquito species. Results of larvicidal tests demonstrated that the leaf essential oils of cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type had an excellent inhibitory effect against Aedes albopictus larvae, and their LC(50) values in 24h were 40.8 microg/ml (LC(90)=81.7 microg/ml) and 46.5 microg/ml (LC(90)=83.3 microg/ml), respectively. Results of the 24-h mosquito larvicidal assays also showed that the effective constituents in leaf essential oils were trans-cinnamaldehyde and benzaldehyde and that the LC(50) values of these constituents against A. albopictus larvae were below 50 mug/ml. In addition, cinnamaldehyde type leaf essential oil and trans-cinnamaldehyde have also exhibited great larvicidal performance against Culex quinquefasciatus and Armigeres subalbatus larvae. Comparisons of mosquito larvicidal activity of trans-cinnamaldehyde congeners revealed that alpha-methyl cinnamaldehyde, benzaldehyde, and trans-cinnamaldehyde exhibited strong mosquito larvicidal activity.     

Antifungal activity of phytochemicals from Eucalyptus hybrid leaves against some plant pathogenic and wood decay fungi

The in vitro fungitoxicity of the essential oil (EO), crude extracts, dried fractions and ursolic acid (UA) isolated from the abundantly available and underutilised leaves of Eucalyptus hybrid (Eucalyptus camaldulensis × Eucalyptus tereticornis) was assessed against three plant pathogenic fungi Aspergillus niger, Fusarium solani and Ganoderma lucidum causing pathogenesis in seeds, seedlings and trees, respectively, and Trametes versicolor and Pycnoporous sanguineus making wood to decay. The EO, methanol extract and UA demonstrated varied antifungal activity against all the fungi with minimum inhibitory concentrations ranging from 0.5 to 3.0%. The results of the study demonstrate a new chemical utilisation approach of the leaves of Eucalyptus hybrid towards the development of biofungicides in the management of above fungi of common occurrence in Indian forestry.     

Screening the antifungal activity of essential oils against decay fungi from palmyrah leaf handicrafts

Background

The whitish tender leaves of Palmyrah are used for making handicrafts. The problem with these articles is discolouration with time and become more brittle due to fungal attack. This could be prevented by some protective coating. Instead of expensive and harmful chemicals we decided to test natural plant essential oils to control fungal attack. Palmyrah leaf article decay fungi were isolated from two different sites of Jaffna peninsula. In this investigation Antifungal Activity of different plant essential oils from neem (Azadirachta indica), castor (Ricinus communis), citronella (Cymbopogon sp) and camphor (Cinnamomum camphora) obtained from local market have been evaluated against isolated fungi. For screening of Antifungal activity, tests and controls were set to determine minimum inhibitory concentration (MIC) and Percentage of Growth Inhibition.

Results

Morphologically three different types of Palmyrah leaf decay fungi were isolated and characterized as Aspergillus niger, Aspergillus flavus and Penicillium sp. Neem and castor oils have recorded no significant (0.05 > P) antifungal activity while citronella and camphor oils showed significantly different antifungal activity compared with control. Camphor oil and Citronella oil showed 100, 58.13% of average growth inhibition for A. niger. 96.38, 51.32% for A.flavus and 84.99, 72.76% for Penicillium sp respectively. Camphor oil showed highest percentage of growth inhibition at lowest minimum inhibitory concentration compared with citronella oil. Camphor oil was found to be highly antifungal and most effective against A niger, and A. flavus, compared with Penicillium sp and gave 100 percentage of growth inhibitions at 5, 1 and 15 ml/dl minimum inhibitory concentration respectively.

Conclusion

Significantly higher broad-spectrum of antifungal activity was observed in camphor oil than other tested oils because it showed highest percentage of growth inhibition at lowest inhibitory concentration. Therefore it could be used for the development of new environmental friendly antifungal agent for the preservation of leafy handicrafts. Further formulation, field experiments are necessary to achieve this target.     

Antifungal activities of the essential oils in Syzygium aromaticum (L.) Merr. Et Perry and Leptospermum petersonii Bailey and their constituents against various dermatophytes

This study was carried out in order to investigate the potential of using plant oils derived from Leptospermum petersonii Bailey and Syzygium aromaticum L. Merr. Et Perry as natural antifungal agents. The antifungal effects of essential oils at concentrations of 0.05, 0.1, 0.15, and 0.2 mg/ml on the dermatophytes Microsporum canis (KCTC 6591), Trichophyton mentagrophytes (KCTC 6077), Trichophyton rubrum (KCCM 60443), Epidermophyton floccosum (KCCM 11667), and Microsporum gypseum were evaluated using the agar diffusion method. The major constituents of the active fraction against the dermatophytes were identified by gas chromatography-mass spectrometry and high-performance liquid chromatography analysis. The antifungal activities of S. aromaticum oil (clove oil) against the dermatophytes tested were highest at a concentration of 0.2 mg/ml, with an effectiveness of more than 60%. Hyphal growth was completely inhibited in T. mentagrophytes, T. rubrum, and M. gypseum by treatment with clove oil at a concentration of 0.2 mg/ml. Eugenol was the most effective antifungal constituent of clove oil against the dermatophytes T. mentagrophytes and M. canis. Morphological changes in the hyphae of T. mentagrophytes, such as damage to the cell wall and cell membrane and the expansion of the endoplasmic reticulum, after treatment with 0.11 mg/ml eugenol were observed by transmission electron microscopy (TEM). At a concentration of 0.2 mg/ml, L. petersonii oil (LPO) was more than 90% effective against all of the dermatophytes tested, with the exception of T. rubrum. Geranial was determined to be the most active antifungal constituent of L. petersonii oil. Taken together, the results of this study demonstrate that clove and tea tree oils exhibited significant antifungal activities against the dermatophytes tested in this study.     

Antifungal activity of essential oils from leaves and flowers of Inula viscosa (Asteraceae) by Apulian region

Some essential oils from several plants (Artemisia verlotorum, Lavandula augustifolia, Ocimum gratissimum) have proved to have acaricidal, antifungal and antibacterial activity. Inula viscosa Ait. (Asteraceae), a plant growing spontaneously in the Mediterranean area, is currently used by popular medicine for its therapeutic effects. Flavonoids, azulenes, sesquiterpenes, and essential oils have been isolated and identified from its leaves. This paper reports the results of the composition and antifungal activity in vitro against dermatophytes and Candida spp. of the four essential oils obtained by steam distillation of the leaves, flowers, whole plant and whole plants without flower extracts of I. viscosa. All the extracts proved to have a significant antifungal activity against dermatophytes even at low concentrations (0.01 mg/ml). The leaf extracts exhibited the greatest antifungal efficacy. The high concentration of the sesquiterpene (carboxyeudesmadiene), occurring in the leaf extracts, may explain its greater antifungal activity.     

Acaricidal and repellent effects of myrtacean essential oils and their major constituents against Tetranychus urticae (Tetranychidae)

Nineteen plant essential oils (EOs) extracted from the family Myrtaceae growing in Australia were screened for their acaricidal and repellent activities against two-spotted spider mite, Tetranychus urticae Koch (Acari: Tetranychidae), in the laboratory by dipping method and choice- and no-choice tests. Acaricidal bioassays showed that five EOs of Callistemon viminalis, Eucalyptus bicostata, Eucalyptus maidenii, Eucalyptus sideroxylm and Eucalyptus approximans significantly increased the mortality of female adult mites and decreased the total number of eggs. In a choice test, Callistemon sieberi, E. bicostata, Eucalyptus ovata, E. sideroxylm, Eucalyptus mannifera, Eucalyptus dives, Eucalyptus elata, Eucalyptus condonocarpa, Kunzea ericoides, Melaleuca armillaris and Melaleuca fulgens demonstrated good repellency to the mite. In another test, C. sieberi, E. bicostata, E. mannifera, E. condonocarpa, K. ericoides, M. armillaris, and M. fulgens EOs decreased the egg production of the females significantly. In the acaricidal and repellent tests, E. bicostata and E. sideroxylon EOs showed both acaricidal and repellent effects (choice test) and decreased the number of eggs on treated bean leaves. The gas chromatograph/mass spectroscopy analyses revealed that the major components of E. bicostata and E. sideroxylon were 1,8-cineole, limonene, and α-pinene. The 1,8-cineole and limonene showed significant repellent effects on the mites, resulting in reduced numbers of eggs in the choice test. Hence, EOs of E. bicostata and E. sideroxylon and limonene and 1,8-cineole may be potential agents to be used in the sustainable management of T. urticae.     

Antifungal activity of essential oils against filamentous fungi determined by broth microdilution and vapour contact methods

AIMS: The in vitro activity of some essential oils (EO) (thyme red, fennel, clove, pine, sage, lemon balm and lavender) against clinical and environmental fungal strains was determined. METHODS AND RESULTS: The minimal inhibitory concentrations were determined by a microdilution method in RPMI 1640 and by a vapour contact assay. The composition of oils was analysed by gas chromatography (GC) and GC/mass spectrometry. The results indicated that the oils antifungal activity depended on the experimental assay used. The inhibiting effects of EO in vapour phase were generally higher than those in liquid state. According to both methods thyme red and clove were found to be the oils with the widest spectrum of activity against all fungi tested. CONCLUSIONS: Despite the differences between the two methods, our results demonstrate that some EO are very active on dermatophytes and dematiaceous fungi. However, more data will be necessary to confirm this good in vitro efficacy. SIGNIFICANCE AND IMPACT OF THE STUDY: This study could identify candidates of EO for developing alternative methods to control environmental and clinically undesirable filamentous fungi.     

Antifungal mechanism of the combination of Cinnamomum verum and Pelargonium graveolens essential oils with fluconazole against pathogenic Candida strains

The present study aimed to investigate the anti-Candida activity of ten essential oils (EOs) and to evaluate their potential synergism with conventional drugs. The effect on secreted aspartic protease (SAP) activity and the mechanism of action were also explored. The antifungal properties of essential oils were investigated using standard micro-broth dilution assay. Only Cinnamomum verum, Thymus capitatus, Syzygium aromaticum, and Pelargonium graveolens exhibited a broad spectrum of activity against a variety of pathogenic Candida strains. Chemical composition of active essential oils was performed by gas chromatography-mass spectrometry (GC-MS). Synergistic effect was observed with the combinations C. verum/fluconazole and P. graveolens/fluconazole, with FIC value 0.37. Investigation of the mechanism of action revealed that C. verum EO reduced the quantity of ergosterol to 83%. A total inhibition was observed for the combination C. verum/fluconazole. However, P. graveolens EO may disturb the permeability barrier of the fungal cell wall. An increase of MIC values of P. graveolens EO and the combination with fluconazole was observed with osmoprotectants (sorbitol and PEG6000). Furthermore, the combination with fluconazole may affect ergosterol biosynthesis and disturb fatty acid homeostasis in C. albicans cells as the quantity of ergosterol and oleic acid was reduced to 52.33 and 72%, respectively. The combination of P. graveolens and C. verum EOs with fluconazole inhibited 78.31 and 64.72% SAP activity, respectively. To our knowledge, this is the first report underlying the mechanism of action and the inhibitory effect of SAP activity of essential oils in synergy with fluconazole. Naturally occurring phytochemicals C. verum and P. graveolens could be effective candidate to enhance the efficacy of fluconazole-based therapy of C. albicans infections.     

Antifungal activity of essential oils evaluated by two different application techniques against rye bread spoilage fungi

AIMS: To study how antifungal activity of natural essential oils depends on the assay method used. METHODS AND RESULTS: Oils of bay, cinnamon leaf, clove, lemongrass, mustard, orange, sage, thyme and two rosemary oils were tested by two methods: (1) a rye bread-based agar medium was supplemented with 100 and 250 microl l-1 essential oil and (2) real rye bread was exposed to 136 and 272 microl l-1 volatile oil in air. Rye bread spoilage fungi were used for testing. Method 1 proved thyme oil to be the overall best growth inhibitor, followed by clove and cinnamon. On the contrary, orange, sage and rosemary oils had very limited effects. Mustard and lemongrass were the most effective oils by the volatile method, and orange, sage and one rosemary showed some effects. Oil compositions were analysed by gas chromatography-mass spectrography. CONCLUSIONS: Antifungal effects of the essential oils depended on the application method. Larger phenolic compounds such as thymol and eugenol (thyme, cinnamon and clove) had best effect applied directly to medium, whereas smaller compounds such as allyl isothiocyanate and citral (mustard and lemongrass) were most efficient when added as volatiles. SIGNIFICANCE AND IMPACT OF THE STUDY: This study proves that the method used for screening essential oils as potential antimicrobials should correspond with the application sought.     

Chemical constituents from the leaves of Cinnamomum parthenoxylon (Jack) Meisn. (Lauraceae)

Phytochemical investigation of the ethanolic extract from the leaves of Cinnamomum parthenoxylon (Jack) Meisn. led to the isolation of (3R, 4R, 3′R, 4′R)-6,6′-dimethoxy-3, 4, 3′, 4′-tetrahydro-2H, 2′H-[3, 3′]bichromenyl-4, 4′-diol (1), 4-hydroxybenzaldehyde (2), 1,2,4-trihydroxybenzene (3), kaempferol-3-O-α-l-rhamnoside (4), herbacetin (5), quercetin-3-O-α-l-rhamnoside (6), daucosterol (7), and β-sitosterol (8). The structures were established by extensive analysis of their MS and NMR spectroscopic data and comparison with literature data. In the present research, all of the isolated compounds 1–8 are reported for the first time in the species C. parthenoxylon. Compounds 1–6 were firstly isolated from genus Cinnamomum. Compounds 1, 3, 5 and 6 have not been reported from any species in Lauraceae family. The chemotaxonomic significance of the isolated compounds is discussed.     

Antifungal activity of essential oil and its constituents from Calocedrus macrolepis var. formosana Florin leaf against plant pathogenic fungi

Resistance to conventional fungicides causes the poor disease control of agriculture. Natural products from plants have great potential as novel fungicide sources for controlling pathogenic fungi. In this study antipathogenic activity of the leaf essential oil and its constituents from Calocedrus macrolepis var. formosana Florin were evaluated in vitro against six plant pathogenic fungi. Chemical analysis of leaf oil by GC/MS allowed identification of alpha-pinene (44.2%), limonene (21.6%), beta-myrcene (8.9%), beta-caryophyllene (8.2%), caryophyllene oxide (2.4%), alpha-cadinol (1.6%), beta-pinene (1.2%), and T-muurolol (1.1%) as main components. Sesquiterpenoid components of the oil were more effective than monoterpenoid components of the oil. In particular, T-muurolol and alpha-cadinol strongly inhibited the growth of Rhizoctonia solani and Fusarium oxysporum, with the IC(50) values < 50 microg ml(-1). These compounds also efficiently inhibited the mycelial growths of Colletotrichum gloeosporioides, P. funerea, Ganoderma australe and F. solani. These results showed that T-muurolol and alpha-cadinol possess antifungal activities against a broad spectrum of tested plant pathogenic fungi and could be used as potential antifungal agents for the control of fungal diseases in plants.     

Antifungal activity of volatile compounds generated by essential oils against fungi commonly causing deterioration of bakery products

AIMS: To investigate the volatile fractions of 16 essential oils for activity against the more common fungi causing spoilage of bakery products, Eurotium amstelodami, E. herbariorum, E. repens, E. rubrum, Aspergillus flavus, A. niger and Penicillium corylophilum. METHODS AND RESULTS: The study applied 50 microl of pure essential oils in a sterilized filter paper, were carried out at pH 6 and at different water activity levels (0.80-0.90). First, a wheat flour based agar medium was used, where cinnamon leaf, clove, bay, lemongrass and thyme essential oils where found to totally inhibit all microorganisms tested. These five essential oils were then tested in sponge cake analogues, but the antifungal activity detected was much more limited. CONCLUSION: Five essential oils showed potential antifungal capacity against all species tested, over a wide range of water availability. Their activity, however, seems to be substrate-dependent. More research is needed to make them work in real bakery products, as in the preliminary study limited effectiveness was found. SIGNIFICANCE AND IMPACT OF THE STUDY: The potential of the cinnamon leaf, clove, bay, lemongrass and thyme essential oils against species belonging to Eurotium, Aspergillus and Penicillium genus has been demonstrated.     

Fumigant toxicity of Apiaceae essential oils and their constituents against Sitophilus oryzae and their acetylcholinesterase inhibitory activity

We evaluated the insecticidal and acetylcholinesterase (AChE) inhibition activities of the essential oils and their constituents of 10 Apiaceae on the adult rice weevil, Sitophilus oryzae. Of the 10 species tested, dill (Anethum graveolens), caraway (Carum carvi), and cumin (Cuminum cyminum) essential oils showed strong fumigant toxicity against adult S. oryzae. LC₅₀ values of caraway, dill, and cumin essential oils were 2.45, 3.29, and 4.75 mg/L air, respectively. Among the test compounds, (+)-carvone, (?)-carvone, cuminaldehyde, dihydrocarvone, linalool oxide, carveol, trans-anethole, and neral demonstrated strong fumigant toxicity against adult S. oryzae with LC₅₀ values of 0.61, 0.84, 1.12, 2.92, 3.76, 4.29, 5.02, and 6.60 mg/L air, respectively. α-Pinene showed the strongest AChE inhibition activity followed by β-pinene and limonene. The measured toxicity of the artificial blends of the constituents identified in dill and cumin oils indicated that (+)-carvone and cuminaldehyde were major contributors to the fumigant toxicity of the artificial blend.     

竹叶楠叶挥发油的化学成分与抗真菌活性研究

利用 GC- MS联用技术从竹叶楠 (Phoebe faberi)叶挥发油中鉴定了 2 6个萜类化合物 ,如(Z) - (R) - (+) - 3,7,11-三甲基 - 1,6 ,10 -十二碳三烯 - 3-醇 (相对含量 39.34% )、β-丁香烯 (2 9.18% )、姜烯 (5.16 % )和氧化丁香烯 (4 .2 1% )。该挥发油具有一定的体外抗真菌活性 ,在培养基油浓度小于2 .0 μL/ m L的情况下 ,能够完全抑制新型隐球菌、申克氏孢子丝菌、羊毛状小孢子菌、石膏样小孢子菌和球毛壳霉等皮肤真菌的生长繁殖。     

Study of antifungal activities of seven essential oils from some Iranian medicinal plants against various postharvest phytopathogenic fungi

The aim of this study was to find the antifungal activities of seven essential oils from some Iranian medicinal plants that have maximum (100%) inhibition effect on the mycelium growth of postharvest phytopathogenic fungi. Among 20 examined species belonging to three families, only 7 species could stop the mycelium growth of phytopathogenic fungi. The selected plants include Trachyspermum ammi, Zataria multiflora Boiss., Satureia hortensis, Caryophillum aromaticus, Menthe piperita, Cuminum cyminum L. and Carum carvi, and fungi include Aspergillus flavus, Botrytis cinerea, Penicillium italicum, Penicillium expansum, Penicillium commune, Rhizopus stolonifer and Rhizopus lyococcus. The results showed that the essential oil of these plants could stop the mycelium growth at 500 ppm, but could not completely inhibit the spore germination, however reduced the spore germination to 80–90%. Among the fungi Rhizopus stolonifer and Rhizopus lyococcus are more resistant to the inhibition effects of essential oils. Among the plants, Cuminum cyminum L. and Carum carvi were slightly weaker than other plants. Also except for Cuminum cyminum L. and Carum carvi, the essential oils of other plants had fungicide effect while these two plants in most cases had fugistatic effect. The results showed that these essential oils can be used as an effective alternative control method.     

粤北阴香不同器官中精油成分研究

采用水蒸汽同步蒸馏法分别对采自粤北的阴香的果、叶、枝条提取精油,并用气质联用仪对所提取的精油进行了成分分析和鉴定。共鉴定了41种成分,主要成分为龙脑（68．5％～73．8％）、芳香醇、丁子香烯、橙花叔醇、榄香烯、柠檬醛、莰烯、葑醇、愈创烯、香叶烯、枞萜、萜品醇、蒎烯等。阴香不同器官（果、叶、枝）中的精油成分及所占比例均有差异。     

Superheated water extraction of essential oils from Cinnamomum zeylanicum (L.)

Introduction – Superheated water extraction (SHWE) potentially provides an environmentally friendly and clean extraction technique which uses a minimum or no organic solvent. The scope and limitations of the technique have still to be fully explored. Objective – To investigate the application of SHWE to cinnamon (Cinnamomum zeylanicum L.) bark and leaves as typical plant materials to determine if this extraction method can yield a higher quality oil. Methodology – Samples of cinnamon bark or leaves were extracted at 200°C with water under pressure. The essential oils were obtained from the aqueous solution using a solid phase extraction cartridge and were then examined by GC‐MS. Results – Using superheated water extraction, cinnamon bark oil with over 80% cinnamaldehyde and cinnamon leaf oil containing up to 98% eugenol were obtained. Alternative solvent extraction methods were also studied but led to emulsion formation apparently because of the presence of cellulose breakdown products. Conclusion – Superheated water extraction offers a cheap, environmentally friendly technique with a shorter extraction time than hydrodistillation and yielded a higher quality oil with a higher proportion of eugenol than hydrodistillation. Copyright © 2010 John Wiley & Sons, Ltd.