Essential oil of trees of the genus Ocotea (Lauraceae) in Costa Rica. I. Ocotea brenesii

The chemical composition of the essential oils from leaves and wood of Ocotea brenesii Standl. growing wild in Costa Rica was determined by capillary GC/FID and GC/MS. From the leaves, 64 compounds were identified, corresponding to 85.9% of the oil, and from the wood 57 compounds were identified corresponding to 69.0% of the oil. The major constituents identified in the leaf oil were alpha-copaene (21. 1%), 8-cadinene (9.2%), spathulenol (7.3%), globulol (5.6%) and beta-caryophyllene (5.2%). The major constituents of the wood oil were alpha-copaene (6.6%), caryophyllene oxide (6.3%). beta-caryophyllene (6.1%) and humulene epoxide (4.6%).     

Antimicrobial activity of six constituents of essential oil from Salvia

The antimicrobial activity of three Salvia species, i.e. S. santolinifolia, S. hydrangea and S. mirzayanii, essential oils were investigated. The essential oils were obtained from the aerial parts of plants and analyzed by GC-MS. The main constituents of aforementioned species were alpha-pinene (72.4%), beta-pinene (6.6%) and limonene (5.3%); beta-caryophyllene (25.1%), 1,8-cineol (15.2%) and caryophyllene oxide (11.5%); alpha-terpinenyl acetate (22.6%), 1,8-cineol (21.2%) and linalool (8.9%), respectively. Bioassays exhibited that the property of the oil of S. myrzayanii was superior to others. The antimicrobial activity of essential oil from Salvia species may well be due to the presence of synergy between six tested compounds (linalool, 1,8-cineol, alpha-pinene, beta-pinene, beta-caryophyllene and limonene) and other constituents of the oils with various degrees of antimicrobial activity. Among these, linalool and 1,8-cineol had the highest antimicrobial activity.     

Chemical composition of the essential oil of Phlomis linearis Boiss. & Bal., and biological effects on the CAM-assay: a safety evaluation

Phlomis linearis Boiss. & Bal. of the Lamiaceae family growing in central, east and southeast Anatolia is an endemic species for Turkey. The essential oil obtained from the aerial parts by hydro distillation was subsequently analyzed by GC/MS. The main components of the oil were found as beta-caryophyllene (24.2%), germacrene D (22.3%) and caryophyllene oxide (9.2%), among 49 identified compounds, representing 94.5% of the total essential oil. The overall biological activity of the essential oil (100 microg/pellet) was tested on the chorioallantoic membrane (CAM) of the fertilized hen's egg in order to examine the anti-angiogenic and anti-inflammatory activity. None of the tests showed pronounced activity, toxicity or irritation at the tested concentration.     

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.     

Antimicrobial activity of some Satureja essential oils

The genus Satureja is represented by fifteen species of which five are endemic and Satureja pilosa and S. icarica have recently been found as new records for Turkey. Aerial parts of the Satureja pilosa, S. icarica, S. boissieri and S. coerulea collected from different localities in Turkey were subjected to hydrodistillation to yield essential oils which were subsequently analysed by GC and GC/MS. The main constituents of the oils were identified, and both antibacterial and antifungal bioassays were applied. Carvacrol (59.2%, 44.8%, 42.1%) was the main component in the oils of S. icarica, S. boissieri and S. pilosa, respectively. The oil of S. coerulea contained beta-caryophyllene (10.6%) and caryophyllene oxide (8.0%) as main constituents.     

小花假泽兰精油化学成分及其抑菌活性初步研究

利用GC-MS技术分析了小花假泽兰全株精油的化学成分及其含量,并初步测定了精油的抑菌效果.从小花假泽兰全株精油中共鉴定出49种成分,占色谱峰总面积的57.28%,主要成分为22,23-二羟基豆甾烷醇(7.34%)、氧化丁子香烯(3.34%)、罗汉柏烯(2.92%)、cubenol(2.81%)等.生长速率法测定表明,小花假泽兰精油对番茄灰霉病菌、小麦纹枯病菌和小麦赤霉病菌菌丝生长抑制作用较强,在1 000 mg/L剂量下抑制率均在90%以上;果实针刺法测试表明,该精油对番茄灰霉病菌具明显保护作用和治疗作用,但治疗效果低于保护效果,在2 000mg/L剂量下,后者达70.79%,前者仅51.79%.     

Essential Oils of Polyalthia suberosa Leaf and Twig and Their Cytotoxic and Antimicrobial Activities

Essential oils from the leaf and twig of Polyalthia suberosa (Roxb.) Thwaites were analyzed using GC/MS/FID. A total of sixty-three constituents were namely identified accounting for 96.03 and 94.12 % in the hydrodistilled oils of the leaf and twig, respectively. Monoterpenes, monoterpenoids, sesquiterpenes, and sesquiterpenoids were characteristic derivatives of P. suberosa essential oils. Sesquiterpenes bicyclogermacrene (26.26 %) and (E)-caryophyllene (7.79 %), and monoterpene β-pinene (12.71 %) were the major constituents of the leaf oil. Sesquiterpenes (E)-caryophyllene (17.17 %) and α-humulene (9.55 %), sesquiterpenoid caryophyllene oxide (9.41 %), and monoterpenes camphene (8.16 %) and tricyclene (6.35 %) were to be main components in the twig oil. The leaf oil indicated cytotoxic activity against three cancer cell lines HepG2, MCF7 and A549 with the IC₅₀ values of 60.96–69.93 μg/mL, while the twig oil inhibited MCF7 with the IC₅₀ value of 66.70 μg/mL. Additionally, the twig oil successfully suppressed the growth of the negative Gram bacterium Pseudomonas aeruginosa, fungus Aspergillus niger, and yeast Candida albicans with the same MIC value of 50 μg/mL, whereas the leaf oil had the same result on the negative Gram bacterium Escherichia coli.     

Antifungal, phytotoxic and insecticidal properties of essential oil isolated from Turkish Origanum acutidens and its three components, carvacrol, thymol and p-cymene

The chemical composition of essential oil isolated by hydrodistillation from the aerial parts of Origanum acutidens was analyzed by GC-MS. Carvacrol (87.0%), p-cymene (2.0%), linalool acetate (1.7%), borneol (1.6%) and beta-caryophyllene (1.3%) were found to be as main constituents. Antifungal, phytotoxic and insecticidal activities of the oil and its aromatic monoterpene constituents, carvacrol, p-cymene and thymol were also determined. The antifungal assays showed that O. acutidens oil, carvacrol and thymol completely inhibited mycelial growth of 17 phytopathogenic fungi and their antifungal effects were higher than commercial fungicide, benomyl. However, p-cymene possessed lower antifungal activity. The oil, carvacrol and thymol completely inhibited the seed germination and seedling growth of Amaranthus retroflexus, Chenopodium album and Rumex crispus and also showed a potent phytotoxic effect against these plants. However, p-cymene did not show any phytotoxic effect. Furthermore, O. acutidens oil showed 68.3% and 36.7% mortality against Sitophilus granarius and Tribolium confusum adults, respectively. The findings of the present study suggest that antifungal and herbicidal properties of the oil can be attributed to its major component, carvacrol, and these agents have a potential to be used as fungicide, herbicide as well as insecticide.     

苦橙叶精油化学成分及抗炎作用研究

为探究苦橙叶精油的抗炎作用。实验采用气相-质谱联用法(GC-MS)分析精油成分,并建立脂多糖(LPS)诱导RAW 264.7细胞炎症模型,用Griess法检测一氧化氮(NO)含量评价其体外抗炎作用,随后进一步通过巴豆油致小鼠耳肿胀模型和鸡蛋清致小鼠足肿胀模型评价其体内抗炎作用。结果表明苦橙叶精油成分以酯类、醇类物质为主;25μg/mL浓度能显著抑制RAW 264.7细胞NO的释放;中浓度苦橙叶精油能明显减轻小鼠耳肿胀程度;低、中、高浓度苦橙叶精油均对小鼠足肿胀模型有炎症缓解作用,并于肿胀前期呈浓度依赖性。以上实验证明苦橙叶精油在体外和体内具有一定抗炎作用。     

GC/MS analysis and potential synergistic effect of mandarin and marjoram oils on Helicobacter pylori

Helicobacter pylori can cause chronic gastritis, peptic ulcer, and gastric carcinoma. This study compares chemical composition and anti-H. pylori activity of mandarin leaves and marjoram herb essential oils, and their combined oil. GC/MS analysis of mandarin oil revealed six compounds (100% identified), mainly methyl-N-methyl anthranilate (89.93%), and 13 compounds (93.52% identified) of marjoram oil, mainly trans-sabinene hydrate (36.11%), terpinen-4-ol (17.97%), linalyl acetate (9.18%), and caryophyllene oxide (8.25%)). Marjoram oil (MIC = 11.40 µg/mL) demonstrated higher activity than mandarin oil (MIC = 31.25 µg/mL). The combined oil showed a synergistic effect at MIC of 1.95 µg/mL (same as clarithromycin). In-silico molecular docking on H. pylori urease, CagA, pharmacokinetic and toxicity studies were performed on major compounds from both oils. The best scores were for caryophyllene oxide then linalyl acetate and methyl-N-methyl anthranilate. Compounds revealed high safety and desirable properties. The combined oil can be an excellent candidate to manage H. pylori.     

Volatile constituents of Cunila polyantha (Lamiaceae) from Costa Rica. A rich source of menthone

The constituents of the volatile oil of Cunila polyantha from Dota, Costa Rica, were investigated using coupled gas chromatography-mass spectrometry (GC-MS) analyses. Menthone (63%), pulegone (14%), beta-caryophyllene (4.5%) and 3-octanyl acetate (3%) were found to be the major constituents of the volatile oil.     

Studies on the antioxidant activity of the essential oil and methanol extract of Marrubium globosum subsp. globosum (lamiaceae) by three different chemical assays

This study is designed to examine the chemical composition and in vitro antioxidant activity of the essential oil and sub-fractions of the methanol extract of Marrubium globosum subsp. globosum. The GC and GC-MS analysis of the essential oil were resulted in the determination of 84 components representing 88.2% of the oil. The major constituents of the oil were spathulenol (15.8%), beta-caryophyllene (9.0%), caryophyllene oxide (7.9%), germacrene D (6.5%), and bicyclogermacrene (3.1%). Antioxidant activities of the samples were determined by three different test systems namely DPPH, beta-carotene/linoleic acid and reducing power assay. In DPPH system, the weakest radical scavenging activity was exhibited by the essential oil (1203.38+/-7.18 microg ml(-1)). Antioxidant activity of the polar sub-fraction of methanol extract was superior to the all samples tested with an EC(50) value of 157.26+/-1.12 microg ml(-1). In the second case, the inhibition capacity (%) of the polar sub-fraction of methanol extract (97.39%+/-0.84) was found the strongest one, which is almost equal to the inhibition capacity of positive control BHT (97.44%+/-0.74). In the case of reducing power assay, a similar activity pattern was observed as given in the first two systems. Polar sub-fraction was the strongest radical reducer when compared with the non-polar one, with an EC(50) value of 625.63+/-1.02 microg ml(-1). The amount of the total phenolics was highest in polar sub-fraction (25.60+/-0.74 microg/mg). A positive correlation was observed between the antioxidant activity potential and total phenolic level of the extracts. On the other hand, total flavonoid content was found equal for the both sub-fractions.     

Anti-inflammation activity of fruit essential oil from Cinnamomum insularimontanum Hayata

In this study, the fruit essential oil of Cinnamomum insularimontanum was prepared by using water distillation. Followed by GC-MS analysis, the composition of fruit essential oil was characterized. The main constituents of essential oil were alpha-pinene (9.45%), camphene (1.70%), beta-pinene (4.30%), limonene (1.76%), citronellal (24.64%), citronellol (16.78%), and citral (35.89%). According to the results obtained from nitric oxide (NO) inhibitory activity assay, crude essential oil and its dominant compound (citral) presented the significant NO production inhibitory activity, IC(50) of crude essential oil and citral were 18.68 and 13.18mug/mL, respectively. Moreover, based on the results obtained from the protein expression assay, the expression of IKK, iNOS, and nuclear NF-kappaB was decreased and IkappaBalpha was increased in dose-dependent manners, it proved that the anti-inflammatory mechanism of citral was blocked via the NF-kappaB pathway, but it could not efficiently suppress the activity on COX-2. In addition, citral exhibited a potent anti-inflammatory activity in the assay of croton oil-induced mice ear edema, when the dosage was 0.1 and 0.3mg per ear, the inflammation would reduce to 22% and 83%, respectively. The results presented that the fruit essential oil of C. insularimontanum and/or citral may have a great potential to develop the anti-inflammatory medicine in the future.     

Chemical composition and antimicrobial activity of essential oil from cones of Pinus koraiensis

The essential oil from the cones of Pinus koraiensis was prepared after removing the seeds, and its chemical composition analyzed using gas chromatography-mass spectrometry (GC-MS). Hydrodistillation of the P. koraiensis cones yielded 1.07% (v/w) of essential oil, which was almost three times the amount of essential oil extracted from the needles of the same plant. Moreover, the antimicrobial activities of the oil against the growth of Gram-positive bacteria, Gram-negative bacteria, and fungi were evaluated using the agar disc diffusion method and broth microdilution method. Eighty-seven components, comprising about 96.8% of the total oil, were identified. The most abundant oil components were limonene (27.90%), alpha-pinene (23.89%), beta-pinene (12.02%), 3-carene (4.95%), beta-myrcene (4.53%), isolongifolene (3.35%), (-)-bornyl acetate (2.02%), caryophyllene (1.71%), and camphene (1.54%). The essential oil was confirmed to have significant antimicrobial activities, especially against pathogenic fungal strains such as Candida glabrata YFCC 062 and Cryptococcus neoformans B 42419. Therefore, the present results indicate that the essential oil from the cones of Pinus koraiensis can be used in various ways as a nontoxic and environmentally friendly disinfectant.     

<Emphasis Type="Italic">Peucedanum japonicum</Emphasis> and<Emphasis Type="Italic">Citrus unshiu</Emphasis> essential oils inhibit the growth of antibiotic-resistant skin pathogens

In this study, the chemical compositions and the anti-bacterial activities of hydrodistilled essential oils of the whole parts ofPeucedanum japonicum and the immature fruits ofCitrus unshiu were investigated. The chemical constituents of theP. Japonicum (PJE) andCitrus unshiu (CuE) essential oils were further analyzed by GC-MS and their major components were β-pinene (66.07%) and limonene (77.93%), respectively. The antibacterial activities of PJE and CuE against drug-susceptible and -resistant skin pathogens were also examined. Anti-bacterial tests using the disk diffusion method and the minimum inhibitory concentration (MIC) values indicated that PJE and CuE have excellent activities. The MIC of PJE against drug-susceptible and -resistant skin pathogens ranged from 0.13 to 5.0 μL/mL, whereas that of CuE ranged from 0.08 to 1.25 μL/mL. In addition, CuE reduced the lipopolysaccharide (LPS)-induced secretion of nitric oxide (NO) in RAW 264.7 cells, indicating that it has anti-inflammatory effects. These findings demonstrate that PJE and CuE have great potential for use in promoting human skin health.     

马缨丹叶片精油化学成分及其对三种害虫的生物活性

【目的】为探讨马缨丹Lantana camara L.叶片精油化学成分以及其对3种害虫的生物活性,以应用于生物防治。【方法】马缨丹叶片经水蒸气蒸馏法提取精油,产率为0.21%。经过气-质联用仪(GCMS)分析,从马缨丹叶片精油中检测出主要的26种化合物,其中α-姜黄烯(α-curcumene,32.76%),β-石竹烯(β-caryophyllene,16.36%),石竹烯氧化物(Caryophyllene oxide,12.22%),桉油烯醇(Spathulenol,10.48%)含量较高,并对3种不同害虫进行生物活性测定。【结果】生物测定结果表明,马缨丹精油对米象Sitophilus oryzae成虫和Ⅳ龄埃及伊蚊Aedes aegypti幼虫的触杀效果显著,LC50分别为0.92 mg/cm2和32.33μg/m L。随着浓度的升高,对白蚁驱避作用增强,白蚁死亡率增加;高浓度精油对白蚁有触杀作用,但较低浓度对白蚁无显著影响。【结论】本研究证明马缨丹叶片精油对3种害虫有良好防治的效果。     

Comparison of Chemical Composition of the Essential Oils from Different Botanical Organs of Pinus mugo Growing in Poland

The essential oils from needles, twigs, bark, wood, cones and young shoots of Pinus mugo were analyzed by GC, GC/MS, and ¹H‐NMR spectroscopy. More than 130 compounds were identified. The oils differed in the quantitative composition. The principal components of the oil from twigs with needles were 3‐carene (23.8 %), myrcene (22.3 %), and α‐pinene (10.3 %). The needle oil contained mainly α‐pinene (18.6 %), 3‐carene (11.3 %), and bornyl acetate (8.3 %). The oils from twigs without needles, young shoots, bark, and wood were dominated by 3‐carene (28.6 %, 15.0 %, 18.5 %, and 34.6 %, respectively) and myrcene (23.4 %, 24.0 %, 24.6 %, and 9.4 %, respectively). In the cone oil (E)‐β‐caryophyllene was the main constituent (24.0 %).     

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。     

Chemical Composition,Antimicrobial, Nitric Oxide Inhibition and Cytotoxic Activity of Essential Oils from Zanthoxylum acanthopodium DC. Leaves and Stems from Vietnam

This study was aimed to investigate the chemical composition and biological activities of leaf and stem essential oils of Zanthoxylum acanthopodium DC. from Vietnam. Their chemical composition was analyzed by GC/MS. Antimicrobial activities were evaluated by microdilution broth assay. Anti-inflammatory activity was evaluated by the ability to inhibit nitric oxide production in macrophage cells. Cytotoxic activity was evaluated using the sulforhodamine B assay on three human cancer cell lines. Forty-four compounds were identified in the leaf oil, among which dehydroaromadendrane (23.4 %), (E)-carpacin (17.6 %), 2-tridecanone (12.2 %), and 9-methyl-2-decanone (11.8 %) were the most abundant. The stem oil contained fifty-five identified constituents, mainly γ-gurjunene (51.1 %) and butyl acetate (11.8 %). Both oils exhibited inhibitory effects on three bacterial strains, namely S. aureus, E. coli, P. aeruginosa and a fungal strain C. albican, while showed insignificant effects on B. subtilis, L. fermentum, and S. enterica. Both oils showed weak NO production inhibition in LPS-induced RAW264.7 cells, but exhibited potent cytotoxic activity against all three tested cell lines SK-LU-1, MCF-7, and HepG2 with the IC₅₀ values ranging from 16.03±0.77 to 35.60±1.62 μg/mL. This is the first report on the antimicrobial, anti-inflammatory and cytotoxic activities of essential oils from the leaves and stems of Z. acanthopodium.     

Phytochemical investigation and evaluation of anti-inflammatory and anti-arthritic activities of essential oil of Strobilanthus ixiocephala Benth

Column chromatographic fractionation of essential oil obtained by hydrodistillation from the flowering tops of S. ixiocephala resulted in the isolation of beta-caryophyllene, fenchyl acetate, T-cadinol and a new sesquiterpene alcohol for which a name ixiocephol has been proposed. The beta-caryophyllene and fenchyl acetate were identified by Co-TLC with authentic samples whereas T-cadinol and ixiocephol were structurally elucidated by UV, IR, 1H NMR, 13C NMR and Mass spectral data. The GC-MS analysis of the essential oil has also revealed the presence of various monoterpenoids and sesquiterpenoids. The essential oil of S. ixiocephala demonstrated a dose dependant anti-inflammatory activity in carrageenan-induced rat paw oedema. It has also revealed good activity in cotton pellet granuloma and adjuvant induced arthritis model in rats.