巴柑檬果皮精油化学成分的研究

用 GC-MS-DS 联用技术、气相色谱双柱保留指数和气相色谱双柱标准品叠加实验,鉴定了我国首次引种成功的巴柑檬果皮精油的化学成分,测定了用不同方法提取的巴柑檬果皮精油各化学成分的相对含量。结果表明:引种的巴柑檬果皮精油的化学成分与国外文献值相符合。     

A Study on Chemical Components of Essential Oils from Citrus bergamia and Its Close Relatives and Its Taxonomy

Citrus bergamia Risso. is a rare perfumery plant. Taxonomists have different views on the taxonomy of C. bergamia. Chemical components of leaf and peel essential oils from C. bergamia, and its close relatives, C. limon, C. aurantifolia and three varieties of C. aurantium, were analyzed by GC and GC-MS. The analytical result shows that the chemical compositions of the leaf essential oils from C. bergamia are basically the same as those from three varieties of C. aurantium. Their main components are linalool (29.19-39.75% )and linalyl acetate (24.73-30.24% )etc., and contents of other components are also similar. But their peel essential oils are different. The peel essential oils from C. bergamia contain less limonene (29.94%) than those from C. aurantium (92.55-94.31% ) and less beta-pinene (3.00%) and y-terpinene(3.48% )than those from C. limon or C. aurantifolia (respectiyely 9.16% and 10.42% ) . The peel essential oils from C. bergamia contain not only as much linalool (22.20%) and linalyl acetate (32.66%)as those in the leaf essential oils from C. aurantium, but also as much limonene(29.94% )as that in the peel essential oils from C. limon or C. aurantifolia . The contents of limonene are close to those of the essential oils from C. aurantifolia. This result shows that C. bergamia may be a natural hybrid between C.aurantium and C. aurantifolia, as proposed by Sinclair W. B.     

无量山种子植物的区系平衡点

在较为完善的分类学处理后所得的包含207科,1026属,2540种植物的名录基础上,本文初步报道了地处滇中南的无量山的种子植物区系组成的初步结果,并在山体各海拔段进行了属的分布区类型每一类分布的详尽统计,得出了热带和温带两大基本成分在无量山达到平衡（各占50％）海拔点,称之为区系平衡点。该点从历史角度看可以反映无量山种子植物区系成分随自然历史变迁所发生的演变,从现实看表明了该地植物区系的过渡性质,同时,寓意着我国亚热带地区客观存在着一条区系平衡线,并且,该点还是热带成分的一个重要性限制点;另一方面可以作为植物引种和选择引种驯化锻炼基地的一个参考指标。     

Toxic effects of six plant oils alone and in combination with controlled atmosphere on Liposcelis bostrychophila (Psocoptera: Liposcelididae).

Six plant essential oils alone as repellent and fumigant, and in combination with the controlled atmosphere against Liposcelis bostrychophila Badonnel were assessed in the laboratory. These essential oils were extracted from the leaves of six source plants: Citrus tangerina Tanaka, Citrus aurantium L., Citrus bergamia Risso et Poiteau, Pinus sylvestris L., Cupressus funebris End]., and Eucalyptus citriodora Hook. The repellency test indicated that L. bostrychophila adults were repelled by filter paper strips treated with six essential oils. Of these essential oils, the C. funebris oil was most effective followed by that of F. sylvestris, C. tangerina, C. bergamia, and E. citriodora. The average repellency of the C. aurantium oil against L. bostrychophila adults was significantly lower than other five test oils by day 14. These essential oils had a high level of toxicity in the fumigation assay against L. bostrychophila adults at both 10 and 20 ppm. When combined with two controlled atmosphere treatments (12% CO2 + 9% O2, and 10% CO2 + 5% O2, balanced N2), the toxicity of plant oils was enhanced significantly.     

Changes in the Volatile Flavor Constituents of Citrus sinensis (L.) Osbeck During Storage

The methods of GC with fused silica capillary column, its Kovats retention index of GC and GC-MS-DS etc. We were used to study the aromatic compounds of the peel essential oil of Citrus sinensis (L.) Osbeck and aromatic concentrates of fruit flesh. 29 chemical constituents from the peels and 40 chemical constituents from the fruit flesh were identified. The trace constituents α-sinensal 0.01% and β-sinensal 0.01% are the special aroma ones for Citrus sinensis. At the same time, the changes flavor components in Citrus sinensis peels and fruit flesh during storage were also explored.     

A Study on the Chemical Components of the Essentialoi from Peel of Citrus medica L. var. muhensis W. D. et Y.

The chemical components of the essential oil from peel of Citrus medica L. var. muliensis W. D. et Y. has been studied by means of the GC-MS-DS, the retention index of eapillarly gas chromatography and the Authentic sample addition process. Twenty-nine constituents has been identified from sixty-four seperated peaks. The main constituents is d-limonene (68.2%), geranial (9.5%), neral (5.37%), nerol (2.72%), β-ocimen (2.47%) and (+)-Carvone.     

蒸馏法与溶剂萃取法提取金柚果皮精油成分的比较分析

采用蒸馏法和溶剂萃取法,提取梅州金柚（Citrus grandis Osbeck cv.）果皮精油,利用GC-MS联用技术测定其化学成分和质量分数,并对两种提取方法进行比较分析。蒸馏法和溶剂萃取法提取的柚皮精油经GC-MS分析,分别鉴定出15个和17个成分,分别占峰面积的99.01%和97.55%,两者共有成分有6个,主要成分均为柠檬烯,梅州金柚果皮可作为柠檬烯的重要资源。此外,溶剂萃取法提取的精油中,质量分数相对较高的9,12-四环辛二烯酸（0.62%）、蛇床子素（0.5%）和谷甾醇（0.5%）,在有关金柚精油成分的研究中尚未见报道。其中蛇床子素有抗骨质疏松、抗病毒等药理活性,谷甾醇有降低血清胆固醇的作用。     

The Chemical Constituents of the Essential Oil from the Flowers,Leaves and Peels of Citrus aurantium

Citrus aurantium L. var. amara Engl., is a better species of sour oranges. There are essential oils in the flowers, the peels, the leaves and the branches of C. aurantium. The flower oil can be used in the preparation of perfumes of high quality. The peel oil is used mainly for the flavor-endowing of soft drinks, alcoholic drinks, bread, confectionaries and cakes. In order to control the quality of the essential oils and to improve them, we have systema- tically studied the chemical constituents of the flowers, the leaves and the peals of C. aurantium with our preparation. 12 main components were separated by silica gel column chromatography. The following 33 chemical components were identified by IR, GC-MS and GC retention index: α-thujene, α-pinene, camphene, β-pinene, myrcene, limonene, β-ocimene, trans-linalooloxide (furanoid), cis-linalooloxide (furanoid), linalool, 1,4-p-methadien-7-ol, trans-pinocarveol, camphor, terpinen-4-ol α-terpineol, nerol, citral-b, geraniol, linalylacetate, citrala, trans-linalooloxide (pyranoid), methyl anthranilate, terpinyl acetate, cis-linalooloxide (pyranoid), neryl acetate. geranyl acetate, nonanal, β-caryophyllene, α-humulene, γ-muurolene, β-nerolidol, farnesol, α- nerolidol. GC retention index of 33 compounds were measured. A fast method for routine determination is presented.     

The Chemical Components of Essential Oils from the Leaves of 110 Species and Cultivars of Citrus Plants

Seventy-two chemical components of essential oils from the leaves of 110 species and cultivars of Citrus were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Among the plants analyzed, there are 3 species in papeda, 12 species and cultivars in Osmocitrus, 18 cultivars in C. aurantium L., 15 cultivars in C. sinensis Osbeck, 16 species and cultivars in Citrophorum, 16 species and cuhivars in Cephalocitrus, 30 species and cultivars in Acrumen. As resources of essential oils, some valuable plants were found such as Citrus hystrix D. C., C. junos (Sieb.) Tan. cv. Xiecheng, C. junos (Sieb.) Tan. cv. Luohancheng and C. tankan Hayata. Our study has provided systematic data of the chemical components of the essential oils for the taxonomic work of Citrus plants.     

Chemical composition and antimicrobial activity of Citrus essences on honeybee bacterial pathogen <Emphasis Type="Italic">Paenibacillus larvae</Emphasis>, the causal agent of American foulbrood

Antimicrobial properties and chemical composition of four citrus fruit essential oils to control Paenibacillus larvae, the causal agent of American foulbrood disease (AFB) were determined. This honeybee larvae disease occurs throughout the world and is found in many beekeeping areas of Argentina. Citrus fruit essential oils tested were those from grapefruit (Citrus paradisi), sweet orange (Citrus sinensis), mandarin (Citrus nobilis) and lemon (Citrus limon). The components of the essential oils were identified by SPME-GC/MS analysis. The antimicrobial activity of the oils against P. larvae were determined by the broth microdilution method. Two way ANOVA tests for minimum inhibitory concentrations (MICs) data and minimal bactericide concentrations (MBCs) data, indicated significant differences between the strains and the oils tested. The antimicrobial assays showed that the oil of C. paradisi inhibited the bacterial strains at the lowest concentrations tested, MICs and MBCs averages of 385.0 mg/l and 770.0 mg/l, respectively. This property could be attributed to the kind and percentage of the volatile components of the oil, like limonene (69.9%) and myrcene (9.6%). The use of essential oils or their specific volatile components individually against pests related to food provision may represent an alternative scope for the control of this serious disease because it does not leave toxic chemical residues in honey nor in its by products.     

Composition of Peel Oil from Citrus Unshu

Constituents of aroma of peel oil (both oleoresin and cold-pressed oil) from Citrus Unshu were isolated by column chromatography and gas chromatography (GLC). and identified mostly by infrared (IR), partially by mass (MS) and nuclear magnetic resonance (NMR) spectroscopy.

One hundred and seven compounds were found in the oil and among them, four sesquiterpene hydrocarbons, five acetates, five carbonyls and five alcohols were identified as a main constituents which contributed to difference in flavor from other citrus peel oils. Characteristics of aroma of C. Unshu was discussed on the basis of quantitative analysis.     

我国特有植物一木里香橼叶精油化学成分的研究

用气相色谱保留指数定性法、色谱-质谱-计算机联用测定和标准品迭加法分析了木里香橼叶精油的化学成分。从分离出的59个色谱峰中鉴定了31个化合物。其中主要成分是柠檬烯(31.730％)、芳樟醇(1.554％)、香茅醛(23.383％)、香茅醇(1.189％)、橙花醇(11.777％)、香叶醛(16.544％),乙酸香茅酯(1.427％)、乙酸橙花酯(2.258％)、乙酸香叶酯(4.714％)等。把木里香橼叶油与木里香橼果皮油与云南野香橼叶油分别作了比较。结果表明木里香橼叶油中含氧化合物醇、醛、酯的含量相当高,是精油的主要成分,可能作为进口橙叶油的较好的代用品,是一种很有潜力的天然香料资源。     

Toxicity of citrus essential oils against Ceratitis capitata (Diptera: Tephritidae) larvae

Citrus peel essential oils are considered to constitute the most important resistance factor of citrus fruits against fruit flies. Essential oils were obtained from three sweet orange varieties, one bitter orange and one lemon variety. Yield, chemical composition and toxicity against neonates of the Mediterranean fruit fly were determined. Based on chemical analysis, the toxicity of commercially purchased major and minor components (monoterpenes and sesquiterpenes) of essential oils was determined. In addition, fractions were prepared to evaluate the role of minor components in the toxicity of crude essential oils. Limonene was by far the most abundant ingredient (96.2–97.4%) in all sweet orange varieties and in bitter orange, while the concentration of limonene was much lower in lemon essential oils (74.3%). Orange and bitter orange essential oils were more toxic than lemon essential oils. The toxicity of orange and bitter orange essential oils was similar to that of their major component limonene. In tests of commercially purchased chemicals, the oxygenated components of essential oils were more toxic than hydrocarbons but their low concentration in citrus essential oils could not affect the toxic activity of essential oils. The presence of α-pinene and β-pinene seems to account for the lower toxicity of lemon essential oils in relation to other citrus essential oils. The importance of understanding the toxicity of essential oils in relation to their composition and their role regarding the resistance of citrus fruits to Ceratitis capitata infestation is discussed.     

Chemical composition and larvicidal activity of edible plant‐derived essential oils against the pyrethroid‐susceptible and ‐resistant strains of Aedes aegypti (Diptera: Culicidae)

The chemical compositions and larvicidal potential against mosquito vectors of selected essential oils obtained from five edible plants were investigated in this study. Using a GC/MS, 24, 17, 20, 21, and 12 compounds were determined from essential oils of Citrus hystrix, Citrus reticulata, Zingiber zerumbet, Kaempferia galanga, and Syzygium aromaticum, respectively. The principal constituents found in peel oil of C. hystrix were β‐pinene (22.54%) and d‐limonene (22.03%), followed by terpinene‐4‐ol (17.37%). Compounds in C. reticulata peel oil consisted mostly of d‐limonene (62.39%) and γ‐terpinene (14.06%). The oils obtained from Z. zerumbet rhizome had α‐humulene (31.93%) and zerumbone (31.67%) as major components. The most abundant compounds in K. galanga rhizome oil were 2‐propeonic acid (35.54%), pentadecane (26.08%), and ethyl‐p‐methoxycinnamate (25.96%). The main component of S. aromaticum bud oil was eugenol (77.37%), with minor amounts of trans‐caryophyllene (13.66%). Assessment of larvicidal efficacy demonstrated that all essential oils were toxic against both pyrethroid‐susceptible and resistant Ae. aegypti laboratory strains at LC₅₀, LC₉₅, and LC₉₉ levels. In conclusion, we have documented the promising larvicidal potential of essential oils from edible herbs, which could be considered as a potentially alternative source for developing novel larvicides to be used in controlling vectors of mosquito‐borne disease.     

Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil

The characteristic aroma compounds of Citrus natsudaidai Hayata essential oil were evaluated by a combination of instrumental and sensory methods. Sixty compounds were identified and quantified, accounting for 94.08% of the total peel oil constituents. Limonene was the most abundant compound (80.68%), followed by gamma-terpinene (5.30%), myrcene (2.25%) and alpha-pinene (1.30%). Nineteen compounds which could not be identified in the original oil were identified in the oxygenated fraction. Myrcene, linalool, alpha-pinene, beta-pinene, limonene, nonanal, gamma-terpinene, germacrene D, and perillyl alcohol were the active aroma components (FD-factor > 3(6)), whereas beta-copaene, cis-sabinene hydrate and 1-octanol were suggested as characteristic aroma compounds, having a Natsudaidai-like aroma in the GC effluent. Three other compounds, heptyl acetate, (E)-limonene oxide and 2,3-butanediol, which each showed a high RFA value (>35) were considered to be important in the reconstruction of the original Natsudaidai oil from pure odor chemicals. The results indicate that 1-octanol was the aroma impact compound of C. natsudaidai Hayata peel oil.     

The effect of lemon, orange and bergamot essential oils and their components on the survival of Campylobacter jejuni, Escherichia coli O157, Listeria monocytogenes, Bacillus cereus and Staphylococcus aureus in vitro and in food systems

AIMS: To investigate the effectiveness of oils and vapours of lemon (Citrus limon), sweet orange (Citrus sinensis) and bergamot (Citrus bergamia) and their components against a number of common foodborne pathogens. METHODS AND RESULTS: The disc diffusion method was used to screen the oils and vapours against Listeria monocytogenes, Staphylococcus aureus, Bacillus cereus, Escherichia coli O157 and Campylobacter jejuni. The survival of each species, demonstrated to be susceptible in the in vitro studies, was tested on cabbage leaf for 60 s by direct contact and on chicken skin for 10 min by direct contact and 24 h by vapour. The results indicate that bergamot was the most inhibitory essential oil (EO) and citral and linalool mimicked its effect (P > 0.001). Citral and linalool vapours produced 6 log reductions in L. monocytogenes, Staph. aureus and B. cereus populations on cabbage leaf after 8-10 h exposure but bergamot vapour exposure, while producing a similar reduction in L. monocytogenes and B. cereus populations, had no effect on Staph. aureus. CONCLUSIONS: Bergamot was the most effective of the oils tested and linalool the most effective anti-bacterial component. Gram-positive bacteria were more susceptible than Gram-negative bacteria in vitro, although Camp. jejuni and E. coli O157 were inhibited by bergamot and linalool oils and by linalool vapour. All bacteria tested were less susceptible in food systems than in vitro. Of the Gram-positive bacteria tested Staph. aureus was the least susceptible to both the oils and the components tested. SIGNIFICANCE AND IMPACT OF THE STUDY: Results suggest the possibility that citrus EOs, particularly bergamot, could be used as a way of combating the growth of common causes of food poisoning.     

柚皮干制前后精油香气成分分析

为明确干制对柚皮中精油香气成分的影响,采用水蒸气蒸馏法提取干制前后柚皮中精油,通过气相色谱-质谱法（GC-MS）对精油进行成分分析.结果表明,从鲜柚皮中共检出74种香气成分,占精油总质量分数的99.61%;从干柚皮中共检出45种香气成分,占精油总质量分数的99.45%;两者共有香气成分44种,相对质量分数分别为98.16%和99.41%.干制后柚皮香气成分中烯烃类化合物的相对质量分数增加;醇类、酯类和酮类化合物的相对质量分数减少.干制对柚皮主体香气成分影响不大.     

Effects of the essential oil from Citrus aurantium L. in experimental anxiety models in mice

Citrus aurantium L. is popularly used to treat anxiety, among other indications suggesting central nervous system action. Previous studies showed anxiolytic effect in the essential oil from peel in mice evaluated on the elevated plus maze [Carvalho-Freitas, M.I.R., Costa, M., 2002. Anxiolytic and sedative effects of extracts and essential oil from Citrus aurantium L. Biological and Pharmaceutical Bulletin 25, 1629-1633.]. In order to better characterize the activity of the essential oil, it was evaluated in two other experimental models: the light-dark box and the marble-burying test, respectively related to generalized anxiety disorder and to obsessive compulsive disorder. Mice were treated acutely by oral route 30 min (single dose) or once a day for 15 days (repeated doses) before experimental procedures. In light-dark box test, single treatment with essential oil augmented the time spent by mice in the light chamber and the number of transitions between the two compartments. There were no observed alterations in the parameters evaluated in light-dark box after repeated treatment. Otherwise, single and repeated treatments with essential oil were able to suppress marble-burying behavior. At effective doses in the behavioral tests, mice showed no impairment on rotarod procedure after both single and repeated treatments with essential oil, denoting absence of motor deficit. Results observed in marble-burying test, related to obsessive compulsive disorder, appear more consistent than those observed in light-dark box.     

Chemotaxonomic Investigations of Peel and Petitgrain Essential Oils from 17 Citron Cultivars

Chemical compositions of essential oils from 17 citron cultivars were studied using GC and GC/MS. To the best of our knowledge, chemical compositions of peel and petitgrain oils from seven of them were reported for the first time. Combined analysis of peel and petitgrain essential oils led to the identification of 37 components (amounting to 98.2–99.9% of the total oil) and 42 components (97.0–99.9%), respectively. Statistical analysis was applied to identify possible relationships between citron cultivars. The levels of seven components, i.e., limonene, β‐pinene, γ‐terpinene, neral, geranial, nerol, and geraniol, indicated that the cultivars could be classified in four main chemotypes for peel and petitgrain oils. Chemotaxonomic investigations were carried out to establish relations between the morphological characteristics of citron cultivars and their corresponding oil compositions.