May/June 2010

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Chemical Composition and Antioxidant Activities of the Essential Oils of Different Parts of Cupressus arizonica Greene

by: S.A. Emami and M. Fakhrjafary, M. Tafaghodi, M.K. Hassanzadeh

The essential oils of different parts of Cupressus arizonica were examined for their potential radical scaveng- ing activity. Fresh leaves and fruits of C. arizonica were steam distilled and the oils were analyzed qualitatively and quantitatively by GC and GC/MS. Different methods of rapid TLC screening, DPPH assay, desoxyribose assay, assay for site-specific reaction and non-enzymatic lipid peroxidation were employed to evaluate possible antioxidant activity of the oils and their main components, as well as the positive controls.

The main components of these essential oils were a-pinene, cymene, myrcene, limonene, sabinene hydrate, cedrane and germacrene D. In rapid TLC screening, the tested compounds mainly showed antioxidant activity. In DPPH assay the stronger antioxidant effects were shown by the fruit oil of C. arizonia. In deoxyribose degradation assay test, most of the tested compounds showed some antioxidant effects. In non-enzymatic lipid peroxidation test, most antioxidant activity was shown by the fruit oil.

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Essential Oil From Organs of Piper truncatum Vell.

by: Ana Paula F. Trindade, Leosvaldo S.M. Velozo, Elsie F. Guimarães, and Maria Auxiliadora C. Kaplan

Essential oils from leaves, stems, roots and inflorescences of Piper truncatum were analyzed by GC and GC/ MS. The main constituents of the oils were; inflorescence oil: camphene (10.3%), germacrene D (56.0%), and an isomer of a-farnesene (10.4%); leaf oil: (Z)-3-hexenol (35.3%), b-caryophyllene (24.2%), germacrene D (11.1%) and (E)-nerolidol (10.5%); stem oil: 6(Z),8(E)-N-isobutyl-decadienamide (16.2%) and root oil: 6(Z),8(E)-N-isobutyldecadienamide (67.6%).

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Volatile Constituents of Aerial Parts of Teucrium scordium L. From Iran

by: Fraiba Sharififar, Zahra Mahdavi, Mansour Mirtajaldini and Amin Purhematy

The essential oil of the aerial parts of Teucrium scordium L. (Lamiaceae), one endemic species growing in Iran was analyzed via GC and GC/MS. Forty components representing about 94.6% of the oil were identified. Pulegone (39.1%) and b-caryophyllene (20.1%) were the main constituents. Additionally, other major compounds were b-farnesene (5.7%), menthofuran (4.2%), 1,8 cineole ( 4.1%) and a-humulene (3.1%). In this oil, the main classes of compounds were found to be oxygenated monoterpenes (54.5%) followed by hydrocarbon sesquiterpenes (28.9%).

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Extraction of Melaleuca cajuputi Using Supercritical Fluid Extraction and Solvent Extraction

by: S.M. Jajaei,* W.R.W. Daud and M. Markom, Z. Zakaria, M. Lo Presti, Rosaria Costa and L. Mondello, and Luca Santi

Extracts of Melaleuca cajuputi were obtained by supercritical (carbon dioxide) extraction and solvent (hexane) extraction methods. This work is aimed at adapting the green technology of using supercritical CO2 (SC-CO2) as solvent in a batch process to extract Melaleuca cajuputi leaves. The plant leaves were collected from Trengganu, Malaysia. Cajuputi extract analyses were performed by GC and GC/MS. The maximum yields obtained were 4.2% and 6.0%, respectively, by supercritical fluid (SFE) and solvent extraction (SE). Several compounds were identified and significant qualitative and quantitative differences were observed under different conditions. The major components of Cajuputi oil consisted of sesquiterpenes (d-elemene, b-elemene, b-caryophyllene, a-humulene, 9-epi-b-caryophyllene), their oxygenated derivatives (viridiflorol, platyphyllol, b-eudesmol, bulnesol, (Z,Z)-farnesol and (E,E)-farnesal) and polyphenolic ketones (isoeugenitine and three unknown compounds).

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Seasonal Variations of Teucrium flavum L. Essential Oil

by: Maria Lo Presti, Maria L. Crupi, Rosaria Costa, G. Dugo and L. Mondello, Salvatore Ragusa and Luca Santi

Essential oils from the aerial parts of Sicilian Teucrium flavum L., isolated by using microwave-assisted hydrodistillation (MHD), were analyzed for the first time at various seasonal stages (vegetative and budding stage) by means of GC/MS and GC-FID; the flowers and fruits were also subjected to examination. More than 80 compounds were identified as oil components. The leaf, flower and fruit oils were characterized by a predominance of sesquiterpenes, such as b-caryophyllene (3–5 g/100 g), germacrene D (4–14 g/100 g), b-bisabolene (32–49 g/100 g); the total amount of sesquiterpene hydrocarbons contained in each oil was 56–70 g/100 g, the oxygenated derivatives were in the range of 9–20 g/100 g. The monoterpene hydrocarbons in all samples (leaves, flowers, fruits) were contained in very low amounts, from 0.2 to 1.6 g/100 g, and were the least representative fraction of the oils. Oxygenated aliphatic compounds, especially esters, were also detected. The results can be useful to support, by means of a safe reliable sample preparation (MHD) and analytical (GC) technique, the research on medicinal plants belonging to Mediterranean flora.

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Combined Analysis of Angelica acutiloba Kitagawa Seed Oil by GC(RI), GC/MS and 13C-NMR

by: Ange Bighelli, Dominique Lesueur, Joseph Casanova, Bui Thi Bang and Pham Van Y

The seed oil of Angelica acutiloba Kit. was submitted, after fractionation over silica gel, to a combined analysis by GC(RI), GC/MS and 13C-NMR. The composition was dominated by non terpenic acyclic alcohols and acetates, and phthalides. The main constituents were dodecyl acetate (33.0%), (Z)-ligustilide (17.4%), dodecanol (7.1%), p-cymene (6.4%), g-terpinene (5.9%) and tetradecyl acetate (5.0%).

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Essential Oil Composition of Globba schomburgkii Hook. f. and Globba ophioglossa Wight

by: Gopan Raj, Varughese George, Mathew Dan and Mathur G. Sethuraman

Essential oils obtained by hydrodistillation of Globba schomburgkii and G. ophioglossa, whole plants (Zingiberaceae) were analyzed by GC-FID and GC/MS. Twenty-two compounds representing 95.2 % of the oil were identified in the analyzed oil from Globba schomburgkii among which b-caryophyllene (31.7%) and caryophyllene oxide (10.3%) were the major constituents. The oil of G. ophioglossa was characterized by its richness in zerumbone (22.0%) and caryophyllene oxide (21.8%), which were among the 16 components comprising 88.3% of the total oil analyzed.

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Volatile Constituents of Centaurea paniculata Subsp. carueliana and C. rupestris s.l. (Asteraceae) From Mt. Ferrato (Tuscany, Italy)

by: Aldo Tava, Silvia Esposti, Mirko Boracchia and Lucia Viegi

The essential oil composition of two endemic species of Centaurea, C. paniculata subsp. carueliana and C. rupestris (Asteraceae) collected on serpentine rocks on Mt. Ferrato (Tuscany, Italy) were investigated by GC and GC/ MS. Several classes of compounds were detected, of which sesquiterpenes, (representing the 25.6% of the total oil from C. paniculata and 74.5% from C. rupestris), alcohols (27.8% in C. paniculata and 4.3% in C. rupestris) and aldehydes (12.0% C. paniculata and 2.0% in C. rupestris) were the most abundant, followed by acids, monoterpenes, esters, ketones, hydrocarbons, diterpenes and miscellaneous. A series of unidentified compounds were also detected. Differences in qualitative and quantitative composition were evidenced and discussed.

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Chemical Composition of the Essential Oil From Solidago puberula Nutt. Growing Wild in the North of Quebec

by: Marianne Piochon, Jean Legault, and André Pichette,

The chemical composition of the essential oil of the aerial parts of downy goldenrod (Solidago puberula Nutt.) growing wild in the north of Quebec (Canada) was investigated for the first time. The oil was analyzed by GC-FID and GC/MS. The main components were myrcene (53.0%), a-farnesene (10.7%), a-pinene (9.4%), (E)-b-ocimene (6.0%), and a-phellandrene (5.7%).

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Volatile Compounds of Seeds of Hesperis bicuspidata, H. bottae and H. podocarpa

by: Nes’e Kirimer, Sengül Gökmen, Betül Demirci, Kemal Hüsnü Can Baser and Ahmet Duran

The volatiles obtained by microdistillation from the crushed seeds of Hesperis bicuspidata (Willd.) Poir., H. bottae Fourn. and H. podocarpa Boiss. (Apiaceae), were analyzed by gas chromatography (GC) and gas chromatography/ mass spectrometry (GC/MS) systems, simultaneously. The major constituent was found as octyl acetate (44%, 29% and 42%) in the volatiles of H. bicuspidata, H. bottae, H. podocarpa, respectively.

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Volatile Constituents of Seeds of Nigella orientalis Cultivated in Poland

by: Anna Wajs and Danuta Kalemba

Volatile organic compounds from the seeds of Nigella orientalis L. were isolated by hydrodistillation and headspace- solid-phase microextraction (HS-SPME). Thirty compounds were identified, 16 of which were new for this plant material. The predominant group of components were sesquiterpene hydrocarbons, among which the major were: b-elemene, d?cadinene and a-selinene. By applying HS?SPME, it was possible to detect more compounds than by means of hydrodistillation. Sesquiterpene hydrocarbons were identified both in hydrodistilled essential oils and those analyzed using HS?SPME, while monoterpenes and low boiling non-terpenes were detectable only by means of HS-SPME method.

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Composition of the Essential Oil From Leaves and Fruits of Hedyosmum colombianum Cuatrec. Grown in Colombia

by: Paula A. Delgado, Clara E. Quijano, Gustavo Morales and Jorge A. Pino

The composition of the essential oils from leaves and fruits of Hedyosmum colombianum Cuatrec. was analyzed by GC and combined GC/MS. Ninety-seven compounds were identified which constitute more than 99% of the composition. The major compounds in both oils were b-pinene (11.4–16.5%) and pinocarvone (13.4–14.2%).

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Composition and Chemical Variability in the Essential Oil from Leaves of Memora nodosa (Silva Manso) Miers

by: Leonice M.F. Tresvenzol, José R. Paula, Pedro H. Ferri and Flavia N.M. Oliveira

The essential oils from leaves of Memora nodosa collected from seven localities of Central Brazilian Cerrado were investigated by GC and GC/MS. Benzaldehyde and 1-octen-3-ol were the major constituents. The results were submitted to Principal Component and Cluster analysis which allowed two groups of oils to be distinguished with respect to sampling site and chemical constituent: cluster I (leaves from Goiânia, Rio Verde, Nerópolis, and Uberlândia sites) containing (E)-2-hexenal (0.3–1.2%) and the highest percentage of 1-octen-3-ol (5.5–8.4%), and cluster II (leaves from Paraúna, Senador Canedo, and Caldas Novas sites) with the highest percentage of benzaldehyde (91.8–94.2%). A strong correlation was obtained between the oil constituent and the geographical coordinates of sampling sites. 1-Octen-3-ol was mainly produced in ecotypes with high altitudes.

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Volatile Constituents of the Aerial Parts of Salvia apiana Jepson

by: Gary R. Takeoka, Christopher Hobbs and Byeoung-Soo Park

Volatile constituents of the aerial parts of fresh white sage (Salvia apiana Jepson) were isolated by extraction with diethyl ether followed by high vacuum distillation with a solvent assisted flavor evaporation (SAFE) apparatus. The isolated volatiles were analyzed by GC and GC/MS. A total of 84 constituents were identified (constituting 95.1% of the total area), 11 of which were tentatively identified. The volatiles were characterized by a high content of hydrocarbon and oxygenated monoterpenes. The major constituents identified were 1,8-cineole (34.5%), camphor (21.7%), b-pinene (7.4%), a-pinene (6.4%), d-3-carene (6.4%), camphene (3.9%), limonene (3.5%), myrcene (3.2%), and terpinolene (1.3%).

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Composition of Tordylium aegyptiacum (L.) Lam. Essential Oil

by: Alev Tosun, Mine Kürkçüoglu and K. Hüsnü Can Baser

The essential oil obtained by hydrodistillation from fruits of Tordylium aegyptiacum (L.) Lam. (syn.: Hasselquistia aegyptiaca L.) (Umbelliferae) was analyzed by GC and GC/MS. In total, 59 compounds were characterized, representing 93.9% of the oil. The main constituents were determined as hexadecanoic acid (40.1%), b-caryophyllene (10.6%), octyl octanoate (8.8%) and caryophyllene oxide (8.5%).

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Volatiles From Mansoa standleyi (Steyerm.) A. H. Gentry

by: Maria das G.B. Zoghbi, Raimunda A. Pereira, Giselle do S. L. de Lima and Giselle M.S.P. Guilhon

Essential oils of Mansoa standleyi collected at four municipalities of the State of Pará were obtained by hydrodistillation and analyzed by GC-FID and GC/MS. All samples analyzed showed a high content of sulfur compounds, among them diallyl disulfide (42.2–69.2%) and diallyl trisulfide (20.1–37.0%) were major. Oils from the leaves, stems, roots, tendrils, seeds, fruit pulp and fruit skin were obtained separately: allyl disulfide was major in seed oil (78.1%), and pulp fruit oil (70.2%), followed by the leaf and stem oils (60.2%). The lowest amount of ally disulfide was in the root oil (51.1%). In all samples the amount of diallyl disulfide was counterbalanced by the amount of diallyl trisulfide.

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Volatiles of Telekia speciosa (Schreb.) Baumg. (Asteraceae) From Serbia

by: Bojan Zlatkovic, Niko Radulovic, Polina Blagojevic and Radosav Palic

The essential oil from the aerial parts of Telekia speciosa (Schreb.) Baumg. obtained by hydrodistillation was analyzed by GC and GC/MS. One hundred and eighty constituents identified accounted for 86.4% of the total oil. The major components of the oil were: (E,Z)-farnesol (12.0%), (E)-nerolidol (10.2%), b-caryophyllene (5.4%), caryophyllene oxide (4.5%), intermedeol (4.2%) and alantolactone (4.1%). The terpenoid fraction represented more than four-fifths of the oil (15.9% monoterpenoids, 64.7% sesquiterpenoids, both classes dominated by oxygenated derivatives). Unlike the root oil, where the eudesmanes were by far the most dominant compound class, the volatiles of the aerial parts were mainly consisted of acyclic-farnesane sesquiterpenoids (26.2%), along side with caryophyllanes (11.6%) and eudesmanes (14.5%).

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Identification of the Volatile Compounds of Flowers of Campomanesia sessiliflora O. Berg and Campomanesia xanthocarpa O. Berg

by: Claudia L. Cardoso, Vanessa M.F. Kataoka and Nilva Ré-Poppi

The essential oils obtained from the flowers from Campomanesia sessiliflora and Campomanesia xanthocarpa were analyzed by GC and GC/MS. Thirty-seven and 34 components were identified in the fruit oil of Campomanesia sessiliflora and Campomanesia xanthocarpa, respectively. In two species the major constituent was ledol (15.6–18.9%).

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Essential Oil Composition of the Endemic Species Thamnosciadium junceum (Sm.) Hartvig

by: Olga Tzakou, Konstantinos Lempesis and Anargyros Loukis

The essential oil of the aerial parts of the endemic Greek species Thamnosciadium junceum was analyzed by GC and GC/MS. Seventy-one compounds representing 98.9% of the total oil were identified. The major constituents were limonene (33.5%), (E)-isomyristicin (15.4%) and terpinolene (9.0%).

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Essential Oils From Beilschmiedia pendula (Sw.) Hemsl. (Lauraceae) From Costa Rica

by: Carlos Chaverri and José F. Cicció

The composition of the essential oil from leaves and branches of Beilschmiedia pendula growing wild in Costa Rica was determined by capillary GC-FID and GC/MS. Sixty eight and 67 compounds were identified in the leaf and branch oils respectively corresponding to about 84.3% and 96.7% of the total amount of the oils. The leaf oil consists mainly of monoterpene hydrocarbons (27.4%), sesquiterpene hydrocarbons (33.0%) and oxygenated sesquiterpenes (16.3%). The major components of the leaf oil were b-pinene (10.4%), b-caryophyllene (8.6%), a-pinene (7.9%) and bicyclogermacrene (7.2%). The branch oil consists mainly of sesquiterpene hydrocarbons (59.3%) and oxygenated sesquiterpenes (24.9%). The major components of the branch oil were b-caryophyllene (17.3%), b-selinene (9.1%), bicyclogermacrene (8.9%), a-cadinol (5.8%) and spathulenol (4.6%).

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Antibacterial Activities Against Staphylococcus aureus of Terpene Alcohols With Aliphatic Carbon Chains

by: Naoko Togashi, Hajime Hamashima, Akiko Shiraishi, Yoshihiro Inoue and Akihito Takano

The antibacterial activities against Staphylococcus aureus of terpene alcohols with aliphatic carbon chains of various lengths were investigated. Farnesol and nerolidol, which each contain two isoprene units, had the strongest antibacterial activities and damaging effects on cell membranes of all the terpene alcohols tested. Plaunotol, which is a diterpene, had antibacterial activity similar to that of sesquiterpenes. The relationship between the length of the carbon chain bonded to the hydroxyl group and activity suggests that the length of the carbon chain is an important determinant of antibacterial activity and cell membrane-damaging activity. It was concluded that the carbon chain length of C10-C12 was appropriate to show the activity.

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Effect of Citronella Oil on Time Kill Profile, Leakage and Morphological Changes of Propionibacterium acnes

by: Pilanthana Lertsatitthanakorn, Suwimol Taweechaisupapong, Channarong Arunyanart, Chantana Aromdee and Watcharee Khunkitti

The aim of this study was to investigate the effect of citronella oil (Java type) (Cymbopogon winterianus Jowitt) on Propionibacterium acnes DMST 14916. Citronella oil compositions were determined by gas chromatography mass spectrometry (GC/MS). Anti-P. acnes activity of citronella oil and its major components were also investigated. After exposure with P. acnes at various concentrations of citronella oil (0–100 mL/mL), time-kill profiles, pentose leakage and electron microscopic characteristics were determined. The GC/MS results revealed that the major constituents of the oil were citronellal, geraniol and citronellol. At all concentrations above Minimum Bactericidal Concentrations (MBCs; 0.625mL/mL), this essential oil killed P. acnes in a dose-dependent manner. The intracellular materials leakage and electron microscopic characteristics evidenced that the major target sites of antibacterial activity appeared to be cell wall, cytoplasmic membrane and intracellular materials. Citronella oil exerted satisfactory bacteriostatic and bactericidal actions against P. acnes.

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Composition and Antimicrobial Activity of the Leaf Essential Oils of Duguetia gardneriana Mart. and Duguetia moricandiana Mart. (Annonaceae)

by: Jackson Roberto Guedes da Silva Almeida, Roselaine Facanali, Maria Aparecida Ribeiro Vieira, Márcia Ortiz Mayo Marques, Ana Sílvia Suassuna Carneiro Lúcio, Edeltrudes de Oliveira Lima, Maria de Fátima Agra and José Maria Barbosa-Filho

As part of their continuing studies on the constituents of the genus Duguetia, these authors have studied the composition and antimicrobial activity of the essential oils obtained from the leaves of two species, and the results are reported here. A hydrodistilled oils obtained from the leaves of Duguetia gardneriana and Duguetia moricandiana were analyzed by GC/MS. The oils showed a total of 33 components. Germacrene D (28.1%), viridiflorene (24.0%), b-pinene (12.6%), a-pinene (9.1%) and b-caryophyllene (5.6%) were found to be the major individual constituents of D. gardneriana oil. The leaf oil of D. moricandiana was dominated by germacrene D (44.3%), a-pinene (13.0%), viridiflorene (9.3%), b-pinene (9.2%) and b-caryophyllene (6.8%). The oils were tested for their antimicrobial activity against 11 pathogenic microorganisms using standard gel diffusion method. The essential oil of D. gardneriana showed activity against Staphylococcus aureus and Candida guilliermondii, while the essential oil of D. moricandiana was more active against Staphylococcus aureus and Candida albicans.

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Chemical Composition and Acaricidal Activity of the Essential Oils From Fruits and Leaves of Protium bahianum Daly

by: Wendel J.T. Pontes, Juliana M.O. Silva, Cláudio A.G. da Camara, Manoel G.C. Gondim-Júnior, José V. Oliveira and Manfred O.E. Schwartz

The essential oils of Protium bahianum fruit and leaves obtained through water distillation were analyzed by GC-FID and GC/MS, and their acaricidal activity was also evaluated using Tetranychus urticae as model. Twentynine components were identified in the oils. The main component of the fruit oil was a-pinene (34.0%) whereas aromadendrene (20.3%) was the major component of the leaf oil. The leaf oil exhibited a higher lethality rate with LC50 of 3.5 mL/L of air after 24 h exposure. The fruits oil showed LC50 of 9.1 mL/L of air and was repellent at 1% concentration.

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Effect of Some Essential Oils as Natural Food Preservatives on Commercial Grated Carrots

by: Flora V. Romeo, Serena De Luca, Amalia Piscopo, Emanuela De Salvo and Marco Poiana

In the present work, the effects of lemon verbena (Lippia citriodora), cypress (Cupressus sempervirens) and lemon-balm (Melissa officinalis) essential oils against the growth of three microorganisms (potentially dangerous to the safety of foods) were evaluated. The three oils were chosen and tested on grated carrots inoculated with bacteria and stored at 8°C until 8 days to simulate the market sale. The most resistant of the three strains against all the tested oils was Escherichia coli, while Listeria strain was the most easily influenced. An important interaction was revealed with the packaging type: oxygen diffusion greatly influenced the bacteria survival at the end of the experiment.

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