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July/August 2007

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Essential Oil Chemical Composition of Annona muricata L. Leaves from Benin (pg.307)

Cosme Kossouoh and Mansour Moudachirou, Victor Adjakidje, Jean-Claude Chalchat* and Gilles Figuérédo

Essential oils from leaves of Annona muricata L. were obtained by steam distillation with a very low percentage. Analysis made by GC and GC/MS showed the presence of 80 compounds. The most abundant constituents were β-caryophyllene (13.6%), δ-cadinene (9.1%), epi-α-cadinol (8.4%), α-cadinol (8.3%).

Essential Oils of Tanacetum elburensis Mozaff. and Tanacetum persicum (Boiss.) Mozaff. from Iran (pg. 310)

Zohreh Habibi, Yahya Hejazi and Siyamak Alipour, Shiva Masoudi, Abdolhossein Rustaiyan*

Water-distilled essential oils from the aerial parts of Tanacetum elburensis Mozaff. and Tanacetum persicum (Boiss.) Mozaff. were analyzed by GC and GC/MS. Thirty-one compounds representing 90.7% of the oil of T.elburensis were identified, among which menthyl isovalerate (20.0%) and 1,8-cineole (16.6%) were the major. The oil of T.persicum was characterized by higher amounts of borneol (24.3%), menthyl acetate (17.3%), isobornyl2-methyl butyrate (16.0%) and artedouglasia oxide D (14.3%) among the twenty-two components comprising 91.8% of the total oil detected. Both oils were richer in oxygenated monoterpenes than sesquiterpenes.

Analysis of the leaf Oil of Syzygium malaccense Merr. et Perry from Nigeria (pg. 313)

A. Karioti and H. Skaltsa* and A.A. Gbolade

The hydrodistilled essential oil from fresh leaves of Syzygium malaccense Merr. et Perry. grown in Nigeria has been studied by GC and GC/MS for the first time. Identification of the substances was made by comparison of mass spectra and retention indices with literature records. The oil was largely composed of monoterpenes (61.1%) characterized mainly by (+)-a-pinene (7.3%), (-)-b-pinene (8.0%), p-cymene (13.5%), and a-terpineol (7.5%). The sesquiterpenes constituted 30.8% of the oil with (-)-b-caryophyllene (9.0%) as the major component.

Chemical Composition of Artemisia absinthium L. from Greece (pg. 316)

A. Basta, O. Tzakou and M. Couladis* and M. Pavlovic´

The hydrodistilled essential oil of the aerial parts of Artemisia absinthium L. was analyzed by GC/MS. Sixty-eight components of the oil were identified representing 93.4%. The main components were caryophyllene oxide (25.3%), p-cymene (16.8%), 1,8-cineole (8.9%) and (Z)-lanceol acetate (7.3%).

Santolina Alcohol as Component of the Essential Oil of Achillea ageratum L. from Corsica Island (pg. 319)

Alain Muselli,* Jean-Marie Desjobert, Antoine-François Bernardini and Jean Costa

The composition of the essential oil of Achillea ageratum L. from Corsica Island was investigated using a combination of gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS) after fractionation over column chromatography. Sixty-eight compounds were identified, the main components being 1,8-cineole (41%), yomogi alcohol (22.3%), santolina alcohol (10%) and artemisyl acetate (7.6%). The chemical composition of Corsican A. ageratum oil differed from those reported in the literature. The use of two capillary columns with different polarity under optimal GC conditions allowed the identification and the quantification of santolina alcohol that was coeluted on both capillary columns used.

Chemical Composition of the Leaf Oils of Myristica malabarica Lam. and Gymnacranthera canarica (King) Warb. (pg. 323)

Baby Sabulal, Rajani Kurup, Sumitha B and Varughese George*

Essential oils from the leaves of Myristica malabarica and Gymnacranthera canarica (Myristicaceae) were isolated by hydrodistillation and analyzed by GC/FID and GC/MS. Seventy-six constituents (98.5%) with β-caryophyllene (27.3%), α−humulene (13.8%) and α−copaene (11.5%) as major components were identified from the leaf oil of M. malabarica. Also, seventy-six constituents (98.1%) with β−caryophyllene (23.4%), linalool (13.4%) and α−humulene (11.3%) as major constituents were identified from the leaf oil of G. canarica. Sesquiterpene hydrocarbons constituted 77.3% in M. malabarica leaf oil and 58.1% in G. canarica leaf oil.

Phenological Variation of the Essential Oil of Artemisia scoparia Waldst. et Kit from Iran (pg. 326)

M.H. Mirjalili*, S.M.F. Tabatabaei and J. Hadian, S. Nejad Ebrahimi and A. Sonboli

Variation in the quantity and quality of the essential oil of Artemisia scoparia Waldst. et Kit at different developmental growth stages including vegetative, floral budding and flowering are reported. The oils were obtained by hydrodistillation of air-dried samples. The yields of oils (w/w %) in different stages were in the order of: flowering (0.9%)> floral budding (0.7%)> vegetative (0.4%). The oils were analyzed by GC and GC/MS. In total, 25, 23 and 18 constituents were identified and quantified in the oils of vegetative, floral budding and flowering plants, representing 98.4 %, 98.5% and 98.7% of the oils, respectively. a- and b-Thujone and 1,8-cineole were the main compounds in all samples. a-Thujone, was lower in the vegetative stage and increased in the subsequent harvesting times to reach maximum in flowering. In contrast, b-thujone, was higher in the vegetative stage and decreased during flowering. Oxygenated monoterpenes were the main group of compounds in flowering (97.9%), floral budding (96.6%) and vegetative (93.4%) stage.

Combined Analysis of the Essential Oil from Tagetes bipinata by GC, GC/MS and 13C-NMR Spectroscopy (pg. 330)

Jean-François Cavalli,* Félix Tomi and Joseph Casanova, Antoine-François Bernardini

Six commercial samples of the essential oil of Tagetes bipinata from Madagascar were analyzed by GC (retention indices), GC/MS and 13C-NMR. Tagetes bipinata produces a monoterpene-rich oil dominated by (Z)-b-ocimene and acyclic unsaturated ketones among which dihydrotagetone was present in the six samples at appreciable content (11.9–24.4%) and is reported for the first time in the oil of T. bipinata.

Chemical Composition of Pulicaria dysenterica (L.) Bernh. from Greece (pg. 333)

A. Basta, O. Tzakou* and M. Couladis and M. Pavlovic´

The chemical composition of the aerial parts oil of Pulicaria dysenterica (L.) Bernh. was examined by GC and GC/MS. Oils hydrodistilled from samples collected from two different locations in Greece were found to possess minor compositional differences but considerable variation in the levels of some components. Fifty-four components were identified representing 80.5% (sample A) and 72.6% (sample B) of the total oils. The main components in sample A were (Z)-nerolidol (11.2%), caryophyllene oxide (9.1%) and (E)-nerolidol (6.6%), while those of sample B were β-caryophyllene (12.8%), caryophyllene oxide (12.8%) and (E)-nerolidol (6.9%).

Chemical Composition of the Essential Oil of Microtoena patchoulii [(C.B. Clarke Ex J.D. Hooker) C.Y. Wu et Hsuan] (pg. 336)

Manami Senpuku, Kazuya Nonaka, Michiho Ito,* and Gisho Honda

The chemical components of the essential oil obtained from the steam-distillation of Microtoena patchoulii leaves were investigated by GC and GC/MS, and twenty-one compounds were identified. The major compounds of the oil were patchouli alcohol (54.4%), 1-octen-3-ol (21.4%), and a-guaiene (2.4%). The composition of M. patchoulii oil is similar to that of commercial patchouli oil, and similar pharmacological effects could be expected when it is used as a substitute for Pogostemon cablin.

Essential Oil from of Guarea macrophylla Vahl var. tuberculata vellozo (Meliaceae) Leaves - Variation in the Chemical Component Proportions (pg. 338)

João Henrique G. Lago* and Paulete Romoff, José R. Pirani, Nídia F. Roque

The essential oils isolated from leaves of Guarea macrophylla var. tuberculata collected monthly during two years (from November 1997 to October 1999) were subjected to GC-FID and GC/MS analysis. The obtained data showed a significant variation in the proportions of the components, which could be associated to species phenological state despite of climatic parameters in each collection.

Composition of an Essential Oil from Agonis fragrans J.R.Wheeler et N.G.Marchant (pg. 342)

Robert F. Lowe,* Michael F. Russell and Ian A. Southwell, Christopher J. Robinson, John Day

The leaf essential oils of Agonis fragrans, isolated by steam distillation and solvent extraction, were analyzed by GC and GC/MS. The major components identified in five of the six samples investigated were 1,8-cineole (28%–34% and 12%–26%, respectively) and a-pinene (14%–28 % and 12%–18% respectively). The remaining sample was almost devoid of 1, 8-cineole (1% in oil and 0% in extract) with higher concentrations of a-pinene (22% and 39%), linalool (25% and 18%) and (+)-(1S, 5R)-myrtenol (20% and 12% respectively). The compositional variation within the species indicated that a breeding project could identify and use the best composition for commercial development.

Chemical Composition of the Leaf Essential Oil of Psidium guajava L. from Taiwan (pg. 345)

Hsin-Chun Chen and Ming-Jen Sheu, Li-Yun Lin and Chung-May Wu*

The composition of the essential oil obtained from the hydrodistillation of the leaves of Psidium guajava L. was analyzed by capillary GC and GC/MS. A total of 50 compounds were identified. The major constituents identified in the oil were: b-caryophyllene (27.7%), a-pinene (14.7%) and 1,8-cineole (12.4%).

Composition of the Essential Oil of the Flowering Aerial Parts of Iranian Crambe orientalis L. (pg. 348)

Javad Safaei-Ghomi,* Abdolhamid Bamoniri and Alireza Hatami and Hossein Batooli

The essential oil of flowering aerial parts of Crambe orientalis L., which belongs to Cruciferae family, was obtained by hydrodistillation method in 0.1% yield and analyzed by GC and GC/MS. Twenty-three compounds representing 98.7% of the oil were identified. Among them 3-butenyl isothiocyanate (51.4%), henicosane (9.3%), epoxy-oleic acid (7.6%) and hexadecanoic acid (7.2%) were the major constituents of the oil.

Composition of the Limonene Dominated Leaf Essential Oil of Nigerian Anacardium occidentale (pg. 351)

D. Olufunke Moronkola*, Adeleke A. Kasali and Olusegun Ekundayo

GC and GC/MS analyses of the fresh leaf oil of Nigerian Anacardium occidentale revealed that there were 51 components representing 99.3%. The most abundant compound was limonene (85.9%). Other major components were β-caryophyllene (1.7%), α–pinene (1.5%), α-terpineol (1.1%) and α-ylangene (1.0%). Forty-six other compounds were also identified which have not been earlier reported in the leaf oil.

Differentiation of Fruiting and Non-fruiting Pimenta dioica (L.) Merr. Trees Based on Composition of Leaf Volatiles (pg. 354)

Donna A Minott* and Heather A Brown

Leaf oil from fruiting female and non-fruiting male Pimenta dioica (L.) Merr. trees, were analyzed by GC. Oil yields from male pimento trees (2.13%) were typically lower than that for female trees (2.67%). Non-fruiting and fruiting trees contained the same volatile components with different relative abundances. The composition of eugenol (p< 0.01), and myrcene, α-phellandrene, γ−terpinene, terpinolene and α-thujene (p< 0.005) were significantly different in the female versus the male pimento trees. Characteristic monoterpenoid profiles were observed for the fruiting and non-fruiting pimento trees which could be used for the early prediction of the berry bearing ability of pimento trees.

Chemical Composition of Leaf and Fruit Oils of Heracleum candolleanum (pg. 358)

Anil J. John, Vrujesh P. Karunakaran, and Varughese George* and Mathur G. Sethuraman

Essential oils from leaves and fruits of Heracleum candolleanum were obtained by hydrodistillation and analyzed by GC and GC/MS. The major components in the leaf oil were sabinene (13.2%), limonene (9.2%), β−caryophyllene (8.6%) and caryophyllene oxide (8.4%), whereas the major constituents in the fruit oil were limonene (70.0%) and octyl acetate (7.2%).

Essential Oil from the Flowers and Leaves of Cassia fistula L. (pg. 360)

O. Tzakou* and A. Loukis and A. Said

The chemical compositions of the flower and leaf essential oil of Cassia fistula L. were examined by GC and GC/MS. Forty-four compounds were identified representing 92.6% and 90.7% of the flower and leaf oil, respectively. The main components of the flower oil were (E)-nerolidol (38.0%), and 2-hexadecanone (17.0%), while the leaf oil consisted mainly of phytol (16.1%).

Eclipta indica L. (Asteraceae): A source of 2-Tridecanone (pg. 362)

Akinola O. Ogunbinu, Isiaka A. Ogunwande a*, Pier L. Cioni and G. Flamini

The volatile oil obtained by hydrodistillation from the leaf of Eclipta indica L. was analyzed for its constituents by means of GC and GC/MS. 2-Tridecanone (89.7%), a straight chain ketone, was the singly most abundant constituent. Caryophyllene oxide (3.9%) and β-caryophyllene (2.6%) were the other compounds occurring in sizeable proportions.

Leaf Essential Oils from Philotheca Species (Rutaceae) in Queensland and Northern New South Wales (pg. 364)

Joseph J Brophy* and Robert J Goldsack, Lachlan M Copeland and Paul I Forster

The leaf oils of the species of Philotheca growing in Queensland and northern New South Wales have been examined by combined GC and GC/MS. Philotheca cuticularis, both subspecies of P. difformis, P. glasshousiensis, P. myoporoides subsp. myoporoides, P. epilosa, P. obovata, P. queenslandica and P. sporadica all produced leaf oils in which the major component (>75%) was α−pinene. In P. acrolopha, the major components were α−pinene (34–42%) and β−caryophyllene (12–22%), while in P. ciliata the principal components were α−pinene (48–54%) and camphor (18–25%). In P. ericifolia the major components were α−pinene (16–25%), myrcene (7–10%), (E)−β−ocimene (18–34%) and the sesquiterpene spathulenol (13–21%). Pilotheca conduplicata produced a monoterpenic oil in which the main components were α−pinene (27.2%), limonene (43.8%) and (E)−β−ocimene (18.3%). In Philotheca papillata α−pinene (43.0%), camphene (9.3%) and elemol (8.8%) were the principal components of the leaf oil. The leaf oil of P. salsolifolia subsp. salsolifolia contained α−pinene (31.9%) and spathulenol (18.1%) as its major components, while in P. salsolifolia subsp. pedicellata sabinene (38%) and bicyclogermacrene (15.2%) were the major components.

Chemical Composition of Essential Oils from Fresh Plant Parts of Korarima (Aframomum corrorima) Cultivated in the Highland of Southern Ethiopia (pg. 372)

Solomon Eyob* and Maigull Appelgren, Jens Rohloff, Admasu Tsegaye and Gezahegn Messele

The essential oils of the leaves, rhizomes, pods and seeds of Aframomum corrorima cultivated in the highlands of southern Ethiopia were obtained by hydrodistillation. The average moisture contents were 80.53% in leaves, 90.30% in rhizomes, 88.00% in pods and 14.19% in seeds when analyzed from fresh samples. The essential oils yield of leaves, rhizomes, pods and seeds were 0.46%, 0.69%, 0.83% and 4.30 % on a w/w dry basis, respectively. The pod and seed oil was analyzed by GC and GC/MS. Forty-two and 40 compounds from pods and seeds consisting of 95% and 99% of the total components were identified from the oils obtained. The major chemical constituents in pod oil were found to be g-terpinene (27.1 %), b-pinene (15.4 %), a-phellandrene (8.5 %), 1,8-cineole (6.7 %) and p-cymene (6.4 %), while seed oil was predominated by 1,8-cineole (39.3 %) being followed by sabinene (10.4 %) and geraniol (6.8 %).

Clastogenic and Anticlastogenic Effect of the Essential Oil from Casearia sylvestris Swart. (pg. 376)

Fabrício G. Sousa, Naira F. Z. Schneider, Caroline E. Mendes, Neusa F. de Moura* and Rosiane B.N. Denardin, Renata Matuo and Mario S. Mantovani

The essential oil composition obtained from the leaves of Casearia sylvestris has been investigated by GC and GC/MS. Thirty-seven compounds were identified in the oil. The major constituents of which were β-caryophyllene (27.5%) and bicyclogermacrene (24.2%). The clastogenic and anticlastogenic effect of the oil was tested by chromosome aberration in cells of tissue hepatoma of Rattus novergicus.The three different concentrations of C. sylvestris oil showed clastogenic effects. However, in the tests of anticlastogenicity, the same three concentrations showed protective activity when associated with ethyl methanesulfonate (EMS).

Composition and Acaricidal Activity of the Resin’s Essential Oil of Protium bahianum Daly Against Two Spotted Spider Mite (Tetranychus Urticae) (pg. 379)

Wendel J.T. Pontes, José C.S. de Oliveira, Claudio A.G. da Camara,* and Adelmo C.H.R. Lopes, Manoel Guedes Corrêa Gondim Júnior and José Vargas de Oliveira, Manfred O. E. Schwartz

The essential oils from two sources of resinous exudates of Protium bahianum obtained by hydrodistillation were analyzed by combinations of GC and GC/MS. Twenty-two and thirteen components were identified in the oils from fresh and aged resins, comprising 95.8 % and 98.6 %, of the oils, respectively. The aged resin oil contained a high percentage of oxygen-containing sesquiterpenes (85.4 %) with a high predominance of β-(Ζ)-santalol acetate (83.1 %). In contrast, no sesquiterpenes were detected in the fresh resin oil and it was constituted basically by monoterpenes hydrocarbons (42.4 %) and oxygen-containing monoterpenes (27.7 %), of which α-phellandrene (13.9 %) and terpinen-4-ol (7.4 %) were the major components, respectively. The acaricidal activities against Tetranychus urticae of the resin oil were also investigated. Both oils showed fumigant toxicity (mortality and fecundity), but only the aged resin oil induced repellence.

Zanthoxylum articulatum Engler (Rutaceae) Essential Oil: Chemical Composition and Larvicidal Activity (pg. 384)

Edinilza Maria A. Feitosa, Angela Martha C. Arriaga,* Telma Leda G. Lemos, Jefferson Q. Lima, Jackson Nunes e Vasconcelos and Maria Conceição F. Oliveira, Gilvandete Maria P. Santiago, Ronaldo F. Nascimento

The leaves of Zanthoxylum articulatum Engler (Rutaceae), collected in Jacobina-Bahia, Northwest of Brazil, was subjected to hydrodistillation and its essential oil was characterized by GC/MS. Twelve compounds were identified representing 90.4% of the oil. Oxygenated sesquiterpenes (65.4%) were the major constituents with viridiflorol (35.4%), spathulenol (9.9%), elemol (9.7%) and globulol (6.5%) being the main compounds. The oil was examined with respect to its larvicidal properties against the larvae of a mosquito (Aedes aegypti) and showed LC50 77.62 ± 0.64 ppm.

Composition and Antimicrobial Activity of the Essential Oil of Tanacetum cadmeum (Boiss.) Heywood subsp. orientale Grierson (Pg. 392)

Gülmira Özek,* Temel Özek, Gökalp Is¸can, K. Hüsnü Can Bas¸er, Ergin Hamzaoglu and Ahmet Duran

Water distilled essential oil of aerial parts of Tanacetum cadmeum (Boiss.) Heywood subsp. orientale Grierson (Asteraceae) was analyzed by GC and GC/MS methods. Ninety three compounds have been characterized representing 97.8% of the oil. 1,8-Cineole (18.9%), p-cymene (15.7%), terpinen-4-ol (14.8%), borneol (9.8%) and γ-terpinene (3.5%) were found to be the major constituents of the oil. Antimicrobial activity of the oil was tested via micro-dilution broth method. Escherichia coli, Staphylococcus aureus, Enterobacter aerogenes, Salmonella typhimurium, Bacillus cereus, Staphylococcus epidermidis, Candida albicans were used as the test microorganisms.

Chemical Analysis and Antimicrobial Activity of Essential Oils from the Aromatic Plants Artemisia afra Jacq. and Leonotis ocymifolia (Burm. F.) lwarsson var. raineriana (Vision1) lwarsson Growing In Tanzania (pg. 396)

K. Vagionas, K. Graikou, I.B. Chinou*, D. Runyoro and O. Ngassapa

Hydrodistilled volatile oils from the aerial parts of Artemisia afra and leaves of Leonotis ocymifolia var. raineriana were investigated, by a combination of GC and GC/MS. From A. afra 37 compounds were identified, representing 95.3% (area percent) of the total oil and from L. ocymifolia var. raineriana, 27 compounds were identified, representing 91.1% of the total oil. Among the identified components camphor (46.2%), a-thujone (15.2%), artemisia ketone (7.4%) and 1,8-cineole (4.2%) were found as the main components of A. afra oil and germacrene D (36.8%), (Z)- b-ocimene (7.9%), b-caryophyllene (7.0%) and (E)-b-ocimene (4.4%) were the major components of L. ocymifolia oil. Furthermore, the oils, as well as nine of their constituents, were evaluated for their antimicrobial activity, against six bacteria, two oral pathogens and three pathogenic fungi. The results showed that the oil of A. afra has a moderate antimicrobial activity, while the oil of L. ocymifolia exhibited a stronger one against Gram-negative bacteria and oral pathogens, and a weaker one against Gram-positive bacteria. This interesting profile can be attributed to the high content of the oil, of germacrene D which is known for its antimicrobial activity.

Analysis of the Volatile Constituents of Five African and Mediterranean Hypericum L. (Clusiaceae,Hypericoideae) Species (pg. 302)

Sara L. Crockett*, Betul Demirci, K. Husnu Can Bas¸er and Ikhlas A. Khan

The volatile constituents of five species of the medicinally and ornamentally valuable genus Hypericum L. (St. John’s Wort; Clusiaceae), with native distributions in Africa and the Mediterranean regions of Europe and Asia, were examined as part of our continuing research on the phytochemistry of Hypericum. The dried and ground aerial material of flowering plants was subjected to microdistillation to isolate volatile compounds, which were subsequently analyzed by GC/MS. The major constituent(s) of H. balearicum were α-pinene (28.5%), β-pinene (20.4%), and β-eudesmol (11.2%); of H. delphicum were caryophyllene oxide (31.5%), β-caryophyllene (18.2%), and undecane (17.5%); of H. roeperanum was γ-curcumene (15.6%); of H. aegypticum ssp. aegypticum was ishwarane (14.4%); and of H. aegypticum ssp. marrocanum were caryophyllene oxide (29.2%) and β-caryophyllene (15.1%). This paper represents the first report, to our knowledge, of volatile constituents for these species.