Sesquiterpenes from carissa edulis

The methanolic extract from the root of Carissa edulis contains about 5% sesquiterpenes. Besides carissone, cryptomeridiol and β-eudesmol, three hitherto unknown sesquiterpenes of the eudesmane-type and a novel germacrane derivate have been isolated.     

Three fragrant sesquiterpenes of agarwood

Three fragrant sesquiterpenes have been isolated as major constituents from the wood of Aquilaria malaccensis and identified as α-agarofuran, (?)-10-epi-γ-eudesmol and oxo-agarospirol.     

Soil acidity elevates some phytohormone and β-eudesmol contents in roots of <Emphasis Type="Italic">Atractylodes lancea</Emphasis>

We examined a low pH effect on root growth of Atractylodes lancea, a Chinese traditional medicinal plant, and accumulation of the major active compound, β-eudesmol. Our results have shown that low pH increases root hair density and root dry weight, but reduces the length of the main root. More acidic pH stimulates production of β-eudesmol in A. lancea roots. Published in Russian in Fiziologiya Rastenii 2009, Vol. 56, No. 1, pp. 147–151. The text was submitted by the authors in English.     

Caespitenone,a new cyclopropanoid pseudoguaiane and ent-sesquiterpenes from Porella species

Six Porella species and one Macvicaria species have been investigated and a new cyclopropane pseudoguaiane was isolated and its structure elucidated by chemical and spectral evidence. Macvicaria ulophylla and the Porella species, except P. caespitans ssp. setigera, contain the diterpene dialdehyde, perrottetianal A. (+)-Aristolone, (?)-α-eudesmol, and related sesquiterpene hydrocarbons and alcohols, enantiomeric to those found in higher plant, have been isolated from the Porella species.     

Terpenoids of Pterocarpus santalinus heartwood

From the heartwood of Pterocarpus santalinus a group of six closely related sesquiterpenes has been isolated which includes three new sesquiterpenes namely isopterocarpolone, pterocarptriol and pterocarpdiolone besides the known β-eudesmol, pterocarpol and cryptomeridiol. Their structures have been determined by spectral and chemical studies. Three triterpenes, acetyl oleanolic aldehyde, acetyl oleanolic acid, and an unidentified compound along with pterostilbene have also been obtained.     

A new sesquiterpene alcohol from Pterocarpus marsupium

The petrol extract of Pterocarpus marsupium afforded a new sesquiterpene alcohol of the eudesmane type, selin-4(15)-en-1β,11-diol, besides β-eudesmol, erythrodiol-3-monoacetate and pterostilbene.     

Composition of essential oil from leaves of Eucalyptus delegatensis

The major components of a dichloromethane extract of mature Eucalyptus delegatensis leaves were cis- and trans-p-2-menthen-1-ol, trans-piperitol, α- and β-eudesmol, 4-phenyl-2-butanone and methyl cinnamate. The major terpenoid was considered to be trans-piperitol, which was responsible for the peppermint aroma of freshly crushed leaves. The steam distillate of the same leaves contained the above compounds together with a number of monoterpene hydrocarbons which were considered to be artefacts. Use of these hydrocarbons as chemotaxonomic markers was considered to be erroneous.     

Biological activity of Cymbopogon schoenanthus essential oil

IntroductionA number of plant species, including Cymbopogon schoenanthus, are traditionally used for the treatment of various diseases. C. schoenanthus is currently, traded in the Saudi markets, and thought to have medicinal value. This study aimed at investigating the biological activities of C. schoenanthus against both Gram-positive and Gram-negative bacteria and to identify its chemical ingredients.Materials and methodsThe inhibitory effects of water extracts of C. schoenanthus essential oils were evaluated against ten isolates of both Gram-positive and Gram-negative bacteria using the agar well diffusion and dilution methods. The minimum inhibitory concentration (MIC) was assayed using the Broth microdilution test on five of the ten isolates. The death rates were determined by the time kill assay, done according to the Clinical Laboratory Standards Institute (CLSI) guidelines. The chemical composition of the essential oils of the plant was performed using GC/MS.ResultsThe C. schoenanthus essential oil was effective against Escherichia coli, Staphylococcus aureus, methicillin-sensitive (MSSA) S. aureus (MRSA) and Klebsiella pneumoniae. The essential oil was not effective against Staphylococcus saprophyticus at the highest concentration applied of >150 μg/ml. The MIC values were as follows: 9.37 μg/ml for E. coli 4.69 μg/ml for S. aureus (MRSA), 2.34 mg/ml for MSSA and 2.34 μg/ml for K. pneumoniae. The time-kill assay indicated that there was a sharp time dependent decline in K. pneumoniae counts in the presence of the oil. This is in contrast to a gradual decline in the case of S. aureus under the same conditions. The eight major components of the essential oil were: piperitone (14.6%), cyclohexanemethanol (11.6%), β-elemene (11.6%), α-eudesmol (11.5%), elemol (10.8%), β-eudesmol (8.5%), 2-naphthalenemethanol (7.1%) and γ-eudesmol (4.2%).ConclusionThe results of the present study provide a scientific validation for the traditional use of C. schoenanthus as an antibacterial agent. Future work is needed to investigate and explore its application in the environmental and medical fields. In addition, to evaluating the efficacy of the individual ingredients separately to better understand the underlying mechanism.     

Chemical composition, antioxidant activity and inhibitory effects of essential oil of Eucalyptus teretecornis grown in north-western Himalaya against Alternaria alternata

The essential oil obtained from fresh leaves of Eucalyptus teretecornis (family Myrtaceae) was analysed by gas chromatography/mass spectrometry (GC/MS). Twenty eight compounds were identified and ??-pinene (22.55%), ??-pinene (22.50%), 1,8-cineole (19.84%), limonene (5.62%), ??-fenchol (3.10%), ??-phellandrene (2.90%), ??-eudesmol (2.66%) and 4-(2-methylcyclohex-1-enyl)-but-2-enal (2.34%) were the main components. The antifungal activity of the essential oil was assayed against Alternaria alternata using bioautography. Two main bioactive components namely a₁ (R _f ?=?0.27) and a₂ (R _f ?=?0.33) were observed that produced inhibition zone of 4?mm and 8?mm in diameter respectively. The minimum inhibitory amount (MIA) of a₁ and a₂ against A. alternata was determined as 28???g and 10???g, respectively using bioautography assay. Components corresponding to a₁ and a₂ were determined as ??-fenchol (oxygenated monoterpene) and ??-eudesmol (oxygenated sesquiterpene) respectively using GC/MS analysis. The antioxidant activity of the essential oil and its bioactive fraction was evaluated by DPPH radical scavenging assay, ??-carotene/linoleic acid bleaching assay, reducing power assay and metal chelating assay. In addition fraction of the essential oil that showed antioxidant activity was analyzed using GC/MS and ??-fenchol, 4-terpineol and carvacrol were the main components.     

Chemical constituents from Flourensia resinosa S.F. Blake (Asteraceae)

β-eudesmol (1), cryptomeridiol (2), ilicic acid (3), 5,7-dihydroxyflavone (chrysin, 4) and 7-O-methyl-chrysin (tectochrysin, 5) were isolated as the major constituents from the acetone extract of the aerial parts of Flourensia resinosa S.F. Blake (Asteraceae), along with flourensiadiol (6), spathulenol (7), p-acetophenol (8), lupeol (9), β-sitosterol (10), triacontanol (11) and squalene (12). Based on previous studies, this chemical composition for F. resinosa is in accordance with the chemical profile of other species of Flourensia. The profile of flavonoids, sesquiterpenes and benzofurans may have chemotaxonomic significance within this genus.     

Larvicidal activity of Amyris balsamifera,Daucus carota and Pogostemon cablin essential oils and their components against Culex pipiens pallens

Larvicidal activities of Amyris balsamifera, Daucus carota, and Pogostemon cablin essential oils were tested against Culex pipiens pallens. All three oils showed 100% larvicidal activity against C. pipiens pallens at 0.1 mg/mL. Among the tested oils, the larvicidal activity of D. carota oil was the strongest followed by P. cablin and A. balsamifera. Four active compounds such as β-eudesmol, elemol, patchoulol, and carotol were isolated from the three oils by open column chromatography. These compounds showed > 90% mortality against C. pipiens pallens at 0.1 mg/mL. In acute toxicity testing of the water flea, Daphnia magna, P. cablin oil was the most toxic followed by A. balsamifera, and D. carota. Among the isolated compounds, carotol was the most toxic to water fleas. The residues of P. cablin, A. balsamifera, and D. carota in water were 67.8%, 59.5%, and 51.2% at 2 days after treatment, respectively. High concentrations of elemol and patchoulol were detected 2 days after treatment compared to those of β-eudesmol and elemol. Whole oils and compounds tested were detected at < 50% after 7 days in water.     

The leaf oil terpene composition of Juniperus occidentalis

The chemical composition of the volatile oil of 10 trees each of two Oregon populations of the western juniper was determined by a computerized GC-MS method. The identity of the major components, sabinene, α-pinene, α- and γ-terpinene, p-cymene, limonene, terpinen-4-ol and bornyl acetate was confirmed. In addition, tricyclene, α-thujene, camphene, β-pinene, α- and β-phellandrene, car-3-ene, trans-ocimene, linalool oxide, terpinolene, trans-sabinene hydrate, camphor, camphene hydrate, borneol, α-terpineol, p-cymenol, methyl citronellate, citronellyl acetate, carvacrol, cuminic aldehyde, β-bourbonene, several cadinene and cadinol isomers, elemol, γ-, β- and α-eudesmol, and manoyl oxide were identified. Santene, citronellol, and aromatic ethers of the safrole-eugenol type were not found. Tree-to-tree variability of the relative percentages of these terpenes was fairly large and chemosystematic implications are discussed briefly.     

Two sinapyl alcohol derivatives from bergamot essential oil

Together with T-cadinol, β-eudesmol, farnesol, sitosterol and suberosin, two derivatives of sinapyl alcohol have been identified in the less volatile     

Variability in essential oil composition of Piper dilatatum L.C. Rich

Twelve samples of air-dried aerial parts of Piper dilatatum L. C. Rich yielded essential oils and their volatile constituents were analyzed by GC and GC–MS. Sesquiterpenes, both hydrocarbons and oxygenated, were the most highly represented classes, the former ranging from 31.5% to 87.7% and the latter varying from 1.8% to 49.4%. Using hierarchical cluster analysis, the oils were divided into seven groups, whose main constituents were: (E)-caryophyllene, α-cadinol and germacrene D (group A); spathulenol, bicyclogermacrene and (Z)-β-ocimene, (group B); spathulenol, germacrene D and (E)-nerolidol, (group C); germacrene D, limonene, α-phellandrene and bicyclogermacrene (group D); β-elemene, germacrene D and β-pinene (group E); curzerene, p-cymene and α-eudesmol (group F); and (Z)-α-bisabolene, curzerene and germacrene D (group G). We have seen that Piper oils from the Amazon present as major constituents terpenoids and phenylpropanoids, always with the predominance of one over another. The essential oils of P. dilatatum presented in this paper, containing only mono- and sesquiterpenes as its major components, is further chemotaxonomic evidence of this dichotomy in the Piper genus.     

Comparative determination of the essential oil composition in Bulgarian endemic plant Achillea thracica Velen. during the process of ex situ conservation

Ex situ conservation of Bulgarian endemic plant Achillea thracica Velen. was achieved by successful in vitro cultivation of mono-nodal segments on MS-B5 medium supplemented with 1.0 mg/L BA for 20 days and subsequent transferring of regenerated plants on hormone free basal MS-B5 medium for root development and accumulation of leaf biomass. In vitro multiplicated plants were successfully acclimated in a growth chamber with 100% survival. GC–MS analysis of the essential oils resulted in the identification of 30, 10 and 28 compounds in in situ grown, in vitro cultivated and ex vitro adapted plants, respectively, constituting 77.7%, 99.9% and 84.1% of the total oils. The wider variety of compounds was found in the essential oils of in situ and ex vitro adapted plants where santolina alcohol, β-eudesmol, 1,8-cineole, germacrene D, α-cadinol and artemisia alcohol were the principal components comprising 68.7% and 69.3 of the oil, respectively. In vitro cultivated plants consist of mainly 1,8-cineole, germacrene D and artemisia alcohol representing 87% of the oil. Different growth conditions affect the composition of essential oils, suggesting their possible involvement in the process of adaptation and surviving in changing environmental conditions.     

Effects of cement dust on volatile oil constituents and antioxidative metabolism of Aleppo pine (Pinus halepensis) needles

The effects of cement dust on the chemical composition of essential oil, lipid peroxidation and antioxidant enzyme activities of Aleppo pine (P. halepensis) needles were studied. Cement dust resulted in a significant decrease in the yield of essential oil with the effect being more pronounced in the close vicinity of the cement factory. A concomitant decrease in all components of the oil was observed and ??-2-carene, trans-carveol, trans-carvyl acetate, ??-terpinyl acetate, ??-copaene, (E,E)-??-farnesene, ??-calacorene, ??-cadinene, spathulenol, humulene oxide II, 8-epi-??-eudesmol, ?-muurolol, cubenol and ethyl hexadecanoate have been proposed as biological indicators of cement dust. Moreover, a redirection of the secondary metabolism toward the biosynthesis of monoterpenes has been evidenced. Malondialdehydes (MDA), a decomposition product of polyunsaturated fatty acids, often considered as a suitable biomarker for lipid peroxidation was induced in the needles exposed to cement dust. Similarly, a remarkable induction of superoxide dismutase (SOD), catalase (CAT) and peroxidase (POD) activities was noticed. The positive relationships were observed among activities of antioxidant enzymes, and between MDA content and activities of antioxidant enzymes, indicating the cooperative action of these antioxidant enzymes to cope with the oxidative stress induced by cement dust. The results obtained indicate that P. halepensis needles are useful bio-monitors of cement dust pollution.     

Analysis of leaf oils from a Eucalyptus species trial

The volatile leaf oils were analysed from adult leaves of five Eucalyptus species growing in a common environment. The trial consisted of two provenances of the species E. globulus and one provenance each of E. nitens and E. denticulata from the southern blue gum group and two provenances each of the species E. delegatensis and E. regnans from the ash group. Oil yields from adult leaves of E. nitens (0.7% dry wt.) and E. denticulata (0.8%) were markedly lower than those from the other three species (3.0–6.1%). Volatile leaf oils of E. delegatensis and E. regnans were rich in α- and β-phellandrene, cis- and trans-p-menth-2-en-1-ol, while E. regnans was also rich in α-, β- and γ-eudesmol. In contrast, volatile leaf oils of E. globulus were rich in 1,8-cineole and α-pinene and E. denticulata rich in γ-terpinene and p-cymene. Oil composition of E. nitens was intermediate between E. globulus and E. denticulata. Differences in oil yield and oil composition between species indicated a strong genetic basis for these variables.     

Chemical composition,antibacterial and antifungal activities of flowerhead and root essential oils of Santolina chamaecyparissus L., growing wild in Tunisia

The antimicrobial properties of essential oil from various Santolina species have not been investigated enough in the previous studies dealing with the biological activities of medicinal plants. In Tunisia, Santolina chamaecyparissus L. (Asteraceae) is the only Santolina species recorded and is used as vermifuge and emmenagogue. The chemical composition, antibacterial and antifungal properties of essential oils from the flowerheads and roots of spontaneous S. chamaecyparissus growing in Tunisia and the chemical composition which leads to the Tunisian chemotype are investigated here for the first time. Essential oils isolated by hydro distillation from flowerheads and roots of S. chamaecyparissus were analyzed by GC and GC/MS. Two methods served for antimicrobial assays of the essential oils: diffusion in a solid medium and micro-well dilution assay. Antifungal tests were carried out by the agar incorporation method. Sixty-seven constituents were identified from the essential oil of the flowerhead. The major constituents were: 1,8-cineole and β-eudesmol. Two non identified compounds were present at the highest concentration in root oil. Flowerhead oil was characterized by high contents in monoterpenes and sesquiterpenes oxygenated compounds. The flowerhead essential oil demonstrated potent of antibacterial properties against Pseudomonas aeruginosa ATCC and Enterococcus faecalis ATCC, with MIC of 0.625 μg/ml. These findings demonstrate that the flowerhead essential oils of S. chamaecyparissus have excellent antibacterial properties and for this reason they could contribute to decrease the problem of microbial resistance to antibiotics.     

Suites of Terpene Synthases Explain Differential Terpenoid Production in Ginger and Turmeric Tissues

The essential oils of ginger (Zingiber officinale) and turmeric (Curcuma longa) contain a large variety of terpenoids, some of which possess anticancer, antiulcer, and antioxidant properties. Despite their importance, only four terpene synthases have been identified from the Zingiberaceae family: (+)-germacrene D synthase and (S)-β-bisabolene synthase from ginger rhizome, and α-humulene synthase and β-eudesmol synthase from shampoo ginger (Zingiber zerumbet) rhizome. We report the identification of 25 mono- and 18 sesquiterpene synthases from ginger and turmeric, with 13 and 11, respectively, being functionally characterized. Novel terpene synthases, (−)-caryolan-1-ol synthase and α-zingiberene/β-sesquiphellandrene synthase, which is responsible for formation of the major sesquiterpenoids in ginger and turmeric rhizomes, were also discovered. These suites of enzymes are responsible for formation of the majority of the terpenoids present in these two plants. Structures of several were modeled, and a comparison of sets of paralogs suggests how the terpene synthases in ginger and turmeric evolved. The most abundant and most important sesquiterpenoids in turmeric rhizomes, (+)-α-turmerone and (+)-β-turmerone, are produced from (−)-α-zingiberene and (−)-β-sesquiphellandrene, respectively, via α-zingiberene/β-sesquiphellandrene oxidase and a still unidentified dehydrogenase.     

Chemical Components in the Bark of Magnolia rostrata W. W. Smith

From the bark of Magnolia rostrata W. W. Smith (Magnoliaceae), the honokiol(1) mp. 87.5 ℃ and the magnolol (Ⅱ) mp. 102 ℃ was isolated. Moreover, it can be proved that the bark of Magnolia rostrata W. W. Smith contains β-eudesmol in the essential oil.