Germacrane-type sesquiterpenoids from the flowers of Chrysanthemum indicum with hepatoprotective activity.

Two new germacrane-type sesquiterpenoids, chrysanthemolides A (1) and B (2), and four known germacrane-type sesquiterpenoids, hanphyllin (3), 3ß-hydroxy-11α,13-dihydro-costunolide (4), costunolide (5), and 6,7-dimethylmethylene-4-aldehyde-1ß-hydroxy-10(15)-ene-(4Z)-dicyclodecylene (6), were isolated and identified from the flowers of Chrysanthemum indicum. The structures of the new compounds were elucidated via high resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR) spectra and electronic circular dichroism (ECD). Meanwhile, all the isolates were tested for their hepatoprotective activity in tert-butyl hydroperoxide (t-BHP) injured AML12 cells. Compounds 1, 2, and 4 showed significant protective effects at 40 µM, comparable with the positive control resveratrol at 10 µM. As the most potent one, compound 1 was chosen for further studies. Compound 1 dose-dependently increased the viability of t-BHP-injured AML12 cells. Furthermore, compound 1 decreased reactive oxygen species accumulation, while increased glutathione level, heme oxygenase-1 level and superoxide dismutase activity, through anchoring in the binding site of Kelch domain of the Kelch-like ECH-associated protein 1 (Keap1) to promote the dissociation of nuclear factor erythroid 2-related factor 2 from Keap1 and translocation to nuclei. In summary, germacrane-type sesquiterpenoids from C. indicum might be further developed to protect liver against oxidative damage.

The essential oil from Kelussia odoratissima Mozaff. fruits exerting potent analgesic and anti-inflammatory effects / El aceite esencial de frutos de Kelussia odoratissima Mozaff. ejerce potentes efectos analgésicos y antiinflamatorios

Kelussia odoratissima fruits are utilized in Persian traditional medicine as a painkiller and to prevent inflammation-based disorders. Considering the higher content of essential oil in the fruits, the oil's anti-inflammatory and analgesic activities were investigated via the paw edema triggered in mice and the writhing test and hot plate technique, respectively. It was observed that the 100, and 200 mg/Kg doses of the oil revealed an analgesic impact (p<0.001) considering the increment in the reaction time needed for the hot plate approach. Furthermore, 100 and 200 mg/Kg doses of the oil caused a reduction in the frequency of writhes in the mice (p<0.01 and p<0.001, respectively). Using all examined doses of theoil (25, 50, and 100 mg/Kg) caused inflammatory reduction (p<0.001). The findings indicated that the oil possess significant activities against acute inflammation. It had both peripheral and central pain-killing impacts. The main components 3-n-butylphthalide (28.3%) and germacrene D (17.3%) can be considered as the responsible compounds to manage the inflammation and pain.

Las frutas de Kelussia odoratissima se utilizan en la medicina tradicional persa como analgésico y para prevenir los trastornos basados en la inflamación. Teniendo en cuenta el mayor contenido de aceite esencial en las frutas, se investigaron las actividades antiinflamatorias y analgésicas del aceite a través del edema de la pata desencadenado en ratones y la prueba de contorsiones y la técnica del plato caliente, respectivamente. Se observó que las dosis de 100 y 200 mg / kg del aceite revelaron un impacto analgésico (p<0,001) considerando el incremento en el tiempo de reacción necesario para el enfoque de placa caliente. Además, dosis de 100 y 200 mg / kg del aceite provocaron una reducción en la frecuencia de retorcimientos en los ratones (p<0,01 y p<0,001, respectivamente). El uso de todas las dosis examinadas del aceite (25, 50 y 100 mg/kg) provocó una reducción inflamatoria (p<0,001). Los hallazgos indicaron que el aceite posee actividades significativas contra la inflamación aguda. Tiene impactos analgésicos tanto periféricos como centrales. Los principales componentes 3-n-butilftalida (28,3%) y germacreno D (17,3%) pueden considerarse como los compuestos responsables del manejo de la inflamación y el dolor.

Gas chromatography coupled to mass spectrometry (GC-MS) characterization and evaluation of antibacterial bioactivities of the essential oils from Piper arboreum Aubl., Piper aduncum L. e Piper gaudichaudianum Kunth.

The objective of this study was to determine the chemical profile and to evaluate the antibacterial activity of the essential oils of Piper species and modulation of the antibiotic activity, using the microdilution method to determine the minimum inhibitory concentration. The chemical components were characterized by gas chromatography coupled to mass spectrometry, which revealed ß-copaen-4-α-ol (31.38%), spathulenol (25.92%), and germacrene B (21.53%) as major constituents of the essential oils of Piper arboreum, Piper aduncum, and Piper gaudichaudianum, respectively. The essential oils analyzed in this study did not present a clinically relevant activity against standard and multiresistant Escherichia coli. However, in the case of multiresistant Staphylococcus aureus, there was a significant activity, corroborating with reports in the literature, where Gram-positive bacteria are more susceptible to antimicrobial activity. The essential oils modulated the effect of the antibiotics norfloxacin and gentamicin, having on the latter greater modulating effect; however, for erythromycin, no statistically significant effect was observed. In conclusion, the results obtained in this study demonstrated that the essential oils of the analyzed Piper species present an inhibitory effect against S. aureus and modulate antibiotic activity, most of which presents synergistic activity.

Chemical investigation and biological activities of the essential oil of Knema kunstleri Warb. from Malaysia.

The chemical composition of the essential oil of Knema kunstleri Warb. (Myristicaceae) was investigated for the first time. The essential oil was obtained by hydrodistillation and fully characterized by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). In total, 36 components were identified in the essential oil, which made up 91.7% of the total oil. The essential oil is composed mainly of ß-caryophyllene (23.2%), bicyclogermacrene (9.6%), δ-cadinene (7.3%), α-humulene (5.7%), and germacrene D (4.3%). The essential oil showed moderate activity towards DPPH free-radical scavenging and lipoxygenase inhibition. To the best of our knowledge, this is the first study of the composition and bioactivities of the essential oil report concerning the genus Knema.

Chemical composition and biological activities of an essential oil from the aerial parts of Artemisia Gmelinii weber ex Stechm.

The aerial parts of Artemisia gmelinii Weber ex Stechm were collected from the northeast of China. The essential oil was obtained by hydrodistillation and analysed by GC-MS. A set of 66 compounds were identified representing 99.1% of the oil composition. The major compounds in the oil were cyclobutaneethanol, endo-borneol, germacrene D, eucalyptol, selin-6-en-4α-ol, bisabolone oxide A, caryophyllene and terpinen-4-ol. Moreover, the essential oil was evaluated for its antioxidant, antidiabetic, and anticholinesterase activities in vitro. Additionally, the antioxidant potential of the oil was evaluated using DPPH and ABTS assays. The oil showed good antidiabetic activity with an IC50 of 63.2 µg/mL, which was similar to that of the positive control acarbose, and weak anticholinesterase activities. These findings demonstrated that the essential oil of Artemisia gmelinii may be a good natural antidiabetic.

Mutagenic and cytostatic activities of the Xylopia laevigata essential oil in human lymphocytes.

Hydro-distilled essential oil from leaves of Xylopia laevigata was characterized by GC-MS. Twenty-seven components were identified and the oil's major constituents comprised germacrene D, bicyclogermacrene, (E)-caryophyllene and germacrene B. The cytotoxicity of the essential oil of X. laevigata (EOXL), determined by MTT and mitotic index methods in cultured human lymphocytes was observed in all tested concentrations. Cultures treated with EOXL demonstrated significant increase in the frequencies of micronuclei in the cytokinesis-block micronucleus assay (CBMN) and reduction of the cytokinesis-block proliferation index (CBPI) rates. Results demonstrated the cytostatic and mutagenic effects of EOXL, the latter for the first time.

Essential Oil Variation within Warburgia salutaris-A Coveted Ethnomedicinal Aromatic Tree.

Warburgia salutaris, known as 'Pepper bark', is an ethnomedicinally important tree found in the southern regions of Africa. A total of 75 fresh leaf specimens of W. salutaris (n=40 wild and 35 cultivated) were collected from the Limpopo (wild) and KwaZulu-Natal provinces (cultivated), two distinct locations in South Africa. In this study, the leaf essential oils obtained by hydrodistillation were characterized using gas chromatography coupled to mass spectrometry/flame ionization detection (GC/MS/FID). More than 15 compounds, accounting for 90-99 % of the total oil composition were identified. The analysis revealed that myrcene (0.6-65.3 %), (E)-ß-ocimene (nd-56.9 %), (Z)-ß-ocimene (nd-19.1 %), α-pinene (nd-19.1 %) and limonene (nd-11.7 %) are major constituents of W. salutaris essential oils. Chemometric analysis revealed two major chemotypes within the essential oils with a modeled variation of approximately 60 %. Linalool and germacrene D were revealed as markers associated with the wild-harvested oils, while cultivated oils were distinguished by higher levels of limonene and α-humulene. The intra-population variation indicated two chemically distinct chemotypes from three different populations, however, the season of harvest did not have a direct influence on the chemical profiles of the essential oils.

Sesquiterpenes rich essential oil from Garcinia celebica L. and its cytotoxic and antimicrobial activities.

Garcinia celebica L., locally known as "manggis hutan" in Malaysia is widely used in folkloric medicine to treat various diseases. The present study was aimed to examine the chemical composition of the essential oil from the leaves of G. celebica L. (EO-GC) and its cytotoxic and antimicrobial potential. EO-GC obtained by hydrodistillation was analysed using capillary GC and GC-MS. Twenty-two compounds were identified, dominated by α-copaene (61.25%), germacrene D (6.72%) and ß-caryophyllene (5.85%). In the in vitro MTT assay, EO-GC exhibited significant anti-proliferative effects towards MCF-7 human breast cancer cells with IC50 value of 45.2 µg/mL. Regarding the antimicrobial activity, it showed better inhibitory effects on Gram-positive bacteria than Gram-negative bacteria and none on the fungi and yeasts tested.

Composition and antioxidant activity of the essential oil of Artemisia annua L.

Artemisia annua L. is an annual Eurasian desert-steppe plant. The composition of essential oils found in Artemisia annua from Russian (Buryatian) flora was analyzed in this work using gas chromatography mass-spectrometry method. Artemisia ketone, ß-selinene, caryophyllene, caryophyllene oxide, germacrene D were the main components of the analyzed essential oils. The comparison of own and literature data showed that the essential oils of A. annua conditionally could be divided into "Asian" and "European" groups. Our samples, referring to "Asian" profile, exhibited higher antiradical activity in comparison with data from previously published studies.

Ocotea pulchellaas an alternative against schistosomiasis: chemical analysis, development of nanoemulsion and biological control activity / Ocotea pulchellacomo una alternativa ante esquistosomiasis: análisis químico, desarrollo de una nanoemulsión y actividad en control biológico

The aim of this work was to evaluate the potential of the essential oil (EO) from Ocotea pulchella leaves as an alternative in the control of schistosomiasis. It was tested O. pulchella EO nanoformulation to assess its activity against adult Biomphalaria glabrata, their spawning and Schistossoma mansoni cercariae. Additionally, the EO chemical composition was investigated by gas-chromatography. Nanoemulsion were elaborated by the low energy method. The adult mollusks, their spawning and cercariae were placed in contact with nanoemulsion to calculate lethal concentrations. Myristicin, bicyclogermacrene and α-Pinene were the main substances in the EO. Nanoemulsion caused mortality of adult B. glabrata, its egg embryos and S. mansoni. These results suggest the use of this nanoemulsion as an alternative in the control of the schistosomiasis cycle.

El objetivo de este trabajo fue evaluar el potencial de los aceites esenciales (AE) de las hojas de Ocotea pulchellacomo una alternativa en el control de esquistosomiasis. Se probó una nanoformulación de AE de O. pulchellapara evaluar su actividad ante adultos de Biomphalaria glabrata, sus huevos y cercarías de Schistossoma mansoni. La nanoemulsión fue elaborada por el método de baja energía. Los moluscos adultos, sus huevos y cercarías se colocaron en contacto con la nanoemulsión para calcular concentraciones letales. Los compuestos mayoritarios en el AE fueron miristicina, biciclogermacreno y α-pineno. La nanoemulsión causó mortalidad en adultos de B. glabrata, sus huevos y a S. mansoni. Los resultados sugieren el uso de esta nanoemulsión como una alternativa en el control del ciclo de esquistosomiasis.

Circadian variation and in vitro cytotoxic activity evaluation of volatile compounds from leaves of Piper regnellii (Miq) C. DC. var. regnellii (C. DC.) Yunck (Piperaceae).

Aiming detection of circadian variation in the chemical composition of volatiles from Piper regnellii, the leaves were collected during four different periods (8, 12, 16 and 20 h) in the same day. After extraction by hydrodistillation and GC/MS analysis, no significant variation was observed for the main compounds: germacrene D (45.6 ± 1.5-51.4 ± 3.1%), α-chamigrene (8.9 ± 1.3-11.3 ± 2.7%) and ß-caryophyllene (8.2 ± 0.9-9.5 ± 0.3%). Evaluation of in vitro cytotoxicity against several cancer and non-tumourigenic cells indicated promising activity, especially to HeLa (human cervical carcinoma) with IC50 ranging from 11 ± 3 to 17 ± 3 µg/mL. The obtained volatile oils were pooled and subjected to fractionation to afford pure ß-caryophyllene, α-chamigrene and germacrene D, being this last compound the more active against HeLa cells with IC50 of 7 ± 1 µg/mL (34 ± 5 µM). Therefore, the predominance of germacrene D in all analysed oils could justify, at least in part, the activity observed for the volatile compounds from P. regnellii leaves.

Chemical composition of Ivorian Artabotrys insignis leaf oil. Combined analysis including 13C NMR, to quantify germacrene A and ß-elemene.

The chemical composition of leaf essential oil from Artabotrys insignis Engler & Diels collected from Cote d'Ivoire was determined by GC(FID), GC-MS and 13C NMR. The main compounds were ß-elemene (66.8%) and germacrene A (17.1%). The true content of germacrene A/ß-elemene was obtained by combining GC(FID) and 13C NMR data.

Variation in Chemical Composition and Antibacterial Activity of the Essential Oil of Wild Populations of Phlomis olivieri.

Various species of the genus Phlomis have been reported to produce metabolites demonstrating significant pharmacological efficiency. In this study, the essential oils from twelve populations of Phlomis olivieri collected from natural habitats were investigated for their chemical components. The hydrodistillated essential oil analyzed by GC-FID and GC/MS. Analyses revealed 27 compounds, constituting 90.52 - 98.51% of the essential oils. Results indicated that the major components of the essential oils from various populations of P. olivieri were germacrene D (26.54 - 56.41%), bicyclogermacrene (6.38 - 30.55%), ß-caryophyllene (5.32 - 24.52%) and α-pinene (1.29 - 15.53%). Principal component analyses (PCA) was used to identify any geographical variations in essential oil composition. Notably, three groups of Iranian P. olivieri populations were determined according to the major compounds. Results of the in vitro antibacterial activity indicated that P. olivieri essential oils showed good inhibitory activities against bacteria, especially Bacillus subtilis. The results of this study gave new insights for cultivation and industrial uses of P. olivieri in Iran.

Chemical composition and antioxidant activity of essential oil from leaves and rhizomes of Curcuma angustifolia Roxb.

The essential oil extracted from rhizome and leaf of Curcuma angustifolia Roxb. (Zingiberaceae) was characterised by gas chromatography-mass spectrometry (GC-MS). The GC-MS analysis revealed the presence of 32 and 35 identified constituents, comprising 92.6% and 92% of total leaf and rhizome oil, respectively. Curzerenone (33.2%), 14-hydroxy-δ-cadinene (18.6%) and γ-eudesmol acetate (7.3%) were the main components in leaf oil. In rhizome oil, curzerenone (72.6%), camphor (3.3%) and germacrone (3.3%) were found to be the major constituents. Antioxidant capacities of oil were assessed by various methods, 2, 2-diphenyl-1-picrylhydrazyl (DPPH), 2, 2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and reducing power ability (RPA). Based on the results, the leaf oil showed more antioxidant potential as compared to rhizome oil and reference standards (ascorbic acid and butylated hydroxytoluene (BHT)). Thus, the leaf essential oil of C. angustifolia can be used as an alternative source of natural antioxidant.

Essential oil composition of Ajuga comata Stapf. from Southern Zagros, Iran.

The chemical composition of essential oil obtained from the aerial parts of Ajuga comata Stapf. was analyzed by GC and GC/MS. Thirty-seven components were identified in the oil. (E)-ß-caryophyllene (30.9%), caryophyllene oxide (24.9%), (E)-ß-farnesene (12.6%), ß-eudesmol (3.2%), δ-cadinene (3.1%) and germacrene D (3.0%) were the main compounds in the EOs. The chemical composition of A. comata Stapf. from the Southern Zagros of Iran is reported for the first time.

Chemical composition, toxicity and non-target effects of Pinus kesiya essential oil: An eco-friendly and novel larvicide against malaria, dengue and lymphatic filariasis mosquito vectors.

Mosquitoes (Diptera: Culicidae) are vectors of important parasites and pathogens causing death, poverty and social disability worldwide, with special reference to tropical and subtropical countries. The overuse of synthetic insecticides to control mosquito vectors lead to resistance, adverse environmental effects and high operational costs. Therefore, the development of eco-friendly control tools is an important public health challenge. In this study, the mosquito larvicidal activity of Pinus kesiya leaf essential oil (EO) was evaluated against the malaria vector Anopheles stephensi, the dengue vector Aedes aegypti and the lymphatic filariasis vector Culex quinquefasciatus. The chemical composition of the EO was analyzed by gas chromatography-mass spectroscopy. GC-MS revealed that the P. kesiya EO contained 18 compounds. Major constituents were α-pinene, ß-pinene, myrcene and germacrene D. In acute toxicity assays, the EO showed significant toxicity against early third-stage larvae of An. stephensi, Ae. aegypti and Cx. quinquefasciatus, with LC50 values of 52, 57, and 62µg/ml, respectively. Notably, the EO was safer towards several aquatic non-target organisms Anisops bouvieri, Diplonychus indicus and Gambusia affinis, with LC50 values ranging from 4135 to 8390µg/ml. Overall, this research adds basic knowledge to develop newer and safer natural larvicides from Pinaceae plants against malaria, dengue and filariasis mosquito vectors.

Chemical Composition and Characteristic Odor Compounds in Essential Oil from Alismatis Rhizoma (Tubers of Alisma orientale).

Chemical composition and potent odorants that contribute to the characteristic odor of essential oil from Alismatis Rhizoma (tubers of Alisma orientale) were investigated by gas chromatography-mass spectrometry (GC-MS), GC-olfactometry (GC-O), aroma extract dilution analysis (AEDA) and relative flavor activity (RFA) methods. Fifty components, representing 94.5% of the total oil, were identified. In this study, we newly identified thirty-nine compounds in the oil from tubers of A. orientale. The major constituents of the essential oil were khusinol (36.2%), δ-elemene (12.4%), germacron (4.1%), alismol (3.8%), ß-elemene (3.1%), and α-bisabolol (1.9%). Through sensory analysis, sixteen aroma-active compounds were detected and the key contributing aroma-active compounds were δ-elemene (woody, flavor dilution (FD)-factor = 4, RFA = 0.3) ß-elemene (spicy, FD = 5, RFA = 0.7), spathulenol (green, FD = 5, RFA = 1.0), γ-eudesmol (woody, FD = 6, RFA = 1.5), and γ-cadinol (woody, FD = 5, RFA = 1.0). These compounds are thought to contribute to the odor from tubers of A. orientale. These results imply that the essential oil from the tubers of A. orientale deserve further investigations in the phytochemical and medicinal fields.

[Simultaneous determination of beta-elemene, curcumol, germacrone and neocurdione in volatile oil of Curcuma phaeocaulis and vinegar products by GC-MS].

This study aims to develop a method for determination of beta-elemene, curcumol, germacrone and neocurdione in the volatile oil of Curcuma phaeocaulis, and to provide the basis of the quality control method for the volatile oil of C. phaeocaulis and the related preparations. Based on GC-MS, the 4 main compounds were simultaneously determined, with the internal standard n-tridecane. The Agilent 19091S-433 column (0.25 microm x 250 microm x 30 m) was adopted at the temperature of 250 degrees C, the programmed temperature method (60 degrees C for 1 min, 5 degrees C x min x to 110 degrees C for 5 min, 1 degrees C x min(-1) to 140 degrees C, 5 degrees C x min(-1) to 160 degrees C, 10 degrees C x min(-1) to 240 degrees C) was used. Helium gas was used as the carrier gas at a constant flow rat of 1 mL x min(-1), with an injection volume of 1 RL. Mass spectra were taken at 70 eV; the ion-source temperature was 200 degrees C. The relation time and character acteristic ions for each target compound were determined by full scan mode and SIM, and m/z 85.1, 93.1, 121.1, 107.1 and 180.1 were the detection ions of n-tridecane, beta-elemene, curcumol, germacrone and neocurdione. As a result, beta-elemene, curcumol, germacrone and neocurdione were all detected with good separation. They were all in a good linear relationship within each concentration scope. The average recovery rates were in the range of 98.2%-101%. So, the method can be used to control the quality of the volatile of C. phaeocaulis Val. and the preparations related.

Impact of gas chromatography and mass spectrometry combined with gas chromatography and olfactometry for the sex differentiation of Baccharis articulata by the analysis of volatile compounds.

The Baccharis genus has more than 400 species of aromatic plants. However, only approximately 50 species have been studied in oil composition to date. From these studies, very few take into consideration differences between male and female plants, which is a significant and distinctive factor in Baccharis in the Asteraceae family. Baccharis articulata is a common shrub that grows wild in south Brazil, northern and central Argentina, Bolivia, Paraguay and Uruguay. It is considered to be a medicinal plant and is employed in traditional medicine. We report B. articulata male and female volatile composition obtained by simultaneous distillation-extraction technique and analyzed by gas chromatography with mass spectrometry. Also, an assessment of aromatic differences between volatile extracts was evaluated by gas chromatography with olfactometry. The results show a very similar chemical composition between male and female extracts, with a high proportion of terpene compounds of which ß-pinene, limonene and germacrene D are the main components. Despite the chemical similarity, great differences in aromatic profile were found: male plant samples exhibited the strongest odorants in number and intensity of aromatic attributes. These differences explain field observations which indicate differences between male and female flower aroma, and might be of ecological significance in the attraction of pollinating insects.

Chemical composition and antioxidant activity of essential oil of six pinus taxa native to China.

The essential oils obtained by steam distillation from needles of six China endemic Pinus taxa (P. tabulaeformis, P. tabulaeformis f. shekanensis, P. tabulaeformis var. mukdensis, P. tabulaeformis var. umbraculifera, P. henryi and P. massoniana) were analysed by GC/MS. A total of 72 components were separated and identified by GC/MS from the six taxa. The major constituents of the essential oils were: α-pinene (6.78%-20.55%), bornyl acetale (3.32%-12.71%), ß-caryophellene (18.26%-26.31%), α-guaiene (1.23%-8.19%), and germacrene D (1.26%-9.93%). Moreover, the essential oils were evaluated for antioxidant potential by three assays (DPPH, FRAP and ABTS) and tested for their total phenolic content. The results showed that all essential oils exhibited acceptable antioxidant activities and these strongly suggest that these pine needles may serve as a potential source of natural antioxidants for food and medical purposes.