Essential Oil Of Chenopodium Ambrosioides Research Articles

Essential oil from <i>Chenopodium ambrosioides L.</i> induces mitochondrial-mediated pathway and endoplasmic reticulum stress-related apoptosis in human liver cancer SMMC-7721 cells

Purpose: To evaluate the cytotoxic effect of essential oil derived from Chenopodium ambrosioides L. in Sichuan Province on human liver cancer SMMC-7721 cells, as well as its possible molecular mechanisms.Methods: Cytotoxicity was characterized by MTT assay and transmission electron microscopy (TEM) of SMMC-7721 cells ultrastructure. The apoptotic effect of the essential oil was evaluated by changes in mitochondrial membrane potential and Western blot assay.Results: MTT assay data indicate that the essential oil was cytotoxic to SMMC-7721 cells, while TEN revealed that there were vacuoles and nucleus fragmentation in the SMMC-7721 cell cytosol, cell swelling, and a large amount of leakage. Mitochondrial membrane potential assay and Western Blot data indicate that the essential oil induced cell apoptosis.Conclusion: The essential oil of Chenopodium ambrosioides L. in Sichuan Province seems to induce apoptosis of human liver cancer SMMC-7721 cells via the mitochondrial-mediated pathway and endoplasmic reticulum stress. Thus, this plant requires further investigation as a potential source of ananti-liver cancer drug.
 Keywords: Chenopodium ambrosioides Essential oil; Anti-tumor activity, Liver cancer Apoptosis, SMMC-7721 cells

Inhibition of the TetK efflux-pump by the essential oil of Chenopodium ambrosioides L. and α-terpinene against Staphylococcus aureus IS-58

The use of natural products is crucial to suppress the development of these micro-organisms and to reduce the concentration necessary to inhibit these microrganisms, reducing the toxicity risks also. In this study, the essential oil from Chenopodium ambrosioides Leaves and its main constituent α-Terpinene were used in the antibacterial and potentiating activity of antibiotics and ethidium bromide assays, against the bacterial strains Staphylococcus aureus IS-58, carriers of efflux pumps. The Minimum Inhibitory Concentration (MIC) was determined using a microdilution method. The capacity of the aforementioned was also tested in combination with tetracycline and ethidium bromide, with the aim of improving the activity of the antibacterials. The MIC of the C. ambrosioides L. essential oil and of α-Terpinene were above 1024 μg/mL, comprising a clinically irrelevant value. However, when associated with the antibiotics, the C. ambrosioides L. essential oil, significantly decreased the MIC of tetracycline and ethidium bromide. The efflux pump is the only mechanism the bacteria possesses to reduce the toxicity of ethidium bromide, and thus this reduction in the MIC demonstrates that the C. ambrosioides L. essential oil is an effective option in the inhibition of the efflux pump present in these micro-organisms.

GC-MS Analysis of Seed Essential Oil of Chenopodium ambrosioides L. Collected from Himalayan Region

The floral twigs of Chenopodium ambrosioides L. were collected from Uttarkashi (Garhwal region) of Uttarakhand state (India). These twigs were shade dried and then seeds were sorted out. The essential oil of seeds of C. ambrosioides L. was analyzed by GC and GC-MS. Ascaridole (40.7 %), isoascaridole (22.7 %), α-terpinene (17.9 %) and p-cymene (8.5 %) were present as major compounds.

Characterization and evaluation of the cytotoxic potential of the essential oil of Chenopodium ambrosioides

The essential oil of Chenopodium ambrosioides L., Amaranthaceae, was obtained by steam distillation in a Clevenger apparatus and characterization was performed using chromatographic and spectroscopic assays (GC-FID, GC/MS, 1H NMR). Two major compounds were identified: p-cymene (42.32%) and ascaridole (49.77%). The ethanolic extract and hydrolate were fractionated by liquid–liquid partitioning and the compounds were characterized by GC/MS. The essential oil, ethanol extract and fractions by partitioning with dicloromethane, ethyl acetate and butanol were tested in tumor cell lines (K562, NALM6, B15, and RAJI). Significant cytotoxic activity was found for essential oil (IC50=1.0μg/ml) for RAJI cells and fraction dicloromethane (IC50=34.0μg/ml) and ethanol extract (IC50=47.0μg/ml) for K562 cells. The activity of the essential oil of C. ambrosioides is probably related to the large amount of ascaridol, since the other major compound, p-cymene, is recognized as a potent anti-inflammatory and has low cytotoxic activity.

The toxicity and physiological effect of essential oil from Chenopodium ambrosioides against the diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae)

In this study, the bioactivities of the essential oil of Chenopodium ambrosioides L. and its two main components, α-terpinene and p-cymene, were evaluated against the diamondback moth (DBM), Plutella xylostella (L.). The contact and fumigant toxicity of the essential oil significantly decreased as the DBM larval instar increased. The essential oil had 30-fold more potent toxicity against third-instar larvae than either α-terpinene or p-cymene. With respect to antifeedant activity, treatment with C. ambrosioides essential oil dose-dependently decreased leaf consumption by third-instar larvae, and the median antifeedant concentration (AFC50) was 66.81 mg/L at 24 h and 78.24 mg/L at 48 h after the treatment. Development of pupae was also inhibited, and the median concentrations of pupae weight inhibition (PWIC50) and percentage inhibition of pupation (PIC50) were 176.5 mg/g leaf and 111.6 mg/g leaf, respectively. In general, contact treatment with the essential oil significantly inhibited the activities of insecticide detoxifying enzyme, including carboxylesterase and glutathione-S-tranferases, whereas, fumigant exposure only altered carboxylesterase activity. At nearly all the tested concentrations, the essential oil induced the activities of superoxide dismutase, peroxidase, and catalase; however, peroxidase activity was inhibited by contact treatment. Thus, the essential oils from C. ambrosioides showed potential as new control products to combat field crop-infesting insect pests, and it may function as fumigant, insecticide synergist, antifeedant, or insect growth regulator.

CARACTERIZAÇÃO QUÍMICA E EFEITO DO ÓLEO ESSENCIAL DE ERVA-DE-SANTA-MARIA SOBRE O ÁCARO-RAJADO DE MORANGUEIRO

O ácaro-rajado, Tetranychus urticae Koch (1836) (Acari: Tetranychidae), é a principal praga na cultura do morangueiro. O objetivo deste trabalho foi a caracterização química do óleo essencial de Chenopodium ambrosioides L. e a avaliação de seus efeitos sobre o ácaro-rajado. Os compostos do óleo essencial foram identificados pelasanálises de CG-DIC e CG-EM. A mortalidade e a oviposição foram avaliadas após a pulverização do óleo (2,5; 5,0; 7,5 e 10,0% v v-1) sobre fêmeas do ácaro-rajado. O rendimento do óleo essencial foi de 0,3%, e os compostos identificados foram (Z)-ascaridol (87%), (E)-ascaridol (5,04%), p-cimeno (4,83%), a- terpineno (1,24%) e piperitona (0,7%). Os maiores valores para mortalidade e redução de oviposição observados foram 85% e 69%, respectivamente. O óleo essencial de C. ambrosioidesé uma opção promissora para o manejo do ácaro-rajado.

Cytotoxicity of Essential Oil of <i>Chenopodium ambrosioides</i> L against Human Breast Cancer MCF-7 Cells

Purpose: To investigate the cytotoxic activity of the essential oil of Chenopodium ambrosioides L. against human breast cancer MCF-7 cells.Methods: Cytotoxicity was characterized by 50 % inhibition (IC50) of human breast cancer cell lines (MCF-7) using 3-(4,5-dimethylthaizol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Apoptosis was analysed by Hoechst33258 staining and DNA ladder. MCF-7 cellular superoxide dismutase (SOD), catalase (CAT) vitality and malondialdehyde (MDA) content were evaluated.Results: The essential oil was cytotoxic to MCF-7 cell line. A dose- and time-dependent inhibition was observed with IC50 values of 18.75, 9.45 and 10.50 μg/ml at 6, 24 and 48 h, respectively. Analyses by Hoechst33258 staining and DNA ladder indicate that the essential oil induced apoptosis. SOD vitality significantly decreased (p＜ 0.05) by 51 % when the concentration of the essential oil increased from 1.25 to 12.5 μg/ml while CAT vitality significantly increased (p ＜ 0.05) by 71 % when essential oil concentration was similarly increased. The MDA content of each treatment group, when compare to control, did not show any significant difference (p ＜ 0.05).Conclusion: The essential oil of C. ambrosioides was cytotoxic to MCF-7 cell line and induced apoptosis.Keywords: Chenopodium ambrosioides L., Essential oil, Cytotoxicity, Apoptosis, Breast cancer, MCF-7 cells.

Composition of essential oil of Chinese Chenopodium ambrosioides and insecticidal activity against maize weevil, Sitophilus zeamais

In a screening programme for new agrochemicals from Chinese medicinal herbs, Chenopodium ambrosioides L. was found to possess strong fumigant activity against the maize weevil Sitophilus zeamais (Motsch.). Essential oil of C. ambrosioides was obtained by hydrodistillation, and the constituents were determined by GC-MS analysis. The active compounds were isolated and identified by bioassay-directed fractionation. Five active compounds [(Z)-ascaridole, 2-carene, ρ-cymene, isoascaridole and α-terpinene] were isolated and identified from the essential oil from Chinese C. ambrosioides. The LC₅₀ values (fumigation) of the crude essential oils and the active compound (Z)-ascaridole against S. zeamais adults were 3.08 and 0.84 mg L⁻¹ air respectively. The LD₅₀ values (contact toxicity) of the crude essential oil and (Z)-ascaridole against S. zeamais adults were 2.12 and 0.86 µg g⁻¹ body weight respectively. The findings suggested that the essential oil of Chenopodium ambrosioides and its main active constituent, (Z)-ascaridole, may be explored as a natural potential fumigant.

Toxic effects of carvacrol, caryophyllene oxide, and ascaridole from essential oil of Chenopodium ambrosioides on mitochondria

Chenopodium ambrosioides have been used for centuries in the Americas as a popular remedy for parasitic diseases. The essential oil of this plant possesses anthelmintic activity and is still used in some regions to treat parasitosis and leishmaniasis. However, the Chenopodium oil caused also some fatalities, leading to its commercial disuse. In this work, we studied the mechanism of toxicity of the essential oil and its major pure ingredients (carvacrol, caryophyllene oxide, and ascaridole, which was synthesized from α-terpinene) with respect to mammalian cells and mitochondria. We observed that all products, but especially caryophyllene oxide, inhibited the mitochondrial electron transport chain. This effect for carvacrol and caryophyllene oxide was mediated via direct complex I inhibition. Without Fe 2+, ascaridole was less toxic to mammalian mitochondria than other major ingredients. However, evidence on the formation of carbon-centered radicals in the presence of Fe 2+ was obtained by ESR spin-trapping. Furthermore, it was shown that Fe 2+ potentiated the toxicity of ascaridole on oxidative phosphorylation of rat liver mitochondria. The increase of the α-tocopherol quinone/α-tocopherol ratio under these conditions indicated the initiation of lipid peroxidation by Fe 2+-mediated ascaridole cleavage. Further ESR spin-trapping experiments demonstrated that in addition to Fe 2+, reduced hemin, but not mitochondrial cytochrome c can activate ascaridole, explaining why ascaridole in peritoneal macrophages from BALB/c mice exhibited a higher toxicity than in isolated mitochondria.

RESPONSE OF TWOSPOTTED SPIDER MITE POPULATIONS TO PROGRAMS OF ABAMECTIN, BIFENAZATE, HEXYTHIAZOX, SPIROMESIFEN, AND AN ESSENTIAL OIL OF CHENOPODIUM AMBROSIOIDES MITICIDES IN FLORIDA STRAWBERRY CROPS

Programs of twospotted spider mite (Tetranychus urticae) management in strawberry were evaluated in two field experiments during 2007 that measured effectiveness of various miticides, a non-ionic surfactant, and their frequency of application. Miticides evaluated included two formulations of abamectin and single formulations of bifenazate, hexythiazox, spiromesifen, and essential oil of Chenopodium ambrosioides. All of the miticides provided significant reductions in spider mites. Three weeks after initial application of treatments the most effective reductions occurred when abamectin, bifenazate, hexythiazox, spiromesifen were used.

1,2:3,4-Diepoxy-p-menthane and 1,4-Epoxy-p-menth- 2-ene: Rare Monoterpenoids from the Essential Oil of Chenopodium ambrosioides L. var ambrosioides Leaves

The composition of the essential oil of leaves from Chenopodium ambrosioides L. var ambrosioides was analyzed by capillary GC and GC/MS. Ten compounds were identified accounting for 94.6% of the total oil. 1,2:3,4-Diepoxy-p-menthane and 1,4-epoxy-p-menth-2-ene were isolated from the oil; it was the first time that these compounds were identified from Chenopodium ambrosioides L. var ambrosioides. The major compounds in the hydrodistillate were α-terpinene (55.6%), p-cymene (16.7%) and 1,4-epoxy-p-menth-2-ene (17.7%).

Combined analysis of the essential oil of Chenopodium ambrosioides by GC, GC‐MS and 13C‐NMR spectroscopy: quantitative determination of ascaridole, a heat‐sensitive compound

A commercial sample of the essential oil of Chenopodium ambrosioides L. from Madagascar was analysed by GC, GC-MS and 13C-NMR. By GC analysis, the major constituents were found to be ascaridole (1) (41.8%), isoascaridole (2) (18.1%), p-cymene (16.2%), alpha-terpinene (9.7%) and limonene (3.8%). However, ascaridole undergoes a partial thermal isomerisation to 2 and hence the amount of 1 is under-estimated by GC analysis. The actual contents of 1 and 2 (55.3 and 4.6%, respectively) were obtained following combined analysis of the sample by GC and 13C-NMR. Several hydroxy- and polyhydroxy-menthanes were identified by 13C-NMR.

Ascaridole-less infusions of Chenopodium ambrosioides contain a nematocide(s) that is(are) not toxic to mammalian smooth muscle

Infusions of Chenopodium ambrosioides (L.) have been used for centuries in the Americas as a popular remedy against intestinal worm infections. The essential oil of Chenopodium ambrosioides contains high levels of ascaridole, which is a potent anthelmintic, but which has also been responsible for human fatalities, leading to its disuse. Almost 90% of the nematocidal activity of Chenopodium ambrosioides infusions was due to a hydrophilic component different from ascaridole. Synthetic ascaridole and the ascaridole from infusions, extracted into hexane, caused a reduction of carbachol-induced contractions in rat gastrointestinal smooth muscle at concentrations required to kill Caenorhabditis elegans (L.). The herbal infusion and the ascaridole-free hexane-extracted aqueous residue of the above infusion, at nematocidal concentractions, had no detectable effect on smooth muscle contraction in the above system. It would appear that the traditional form of useage of Chenopodium ambrosioides infusions as a vermifuge is safer than the use of the herb’s essential oil.

Ascaridole-less infusions of Chenopodium ambrosioides contain a nematocide(s) that is(are) not toxic to mammalian smooth muscle

Infusions of Chenopodium ambrosioides (L.) have been used for centuries in the Americas as a popular remedy against intestinal worm infections. The essential oil of Chenopodium ambrosioides contains high levels of ascaridole, which is a potent anthelmintic, but which has also been responsible for human fatalities, leading to its disuse. Almost 90% of the nematocidal activity of Chenopodium ambrosioides infusions was due to a hydrophilic component different from ascaridole. Synthetic ascaridole and the ascaridole from infusions, extracted into hexane, caused a reduction of carbachol-induced contractions in rat gastrointestinal smooth muscle at concentrations required to kill Caenorhabditis elegans (L.). The herbal infusion and the ascaridole-free hexane-extracted aqueous residue of the above infusion, at nematocidal concentractions, had no detectable effect on smooth muscle contraction in the above system. It would appear that the traditional form of useage of Chenopodium ambrosioides infusions as a vermifuge is safer than the use of the herb’s essential oil.

Essential Oil of Chenopodium ambrosioides L. from Cuba

The chemical composition of the essential oil obtained from aerial parts of Chenopodium amhrosioides from Cuba was examined by combined GC/M S. The oil was characterized by the presence of α-terpinyl acetate (73.9 %) and p-cymene (4.3 %).

Chemical Examination of the Essential Oil of Chenopodium ambrosioides L. from the Southern Hills of India

The hydrodistilled essential oil from the aerial parts of Chenopodium ambrosioides L. was analyzed by GC and GC/MS. Fifteen constituents, representing 95% of the oil, having six monoterpene hydrocarbons (85%) and nine oxygenated monoterpenes (10%), were characterized. The major components were α-terpinene (64%), p-cymene (19%) and ascaridole (7%).

Chemical Composition of Essential Oils of Chenopodium ambrosioides L. from Rwanda

The essential oil of Chenopodium ambrosioides is well known. The oil from Rwanda is composed mainly of α-terpinene, and contains only a small proportion of ascaridole, which is usually present in large amounts.

Volatile Constituents from the Leaves ofChenopodium ambrosioidesL.

ABSTRACT The composition of the essential oil of Chenopodium ambrosioides L. was analyzed by capillary GC and GC/MS. Forty-nine compounds were identified accounting for 96.86% of the oil. The major compounds were limonene (32.5%) and trans-pinocarveol (26.7%).

Toxicity and Repellency of Chenopodium Oil To Four Species of Stored-Product Insects2

Chenopodium oil, an essential oil of Chenopodium ambrosioides L., was evaluated for its toxicity and repellency to adults of Callosobruchus machulatus (F.), Sitophilus oryzae (L.), Lasioderma serricorne (F.), and Tribolium confusum Jacquelin du Val. Topically applied, the oil was highly toxic to C. maculatus (100% mortality at 40 μg/insect) and L. serricorne (92.5% mortality at 50 μg/insect), moderately toxic to S. oryzae (52.5% mortality at 50 μg/insect), and only slightly toxic to T. confusum at 50 μg/insect. When applied to the surface of wheat, the oil was highly repellent to S. oryzae. When applied to wheat or black-eyed peas, the oil reduced infestations of S. oryzae and C. maculatus at dosages of 2000 and 1000 ppm, respectively.

野生アリタソウの精油成分に就いて (第3報)

It has previously been shown that crystals of m.p. 105-106°, C10H14O, had been obtained as the component of the essential oil of Chenopodium ambrosioides L. The molecular composition is now corrected to C20H28O2, confirmed as the dimer of l-pinocarvone, and its structure was assumed as follows: