Identification of the main volatile compounds in the leaf and flower of <Emphasis Type="Italic">Tithonia diversifolia</Emphasis> (Hemsl) Gray

The composition of the essential oils of the leaves and flowers of Tithonia diversifolia (Hemsl) A. Gray, Mexican sunflower, are reported. The oils were obtained by hydrodistillation in an all-glass Clevenger-type apparatus and analyzed by GC–MS. The leaf oil was comprised of an abundance of α-pinene (32.9%), β-caryophyllene (20.8%), germacrene D (12.6%), β-pinene (10.9%) and 1, 8-cineole (9.1%). Germacrene D (20.3%), β-caryophyllene (20.1%) and bicyclogermacrene (8.0%) characterized the oil of the flower. A number of aliphatic fatty acids and a diterpenoid compound, sandaracopimaradiene, that were present in the flower, could not be detected in the leaf oil.     

Composition of the essential oil from the root of <Emphasis Type="Italic">Artemisia annua</Emphasis>

Upon hydrodistillation, dried roots of Artemisia annua L. cultivar Jwarharti gave a pleasantly fragrant essential oil with a yield of 0.25%. GC and GC–MS analyses of the oil enabled the identification of 52 components representing 83.2% of the oil. The oil was rich in sesquiterpenes and oxygenated sesquiterpenes and had cis-arteannuic alcohol (25.9%), (E)-β-farnesene (6.7%), β-maaliene (6.3%), β-caryophyllene (5.5%), caryophyllene oxide (4.4%) and 2-phenylbenzaldehyde (3.5%) as its major components. The oil was found to possess considerable fumigant activity and ability to repel adult Tribolium castaneum beetles.     

Antitumour Activity of the Microencapsulation of Annona vepretorum Essential Oil

Annona vepretorum Mart. (Annonaceae), popularly known as ‘bruteira’, has nutritional and medicinal uses. This study investigated the chemical composition and antitumour potential of the essential oil of A. vepretorum leaf alone and complexed with β‐cyclodextrin in a microencapsulation. The essential oil was obtained by hydrodistillation using a Clevenger‐type apparatus and analysed using GC‐MS and GC‐FID. In vitro cytotoxicity of the essential oil and some of its major constituents in tumour cell lines from different histotypes was evaluated using the alamar blue assay. Furthermore, the in vivo efficacy of essential oil was demonstrated in mice inoculated with B16‐F10 mouse melanoma. The essential oil included bicyclogermacrene (35.71%), spathulenol (18.89%), (E)‐β‐ocimene (12.46%), α‐phellandrene (8.08%), o‐cymene (6.24%), germacrene D (3.27%) and α‐pinene (2.18%) as major constituents. The essential oil and spathulenol exhibited promising cytotoxicity. In vivo tumour growth was inhibited by the treatment with the essential oil (inhibition of 34.46%). Importantly, microencapsulation of the essential oil increased in vivo tumour growth inhibition (inhibition of 62.66%).     

Chemical Composition of Essential Oils from Leaves and Twigs of Pistacia lentiscus,Pistacia lentiscus var. chia,and Pistacia terebinthus from Turkey

The composition of the essential oils from the leaves and twigs of Pistacia lentiscus L., Pistacia lentiscus var. chia (L.), and Pistacia terebinthus L. of Turkish origin were analyzed by gas chromatography/mass spectrometry (GC/MS). Seventy-seven constituents were characterized from the essential oil of P. terebinthus leaves with α-cadinol (6.9%), phytol (5.4%), δ-cadinene (5.1%), α-terpineol (5.0%), and bornyl acetate (4.4%) as major constituents. Germacrene D (10%), β-pinene (7.5%), bornyl acetate (6.0%), α-cubebene (5.9%), and cubebol (5.4%) were found to be the main components among the 61 compounds characterized in the essential oil of P. terebinthus twigs. Forty-six compounds were characterized from the essential oil of P. lentiscus twigs with sabinene (23.2%), α-pinene (19.4%), germacrene D (14.1%), limonene (6.9%), β-phellandrene (6.5%), terpinene-4-ol (5.7%), and β-caryophyllene (5.7%) as the main constituents. Terpinene-4-ol (29.2%), β-caryophyllene (29.2%), and p-cymene (7.1%) were identified as the major components among the 64 compounds characterized in the essential oil of P. lentiscus leaves. Sixty-eight compounds were found on the essential oil of P. lentiscus var. chia leaves with germacrene D (20.1%), myrcene (13.9%), β-caryophyllene (10.8%), and α-terpinyl acetate (4.8%) as the major constituents. Myrcene (27.4%), germacrene D (21.7%), and β-caryophyllene (7.2%) were found to be the main components among 50 compounds characterized in the essential oil of P. lentiscus var. chia twigs.     

Chemical composition and antibacterial activity of essential oils of <Emphasis Type="Italic">Eugenia</Emphasis> species

The essential oils of the leaves of Eugenia brasiliensis, Eugenia beaurepaireana, and Eugenia umbelliflora were analyzed by GC–MS. The major compounds found in the oil of E. brasiliensis were spathulenol (12.6%) and τ-cadinol (8.7%), of E. beaurepaireana were β-caryophyllene (8.0%) and bicyclogermacrene (7.2%), and of E. umbelliflora were viridiflorol (17.7%) and β-pinene (13.2%). These oils were assayed to determine their antibacterial activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli. All of the oils analyzed showed antibacterial activity, ranging from moderate to strong, which was most accentuated for the E. umbelliflora and E. brasiliensis oils, which strongly inhibited the growth of S. aureus giving values of MIC = 119.2 and 156.2 μg/mL, respectively.     

Variability,toxicity, and antioxidant activity of Eupatorium cannabinum (hemp agrimony) essential oils

Content: Eupatorium cannabinum L. (Asteraceae) is as a potential source of biologically active compounds. The plant is used in traditional medicine for the treatment of diarrhea and livers diseases.

Objective: The present study provides investigation on pharmacological properties (antioxidant and toxic activities) of essential oils of E. cannabinum, collected from 11 wild populations in Lithuania.

Materials and methods: Twenty-two hemp agrimony essential oil samples were prepared by hydrodistillation according to the European Pharmacopoeia, and their chemical composition was determined by GC–FID and GC–MS. Compositional data were subjected to principal components analysis (PCA). Instead of conventional spectrophotometric methods, cyclic voltammetry (CV) and square wave voltammetry (SWV) techniques were applied to determine antioxidant activity of hemp agrimony essential oils. Meanwhile, toxicity of the oils was determined using brine shrimp (Artemia sp.) assay.

Results: Chemical profiles of E. cannabinum oils were described according to the first predominant components: germacrene D (≤22.0%), neryl acetate (≤20.0%), spathulenol (≤27.2%), and α-terpinene (11.5%). For the first time, α-zingiberene (≤7.8%) was found to be among three major constituents (as the second one) for hemp agrimony oils. SWV measurements revealed that oxidation potentials of compounds present in the oils are lower (below 0.1 V) compared with that of well-known antioxidant quercetin (0.15 V). Toxicity tests evaluated that hemp agrimony oils containing predominant amounts of germacrene D and neryl acetate were notably toxic (LC₅₀ value 16.3–22.0 μg/mL).

Conclusion: The study provided some new data concerning chemical composition and pharmaceutical properties of E. cannabinum essential oils.     

Volatile oil profiles of the aerial parts of Jordanian garland,Chrysanthemum coronarium

Objective: The study evaluates, qualitatively and quantitatively, the volatile oil profiles of the aerial parts of Jordanian garland Chrysanthemum coronarium L. (Asteraceae) and compares the findings with literature reports of garland of other sources, in terms of general composition and content of potentially active components.

Materials and methods: The chemical composition of the essential oils isolated by hydrodistillation from dried material composed of flowerheads (FH) and aerial parts except for flowerheads (AEF) was assessed by GC-FID and GC-MS.

Results and discussion: More than 60 components were identified in the studied oils, corresponding to about 99.6 and 99.7% of total oil constituents of FH and AEF, respectively. The oil was characterized by substantial levels of monoterpenes (76.9% in FH and 61.9% in AEF) and moderate levels of sesquiterpenes (15.7% in FH and 27.7% in AEF). The oil from FH was characterized by high levels of oxygenated monoterpenes (64.3%, compared to 15.3% in AEF) and moderate levels of both monoterpene-hydrocarbons (12.6%, compared to 46.6% in AEF as the major fraction) and sesquiterpene-hydrocarbons (14.7%, compared to 23.5% in AEF), while very low levels of oxygenated sesquiterpenes were observed in both oils (1.0% in FH and 4.2% in AEF). The principal oil component was camphor (17.5%) in FH and myrcene (36.7%) in AEF. Other major components identified in the FH oil were santolina triene (4.3%), neoiso-3-thujanol (5.6%), cis-chrysanthenyl acetate (10.8%), perilla aldehyde (11.7%), iso-italicene (4.7%), phenylpropyl butanoate (4.9%), and germacrene D (4.3%), while Z-β-ocimene (5.2%), isobornyl acetate (5.2%), E-β-farnesene (12.1%), and germacrene D (4.5%) were the major constituents of AEF oil.     

Chemical composition and cytotoxic activity of the leaf essential oil of <Emphasis Type="Italic">Eugenia zuchowskiae</Emphasis> from Monteverde,Costa Rica

The leaf essential oil of Eugenia zuchowskiae from Monteverde, Costa Rica, has been obtained by hydrodistillation and analyzed by GC–MS. The principal constituents of E. zuchowskiae leaf oil were α-pinene (28.3%), β-caryophyllene (13.2%), α-humulene (13.1%), and α-copaene (8.1%). The leaf essential oil of E. zuchowskiae showed pronounced in-vitro cytotoxic activity against MCF-7, MDA-MB-468, and UACC-257 human tumor cell lines. The major components showed cytotoxic activities comparable to doxorubicin (LC₅₀ 14–70 μg/ml).     

Composition and antibacterial activity of the essential oils from Zanthoxylum rhoifolium

The essential oils from the aerial parts of leaves, fruits and flowers of Zanthoxylum rhoifolium of Southern Brazil (Rio Grande do Sul), were analysed by GC, GC/MS, and chiral phase gas chromatography (CPGC). Forty-eight compounds were identified from the essential oils. The major constituents of the essential oil of the leaves were germacrene D (34 %) and bicyclogermacrene (23 %) and of the fruits, menth-2-en-1-ol (46.2 %), beta-myrcene (30.2 %), (-)-linalool (15 %) and (-)-alpha-terpineol (8.45 %). beta-Myrcene (65 %) and menth-2-en-1-ol (5.4 %) dominate the essential oil of the flowers. The oils of the leaves and fruits were bioactive with antibacterial activity against Staphylococcus aureus (Gram positive), and Klebsiella pneumoniae and Salmonella setubal bacteria (Gram negative) microorganisms, while the essential oil of the flowers was inactive.     

Comparative study on volatile components of Nardostachys Rhizome

Volatile components in 13 crude drug samples derived from Nardostachys chinensis or Nardostachys grandiflora were studied by solid phase micro extraction (SPME)-GC and SPME-GC–MS. Twenty-three compounds accounting for 81.3 and 70.0% of volatile components in newly collected samples of two species were identified. β-Maaliene, 9-aristolene, calarene and patchouli alcohol were identified as the major volatile constituents of N. chinensis, whereas aromadendrene, cube-11-ene, epi-α-selinene, spirojatamol and valeranone were identified as those of N. grandiflora. Using the peaks of β-maaliene and 9-aristolene in GC profiles as the marker, two Nardostachys species were clearly distinguished among the samples examined.     

Extraction of essential oils from garlic (Allium sativum) using ligarine as solvent and its immunity activity in gastric cancer rat

The chemical composition of essential oil from magnolia collected in Suzhou city, China, was studied using gas chromatography-mass spectroscopy. Fifty-four volatile compounds were identified in the essential oil, with eucalyptol (21.55%), β-Pinene(11.07%), D-Limonene (8.93%), 1R-α-Pinene (7.86%), Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)-(6.46%), Cyclohexene, 4-methylene-1-(1-methylethyl)- (5.30%), 1,4-Cyclohexadiene, 1-methyl-4-(1-methylethyl)- (5.10%), camphene (4.72%), being the major chemical constituents. In an in vivo approach, the protective effect of the essential oil against oxidative stress in gastric cancer (GC) mice was also investigated in terms of superoxide dismutase, CAT, and glutathione peroxidase activities. Our results indicate that the essential oil has an effective capability to enhance serum antioxidant enzyme activities and sCD40L, and decrease phosphorylate-activate Akt protein levels in a dose-dependent manner in gastric cencer mice. Overall, essential oil from magnolia appears to be an effective antioxidant and is quite suitable for further biological evaluation.     

A new furostanol saponin from <Emphasis Type="Italic">Asparagus cochinchinensis</Emphasis>

A new furostanol saponin, (25S)-26-O-β-d-glucopyranosyl-5β-furost-20(22)-en-3β, 15β,26-triol-3-O-[α-l-rhamnopyranosyl-(1–4)]-β-d-glucopyranoside, namely, aspacochioside D (1) were isolated from Asparagus cochinchinensis (Lour.) Merr, along with three known saponins, aspacochioside C (2), (25S)-5β-spirostan-3β-yl-O-[O-α-l-rhamnopyranosyl-(1–4)]-β-d-glucopyranoside (3), and pseudoprotoneodioscin (4). The structure of 1 was elucidated on the basis of chemical reactions and spectral analysis (IR, GC, ESI-MS, ¹H-NMR, ¹³C-NMR, DEPT, HMBC, HMQC and NOESY). The antiproliferative effects of 1–4 were evaluated in a cytotoxicity assay against the human tumor cell line, A549. Compound 2 (Aspacochioside C) exhibited moderate cytotoxicity against A-549, with an IC₅₀ value of 3.87 μg/mL.     

A new triterpenoid from <Emphasis Type="Italic">Panax ginseng</Emphasis> exhibits cytotoxicity through p53 and the caspase signaling pathway in the HepG2 cell line

A new triterpenoid, 20(R),22(ξ),24(S)-dammar-25(26)-ene-3β,6α,12β,20,22,24-hexanol (1), and three known triterpenoids, β-D-glucopyranoside,(3β,12β)-12,20-dihydroxydammar-24-en-3-yl,6-acetate (2), 20(R)-ginsenoside Rg₃ (3), and 20(R)-ginsenoside Rh₂ (4), were isolated from the leaves of Panax ginseng. Their structures were determined by chemical analysis and spectral methods (IR, 1D and 2D NMR, HR-ESI-MS). Compounds 1–4 were exhibited various degrees of cytotoxicity in the human hepatoma cell line, HepG2. Compound 1 had the highest cytotoxic potency, with an IC₅₀ value of 20.1 μM, by stimulating p53-mediated cell cycle arrest at the G1 to S phase transition, leading to apoptosis via activation of the caspase signaling pathway.     

Baimantuoluosides D-G,four new withanolide glucosides from the flower of <Emphasis Type="Italic">Datura metel</Emphasis> L.

In our search for bioactive anti-psoriasis compounds from the flower of Datura metel L, we isolated four new withanolide glucosides, baimantuoluosides D, E, F and G (1–4). The structures of the new compounds are (5α,6α,7β,22R)-5,6,7,27-tetrahydroxy-1-oxowitha-2,24-dien-27-O-β-D-glucopyranoside (1), (5α,6β,7α,22R)-5,6,7,27-tetrahydroxy-1-oxowitha-2,24-dien-27-O-β-D-glucopyranoside (2), (5α,6β,7α,12β,22R)-5,6,7,12,27-pentahydroxy-1-oxowitha-2,24-dien-27-O-β-D-glucopyranoside (3), and (5α,6β,22R)-5,6,27-trihydroxy-1-oxowitha-2,24-dien-27-O-β-D-glucopyranoside (4) on the basis of chemical and physicochemical evidence.     

Identification of the main aroma compounds in dried seeds of Brassica hirta

The composition of the volatile oil from Sinapis Semen, dried seeds of Brassica hirta (Cruciferae), have been investigated using capillary GC and GC/MS. The important odor-active compounds in the oil were also detected by means of GC-olfactometry (GC-O) and aroma extract dilution analysis (AEDA). The oil was found to contain 68 components, representing 95.36% of the total oil. The main constituents were 4-hydroxy-benzeneacetonitrile (29.63%), palmitic acid (14.55%), linoleic acid and oleic acid (9.67%). The AEDA and GC-O analyses showed that heptanal, phenylethylalcohol, (2E)-octenal and (2E, 4E)-dodecadienal are to a large extent responsible for the characteristic flavor of Sinapis Semen.     

Chemical composition and biological activity of total bufadienolides from the Central-Asian <Emphasis Type="Italic">Bufo viridis</Emphasis> toad venom

The chemical composition of bufadienolides isolated from the venom of Bufo viridis green toad occurring in Central Asia was determined and their biological properties were studied. Six individual bufadienolides were isolated by reverse-phase chromatography on a Lichrosorb RP-8 (10 μ) column in amounts sufficient for qualitative analysis. Two of these were previously identified as arenobufagin and gamabufotalin by NMR spectroscopy and x-ray diffraction methods. The chemical structures of four other bufadienolides are now established by NMR spectroscopy and HPLC. These compounds have been identified as telocinobufagin (3β,5β,14β-trihydroxybufa-20,22-dienolide), marinobufagin (3β, 5β-hydroxy-14,15β-epoxybufa-20,22-dienolide), bufarenogin (3β,12β,14β-hydroxybufa-20,22-dienolide), and bufalin (3β,14β-hydroxybufa-20,22-dienolide). __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 41, No. 11, pp. 33–37, November, 2007.     

Cyclooxygenase-2 inhibitory effects and composition of the volatile oil from the dried roots of Lithospermum erythrorhizon

The composition of the volatile oil from Lithospermi Radix, the dried roots of Lithospermum erythrorhizon (Boraginaceae), has been investigated by capillary GC and GC–MS. To investigate the anti-inflammatory activity of the oil, in-vitro inhibition of ovine cyclooxygenase-1 and 2 (COX-1 and COX-2) activity by the oil was studied. Fifty-four components of the oil were identified, representing 92.74% of the oil. The main components were 2-methylbutanoic acid (21.50%), 3-methylbutanoic acid (12.61%), 2-methylpropanoic acid (8.99%), methyl linoleate (8.76%), methyl oleate (6.27%), methyl palmitate (6.06%), and 2-methyl-2-butenoic acid (5.74%). Highly selective COX-2 inhibition was observed; at 50 μg/ml the oil inhibited 38.8% of COX-2 activity.     

Modulation of immunoreactive protein kinase C-α and β isoforms and G proteins by acute and chronic treatments with morphine and other opiate drugs in rat brain

The abundance of protein kinase C-α and β isoforms (PKC-αβ), PKC-α messenger (m) RNA and guanine nucleotide-binding G protein subunits (Gα_i1/2, Gα_o and Gβ) were quantitated in the rat cerebral cortex after acute and chronic treatments with various opiate drugs. Acute (100mg/kg for 2h) and chronic (10 to 100mg/kg for 5 days) treatment with morphine decreased similarly the immunoreactivity of PKC-αβ (28% and 32%, respectively). Acute (2h) and chronic treatment (5 days) with other μ-agonists heroin (30mg/kg and 10 to 30mg/kg) and methadone (30mg/kg and 5 to 30mg/kg) also induced similar decreases of PKC-αβ (acute: 25% and 23%; chronic: 28% and 18%). After the chronic treatments, spontaneous (48h) or naloxone (2mg/kg)-precipitated opiate withdrawal (2h) resulted in up-regulation of PKC-αβ above control levels (30-38%), and in the case of morphine withdrawal in a concomitant marked increase in the expression of PKC-α mRNA levels (2.3-fold). Acute (2h) treatments with pentazocine (80mg/kg, mixed κ/δ-agonist and μ-antagonist), spiradoline (30mg/kg, selective κ-agonist) and [D-Pen², D-Pen⁵] enkephalin (14nmol i.c.v., selective δ-agonist) induced significant decreases of PKC-αβ (19–33%). Chronic (5 days) treatment with pentazocine (10 to 80mg/kg), but not spiradoline (2 to 30mg/kg), also induced a similar decrease of PKC-αβ (35%). In pentazocine- or spiradoline-dependent rats, naloxone (2mg/kg) did not induce up-regulation of brain PKC-αβ. Acute (10mg/kg for 2h) and chronic (2×10mg/kg for 5 and 14 days) treatment with naloxone did not alter PKC-αβ immunoreactivity. Chronic, but not acute, treatment with μ-agonists (morphine, heroin and methadone) increased the immunoreactivities of Gα_i1/2 (33-37%), Gα_o (25-41%) and Gβ (10-33%) protein subunits. In heroin- and methadone-dependent rats naloxone (2mg/kg)-precipitated withdrawal (2h) did not modify the up-regulation of these G proteins induced by chronic μ-opiate treatment. In marked contrast to μ-agonists, chronic treatment with high doses of pentazocine and spiradoline or acute treatment with [D-Pen², D-Pen⁵] enkephalin did not result in up-regulation of these G protein subunits. After chronic treatment with μ-agonists, significant negative correlations were found when the percentage changes in immunoreactivity of PKC-αβ were related to the percentage changes in immunoreactivity of Gα_i1/2 (r =-0.53, n = 29) and Gβ (r =-0.41, n = 24) in the same brains. PKC-αβ abundance did not correlate significantly with the density of Gα_o (r =-0.21, n = 28). Together the results indicate that the brain PKC-αβ system may play a major regulatory role in opiate tolerance and dependence. Moreover, the possible in vivo cross-communication between this regulatory enzyme and specific inhibitory G proteins may also be of relevance in the cellular and molecular processes of opiate addiction. Received: 15 July 1996 / Accepted: 22 November 1996     

Inhibitory effects of devil’s claw (secondary root of <Emphasis Type="Italic">Harpagophytum procumbens</Emphasis>) extract and harpagoside on cytokine production in mouse macrophages

Successive oral administration (50 mg/kg) of a 50% ethanolic extract (HP-ext) of devil’s claw, the secondary root of Harpagophytum procumbens, showed a significant anti-inflammatory effect in the rat adjuvant-induced chronic arthritis model. HP-ext dose-dependently suppressed the lipopolysaccharide (LPS)-induced production of inflammatory cytokines [interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α)] in mouse macrophage cells (RAW 264.7). Harpagoside, a major iridoid glycoside present in devil’s claw, was found to be one of the active agents in HP-ext and inhibited the production of IL-1β, IL-6, and TNF-α by RAW 264.7.