Showing papers in "Natural Product Communications in 2010"
TL;DR: Eugenol possesses significant antioxidant, anti-inflammatory and cardiovascular properties, in addition to analgesic and local anesthetic activity, and the design of new drugs based on the pharmacological effects of eugenol could be beneficial.
Abstract: Eugenol, the major constituent of clove oil, has been widely used for its anesthetic and analgesic action in dentistry. Eugenol exhibits pharmacological effects on almost all systems and our aim is...
177 citations
TL;DR: The essential oils from Foeniculum vulgare commercial aerial parts and fruits were isolated by hydrodistillation, with different distillation times, and analyzed by GC and GC-MS, showing a very low antimicrobial activity.
Abstract: The essential oils from Foeniculum vulgare commercial aerial parts and fruits were isolated by hydrodistillation, with different distillation times (30 min, 1 h, 2 h and 3 h), and analyzed by GC and GC-MS. The antioxidant ability was estimated using four distinct methods. Antibacterial activity was determined by the agar diffusion method. Remarkable differences, and worrying from the quality and safety point of view, were detected in the essential oils. trans-Anethole (31-36%), alpha-pinene (14-20%) and limonene (11-13%) were the main components of the essentials oil isolated from F. vulgare dried aerial parts, whereas methyl chavicol (= estragole) (79-88%) was dominant in the fruit oils. With the DPPH method the plant oils showed better antioxidant activity than the fruits oils. With the TBARS method and at higher concentrations, fennel essential oils showed a pro-oxidant activity. None of the oils showed a hydroxyl radical scavenging capacity > 50%, but they showed an ability to inhibit 5-lipoxygenase. The essential oils showed a very low antimicrobial activity. In general, the essential oils isolated during 2 h were as effective, from the biological activity point of view, as those isolated during 3 h.
101 citations
TL;DR: Tulsi (Ocimum sanctum Linn.) essential oil (TEO) was found to be the most effective, followed by Peppermint essential oil, and Aloe vera aqueous leaf extract, while inhibition of H+ extrusion appeared to be a synergistic function of the lead molecules.
Abstract: Aqueous extracts and oils of five Indian medicinal plants, traditionally used for their antimicrobial activities, were evaluated against two of the most prevalent Candida species causing candidiasis, C. albicans and C. tropicalis. Of these plant materials, three showed varying degrees of antifungal activity against both species. Tulsi (Ocimum sanctum Linn.) essential oil (TEO) was found to be the most effective, followed by Peppermint essential oil, and Aloe vera aqueous leaf extract. The product with the lowest MIC was further studied along with its lead molecules to explore the possible mechanism of action of the most active constituents. Eugenol, methyl eugenol, linalool, and 1, 8-cineole, along with TEO were then evaluated at the same. The pattern and extent of inhibition was studied using growth and WST1 cytotoxicity assays. Proton pumps are important for growth and metabolism of Candida species and so H+ extrusion studies were performed to explore the possible mechanism of the test compounds. Linalool was the most active constituent of TEO, whereas inhibition of H+ extrusion appeared to be a synergistic function of the lead molecules.
98 citations
TL;DR: The results showed that curcumin and its new derivatives have remarkable antiviral effects on HSV-1 in cell culture.
Abstract: Antiviral drug resistance is one of the most common problems in medicine, and, therefore, finding new antiviral agents, especially from natural resources, seems to be necessary. This study was designed to assay the antiviral activity of curcumin and its new derivatives like gallium-curcumin and Cu-curcumin on replication of HSV-1 in cell culture. The research was performed as an in vitro study in which the antiviral activity of different concentrations of three substances including curcumin, Gallium-curcumin and Cu-curcumin were tested on HSV-1. The cytotoxicity of the tested compounds was also evaluated on the Vero cell line. The CC50 values for curcumin, gallium-curcumin and Cu-curcumin were 484.2 µg/mL, 255.8 µg/mL and 326.6 µg/mL, respectively, and the respective IC50 values 33.0 µg/mL, 13.9 µg/mL and 23.1 µg/mL. The calculated SI values were 14.6, 18.4 and 14.1, respectively. The results showed that curcumin and its new derivatives have remarkable antiviral effects on HSV-1 in cell culture.
95 citations
TL;DR: A concise review of the scientific literature pertaining to constituents of Hypericum essential oils and volatile fractions is presented.
Abstract: The flowering plant genus Hypericum (Hypericaceae) contains the well-known medicinally valuable species Hypericum perforatum (common St. John's wort). Species of Hypericum contain many bioactive constituents, including proanthocyanins, flavonoids, biflavonoids, xanthones, phenylpropanes and naphthodianthrones that are characterized by their relative hydrophilicity, as well as acylphloroglucinols and essential oil components that are more hydrophobic in nature. A concise review of the scientific literature pertaining to constituents of Hypericum essential oils and volatile fractions is presented.
83 citations
TL;DR: The aim of the present review is to discuss the biosynthesis and regulation of essential oils in the genus Cymbopogon with given emphasis to two elite members, lemongrass and palmarosa, and to propose C. flexuosus as a model system for the study of essential oil metabolism beyond the much studied plant family Lamiaceae.
Abstract: Essential oils distilled from Cymbopogon species are of immense commercial value as flavors and fragrances in the perfumery, cosmetics, soaps, and detergents and in pharmaceutical industries. Two major constituents of the essential oil, geraniol and citral, due to their specific rose and lemon like aromas are widely used as flavors, fragrances and cosmetics. Citral is also used for the synthesis of vitamin A and ionones (for example, beta-ionone, methyl ionone). Moreover, Cymbopogon essential oils and constituents possess many useful biological activities including cytotoxic, anti-inflammatory and antioxidant. Despite the immense commercial and biological significance of the Cymbopogon essential oils, little is known about their biosynthesis and regulatory mechanisms. So far it is known that essential oils are biosynthesized via the classical acetate-MVA route and existence of a newly discovered MEP pathway in Cymbopogon remains as a topic for investigation. The aim of the present review is to discuss the biosynthesis and regulation of essential oils in the genus Cymbopogon with given emphasis to two elite members, lemongrass (C. flexuosus Nees ex Steud) and palmarosa (C. martinii Roxb.). This article highlights the work done so far towards understanding of essential oil biosynthesis and regulation in the genus Cymbopogon. Also, based on our experiences with Cymbopogon species, we would like to propose C. flexuosus as a model system for the study of essential oil metabolism beyond the much studied plant family Lamiaceae.
77 citations
TL;DR: Results indicate, for the first time, that black currant skin containing an anthocyanin-rich fraction inhibits the proliferation of liver cancer cells, possibly due to additive as well as synergistic effects.
Abstract: Dietary antioxidants, such as anthocyanins, are helpful in the prevention and control of various diseases by counteracting the imbalance of oxidative and antioxidative factors in the living systems. Black currant (Ribes nigrum L., Grossulariaceae) is known to contain high amounts of anthocyanins (250 mg/100 g fresh fruit). Black currant fruits have been used in Asian and European traditional medicine for the treatment of a variety of diseases. Black currant extract has recently been found to be the second most effective amongst nine different berry extracts studied for their free radical scavenging activity. Constituents present in black currant juice have been found to exert a number of health-promoting effects, including immunomodulatory, antimicrobial and antiinflammatory actions, inhibition of low-density lipoprotein, and reduction of cardiovascular diseases. Although antioxidant and antiinflammatory effects of black currant juice could be of value in preventing and treating oxidative stress- and inflammation-driven cancers, no experimental evidence is available to now. The objective of the present study was to evaluate the potential antiproliferative effects of black currant fruit skin extract against HepG2 human liver cancer cells. The aqueous extract yielded an anthocyanin-rich fraction with cyanidin-3-O-rutinoside as one of the major anthocyanins. This fraction exhibited a potent cytotoxic effect on HepG2 cells and this effect was more pronounced than that of delphinidin and cyanidin, two major aglycones of anthocyanins present in black currant. Our results indicate, for the first time, that black currant skin containing an anthocyanin-rich fraction inhibits the proliferation of liver cancer cells, possibly due to additive as well as synergistic effects. This product could be useful in the prevention and treatment of human hepatocellular carcinoma.
68 citations
TL;DR: It is demonstrated that the two enantiomers of linalool have similar qualitative anticonvulsant activity, but show different potencies.
Abstract: The anticonvulsant activity of the racemate and enantiomers of linalool have been evaluated. Pretreatment of the mice with (S)-(+)-, (R)-(-)- and rac-linalool increased the latency of convulsions significantly in the PTZ model. Only rac-linalool had an effect at the dose of 200 mg/kg. The enantiomers and their racemic mixture were effective in inhibiting the convulsant effect of PTZ at the dose of 300 mg/kg. The linalools presented pharmacological activity close to that of diazepam. In the PIC seizure model, (R)-(-)-linalool and rac-linalool presented activity at the dose of 200 mg/kg, but the rac-linalool was more potent than (R)-(-)-linalool; (S)-(+)-linalool had no effect at this dose. On the other hand, at the dose of 300 mg/kg this enantiomer was effective, but less potent than (R)-(-)-linalool and rac-linalool. In the MES model, linalools decreased the convulsion time of the mice in the doses of 200 and 300 mg/kg. rac-Linalool presented maximum effect at 300 mg/kg. Surprisingly, it increased significantly the convulsion time at a dose of 100 mg/kg. Using the parameter of tonic hind convulsions, only (R)-(-)-linalool produced protection from tonic extension at the dose of 200 mg/kg. When the (+)- and (-)-enantiomers, and rac-linalool were administered at the dose of 300 mg/kg they were also effective in preventing tonic convulsions induced by transcorneal electroshock in the animals. The (+)- and (-)-forms were equipotent and the rac-linalool was more effective than phenytoin. We have demonstrated that the two enantiomers have similar qualitative anticonvulsant activity, but show different potencies.
67 citations
TL;DR: This paper compiles all 307 naturally occurring diarylheptanoids from 46 plants as reported in 137 references with their distributions, physiological activities and 13C-NMR spectral data.
Abstract: Diarylheptanoids, natural products with a 1,7-diphenylheptane structural skeleton, are mainly distributed in the roots, rhizomes and bark of Alpinia, Zingiber, Curcuma and Alnus species They have become of interest in natural product research over the past twenty years because of their remarkable anti-cancer, anti-emetic, estrogenic, anti-microbial and anti-oxidant activity This paper compiles all 307 naturally occurring diarylheptanoids from 46 plants as reported in 137 references with their distributions, physiological activities and 13C-NMR spectral data
66 citations
TL;DR: Overall, the results suggest that black pepper and its constituents like hot pepper, exhibit antiinflammatory, antioxidant and anticancer activities.
Abstract: Black pepper (Piper nigrum) and hot pepper (Capsicum spp.) are widely used in traditional medicines. Although hot Capsicum spp. extracts and its active principles, capsaicinoids, have been linked with anticancer and anti-inflammatory activities, whether black pepper and its active principle exhibit similar activities is not known. In this study, we have evaluated the antioxidant, anti-inflammatory and anticancer activities of extracts and compounds from black pepper by using proinflammatory transcription factor NF-kappaB, COX-1 and -2 enzymes, human tumor cell proliferation and lipid peroxidation (LPO). The capsaicinoids, the alkylamides, isolated from the hot pepper Scotch Bonnet were also used to compare the bioactivities of alkylamides and piperine from black pepper. All compounds derived from black pepper suppressed TNF-induced NF-kappaB activation, but alkyl amides, compound 4 from black pepper and 5 from hot pepper, were most effective. The human cancer cell proliferation inhibitory activities of piperine and alklyl amides in Capsicum and black pepper were dose dependant. The inhibitory concentrations 50% (IC50) of the alklylamides were in the range 13-200 microg/mL. The extracts of black pepper at 200 microg/mL and its compounds at 25 microg/mL inhibited LPO by 45-85%, COX enzymes by 31-80% and cancer cells proliferation by 3.5-86.8%. Overall, these results suggest that black pepper and its constituents like hot pepper, exhibit anti-inflammatory, antioxidant and anticancer activities.
64 citations
TL;DR: All cumin oils and cuminic aldehyde exhibited a considerable inhibitory effect against all the organisms tested, except Pseudomonas spp.
Abstract: Cumin oil samples (Cuminum cyminum L.) from four different geographical origins were analyzed using GC-MS and GC-FID for their qualitative and quantitative composition. The major compounds in all cumin oils were the monoterpenes beta-pinene, p-cymene and gamma-terpinene and the terpenoid aldehydes cuminic aldehyde and the isomeric menthadien carboxaldehydes. All essential oils, and cuminic aldehyde, were tested, using agar diffusion and serial dilution methods, against different Gram-positive and Gram-negative bacteria isolated from different sources of food (pork fillet, minced meat and sausages) and clinical isolates, as well as three different Candida albicans isolates. All cumin oils and cuminic aldehyde exhibited a considerable inhibitory effect against all the organisms tested, except Pseudomonas spp.
TL;DR: Essential oils from Ocimum basilicum L. basilicum, C. sativum var.
Abstract: Essential oils from Ocimum basilicum L. and Coriandrum sativum L. varieties originating from Turkey were investigated for their antimicrobial properties. The antimicrobial effects of the oil variet...
TL;DR: Volatile oils of Aquilaria malaccensis Benth.
Abstract: Volatile oils of Aquilaria malaccensis Benth. (Thymelaeaceae) from Malaysia were obtained by hydrodistillation and subjected to detailed GC-FID and GC/MS analyses to determine possible similarities and differences in their chemical composition in comparison with the commercial oil. A total of thirty-one compounds were identified compared with twenty-nine identified in the commercial oil. The major compounds identified were 4-phenyl-2-butanone (32.1%), jinkoh-eremol (6.5%) and alpha-guaiene (5.8%), while the major compounds in the commercial oil were alpha-guaiene (10.3%), caryophellene oxide (8.6%), and eudesmol (3.2%). The results of the present study showed that more than nine sesquiterpene hydrocarbons were present, which is more than previously reported. Analysis also showed that the number of oxygenated sesquiterpenes in this study were much less than previously reported. Among the compounds detected were alpha-guaiene, beta-agarofuran, alpha-bulnesene, jinkoh-eremol, kusunol, selina-3,11-dien-9-one, oxo-agarospirol and guaia-1 (10), 11-dien-15,2-olide.
TL;DR: The leaf and fruit essential oils of Litsea cubeba, extracted by hydrodistillation, were assessed for anticancer activities and the fruit oil, but not that of the leaf, exhibited cytotoxic activity against human lung, liver and oral cancer cells.
Abstract: The leaf and fruit essential oils of Litsea cubeba, extracted by hydrodistillation, were assessed for anticancer activities. A total of 53 and 50 compounds were identified, respectively from the le...
TL;DR: The obtained results show the potential use of the endophytic fungus for its biological role in providing its host plant with protection, as well as the possible development of beauvericin as an antibacterial.
Abstract: From the fungal endophyte, Fusarium redolens Dzf2, isolated from rhizomes of the Chinese medicinal plant Dioscorea zingiberensis, beauvericin was obtained by TLC in combination with bioautographic antibacterial assay. The compound was identified by spectroscopic and physicochemical means. The median effective inhibitory concentration (IC50) values of beauvericin against six test bacteria (Bacillus subtilis, Staphylococcus haemolyticus, Pseudomonas lachrymans, Agrobacterium tumefaciens, Escherichia coli and Xanthomonas vesicatoria) were between 18.4 and 70.7 microg/mL. The beauvericin content of F. redolens Dzf2 mycelia was 9.60 mg/g dw, and beauvericin yield 62.4 mg/L. The obtained results show the potential use of the endophytic fungus for its biological role in providing its host plant with protection, as well as the possible development of beauvericin as an antibacterial.
TL;DR: The addition of the polymer coating did not enhance antimicrobial activity, but owing to their positive effects on membrane stability, its presence is important as a means of extending the shelf life of these formulations.
Abstract: Essential oils and their constituents are known to possess antimicrobial activity; however, their inherent volatility is a limiting factor. In order to exploit the antimicrobial efficacy of essential oils, encapsulation within polymeric liposomal systems was undertaken. The liposomes were subsequently polymer-coated in order to further enhance the stability of the formulations. Essential oils distilled from Artemisia afra, Eucalyptus globulus and Melaleuca alternifolia were encapsulated into diastearoyl phosphatidylcholine and diastearoyl phosphatidylethanolamine liposomes employing a reverse phase evaporation methodology. A polyelectrolyte coating was then applied via the layer-by-layer self-deposition technique. A batch of the liposomes was polymer-coated with a 0.15%w/v chitosan solution. Using the minimum inhibitory concentration assay, the liposome-encapsulated, unencapsulated and polymer-coated liposome-encapsulated essential oils were compared in order to observe whether the antimicrobial efficacy was improved with encapsulation and polymer coating. Fractional inhibitory concentrations (FICs) were calculated in order to determine the antimicrobial interactions amongst the lipoid components, polymer coating and essential oils (synergistic, additive, indifferent and antagonistic interactions). With the exception of A. afra, microbial growth was inhibited at lower concentrations for the encapsulated formulations in comparison with the nonencapsulated oils. Synergistic to additive interactions were noted for encapsulated E. globulus (sigmaFIC values 0.25-0.45) and M alternifolia (sigmaFIC values 0.26-0.52) formulations. The addition of the polymer coating did not enhance antimicrobial activity, but owing to their positive effects on membrane stability, its presence is important as a means of extending the shelf life of these formulations. Additionally, the presence of the polymeric coating availed the essential oil at a slower rate. This investigation is a stepping stone towards the promotion of the antimicrobial use of essential oils. The added benefits are that essential oils not only provide effective antimicrobial efficacy, but also promote a "greener" consumerism. Within liposomes, they will enhance dermato-cosmetic properties and increase the marketing image of the final product.
TL;DR: The essential oils were screened for their antifungal activities against common phytopathogenic fungi using the paper disk diffusion method and they showed activity at low doses against the fungi tested.
Abstract: Essential oil (EO) from aerial parts of Eucalyptus camaldulensis Dehnh., growing wild in different localities of Sardinia (Italy), was extracted by steam distillation and analyzed by gas chromatography (GC) FID and GC-ion trap mass spectrometry (ITMS). The yields of EO (v/dry wt) ranged between 0.2-0.5%. Samples were harvested between April and December to study the seasonal chemical variability of the EO. The chemical composition varied depending on the different origins and showed strong fluctuation during the vegetative stage. Thirty-seven compounds, accounting for at least 97.7% of the total EOs were identified, the major components being p-cymene (27.8-42.7%), 1,8-cineole (4.1-39.5%), beta-phellandrene (3.9-23.8%), spathulenol (2.1-15.5%) and cryptone (3.2-10.2%). The oils possessed moderate amounts (1.4-4.7%) of two uncommon aldehydes, cuminal and phellandral. The essential oils were screened for their antifungal activities against common phytopathogenic fungi using the paper disk diffusion method and they showed activity at low doses against the fungi tested. The antioxidant activity, assessed by DPPH-test and expressed as Trolox equivalent antioxidant capacity, showed values ranging between 0.5 and 5.8 mmol/L.
TL;DR: This paper could provide a reference for strengthening the triterpenoid saponin-synthesizing capability of specific medicinal plants at enzyme and/or gene expression levels in order to improve the plants’ commercial values.
Abstract: Triterpenoid saponins are one of the key active components of many medicinal plants. The biosynthetic pathway of triterpenoid saponins in higher plants and a lot of experimental results both indicated that the key enzymes involved in triterpenoid saponin synthesis are squalene synthase (SS), squalene epoxidase (SE), lupeol synthase (LS), dammarenediol synthase (DS), beta-amyrin synthase (beta-AS), cytochrome P450-dependent monooxygenase (PDMO), and glycosyltransferase (GT). The activities and coding genes of the key enzymes could be induced by a range of factors in various plant species. However, the effects of the factors on the content and composition of the triterpenoid saponins in specific plants are not certainly coincident, and different factors appear to induce the gene expressions of the key enzymes by different signal pathways and at different levels. This paper could provide a reference for strengthening the triterpenoid saponin-synthesizing capability of specific medicinal plants at enzyme and/or gene expression levels in order to improve the plants' commercial values.
TL;DR: This is the first report of the quantification of C and DHC in Bhut Jolokia, comparison of capsaicinoids content in BhUT Jolokia with Jalapeno and Scotch Bonnet hot peppers and the COX and LPO inhibitory activities of C.
Abstract: Hot peppers are known for medicinally important capsaicinoids. Bhut Jolokia, Capsicum chinense/Capsicum frutescens, is the hottest pepper in the world. However, its bioactivity and quantity of heat principles are not reported. We have now quantified capsaicin (C) and dihydrocapsaicin (DHC) in Bhut Jolokia and compared it with commonly consumed hot peppers, Jalapeno (Capsicum annuum) and Scotch Bonnet (Capsicum chinense). The concentration of C and DHC in Bhut Jolokia was 5.36%, which is about 338 and 18 times greater than in Scotch Bonnet and Jalapeno, respectively. We have also isolated capsaicin (C) and dihydrocapsaicin (DHC) in pure form and determined lipid peroxidation (LPO) and cyclooxygenase (COX-1 and -2) enzymes inhibitory concentrations. This is the first report of the quantification of C and DHC in Bhut Jolokia, comparison of capsaicinoids content in Bhut Jolokia with Jalapeno and Scotch Bonnet hot peppers and the COX and LPO inhibitory activities of C and DHC.
TL;DR: Compared with placebo, jasmine oil caused significant increases of breathing rate, blood oxygen saturation, and systolic and diastolic blood pressure, which indicated an increase of autonomic arousal.
Abstract: The aim of this study was to investigate the effect of aromatherapy massage with jasmine oil (Jasminum sambac L, Oleaceae) on humans Human autonomic parameters, ie blood pressure, pulse rate, blood oxygen saturation, breathing rate, and skin temperature, were recorded as indicators of the arousal level of the autonomic nervous system In addition, subjects had to rate their emotional condition in terms of relaxation, vigor, calmness, attentiveness, mood, and alertness in order to assess subjective behavioral arousal Forty healthy volunteers participated in the experiments Jasmine oil was applied topically to the skin of the abdomen of each subject Compared with placebo, jasmine oil caused significant increases of breathing rate, blood oxygen saturation, and systolic and diastolic blood pressure, which indicated an increase of autonomic arousal At the emotional level, subjects in the jasmine oil group rated themselves as more alert, more vigorous and less relaxed than subjects in the control group This finding suggests an increase of subjective behavioral arousal In conclusion, our results demonstrated the stimulating/activating effect of jasmine oil and provide evidence for its use in aromatherapy for the relief of depression and uplifting mood in humans
TL;DR: All the investigated compounds were active against Gram-positive bacteria, especially β-caryophyllene against Enterococcus faecalis, but only few substances showed activity towards Gram-negative bacteria, except for cinnamic acid, which was active against all (MIC 60 ppm).
Abstract: Commercially available aroma samples were evaluated for their olfactory quality by professional perfumers and tested for their antimicrobial activity. Agar diffusion and agar-dilution were used as ...
TL;DR: Circular dichroism (CD) spectra showed that the stereochemistry of compounds 1, 3, and 6-8 belongs to the normal series of abietane diterpenes, which confirmed the absolute stereochemical identity of the isolated compounds.
Abstract: Chromatographic separation of the roots of a Kenyan medicinal plant, Clerodendrum eriophyllum, led to the isolation of ten abietane diterpenoids (1-10), one of which (1) was isolated for the first time from a natural source. Using spectroscopic data, the structure of 1 was determined to be 12-hydroxy-8,12-abietadiene-3,11,14-trione. Circular dichroism (CD) spectra showed that the stereochemistry of compounds 1, 3, and 6-8 belongs to the normal series of abietane diterpenes, which confirmed the absolute stereochemistry of the isolated compounds. Compounds 1-10 were evaluated for their in vitro antiplasmodial, antileishmanial, antifungal and antibacterial activities. Compounds 3 and 7 exhibited potent antifungal activity (IC50/MIC 0.58/1.25 and 0.96/2.5 microg/mL, respectively) against C. neoformans, whereas 3, 6 and 7 showed strong antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with IC50/MIC values between 1.33-1.75/2.5-5 and 0.96-1.56/2.5 microg/mL, respectively. In addition, compounds 3 and 9 exhibited potent antileishmanial activity (IC50 0.08 and 0.20 microg/mL, respectively) against L. donovani, while 3 and 7 displayed weak antimalarial activity against Plasmodium falciparum, but 9 was inactive.
TL;DR: With the exception of trigonelline in the Laminaria species, the betaine yields from the various samples of L. digitata, L. hyperborea and F. serratus showed little variation, regardless of either the place or date of collection.
Abstract: Ascophyllum nodosum, and to a lesser extent, Laminaria digitata, L. hyperborea and Fucus serratus, are marine algal species utilized in the commercial production of seaweed extracts used in agricul...
TL;DR: From the roots of Ligularia oligonema and an unidentified sample of LIGularia collected in Yunnan Province of China, two new sesquiterpenoids, 3 β-acetoxy-6β-(2-methylbutyryloxy)furanoeremophilan-10β-ol and 3β- acetoxy- 6β-isobutyryLoxy-furanoermophilian-10 β-ol, were isolated.
Abstract: From the roots of Ligularia oligonema and an unidentified sample of Ligularia collected in Yunnan Province of China, two new sesquiterpenoids, 3 beta-acetoxy-6 beta-(2-methylbutyryloxy)furanoereinophilan-10 beta-ol and 3 beta-acetoxy-6 beta-isobutyryloxyfuranoeremophilan-10 beta-ol, were isolated. DNA sequencing showed that the unidentified sample was likely to be L. oligonema. In addition, the DNA data suggested that the chemical evolution among L. oligonema and related Ligularia species is rather complex.
TL;DR: A phenylpropanoid-substituted flavanol showed the most potent cytotoxicity against A549 cells and HT-1080 cells, stronger than those of the clinically used anticancer drug, 5-fluorouracil (IC50, 7.5 μM and 5.4 μM, respectively).
Abstract: The cytotoxicity of 39 compounds, including eighteen flavonoids (flavanones, 1–10; flavones, 11–17; flavanol, 18), sixteen phenolic acid derivatives (aromatic acids, 19–24; aldehyde, 25; esters, 26...
TL;DR: All the behavioral assessments indicated that inhalation of AZEO had a positive anxiolytic effect, and it is necessary to consider tissue distribution for investigating the effects of essential oil inhalation.
Abstract: The use of essential oils is common throughout the world, and clarification of their detailed effects and pharmaceutical potencies is necessary. Additionally, detailed information regarding the pharmacokinetics of essential oils is needed. In this report, GC-MS analysis was used to observe the tissue distribution of the multiple components of Alpinia zerumbet (Pers.) B.L. Burtt. et Sm. Anxiety-related behavior was evaluated by the light and dark box test (LD), open field test (OF), and elevated plus maze test (EPM). GC-MS quantification of the major components of A. zerumbet essential oil (AZEO) (alpha-pinene, p-cymene, 1,8-cineole, and limonene) was almost identical using either the injection or headspace injection method. All the behavioral assessments indicated that inhalation of AZEO had a positive anxiolytic effect. This was especially evident in the EPM (time spent in the open arms), where anxiolytic effects were clearly observed (P < 0.05). Alpha-Pinene accumulated in the brain at almost the same rate as in the liver. However, the oil components chiefly accumulated in the kidney. Therefore, the essential oil component in the largest proportion will not necessarily be distributed to organs throughout the body in the same quantities and/or ratios. It is necessary to consider tissue distribution for investigating the effects of essential oil inhalation.
TL;DR: The essential oil from P. claussenianum fresh leaves, which was rich in (E)-nerolidol, showed effective growth inhibition of L. amazonensis due to the high percentage of this metabolite in the mixture.
Abstract: Analyses of essential oils obtained from fresh and dried leaves and inflorescences of Piper clausenianum were performed using GC-FID, GC-MS and NMR techniques. Forty compounds were detected for these four oils with the total of identified constituents ranging from 88.7% for the dried inflorescences to 97.7% for the dried leaves. Sesquiterpenes were the main constituents in the volatile fraction from leaves with a high percentage of (E)-nerolidol (up to 83%). However, monoterpenes were identified in greater amount in the inflorescences, with linalool percentages from 50% up. The essential oils from fresh leaves and inflorescences were submitted to anti-parasitic activity against a strain of Leishmania amazonensis. Both samples showed biological activity, but the essential oil from P. claussenianum fresh leaves, which was rich in (E)-nerolidol, showed effective growth inhibition of L. amazonensis due to the high percentage of this metabolite in the mixture.
TL;DR: The chemical compositions of the essential oils from the peel of ripe and unripe fruits of Hymenaea courbaril L., obtained by hydrodistillation, were analyzed by GC and GC-MS and the first report of this sesquiterpene caryolane-1,9β-diol was reported, to the best of the authors' knowledge.
Abstract: The chemical compositions of the essential oils from the peel of ripe and unripe fruits of Hymenaea courbaril L., obtained by hydrodistillation, were analyzed by GC and GC-MS. The main constituents of the essential oil from the peel of the ripe fruits were the sesquiterpenes alpha-copaene (11.1%), spathulenol (10.1%) and beta-selinene (8.2%), while germacrene-D (31.9%), beta-caryophyllene (27.1%) and bicyclogermacrene (6.5%) were the major compounds in the oil from unripe fruits. The essential oils were tested against Aedes aegypti larvae and showed LC50 values of 14.8 +/- 0.4 microg/mL and 28.4 +/- 0.3 microg/mL for the ripe and unripe fruit peel oils, respectively. From the peel of the ripe fruits, the diterpenes zanzibaric acid and isoozic acid were isolated, along with the sesquiterpene caryolane-1,9beta-diol. To the best of our knowledge, this is the first report of this sesquiterpene in the genus. The structures of all compounds isolated were identified on the basis of their spectral data (IR, MS, 1D- and 2D-NMR) and by comparison with literature spectral data.
TL;DR: Essential oil yield was fairly strongly related to the concentrations of Ca2+ and K+ and percentage of organic matter, altitude, temperature, and soil texture, and some environmental factors revealed a significant relationship between oil components and environmental factors.
Abstract: Essential oils of the air-dried aerial parts of five populations of Thymus migricus Klokov & Desj.-Shost. collected from northwest Iran were obtained by hydrodistillation with yield of 1.1 – 3.3% (...
TL;DR: All the caffeoylquinic acid derivatives, in a dose-dependent fashion, were able to inhibit monocyte chemoattractant protein-3 synthesis/release, with 4,5-DCQ being the most potent at the highest tested concentration.
Abstract: In this study we aimed at evaluating the effect of the major polar constituents of the medicinal plant Lychnophora ericoides on the production of inflammatory mediators produced by LPS-stimulated U-937 cells. The 6,8-di-C-beta-glucosylapigenin (vicenin-2) presented no effect on tumor necrosis factor (TNF)-alpha production, but inhibited, in a dose-dependent manner, the production of prostaglandin (PG) E2 without altering the expression of cyclooxygenase (COX)-2 protein. 3,5-Dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid, at lower concentrations, had small but significant effects on reducing PGE2 levels; at higher doses these compounds stimulated PGE2 and also TNF-alpha production by the cells. All the caffeoylquinic acid derivatives, in a dose-dependent fashion, were able to inhibit monocyte chemoattractant protein-3 synthesis/release, with 4,5-DCQ being the most potent at the highest tested concentration. These results add important information on the effects of plant natural polyphenols, namely vicenin-2 and caffeoylquinic acid derivatives, on the production of inflammatory mediators by cultured cells.