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Essential oil composition of the leaves and stems of Meum athamanticum Jacq., from Spain1
Abstract
The essential oil of the leaves and stems of Meum athamanticum Jacq., has been extracted by steam distillation and analysed by gas chromatography (GC) and gas chromatography coupled to mass spectrometry (GC-MS). The monoterpene fraction was predominant while the sesquiterpene one was practically absent. The principal constituents have been identified as (E)-beta-ocimene (29.6%), gamma-terpinene (17.9%), terpinolene (17.0%) and p-cymene (9.7%). Our results show that the chemical composition of the essential oil obtained of the leaves and stems of M. athamanticum from Spain is different to that obtained from plants of Germany, Italy and France.
... In addition, it has been shown to have antiviral activity (including HIV). Active ingredients include mainly saponins, terpenes, carbohydrates, phenolic compounds, and flavonoids [30,31]. ...
... Meum athamanticum L. is also well known to have high antioxidant activity. Active ingredients include mainly essential oil, saponins, phenolic compounds, and flavonoids [30,[54][55][56]. Some of the components isolated from the extracts of M. athamanticum were cinnamic acid esters (methyl ferulate, methyl caffeate, quinic acid, and feruloyl quinic acid), phthalide derivatives (ligustilide, butylidenephthalide, and butylphthalide), and sterol derivatives (cetyl alcohol and sitosterol) [57][58][59]. ...
Plant materials play a very significant role as components of products being used both for medicinal and cosmetic purposes. Due to the high content of active substances, they can play an important role as extracts with antioxidant, regenerative, and antiaging properties. The skin aging process depends on various pathological and physiological processes, among which the degradation of extracellular matrix biomolecules such as collagen and elastin, which significantly affect the maintenance of good skin condition, is very important. The secondary metabolites and plant extracts may have collagenase and elastase inhibitory activity. This activity is mainly due to the high content of a wide range of various biologically active compounds, such as polyphenols, which include, among others, flavonoids, phenolic acids, tocopherols, and tannins. The work involved a comprehensive assessment of the plant from Apiaceae family such as Meum athamanticum L., Centella asiatica L., and Aegopodium podagraria L. extract as a multifunctional raw material. During study antioxidant properties, phenolic compounds and flavonoids content, effect on collagenase and elastase enzyme activity (antiaging effect), cytotoxic properties on skin cells (keratinocytes and fibroblasts), and cell migration capacity were analyzed. It has been shown that the highest antioxidant capacity can be observed for the extract of herb of Aegopodium podagraria L. When the concentration reached 5% all tested extracts had a positive effect on the cell proliferation of both keratinocytes and fibroblasts. It turned out that the most promising inhibitor of collagenase and elastase enzymes was the extract from Aegopodium podagraria, which inhibits the activity of both enzymes by over 70% in the concentration of 5% positively affecting the condition of skin cells.
... Although the organismic source is unknown, it has been speculated that these derivatives are formed via oxidation of the C-26 methyl group of the hopane skeleton followed by rearrangement and migration of the C-8ÀC-14 bond. In biodegraded oils from seeps in Pakistan, 8,14-seco-hopanes (191À196) were characterized as a homologous series of a diastereomeric ensemble of six isomers of configurations, 8βH,14αH,17α,21βH, 8βH,14αH,17β,21αH, 8αH,14βH,17α,21βH, 8αH,14αH,17α,21βH, 8αH,14αH,17β,21βH, and 8αH,14βH,17β,21βH [105] (Fig. 35). As these compounds seem to be highly bioresistant, and also occur in non-biodegraded Paleogene brown coal from the Zhoujing mine, Baise Basin, in 35 8,14-seco-Hopane diastereomers 8βH,14αH,17α,21βH-, 8βH,14αH,17β,21αH-, 8αH,14βH,17α,21βH-, 8αH,14αH,17α,21βH-, 8αH,14αH,17β,21βH-, 8αH,14βH,17β,21βH-191 to 8βH,14αH,17α,21βH-, 8βH,14αH,17β,21αH-, 8αH,14βH,17α,21βH-, 8αH,14αH,17α,21βH-, 8αH,14αH,17β,21βH-, 8αH,14βH,17β,21βH-196, and monoaromatic seco-hopane series 197-203 and 204-210 southern mainland China [106], these molecular fossils may either have a direct biological precursor or may have formed during early diagenesis. ...
... As noted in Beck and Chou's review on phthalides [2], the structure of celephthalide C (61) was found to be similar to that of neocnidilide (6). The accumulation of some secondary metabolites of Ligusticum chuanxiong (including phthalides) has been correlated with the developmental stages of the plant [103], with (Z )-butylidenephthalide (3) and (Z )-ligustilide (8) found as volatiles of Angelica tenuissima Nakai [104] and Meum athamanticum [105]. ...
Phthalides are a relatively small group of natural compounds confined to several plant families and some genera of fungi and liverworts. They are divided into two structural groups, the monomeric and dimeric phthalides, and known mainly as bioactive constituents of different plant species used traditionally for medicinal purposes in Asia, Europe, and North America.
The first reports on the chemistry of phthalides appeared at the end of the nineteenth century, in which they were identified as the odor constituents of the essential oil of celery (Apium graveolens) by Ciamician and Silber (1897). In the first half of the last century, phthalides were isolated from Cnidium officinale and Ligusticum acutilobum, species widely used in Asian traditional medicine, and from Levisticum officinale, a species used as food and condiment. Throughout the second part of the twentieth century, phthalides have been characterized from several plant families, namely Asteraceae, Leguminosae, Orchidaceae and Rutaceae, among others, but mainly from the Umbelliferae (syn Apiaceae) family, and the major contributors have been the following species used in traditional medicine: Ligusticum chuanxiong (Chinese name: Chuanxiong), Angelica sinensis (Chinese name: Danggui), Cnidium officinale (Japanese name: Senkyu), Angelica acutiloba (Japanese name: Toki), and Ligusticum porteri (Hispanic name: Oshá). Phthalides are also constituents of several genera of fungi, such as Penicillium, Alternaria and Pestalotiopsis, and some liverworts.
Different chromatographic, spectrometric, and two-dimensional nuclear magnetic resonance (NMR) techniques have been used for the isolation and structural characterization of phthalides in extracts, and for assessing the quality of plant material containing this type of compound. Isotopic labeling has established the biosynthesis of phthalides via linkage of acetate units forming polyketide intermediates.
Chemical transformations of monomeric phthalides have included oxidation, reduction, addition, elimination, and cycloaddition reactions, and treatments with Lewis acids of (Z)-ligustilide have afforded linear dimers. Some intramolecular condensations and differentiated cyclizations of the dimeric phthalides have been carried out, providing evidences for the particular chemical reactivity of these compounds.
Several structural modifications of phthalides have been carried out subjecting them to microbial transformations by different species of bacteria, fungi and algae, and these included resolutions of racemic mixtures and oxidations, among others.
The [π4s + π2s] and [π2s + π2s] cycloadditions of (Z)-ligustilide for the synthesis of dimeric phthalides have been reported, and different approaches involving cyclizations, Alder–Rickert reactions, Sharpless asymmetric hydroxylations, or Grignard additions have been used for the synthesis of monomeric phthalides. The use of phthalides as building blocks for divergent oriented synthesis has been proven.
Many of the naturally occurring phthalides display different biological activities including antibacterial, antifungal, insecticidal, cytotoxic, and anti-inflammatory effects, among many others, with a considerable recent research on the topic. In the case of compounds isolated from the Apiaceae, the bioactivities correlate with the traditional medicinal uses of the natural sources. Some monomeric phthalides have shown their ability to attenuate certain neurological diseases, including stroke, Alzheimer’s and Parkinson’s diseases.
The present contribution covers the distribution of phthalides in nature and the findings in the structural diversity, chemical reactivity, biotransformations, syntheses, and bioactivity of natural and semisynthetic phthalides.
... Thus, fi ngerprint can be performed in complex matrix analysis. Paúl et al., (2004) analyzed volatiles substances in Meum athamanticum, generating a profi le of 46 components that were used to monitor seasonal and geographic chemical variations. Lu et al. (2006) used this methodology to create a fi ngerprint of Houttuynia cordata, a plant widely used to treat disease in China and produced by about 40 factories. ...
... Lu et al. (2006) suggested that only 15 components could be investigated as marker for quality control in Houttuynia cordata. Paúl et al. (2004) used 46 components to monitor seasonal modifi cations in Meum athamanticum. ...
The Laboratory of Chemistry of Natural Products has an ex situ collection of extracts from organisms of the biodiversity aiming at bioprospecting. Nowadays the collection has about 4000 extracts from 1000 different species. Extracts are used to identify new bioactive compounds that could be useful for developing new drugs against neglected diseases like leishmaniosis, Chagas disease, malaria and tuberculosis. After biologic assays, the bioactive extracts need to be prepared in larger quantity to allow isolation and characterization of the bioactive component. At this time, it is important to not only confirm the bioactivity of new extract but also check if its composition is similar to the old one. It was evaluated the ability of Solid Phase Microextraction and Gas Chromatography-Mass Spectrometry analysis (SPME-GC-MS). It was used the AMDIS (Automatic Mass Spectral Deconvolution and Identification System) software as tools to collect and to compare the chromatographic profiles of each extract (fingerprint). Forty six samples were analyzed, it was possible to infer from the composition of each sample and common compounds. Nine groups of samples, collected at different time, were analyzed and seasonal modifications between then could be elucidated. The results showed that this methodology can be used to monitor the composition of extracts, allowing to monitor chemical changes that may occur during storage periods and to investigate the occurrence of a determined component in different extracts.
... Trace amounts (t) were present at <0.1%. RRI, relative retention index calculated on the basis of retention of n-alkanes; Pub RRI, relative retention index published in a [41], b [42], c [43], d [44], e [45], f [46], g [47], h [48], i [31], j [49], k [50], and l [51]. # Tentatively identified using Wiley and MassFinder mass spectra libraries and published RRI. ...
Grindelia squarrosa (Pursh) Dunal is used in traditional medicine for treating various diseases; however, little is known about the immunomodulatory activity of essential oils from this plant. Thus, we isolated essential oils from the flowers (GEOFl) and leaves (GEOLv) of G. squarrosa and evaluated the chemical composition and innate immunomodulatory activity of these essential oils. Compositional analysis of these essential oils revealed that the main components were α-pinene (24.7 and 23.2% in GEOFl and GEOLv, respectively), limonene (10.0 and 14.7%), borneol (23.4 and 16.6%), p-cymen-8-ol (6.1 and 5.8%), β-pinene (4.0 and 3.8%), bornyl acetate (3.0 and 5.1%), trans-pinocarveol (4.2 and 3.7%), spathulenol (3.0 and 2.0%), myrtenol (2.5 and 1.7%), and terpinolene (1.7 and 2.0%). Enantiomer analysis showed that α-pinene, β-pinene, and borneol were present primarily as (−)-enantiomers (100% enantiomeric excess (ee) for (−)-α-pinene and (−)-borneol in both GEOFl and GEOLv; 82 and 78% ee for (−)-β-pinene in GEOFl and GEOLv), while limonene was present primarily as the (+)-enantiomer (94 and 96 ee in GEOFl and GEOLv). Grindelia essential oils activated human neutrophils, resulting in increased [Ca2+]i (EC50 = 22.3 µg/mL for GEOFl and 19.4 µg/mL for GEOLv). In addition, one of the major enantiomeric components, (−)-borneol, activated human neutrophil [Ca2+]i (EC50 = 28.7 ± 2.6), whereas (+)-borneol was inactive. Since these treatments activated neutrophils, we also evaluated if they were able to down-regulate neutrophil responses to subsequent agonist activation and found that treatment with Grindelia essential oils inhibited activation of these cells by the N-formyl peptide receptor 1 (FPR1) agonist fMLF and the FPR2 agonist WKYMVM. Likewise, (−)-borneol inhibited FPR-agonist-induced Ca2+ influx in neutrophils. Grindelia leaf and flower essential oils, as well as (−)-borneol, also inhibited fMLF-induced chemotaxis of human neutrophils (IC50 = 4.1 ± 0.8 µg/mL, 5.0 ± 1.6 µg/mL, and 5.8 ± 1.4 µM, respectively). Thus, we identified (−)-borneol as a novel modulator of human neutrophil function.
... The differences found in this work can be caused by the effect of the location and time of collection (Palá-Paúl et al., 2004;Sá et al., 2016), as well as by extraction methods, where MADH would promote the extraction of certain compounds (Jordán et al., 2013;Ajayi et al., 2016). ...
Acantholippia deserticola (Rica rica; RR) and Artemisia copa (Copa copa; CC) are herbs native to the Chilean highlands and have historically been used for medicinal purposes by the Atacameños people. The essential oils were analized by GC/MS, the principal compounds found in RR essential oil (RR_EO) were β-thujone (45%), β-linalool (16%), and eucalyptol (9%) and were butyric acid (38%), γ-terpinene (16%), and cis-2-menthenol (12%) in CC essential oil (CC_EO). The total polyphenol content (TPC) and the antioxidant capacity (AC) were evaluated. The TPC was 25 and 20 mg/mL for CC_EO and RR_EO, respectively, and the respective AC values were 740 and 320 μg eq Trolox/mL by the ferric reducing antioxidant power (FRAP) method. The IC 50 (1,1-diphenyl-2-picrylhydrazyl; DPPH) values were 316.9 and 485.8 μg/mL for CC_EO and RR_EO, respectively. Antimicrobial activity was evaluated against 32 bacteria using the agar disc diffusion method. CC_EO exerted a significant inhibitory effect (> 20 mm) against 9 bacteria, including Listeria monocytogenes and Staphylococcus aureus, and RR_EO significantly inhibited Escherichia coli. The CC_EO MIC values were 0.39 μg/mL for Corynebacterium. The RR_EO MIC value was 6.25 μg/mL for S. viridans. Neither EO showed toxicity against the nematode C. elegans at 2.5 mg/mL. The essential oils of RR and CC, extracted by MAHD have important bioactive potential and low toxicity, which would allow their use of active ingredients that could potentially be used in areas such as the clinic, food, cosmetics, sanitizers, and detergents, among others.
... They found 15 compounds that could be used as markers to identify and evaluate the consistency in 40 different factories and different batches. Paul et al. [54] analyzed volatile substances in Meum athamanticum to generate a profile of 46 components that was used to monitor seasonal and geographic chemical variation. In this study, we described the fingerprints of RS1S extract that could allow for monitoring the stability and comparing the composition of selected extracts for further isolation and characterization of the active principle/s as well as other in vivo and in vitro studies in the future. ...
... They found 15 compounds that could be used as markers to identify and evaluate the consistency in 40 different factories and different batches. Paul et al. [54] analyzed volatile substances in Meum athamanticum to generate a profile of 46 components that was used to monitor seasonal and geographic chemical variation. In this study, we described the fingerprints of RS1S extract that could allow for monitoring the stability and comparing the composition of selected extracts for further isolation and characterization of the active principle/s as well as other in vivo and in vitro studies in the future. ...
Background
Rhazya stricta Decne. is a medicinal plant that is widespread in Saudi Arabia and desert areas of the Arabian Peninsula. Its extract contains alkaloids, tannins, and flavonoids that are involved in different biological activities. The study aim was to evaluate the effects of Rhazya stricta plant extracts on the proliferation and differentiation of NTERA-2 (NT2) pluripotent embryonal carcinoma cells.
Methods
Soxhlet extraction was carried out using different solvents to extract stems, leaves and fruit parts of this plant. Cytotoxicity was evaluated by an MTS cell viability assay. The ability of the plant extract to induce cell differentiation was examined phenotypically using an inverted light microscope. The expression of pluripotency markers was investigated by reverse transcriptase polymerase chain reaction (RT-PCR) and immunocytochemistry. Phytochemical screening of chloroform stem extracts was carried out and a chromatographic fingerprint was generated using gas chromatography – mass spectrometry (GC-MS).
Results
Chloroform stem extract induced differentiation of NT2 cells at 5 μg/ml, and the differentiated cells exhibited neurite formation. Following induction of differentiation, there was significant down-regulation of the pluripotency marker genes Oct4 and Sox2. In addition, the surface antigen pluripotency marker, TRA-1-60, was strongly down-regulated. Phytochemical analysis of the extract showed the presence of alkaloids and saponins. The chromatogram revealed the presence of fifteen compounds with different retention times.
Conclusion
Our results demonstrate for the first time that chloroform stem extract of R. stricta can induce neuronal differentiation of stem cells at an early stage and may contain potential therapeutic agent that can be used in neurodegenerative diseases.
... Chromatograms were determined using MS (mass spectrometer) or MS/MS. The data were determined using internal standards [40]. ...
Essential oils (herbal volatile oils) as alternatives to antibiotics are considered the most powerful natural feed additives. The aim of this study was to determine the effects of volatile oils and their mixtures (VOM) dietary supplementation on the performance, serum and tibia characteristics of broilers. A total of 800 male Ross 308 broiler chicks were equally divided into 8 groups of 100 chicks (10 replicates of 10 chicks each). The study included a control (NC) and diets supplemented with oils according to the following 7 treatments: 200 mg alpha-tocopherol acetate/kg (PC); 100 mg oregano oil/kg (OVO); 100 mg rosemary oil/kg (RVO); 100 mg fennel oil (FVO); oregano oil + rosemary oil + fennel oil - equally mixed - (100, 200, and 400 mg/kg, VOM-1, VOM-2 and VOM-3, respectively). The experiment was conducted for 42 d. At the end of the experiment, no significant differences were observed in feed intake and carcass yield. Dietary supplementation with mixed volatile oils (VOM-2 and VOM-3) and OVO improved the final body weight. Dietary treatments significantly influenced the feed conversion ratio (FCR) and bone ash (P<0.001). Furthermore, the hot carcass weights of the OVO and RVO group and the volatile oil mixture group (VOM-2 and VOM-3) were significantly higher than for the NC group. FVO and VOM supplementation at both inclusion levels (VOM-2 and VOM-3) in the broiler diet significantly increased the bone Ca level compared with the other groups (p<0.001). Moreover, the bone phosphorus percentage of the same groups (FVO, VOM-2 and VOM-3) were also significantly enhanced (p<0.001) compared to the control groups (NC and PC). In conclusion, the results of this study showed encouraging improvement in performance and in tibia Ca levels in broilers when their diets were supplemented with VOM-3.
... Chromatograms were determined using MS (mass spectrometer) or MS/MS. Data were calculated using internal standards (Pala-Paul et al., 2004). ...
The aim of this study was to determine the possible effects of various levels of rosemary and oregano volatile oil mixture dietary supplementation on oxidative status parameters in the blood and various organs of quails. A total of 880 one-day-old Pharaoh quails (Coturnix coturnix Pharaoh) including both males and females, were divided into four groups containing 220 quails and treated as follows: a control group with 0 mg volatile oil (VO)/kg of diet; group I, with 100 mg/kg rosemary VO (RVO) plus 100 mg/kg oregano VO (OVO, 50:50%); group II, 60 mg/kg rosemary VO plus 140 mg/kg oregano VO (30:70%); and group III, 140 mg/kg rosemary VO plus 60 mg/kg oregano VO (70:30%). The diets were prepared fresh for each treatment. The experiment was carried out for 42 days. The quails were euthanized and then serum, erythrocyte, heart, liver and spleen were obtained. Serum malondialdehyde (MDA), nitric oxide (NO), antioxidant activity (AOA), glutathione (GSH), vitamin A (VA), vitamin C (VC), erythrocyte superoxide dismutase (SOD), as well as MDA, NO and SOD levels from the heart, liver and spleen were determined by enzyme-linked immunosorbent assay (ELISA). The results of the study show that whereas the lowest serum MDA and serum NO values were observed in group III (p< 0.05), the highest serum MDA and serum NO values were in group I (p<0.05). Moreover, the highest NO and SOD levels in group I were found in the liver and spleen, respectively (p<0.05). In conclusion, supplementation with a rosemary and oregano VO mixture to the diets of quails may alter the antioxidant activity depending on the diets, and the most effective doses of rosemary and oregano VO mixture were 70 and 30%, respectively.
... Our results concerning the effect of part of plant on yield are in good accordance with the literature. In fact, palá paúl et al. reported that the yields of the essential oil from O. basilicum were 0.82 % for flowers and 0.49 % (v/w) for leaves25 . The yields of Eryngium bourgatii Gouan flowers and leaves were 0.33 % and 0.11 % (v/w) respectively 26 . ...
Air-dried aerial parts of wild Ormenis mixta were collected from five different regions of Morocco (Kenitra, Tamesna, Sidi allal lbahraoui, Settat and Benguerir) during 2011. The essential oil obtained separately from the leaves and flowers of O.mixta has been extracted by Clevenger apparatus and analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The flowers gave the most important yield in all the regions. The yield obtained varies greatly with a range of 0.83 to 1.67 % for flowers and 0,56 to 0,86 % for leaves. Significant differences were found in the chemical composition of leaves and flowers. The main components of flowers were camphor (14,4-29 %), trans-β-farnesene (8.3 %) and 2-tridecanone (21.5 %). For the leaves, the major components were trans-nerolidol (44.1 %), β-myrcene (12.4 %) and camphor (11-33 %). Cluster analysis of the essential oil composition from the five populations studied confirmed a major chemical variability.
... Chromatograms were determined using MS (Mass spectrometry) or MS/MS. The data were determined using internal standards (Pala-Paul et al., 2004). ...
Abstract 1. The aim of this study was to determine the effects of juniper oil (JO) dietary supplementation on the laying performance, egg traits and egg malondialdehyde (MDA) concentrations of quail. 2. A total of 400 female Pharaoh quail were equally divided into 4 groups containing 100 quail (5 replicates of 20 quail each). The study included a control treatment with no diet additives, and the treatments were as follows: (Group 1) 100 mg/kg JO; (Group 2) 200 mg/kg JO; (Group 3) 300 mg/kg JO. The experiment was carried out for 60 d. 3. At the end of the experiment, there were no significant differences in body weight, egg weight, egg mass, egg shape index, yolk colour, egg production, feed consumption or feed efficiency. 4. The Haugh unit was increased in groups 2 and 3 compared to the control group. Dietary fortification with JO improved egg shell thickness and breaking strength compared to the control group. Furthermore, the damaged egg ratio was significantly decreased in group 3 compared to the control. The increasing concentration of JO (200 and 300 mg/kg) caused a significant decrease in egg yolk MDA concentration after 15 and 30 d of storage at 20°C. 5. It was concluded that inclusion of JO in layer diets can improve egg quality characteristics in terms of Haugh unit, egg shell thickness and breaking strength. Moreover, supplementation of JO in the diets of quail may enhance the antioxidant status of eggs, and the most effective doses of JO were 200 and 300 mg/kg.
... Chromatograms were determined using MS (mass spectrometer) or MS/MS. The data were calculated using internal standards (Palá-Paúl et al., 2004). ...
Abstract 1. This study aimed to evaluate the effects of juniper oil on growth performance and meat quality in quails to determine its use as a safe and natural method to reduce overdependence on the use of antibiotic. 2. A total of 1000 1-d-old Pharaoh (Coturnix coturnix Pharaoh) quails, including both males and females, were divided into 4 groups containing 250 quails and treated as follows: (1) a control group with 0 mg volatile oil/kg diet; (2) 100 mg/kg juniper oil; (3) 150 mg/kg juniper oil and (4) 200 mg/kg juniper oil. The diets were prepared fresh for each treatment. The experiment was carried out for 42 d. 3. The results of the study showed that supplementation with juniper oil (100 and 150 mg/kg) caused a significant increase in live weight, live weight gain and carcass yields during the growing and finishing periods. Feed intake and feed conversion rate were not significantly influenced by treatments. 4. The quails given rations containing Juniper oil had reduced thiobarbituric acid levels in raw thigh meat samples at different storage times. Juniper oil was found to have significant antioxidant activity and prevented lipid oxidation in stored meat. 5. In conclusion, natural antioxidants such as a juniper oil can be used instead of synthetic antioxidants to retard lipid oxidation in animal diets to improve meat product quality and animal performance.
... They have smooth muscle relaxant activity , vasorelaxing activity (Chan et al. 2006), analgesic, neuroprotective (Peng et al. 2007;Kuang et al. 2006), antisclerotic, antihypertensive (Lu et al. 2006), serotonergic (Deng et al. 2006a), GABAergic (Deng et al. 2006b), antiproliferative (Liang and He 2006), antihyperglycemic (Brindis et al. 2011), sedative and spasmolytic (León et al. 2011). These compounds have been found in some genera of the Apiaceae including Angelica (Lao et al. 2004), Anethum (Fischer and Gijbels 1987), Apium (MacLeod et al. 1988), Bifora (Gijbels et al. 1985), Capnophyllum (Gijbels et al. 1984), Cnidium (Gijbels et al. 1981), Conioselinum (Gijbels et al. 1979), Levisticum (Santos et al. 2005), Ligusticum (Delgado et al. 1988), Lomatium (Bairamian et al. 2004), Opopanax (Gijbels et al. 1983), Petroselinum (Gijbels et al. 1985), Peucedanum (Gijbels et al. 1984) and Meum (Palá-Paúl et al. 2004). ...
The morphogenetic response of Ligusticum porteri, a medicinal and ceremonial plant, was investigated as part of the conservation strategy of this wild species and was compared to that of a cultivated species, Petroselinum crispum. Seeds were germinated in half strength Murashige and Skoog medium. Plantlets were excised into root, cotyledon, petiole, stem and leaf explants and cultured in an induction medium supplemented with the range of 0–18.09 μM 2,4-dichlorophenoxyacetic acid (2,4-D) or 0–21.48 μM α-naphthaleneacetic acid in combination with 0–13.31 μM 6-benzylaminopurine. Calli derived from leaf, seeds, petiole, stem and roots, mature aerial parts and roots extracts of L. porteri and P. crispum were analyzed by thin layer chromatography and gas chromatography coupled to mass spectrometry. 3-Butylidenephthalide (6.3%) was identified along with other 23 compounds from mature aerial parts extract of L. porteri and also in its roots (20.8%). 3-n-Butylphthalide (0.7%) and 3,6,7,-trimethoxy-isobenzofuran-13(H)-one (4.9%) were identified from the roots of P. crispum. 3-Butylidenephthalide was identified from two petiole (0.9%; 0.26%) and one stem (0.8%) callus extracts of L. porteri. This is the first report on phthalides production from in vitro cultures of L. porteri. The results indicated that in vitro cultures of this plant possess the biosynthetic machinery for the biosynthesis of these highly valuable compounds.
... Chromatograms were determined using MS (Mass spectrometry) or MS/MS. The data were determined using internal standards (Pala-Paul et al., 2004). ...
Abstract 1. This study was conducted to determine the effects of volatile oil mixture on quail laying performance, egg traits and egg malondialdehyde (MDA) concentration. 2. A total of 260 Pharaoh quails (Coturnix coturnix Pharaoh) aged 6 weeks were equally divided into 5 groups of 65 (4 replicates of 13 quails each). The mixture of diets was as follows: a control treatment with 0 mg volatile oil/kg of diet; (1) 200 mg/kg rosemary volatile oil; (2) 200 mg/kg oregano volatile oil; (3) 40 mg/kg rosemary volatile oil plus 160 mg/kg oregano volatile oil (ratio 20:80) and (4) 160 mg/kg rosemary volatile oil plus 40 mg/kg oregano volatile oil (ratio 80:20). The diets were prepared fresh for each treatment. The experimental period lasted 10 weeks. 3. At the end of the experiment, there were no significant differences amongst the groups in body weight, egg weight, egg mass, egg shape index, Haugh unit, egg shell thickness or egg shell-breaking strength. 4. Diets containing rosemary volatile oil increased the egg production significantly. Feed intake significantly increased in the groups containing volatile oil mixture (groups 4 and 5). The inclusion of rosemary volatile oil at 200 mg/kg improved feed efficiency. 5. Egg albumen and egg yolk index values showed significant increases in the group given diets containing rosemary volatile oil. Egg yolk colour became darker with the addition of rosemary and oregano volatile oil. The treatment group had lower egg yolk MDA concentration than the control group. 6. It is concluded that, alone or in combination, rosemary and oregano volatile oil can be used in quail diets without adverse effects on the measured parameters. Inclusion of rosemary and oregano volatile oil in quail diets enhanced the antioxidant status of eggs.
... Chromatograms were determined using MS (Mass spectrometry) or MS/MS. The data were determined using internal standards (Pala-Paul et al., 2004). ...
1. This study was conducted to determine the utility of a volatile oil (VO) mixture in quail diets as a natural growth promoter. Different levels of VO mixtures, derived from rosemary and oregano, were added to a basal diet to determine the effects of the mixture on live weight (LW), live weight gain (LWG), feed intake, feed conversion ratio (FCR), carcase yield (CY), lipid oxidation level in thigh meat samples, and blood constituents.
2. A total of 880 one-day-old Pharaoh (Coturnix coturnix Pharaoh) quails, including both males and females, were divided into 4 groups containing 220 quails and treated as follows: (1) a control treatment with 0 mg VO/kg of diet; (2) 100 mg/kg rosemary VO plus 100 mg/kg oregano VO (50:50%); (3) 140 mg/kg oregano VO plus 60 mg/kg rosemary VO (70:30%); and (4) 60 mg/kg oregano VO plus 140 mg/kg rosemary VO (30:70%). The diets were prepared fresh for each treatment. The experiment was carried out for 42 d.
3. The results of the study showed that the highest concentration of rosemary oil (140 mg/kg) caused a significant increase in live weight, live weight gain and carcase yields during the growing and finishing periods. However, feed intake and FCR were not significantly influenced by treatments.
4. The quails fed with rations containing the VO mixture derived from rosemary and oregano had reduced thiobarbituric acid levels (TBA) in raw breast meat samples at different storage times. There is possibly a synergistic effect between oregano and rosemary volatile oils in preventing lipid oxidation in stored meat.
5. In this study, the haemoglobin (PCV) and haematocrit values and the heterophile/lympohocyte (H/L) ratio increased in the blood samples taken from Treatment 2.
6. In conclusion, a volatile oil containing a mixture of rosemary and oregano oils could be a potential natural growth promoter for quails, depending on the plants from which the VOs were extracted, the dosage and the synergetic effects of the mixture.
... Oils from the aerial parts of Meum athamanticum (L.) Jacq. contained mainly monoterpenes, such as E-β-ocimene, γ-terpinene and limonene [8,76,77], whereas the root oil had Z-ligustilide as its main compound [76]. Another root oil from M. athamanticum, cultivated in a botanical garden, contained, besides bicyclo-germacrene, germacrene D, β-bisabolene, α-chamigrene, germacrene B and βelemene, the sesquiterpene hydrocarbons β-bazzanene, α-barbatene and β-barbatene, typical compounds of liverworts (Hepaticae) [78]. ...
In this overview, the essential oil composition of more than 150 species from about 50 genera of the Apiaceae is reviewed. Essential oil components encountered in Apiaceae proved to be very diverse; they include monoterpenes, sesquiterpenes, rarely diterpenes, phenylpropanoids, phthalides, octanol and octyl esters, trimethylbenzaldehydes and aliphatic aldehydes. In assessing the data one has to keep in mind that the essential oil amount and composition is influenced by many factors, including geographic and genetic variation, physiological aspects and environmental conditions. In some species the occurrence of chemotypes could be demonstrated, but in many cases the data available do not allow the evaluation of infraspecific variability.
In this study, the effect of dietary supplementation of oregano and rosemary essential oils (EO) on growth performance and cecal microbiota of broilers were investigated. A total of 450 1-d-old male Ross-308 broilers were divided into 5-experimental groups (10 replicates of 9 chickens): a Control (C), fed a basal diet; four treatments, which received a basal diet supplemented with oregano and rosemary EOs individually (O, 300 mg/kg oregano EO; R, 300 mg/kg rosemary EO) and combined (OR1, 150 mg/kg oregano EO + 150 mg/kg rosemary EO; OR2, 200 mg/kg oregano EO + 200 mg/kg rosemary EO). Body weight (BW), feed intake (FI), body weight gain (BWG), feed conversion ratio (FCR), and cecal microbiota (coliforms, clostridia and lactobacilli) were determined weekly, and at 42 d, respectively. BW in R (p<0.05) and OR2 (p<0.001), and BWG and FCR in OR2 (p<0.05) were significantly higher than C at 42 d, despite no difference in FI in any group during experimental period. Counts of cecal coliforms (p<0.001) and clostridia (p<0.01) decreased, and lactobacilli (p<0.001) increased substantially between C and treatment groups. Results indicated that combined oregano and rosemary EO (200 mg/kg ea) supplementation significantly increased BW and BWG, improved FCR in 1-42 d, lowered coliform and clostridial, and increased lactobacilli counts suggesting a beneficial shift in cecal microbiota.
Plants are rich in phytochemicals and they use them for their basic processes including growth and development. Besides playing pivotal roles in the plants, phytochemicals also have different biological activities such as antiviral, antitumour, anti-inflammatory and antimicrobial activity. Many of the plant-based compounds have shown health-promoting activities. Medicinal plants are still used in various countries for primary health-care purposes due to their bioactivities. Scientists have tried to isolate the active compounds from the plants which have medicinal properties during the nineteenth and twentieth centuries. Secondary metabolites including alkaloid, saponins, lignans and terpenes are produced through numerous biosynthetic pathways, including shikimate, malonyl-CoA, mevalonate and pentose phosphate pathways. Among the angiosperms, it has been reported that Amaranthaceae, Apiaceae, Cucurbitaceae, Lamiaceae, Lauraceae, Poaceae, Rutaceae and Solanaceae are the major plant families rich in phytochemicals. Due to their huge medicinal importance, researchers are now attempting to obtain plant-derived bioactive compounds in higher amounts for their usage in nutraceuticals and medicinal industries. This book chapter includes information about phytochemical extraction, biosynthesis and their biological activities in some important plant families including Amaranthaceae, Apiaceae, Cucurbitaceae, Lamiaceae and Lauraceae.
Five batches of resin from the Pili tree (Canarium ovatum Engl.) were distilled and their essential oils and hydrosols analyzed by gas chromatography. The oils, obtained in yields of 13.4‐19.7% v/m, featured α‐phellandrene in high proportions (50‐65%), alongside limonene, β‐phellandrene and para‐cymene. Chiral GC analysis confirmed that both phellandrenes were in fact >95% (S)‐(+) enantiomers, while the other monoterpenes featured less pronounced enantiomeric excesses. The hydrosols were rich in α‐phellandrene oxidation products including cis‐α‐phellandrene epoxide and a series of para‐menth‐5‐ene‐1,2‐diol isomers. Both essential oils and hydrosols were tested for their antibacterial activity against Escherichia coli and Staphylococcus aureus and exhibited MIC90 of less than 5 and 0.5 mg/mL of total volatiles, respectively. The essential oil features some potential as a source of readily available natural (S)‐(+)‐α‐phellandrene.
The newly developed gas chromatography–tandem mass spectrometry method allows the analysis of non-volatile, polar substances in cigarette ash. Only a few mg of ash, derivatized by two-step silanization with hexamethyldisilazane and N,O-bis(trimethylsilyl)trifluoroacetamide, are necessary for the analysis. Samples are directly analyzed after derivatization, without the need of extraction as a next purification step. Differences in chromatographic profiles reflect the composition uniqueness of each matrix and can be used for product authentication by chromatographic fingerprint method. The method was used to differentiate between cigarette ash samples of three cigarette brands (Marlboro, Davidoff, and West) and can be useful for forensic purposes.
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1. The aim of this study was to investigate the individual and combined effects of rosemary, oregano and fennel volatile oil supplementation on the performance and ilio-caecal bacteriological flora of broiler chickens. 2. A total of 800 male Ross-308 broiler chickens were divided equally into 8 groups; each contained 100 chickens. The study included a control treatment (NC) with no dietary additives that was supplemented with oils according to the following 7 treatments: 200 mg α-tocopherol acetate/kg (PC), 100 mg oregano volatile oil /kg (OVO), 100 mg rosemary volatile oil /kg (RVO), 100 mg fennel volatile oil/kg (FVO), and an equal mixture of oregano+rosemary+fennel volatile oil (100, 200, 400 mg/kg, VOM-1, VOM-2 and VOM-3, respectively). The experiment lasted for 6 weeks. 3. At the end of the experiment, dietary supplementation with α-tocopherol, oregano, rosemary and fennel volatile oil and two different volatile oil mixtures (VOM-2; VOM-3) significantly increased the body weights of broilers at 7, 14 and 21 d of age compared to the NC (-) and VOM-1 groups. At 0-42 d, birds fed on VOM-3 were considerably heavier and also gained more weight than NC (-) and VOM-1 groups. 4. The blend of VOs at 400 mg/kg significantly increased Lactobacillus spp. in faeces. The blends of oregano, rosemary and fennel volatile oils (VOM-3) at 400 mg/kg concentration and also VOM-3 group exhibited stronger antibacterial activity against coliform bacteria compared to the NC(-) group. 5. In conclusion, the blend of oregano, rosemary and fennel VOs at higher concentrations (400 mg/kg concentration) in diets can be used to stimulate the growth and can improve the intestinal microbial balance (including a reduction of coliform bacteria and an increase in Lactobacillus spp. counts) of broiler chickens.
The chemical composition of the essential oil from PINELLIA TUBER (Japanese name: Hange), the dried rhizome of Pinellia ternata, was investigated by capillary gas chromatography (GC) and GC-mass spectrometry (MS) analyses. The oil obtained from Pinellia tuber was revealed the presence of 114 compounds, representing 90.6% of the total oil identified. This colorless oil had a spicy and woody odor. The main components of the oil were β-cubebene (8.8%), atractylon (7.8%), methyl eugenol (6.2%), and δ-cadinene (5.3%). Fifteen major odor-active compounds were identified in the essential oil from PINELLIA TUBER by the GC-olfactometry (GC-O) and aroma extract dilution analysis (AEDA). Among these, safrole (spicy) and β-vatirenene (woody) showed the highest flavor dilution (FD) factor (128), followed by paeonol (FD = 64; woody, spicy), α-humulene (FD = 64; woody), and β-phenylnaphthalene (FD = 64; spicy).
A new phthalide, 3-but-2′-enylidene-4,5,6,7-tetrahydrophthalide (3.5%), was isolated from the essential oil of the aerial parts of Meum athamanticum (L.) Jacq., together with (Z)-ligustilide (0.1%) and sedanonic acid lactone (0.5%), and their structures established by MS and NMR techniques. In addition, a total of 23 components, accounting for 93.2% of the oil, could be identified by GC–MS. The major components of the oil were found to be monoterpene hydrocarbons, limonene (33.5%), α-phellandrene (15.3%), myrcene (13.4%) and (E)-β-ocimene (11.6%). Copyright © 2006 John Wiley & Sons, Ltd.
The study was conducted to determine the effects of dietary supplementation rosemary aromatic plant, rosemary volatile oil and α-tocopherol acetate (Vitamin E) on serum variables of broilers fed on maize-soybean meal based diets. Eight hundred 1-d-old Ross-308 male chickens were weighed and randomly divided into 1 control and 7 experimental groups each with 10 replicates of 10 birds. There were 8 dietary treatments: (VitE1) control without rosemary and rosemary volatile oil only with 50 mg/kg vitamin E; (R1) 5.7 g/kg ground rosemary leaves; (R2) 8.6 g/kg ground rosemary leaves; (R3) 11.5 g/kg ground rosemary leaves; (RO1) 100 mg/kg rosemary volatile oil; (RO2) 150 mg/kg rosemary volatile oil; (RO3) 200 mg/kg rosemary volatile oil and (VitE2) 200 mg/kg vitamin E. Broilers consumed the diets and water ad libitum. After 42 days, 80 animals were randomly selected for serum biochemical profile analysis involving ceruloplasmin, superoxide dismutase activity (SOD), transferring, albumin globulins ratio (A/G), total cholesterol, creatin, urea, alanine aminotransferase (ALT) and aspartate amino transferase (AST). While serum transferrin, urea level and ALT-AST activity were not statistically different among groups serum ceruloplasmin (p< 0.000), SOD activity (p<0.05), albumin/globulin ratio (p< 0.000), total cholesterol (p<0.001), creatinin (p<0.05) and AST (p< 0.000) level were found to be significantly different. In conclusion, the Rosmarinus officinalis plant and its volatile oil have increasing effect on serum SOD activity and effect positively oxidation mechanism. On the other hand, it can be assumed that rosemary plant created hypocholesterolemic effect in this study.
1. The current study was conducted to evaluate the effects of dietary supplementation with vitamin E (as alpha-tocopherol acetate), dried rosemary leaves and rosemary volatile oil on the performance, meat quality (measured as sensory variables, pH, colour, malondialdehyde (MDA) level, and bacteria count) and serum superoxide dismutase (SOD) activity in broilers fed on maize-soybean meal based diets. 2. A total of 800 broiler chicks were randomly allocated to 8 dietary treatments, which were set up with 1 control group and 7 experimental groups. The control group (VitE1) was given a basal diet including 50 mg/kg alpha-tocopherol acetate, while the experimental groups were given 5 x 7 g/kg rosemary plant (R1), 8 x 6 g/kg plant (R2), 11 x 5 g/kg plant (R3), 100 mg/kg plant oil (RO1), 150 mg/kg plant oil (RO2), 200 mg/kg plant oil (RO3) or 200 mg/kg alpha-tocopherol acetate (VitE2). 3. Although there were no statistical differences observed for feed consumption, other performance variables including live weight gain, feed efficiency and carcase yield were significantly affected. The addition of rosemary volatile oil had more effect on the performance variables than did the rosemary plant itself. 4. As a measure of meat shelf life, TBA analyses were performed on the meat samples on d 1, 3 and 5 after culling. Meat MDA levels of groups fed diets with rosemary and rosemary volatile oil were significantly lower than that of groups fed diets containing alpha-tocopherol acetate alone. 5. Significant differences were also seen between the control and experimental groups for meat colour and meat pH values as well as for sensory analyses. 6. Microbiological analyses conducted at the end of the experiment showed that E. coli counts were significantly reduced in meat samples from the experimental groups. 7. In conclusion, dietary supplementation with rosemary and its volatile oil improved broiler meat quality. Moreover growth performance was positively affected by the rosemary volatile oil supplementations.
Phthalides, and their corresponding dihydro and tetrahydro analogues, are components of several genera of the plant family Apiaceae. These taxa have been reported as exhibiting a wide range of bioactivities against experimental models of several illnesses and physiological conditions, including microbial and viral infections, stroke, tuberculosis, and vasoconstriction. Many of these genera are purported to possess medicinal values, and of these several are considered to be traditional herbal medicines. This review provides an overview of the methods of investigation, the structural diversity, and the bioactivity of phthalides, dihydrophthalides, tetrahydrophthalides, and dimers from plants in the Apiaceae.
Relations between the distribution of Arrhenatheretalia species from roadside grasslands of southern Belgium and variations in climatic parameters are described on the basis of a statistical sampling procedure integrating multivariate techniques (cluster analysis and DCA-ordination). The authors examine the influence of small macroclimate features, such as mean annual rainfall (1100-1400 mm), mean annual temperature (7.0-8.2 °C), mean annual number of frost days (90-120) and mean annual number of snow days (28-35), on the floristic composition of roadside grasslands from High Ardennes (525-570 m a.s.l.) (19 samplings) and Middle Ardennes ecological sectors (330-500 m a.s.l.) (26 samplings). Cluster analysis revealed two distinct clusters of vegetation samples which are likely to be arranged along a climatic gradient. Sample scores on the first DCA-axis were significantly correlated with climatic parameters. Mean annual number of frost days was the factor which best explained the differences between plots, when analysed with a linear regression. These results indicate that very small macroclimate variations in general and in the number of frost days in particular, are determinant of compositional variation in roadside plant communities.
The sesquiterpene hydrocarbons β-bazzanene and α- and β-barbatene, typical constituents of liverworts (Hepaticae), were identified for the first time as constituents of a higher plant in the roots of Meum athamanticum (L.) Jacq. In addition, isobazzanene and isobarbatene, together with a variety of common sesquiterpene hydrocarbons, were identified. For α- and β-barbatene and isobarbatene the opposite configurations from those in liverworts were determined by enantioselective GC using modified cyclodextrins as chiral stationary phases. The configuration of β-bazzanene and isobazzanene could not be assigned. Isobarbatene was found for the first time as a natural compound.
The essential oils from the epigeous (above ground) and hypogeous (below ground) parts of Meum athamanticum Jacq., which were obtained by hydro-distillation, were subjected to analysis by GC and GC/MS. The major components were found to be (E)-β-ocimene (34.9%), p-cymene (12.1%), (Z)-β-ocimene (10.2%) and δ-3-carene (6.2%) in the epigeous part oil and (Z)-ligustilide (36.2%), (E)-β-ocimene (14.4%) and (Z)-3-butylidene phthalide (6.3%) from the hypogeous part oil.
The volatile constituents of fruit, herb and underground parts of Ligusticum mutellina (L.) Crantz were studied by GC and GC/MS. The oils showed a different composition with the main class of compounds being phenylpropanoids with 57.6% (fruit), 49.5% (herb) and 30.2% (rhizome/roots). The major constituents are myristicin (35.1%) and apiole (17.4%) in the fruit oil, myristcin (39.3%) and α-phellandrene (23.4%) in the herb oil and myristicin (26.8%) and (Z)-ligustilide (19.1%) in the oil of the underground parts. Phthalides (23.9%) are characteristic compounds of the root/rhizome oil and could not be detected in the aerial parts of this plant.
The volatile components from nine plants growing on natural grasslands in Auvergne, central France, selected for the broad qualitative and quantitative diversity of their terpenoid fractions, were analyzed by high-resolution gas-phase chromatography and mass spectrometry (HRGC-MS) after static headspace solid-phase microextraction (SHS-SPME). SHS-SPME allowed all the plant material to be analyzed under the same conditions despite its wide-ranging composition. This is not always possible with other extraction methods. Using an apolar poly(dimethylsiloxane) (PDMS) phase, numerous terpenoid hydrocarbons, together with alcohols, cyclic ethers, and esters, were extracted. Its ease of use and the high resolution of the chromatographic profiles obtained make SHS-SPME well suited to the rapid characterization of the main components of the volatile fraction of plants. Of the nine plants studied, four (Meum athamanticum, Pimpinella saxifraga, Achillea millefolium, and Thymus pulegioides) exhaled more than 60 different volatile components. Certain terpenes present in large amounts in these plants might help link dairy products to grazing pasture, thus improving food traceability.