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1.
Plants (Basel) ; 12(3)2023 Jan 31.
Article in English | MEDLINE | ID: mdl-36771704

ABSTRACT

Origanum vulgare L. is a well-known aromatic and medicinal plant, whose essential oil (EO) has recognised flavouring and medicinal properties. In this study, Origanum vulgare subsp. virens (Hoffmanns. & Link) Ietsw. EOs, isolated from accessions grown in experimental fields, were evaluated. The plant material was grown from rooted cuttings or nutlets (fruits), originally collected in 20 regions in mainland Portugal and harvesting for EO isolation was performed in two years. EOs were isolated by hydrodistillation and analysed by gas chromatography and gas chromatography-mass spectrometry, for EO quantification and identification, respectively. EO yields ranged from <0.05-3.3% for rooted cuttings, with oregano samples obtained in Portalegre and Alandroal, respectively. Ninety-one compounds were identified, mainly grouped in oxygen-containing monoterpenes and monoterpene hydrocarbons. EO agglomerative cluster analysis evidenced two main clusters, with the first subdivided into four subclusters. From the obtained data, the putative O. vulgare subsp. virens chemotypes are carvacrol, thymol and linalool, with γ-terpinene, p-cymene, cis- and trans-ß-ocimene also contributing as these EOs chemical descriptors. The comparison between the present data and a survey of the existing literature on Portuguese O. vulgare reinforces the major variability of this species' EOs and emphasises the importance of avoiding wild collections to obtain a defined chemical type of crop production of market relevance.

2.
Heliyon ; 8(12): e12647, 2022 Dec.
Article in English | MEDLINE | ID: mdl-36636210

ABSTRACT

The evaluation of the elemental content of moringa leaves and flowers by Energy Dispersive X-Ray Fluorescence Spectrometry revealed that the leaves are a good source of some macro (Ca and K) and micronutrients (Mn) beyond the presence of important polyunsaturated fatty acids (PUFAs), essential in human nutrition. Total soluble sugars prevail in the flowers which may be linked to insect attraction and the pollination process. M. oleifera leaves, flowers and seeds essential oils (EOs) were isolated by hydrodistillation. Gas chromatography and gas chromatography-mass spectrometry analysis (GC-MS) showed EOs dominated by alkanes and fatty acids in diverse ratios in the analyzed plant parts. The nutritional characterization of M. oleifera cultivated in Portugal showed some important nutrients to human physiology. Further studies will allow determining if its consumption may overcome the nutritional imbalances of daily modern households, preventing the emergence of hypertension and diabetes.

3.
Phytochemistry ; 169: 112159, 2020 Jan.
Article in English | MEDLINE | ID: mdl-31600652

ABSTRACT

In Portugal, the pine black sawyer Monochamus galloprovincialis is the principal vector of the pinewood nematode, Bursaphelenchus xylophilus, the causal agent of pine wilt disease (PWD), a lethal phyopathogen with major ecological and economic consequences to European forestry. The aim of this study was to determine the influence of M. galloprovincialis feeding on the volatiles emitted by pine trees. This study focused on the pine species which are most relevant to Portugal, that is, Pinus pinaster (maritime pine) and Pinus pinea (stone or umbrella pine), assessing to what extent pine chemotypes might influence feeding by the insect vector. Preliminary evaluation of each maritime pine essential oil allowed recognizing the existence of two main chemotypes (C1 and C2) and absence of chemical variability in P. pinea. Emission of volatiles from pine trees was evaluated before and during 24 h of feeding by a mixed-sex pair of newly emerged, unfed M. galloprovincialis. Volatiles were also collected from the oleoresin released from the feeding wounds as well as from the insects after feeding. Pine volatiles were collected by solid phase microextraction (SPME) and insect volatiles extracted with pentane, and all analysed by gas chromatography-mass spectrometry (GC-MS) and by GC for component identification and quantification, respectively. Of the seventeen emitted volatiles detected in SPME analyses of P. pinaster, ß-pinene, α-pinene, ß-caryophyllene, and germacrene D showed the highest average fold increases as a result of M. galloprovincialis feeding. When grouped by P. pinaster chemotype, C1 and C2 groups of trees showed different patterns of responses. ß-Caryophyllene and germacrene D showed the highest fold increase in C1 trees, whereas ß-pinene and α-pinene clearly dominated in C2 trees. Likewise, the oleoresin volatiles from C1 trees were dominated by δ-3-carene and/or ß-pinene, whereas α-pinene and ß-pinene were the main volatile components from oleoresin of C2 trees. Nine components were detected in P. pinea volatiles, of which limonene showed the highest fold increase as a result of insect feeding. The volatiles collected from the insects after they had fed on P. pinaster included α-pinene, ß-pinene, and abietic acid, and by the straight-chain n-alkanes n-C27, n-C29, and n-C25, together with the methyl-branched hydrocarbons 3-meC29, 2-meC28, and 3-meC27. A better understanding of the responses of different P. pinaster chemotypes to feeding by M. galloprovincialis may be helpful in the development of new lures to improve pine sawyer trapping in integrated pest management for control of PWD.


Subject(s)
Animal Feed , Coleoptera/drug effects , Pinus/chemistry , Plant Extracts/chemistry , Volatile Organic Compounds/pharmacology , Animals , Gas Chromatography-Mass Spectrometry , Portugal , Solid Phase Microextraction , Volatile Organic Compounds/chemistry , Volatile Organic Compounds/isolation & purification
4.
Chem Biodivers ; 14(1)2017 Jan.
Article in English | MEDLINE | ID: mdl-27623247

ABSTRACT

Pinewood nematode (PWN), Bursaphelenchus xylophilus, is the causal agent of pine wilt disease, a serious threat to global forest populations of conifers, especially Pinus spp. A time-course study of the essential oils (EOs) of 2-year-old Pinus halepensis, Pinus pinaster, Pinus pinea and Pinus sylvestris following inoculation with the PWN was performed. The constitutive and nematode inoculation induced EOs components were analyzed at both the wounding or inoculation areas and at the whole plant level. The enantiomeric ratio of optically active main EOs components was also evaluated. External symptoms of infection were observed only in P. pinaster and P. sylvestris 21 and 15 days after inoculation, respectively. The EO composition analysis of uninoculated and unwounded plants revealed the occurrence of chemotypes for P. pinaster, P. halepensis and P. sylvestris, whereas P. pinea showed a homogenous EO composition. When whole plants were evaluated for EO and monoterpene hydrocarbon enantiomeric chemical composition, no relevant qualitative and quantitative differences were found. Instead, EO analysis of inoculated and uninoculated wounded areas revealed an increase of sesquiterpenes and diterpenic compounds, especially in P. pinea and P. halepensis, comparatively to healthy whole plants EOs.


Subject(s)
Oils, Volatile/analysis , Pinus/chemistry , Animals , Monoterpenes/analysis , Nematoda/pathogenicity , Nematode Infections/metabolism , Oils, Volatile/chemistry , Plant Diseases/parasitology , Terpenes/analysis
5.
J Agric Food Chem ; 64(40): 7452-7458, 2016 Oct 12.
Article in English | MEDLINE | ID: mdl-27653470

ABSTRACT

As a nematotoxics screening biotechnological system, Solanum tuberosum hairy roots (StHR) and S. tuberosum hairy roots with Meloidogyne chitwoodi co-cultures (StHR/CRKN) were evaluated, with and without the addition of the essential oils (EOs) of Satureja montana and Ruta graveolens. EOs nematotoxic and phytotoxic effects were followed weekly by evaluating nematode population density in the co-cultures as well as growth and volatile profiles of both in vitro cultures types. Growth, measured by the dissimilation method and by fresh and dry weight determination, was inhibited after EO addition. Nematode population increased in control cultures, while in EO-added cultures numbers were kept stable. In addition to each of the EOs main components, and in vitro cultures constitutive volatiles, new volatiles were detected by gas chromatography and gas chromatography coupled to mass spectrometry in both culture types. StHR with CRKN co-cultures showed to be suitable for preliminary assessment of nematotoxic EOs.


Subject(s)
Oils, Volatile/pharmacology , Plant Roots/drug effects , Ruta/chemistry , Satureja/chemistry , Solanum tuberosum/parasitology , Tylenchoidea/pathogenicity , Animals , Coculture Techniques , Gas Chromatography-Mass Spectrometry , Oils, Volatile/analysis , Oils, Volatile/chemistry , Plant Roots/growth & development , Plant Roots/parasitology , Solanum tuberosum/cytology , Solanum tuberosum/drug effects , Tylenchoidea/drug effects
6.
Nat Prod Commun ; 11(7): 1029-1038, 2016 Jul.
Article in English | MEDLINE | ID: mdl-30452188

ABSTRACT

The in viro antioxidant, anti-inflammatory, anti-hyperglycaemic, and anti-acetylcholinesterase activities of the essential oils (EOs) isolated from six Lamiaceae species (Thymbra capitata,. Thymus albicans, Th. caespititius, Th. carnosus, Th. lotocephalus and Th. mastichina) grown in Portugal, were evaluated. Th. caespititius and T. capitata carvacrol/thymol-rich EOs showed the best capacity for preventing lipid peroxidation, and scavenging the 2,2'-azino- bis(3-ethylbenzothiazoline-6-sulphonid acid) (ABTS) and peroxyl free radicals, as well as for inhibiting lipoxygenase and a-amylase. However, Th. caespititius and Th. lotocephalus 1,8-cineole and linalool rich EOs were the best inhibitors of a-glucosidase. T capitata, Th. lotocephalus and Th. albicans EOs were the: most active for inhibiting acetyleholinesterase. Th. caespititius and Th. mastichina EOs were the main scavengers of nitric oxide (NO) radicals. The comparison between the present data with a survey of the existing literature on the in vitro biological activities of the essential oils isolated from the same species from Portuguese origin, using other.methodologies, showed some differences. For instance the use of two oxidizable substrates (egg yolk andlecithin liposomes) led to distinct results mainly for those samples with relatively low activity. In addition, the EOs capacity for scavenging peroxyl radicals-was also influenced by the presence of cyclodextrins, as a synergism seemed to occur between EOs and those carbohydrates.


Subject(s)
Anti-Inflammatory Agents/chemistry , Antioxidants/chemistry , Hypoglycemic Agents/chemistry , Lamiaceae/chemistry , Plant Oils/pharmacology , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/pharmacology , Hypoglycemic Agents/pharmacology , Lecithins/chemistry , Lipid Peroxidation , Liposomes/chemistry , Lipoxygenase Inhibitors/chemistry , Lipoxygenase Inhibitors/pharmacology , Oils, Volatile/chemistry , Oils, Volatile/pharmacology , Plant Oils/chemistry , alpha-Amylases/antagonists & inhibitors , alpha-Glucosidases/metabolism
7.
Article in English | MEDLINE | ID: mdl-26229547

ABSTRACT

The antioxidant and antiproliferative activities of the essential oils from Thymbra capitata and Thymus species grown in Portugal were evaluated. Thymbra and Thymus essential oils were grouped into two clusters: Cluster I in which carvacrol, thymol, p-cymene, α-terpineol, and γ-terpinene dominated and Cluster II in which thymol and carvacrol were absent and the main constituent was linalool. The ability for scavenging ABTS(•+) and peroxyl free radicals as well as for preventing the growth of THP-1 leukemia cells was better in essential oils with the highest contents of thymol and carvacrol. These results show the importance of these two terpene-phenolic compounds as antioxidants and cytotoxic agents against THP-1 cells.

8.
Planta ; 241(6): 1325-36, 2015 Jun.
Article in English | MEDLINE | ID: mdl-25677754

ABSTRACT

MAIN CONCLUSION: Co-cultures of Pinus pinaster with Bursaphelenchus xylophilus were established as a biotechnological tool to evaluate the effect of nematotoxics addition in a host/parasite culture system. The pinewood nematode (PWN), Bursaphelenchus xylophilus, the causal agent of pine wilt disease (PWD), was detected for the first time in Europe in 1999 spreading throughout the pine forests in Portugal and recently in Spain. Plant in vitro cultures may be a useful experimental system to investigate the plant/nematode relationships in loco, thus avoiding the difficulties of field assays. In this study, Pinus pinaster in vitro cultures were established and compared to in vivo 1 year-old plantlets by analyzing shoot structure and volatiles production. In vitro co-cultures were established with the PWN and the effect of the phytoparasite on in vitro shoot structure, water content and volatiles production was evaluated. In vitro shoots showed similar structure and volatiles production to in vivo maritime pine plantlets. The first macroscopic symptoms of PWD were observed about 4 weeks after in vitro co-culture establishment. Nematode population in the culture medium increased and PWNs were detected in gaps of the callus tissue and in cavities developed from the degradation of cambial cells. In terms of volatiles main components, plantlets, P. pinaster cultures, and P. pinaster with B. xylophilus co-cultures were all ß- and α-pinene rich. Co-cultures may be an easy-to-handle biotechnological approach to study this pathology, envisioning the understanding of and finding ways to restrain this highly devastating nematode.


Subject(s)
Biotechnology/methods , Coculture Techniques/methods , Pinus/growth & development , Plant Diseases/parasitology , Tylenchida/physiology , Animals , Pinus/ultrastructure , Plant Shoots/growth & development , Plant Shoots/ultrastructure , Volatile Organic Compounds/analysis , Water
9.
Chem Biodivers ; 11(5): 719-32, 2014 May.
Article in English | MEDLINE | ID: mdl-24827682

ABSTRACT

Volatile-oils chemical composition and bioactivity of the essentail oils from Plectranthus barbatus, P. neochilus, and P. ornatus (Lamiaceae) were assessed. Aerial parts from these three related Plectranthus species were collected from cultivated plants grown in Portugal, during vegetative and flowering phases. Volatiles, isolated by distillation-extraction, were analyzed by GC and GC/MS. Monoterpene hydrocarbons (12-74%) and sesquiterpene hydrocarbons (4-45%) constituted the main fractions in all volatiles. α-Pinene (3; 12-67%), oct-1-en-3-ol (6; traces-28%), ß-pinene (7; 0.1-22%), and ß-caryophyllene (50; 7-12%) dominated P. barbatus volatiles. P. neochilus major volatile components were α-terpenyl acetate (41; traces-48%), α-thujone (2; 2-28%), ß-caryophyllene (50; 2-28%), ß-pinene (7; 1-25%), and α-pinene (3; 1-19%). Oct-1-en-3-ol (6; 13-31%), ß-pinene (7; 11-24%), α-pinene (3; 11-19%), and ß-caryophyllene (50; traces-11%) were the main constituents from P. ornatus volatiles. These chemical compositions were rather different from those previously found for specimens harvested in Africa and Brazil. Moreover, the volatiles from the flowers are herewith reported for the first time. Essential oils, isolated by hydrodistillation from leaves and stems, showed a yellowish color and unpleasant odor, with yields ranging from 0.08% to 0.84% (v/dry weight). Antioxidant and antimicrobial activities of the essential oils were evaluated by DPPH· and TBARS assays, and agar disc-diffusion method, respectively. Results showed low or moderate antioxidant capacity and significant antimicrobial activity against Gram-positive bacteria.


Subject(s)
Anti-Infective Agents/chemistry , Antioxidants/chemistry , Oils, Volatile/chemistry , Plant Oils/chemistry , Plectranthus/chemistry , Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Antioxidants/isolation & purification , Antioxidants/pharmacology , Bacteria/drug effects , Bacterial Infections/drug therapy , Fungi/drug effects , Humans , Mycoses/drug therapy , Oils, Volatile/isolation & purification , Oils, Volatile/pharmacology , Plant Oils/isolation & purification , Plant Oils/pharmacology
10.
Nat Prod Commun ; 9(4): 587-94, 2014 Apr.
Article in English | MEDLINE | ID: mdl-24868891

ABSTRACT

Essential oils (EO) possess antimicrobial, anti-inflammatory, insect repellent, anti-cancer, and antioxidant properties, among others. In the present work, the antioxidant, anti-inflammatory and anti-proliferative activities of Moroccan commercial EOs (Citrus aurantium, C. limon, Cupressus sempervirens, Eucalyptus globulus, Foeniculum vulgare and Thymus vulgaris) were evaluated and compared with their main constituents. T. vulgaris EO showed the best free radicals scavenging capacity. This EO was also the most effective against lipid peroxidation along with C. limon and F. vulgare EOs. C. sempervirens EO was the most effective in scavenging NO free radicals, whereas C. limon EO showed the best chelating power. Not all of the major compounds of the EO were responsible for the whole activity of the EOs. T. vulgaris EO showed the best anti-proliferative activity against THP-1 cells in contrast to that of F. vulgare. The antioxidant and anti-inflammatory activities of the EOs were plant species dependent and not always attributable to the EOs main components. Nevertheless, the EOs anti-proliferative activities were more related to their main components, as with T. vulgaris, C. limon, E. globulus and C. sempervirens.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Antioxidants/pharmacology , Magnoliopsida/chemistry , Oils, Volatile/chemistry , Plant Oils/pharmacology , Animals , Anti-Inflammatory Agents/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antioxidants/chemistry , Cell Line, Tumor , Morocco , Plant Oils/chemistry
11.
Phytochemistry ; 94: 220-8, 2013 Oct.
Article in English | MEDLINE | ID: mdl-23829930

ABSTRACT

The Portuguese pine forest has become dangerously threatened by pine wilt disease (PWD), caused by the pinewood nematode (PWN), Bursaphelenchus xylophilus. Synthetic chemicals are the most common pesticides used against phytoparasitic nematodes but its use has negative ecological impacts. Phytochemicals may prove to be environmentally friendly alternatives. Essential oils (EOs) and decoction waters, isolated from 84 plant samples, were tested against B. xylophilus, in direct contact assays. Some successful EOs were fractionated and the fractions containing hydrocarbons or oxygen-containing molecules tested separately. Twenty EOs showed corrected mortalities ⩾96% at 2 µL/mL. These were further tested at lower concentrations. Ruta graveolens, Satureja montana and Thymbra capitata EOs showed lethal concentrations (LC100)<0.4µL/mL. Oxygen-containing molecules fractions showing corrected mortality ⩾96% did not always show LC100 values similar to the corresponding EOs, suggesting additive and/or synergistic relationships among fractions. Nine decoction waters (remaining hydrodistillation waters) revealed 100% mortality at a minimum concentration of 12.5µL/mL. R. graveolens, S. montana and T. capitata EOs are potential environmentally friendly alternatives for B. xylophilus control given their high nematotoxic properties. Nematotoxic activity of an EO should be taken in its entirety, as its different components may contribute, in distinct ways, to the overall EO activity.


Subject(s)
Nematoda/drug effects , Oils, Volatile/pharmacology , Plant Oils/pharmacology , Plants/chemistry , Animals , Chemical Fractionation , Cluster Analysis , Dose-Response Relationship, Drug , Host-Parasite Interactions/drug effects , Lamiaceae/chemistry , Nematoda/physiology , Oils, Volatile/classification , Oils, Volatile/isolation & purification , Pinus/parasitology , Plant Diseases/parasitology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Oils/classification , Plant Oils/isolation & purification , Plants/classification , Ruta/chemistry , Satureja/chemistry , Species Specificity , Water/chemistry
12.
Planta ; 238(1): 191-204, 2013 Jul.
Article in English | MEDLINE | ID: mdl-23624978

ABSTRACT

The identification, isolation and functional characterization of two genes encoding two monoterpene synthases-γ-terpinene synthase (Tctps2) and α-terpineol synthase (Tctps5)-from three chemically distinct Thymus caespititius (Lamiaceae) genotypes were performed. Genomic exon-intron structure was also determined for both terpene synthase genes, revealing an organization with seven exons and six introns. The cDNA of Tctps2 was 2,308 bp long and had an open reading frame of 1,794 bp encoding for a protein with 598 amino acids. Tctps5 was longer, mainly due to intron sequences, and presented high intraspecific variability on the plants analyzed. It encoded for a protein of 602 amino acids from an open reading frame of 1,806 bp comprising a total of 2,507 bp genomic sequence. The amino acid sequence of these two active Tctps genes shared 74 % pairwise identity, ranging between 42 and 94 % similarity with about 50 known terpene synthases of other Lamiaceae species. Gene expression revealed a multi-product Tctps2 and Tctps5 enzymes, producing γ-terpinene and α-terpineol as major components, respectively. These enzymatic results were consistent with the monoterpene profile present in T. caespititius field plants, suggesting a transcriptional regulation in leaves. Herewith reported for the first time for this species, these two newly characterized Tctps genes improve the understanding of the molecular mechanisms of reaction responsible for terpene biosynthesis and chemical diversity found in T. caespititius.


Subject(s)
Alkyl and Aryl Transferases/genetics , Lamiaceae/enzymology , Lamiaceae/genetics , Alkyl and Aryl Transferases/metabolism , Amino Acid Sequence , Base Sequence , Cloning, Molecular , Gene Expression Regulation, Plant , Introns , Lamiaceae/metabolism , Molecular Sequence Data , Phylogeny , Plant Proteins/genetics , Plant Proteins/metabolism , Sequence Homology, Amino Acid
13.
Nat Prod Res ; 27(8): 743-9, 2013 Apr.
Article in English | MEDLINE | ID: mdl-22724515

ABSTRACT

The variability of the volatile profile of 70 propolis samples from acaricide-treated and -untreated beehives maintained at Algarve (Portugal) was evaluated. Propolis samples were collected in three regions of Algarve at three different periods. Cluster analysis based on the propolis volatiles' chemical composition defined two main clusters, not related to the time of year, collection site, altitude, temperature or humidity ranges, and was based mainly on the relative amounts of viridiflorol, n-tricosane and n-nonadecane for cluster I. Cluster II was mainly characterised by the high thymol content, followed by viridiflorol, n-tricosane and n-nonadecane. The presence of higher thymol levels in propolis samples from cluster II may reflect the long use of an acaricide with thymol as main active ingredient. All samples showed an intense rock-rose aroma supported by the presence of characteristic Cistus and labdanum oil volatile components. Given the nowadays frequent propolis household use, volatiles thorough characterisation may assist in its quality assessment.


Subject(s)
Acaricides , Oils, Volatile/chemistry , Propolis/chemistry , Thymol , Animals , Beekeeping , Bees , Cluster Analysis , Portugal
14.
Rev. bras. farmacogn ; 21(6): 1012-1024, Nov.-Dec. 2011. graf, tab
Article in English | LILACS | ID: lil-602297

ABSTRACT

Thyme essential oils are well recognized by their excellent biological activities and the antimicrobial activity of Portuguese thyme essential oils has been investigated with promising results, particularly against food borne pathogens. In this study the potential antimicrobial activity of the essential oils of five species of Thymus (Lamiaceae), namely Th. caespititius Brot., Th. camphoratus Hoffmanns. & Link, Th. capitellatus Hoffmanns. & Link., Th. carnosus Boiss. and Th. zygis L. was evaluated against Candida albicans, Haemophilus influenza, Helicobacter pylori, Listeria monocytogenes, Salmonella enterica and Streptococcus pneumoniae. H. pylori strains were the most susceptible bacteria, particularly to the essential oils of Th. caespititius (Planalto Central), Th. zygis (Rebordãos) and Th. caespititius (Pico) which minimum inhibitory concentration (MIC) values ranged from 0.05 to 0.08 mg.mL-1. Th. caespititius essential oil from Planalto Central or its main component, carvacrol significantly (p<0.05) inhibited the intracellular growth of H. pylori, and showed no citotoxicity to the gastric cell line. Our results suggest the potential of this essential oil and its main component as a promising tool as anti-Helicobacter agent potentiating the eradication of this important gastroduodenal pathogen.

15.
Nat Prod Commun ; 5(9): 1465-76, 2010 Sep.
Article in English | MEDLINE | ID: mdl-20923010

ABSTRACT

Thyme is the common name of many taxa belonging to the Thymbra and Thymus genera. Given the economic importance of thyme oils, many thyme species have been studied and their essential oils and other volatile-containing extracts chemically characterized. Thymbra and Thymus species are frequent in the west Mediterranean region, considered to be the centre of origin of the genus Thymus, and extend further westwards in the Iberian Peninsula and northwest Africa, to the Macaronesian region in the Atlantic Ocean. The present work gives an overview of the chemical composition of the volatiles from the taxa of these two genera occurring in the above geographic area.


Subject(s)
Oils, Volatile/analysis , Thymus Plant/chemistry , Mediterranean Region , Portugal , Thymus Plant/classification
16.
Biotechnol Lett ; 31(6): 897-903, 2009 Jun.
Article in English | MEDLINE | ID: mdl-19205895

ABSTRACT

Two oxygen-containing monoterpene substrates, menthol or geraniol (25 mg l(-1)), were added to Anethum graveolens hairy root cultures to evaluate the influence of the biotransformation capacity on growth and production of volatile compounds. Growth was assessed by the dissimilation method and by fresh and dry weight measurement. The volatiles were analyzed by GC and GC-MS. The total constitutive volatile component was composed, in more than 50%, by falcarinol (17-52%), apiole (11-24%), palmitic acid (7-16%), linoleic acid (4-9%), myristicin (4-8%) and n-octanal (2-5%). Substrate addition had no negative influence on growth. The relative amount of menthol quickly decreased 48 h after addition, and the biotransformation product menthyl acetate was concomitantly formed. Likewise, the added geraniol quickly decreased over 48 h alongside with the production of the biotransformation products. The added geraniol was biotransformed in 10 new products, the alcohols linalool, alpha-terpineol and citronellol, the aldehydes neral and geranial, the esters citronellyl, neryl and geranyl acetates and linalool and nerol oxides.


Subject(s)
Anethum graveolens/metabolism , Menthol/metabolism , Terpenes/metabolism , Acyclic Monoterpenes , Anethum graveolens/chemistry , Anethum graveolens/growth & development , Biomass , Biotransformation , Gas Chromatography-Mass Spectrometry , Oils, Volatile/metabolism , Plant Roots/growth & development , Plant Roots/metabolism
17.
Planta Med ; 75(4): 387-91, 2009 Mar.
Article in English | MEDLINE | ID: mdl-19156598

ABSTRACT

The biotransformation capacity of Levisticum officinale W.D.J. Koch hairy root cultures was studied by evaluating the effect of the addition of 25 mg/L menthol or geraniol on morphology, growth, and volatiles production. L. officinale hairy root cultures were maintained for 7 weeks in SH medium, in darkness at 24 degrees C and 80 r.p.m., and the substrates were added 15 days after inoculation. Growth was evaluated by measuring fresh and dry weight and by using the dissimilation method. Volatiles composition was analyzed by GC and GC-MS. Hairy roots morphology and growth were not influenced by substrate addition. No new volatiles were detected after menthol addition and, as was also the case with the control cultures, volatiles of these hairy roots were dominated by (Z)-falcarinol (1-45%), N-octanal (3-8%), palmitic acid (3-10%), and (Z)-ligustilide (2-9%). The addition of geraniol induced the production of six new volatiles: nerol/citronellol/neral (traces-15%), alpha-terpineol (0.2-3%), linalool (0.1-1.2%), and geranyl acetate (traces-2%). The relative amounts of the substrates and some of their biotransformation products decreased during the course of the experiment. Following the addition of beta-glycosidase to the remaining distillation water, analysis of the extracted volatiles showed that lovage hairy roots were able to convert both substrates and their biotransformation products into glycosidic forms. GC:gas chromatography GC-MS:gas chromatography-mass spectrometry SH:Schenk and Hildebrandt (1972) culture medium.


Subject(s)
Levisticum/metabolism , Menthol/metabolism , Plant Roots/metabolism , Terpenes/metabolism , Acyclic Monoterpenes , Glycosylation , Tissue Culture Techniques
18.
Biotechnol Lett ; 30(7): 1265-70, 2008 Jul.
Article in English | MEDLINE | ID: mdl-18273553

ABSTRACT

Six-year-old Levisticum officinale (lovage) hairy root cultures were used to study the effect of eight different NH(4) (+):NO(3) (-) ratios on their growth and volatile components. All cultures were kept at 24 degrees C on orbital shakers at 80 rpm, in darkness or in a 16 h light/8 h dark photoperiod. Growth was evaluated by dry and fresh weight determination. The volatiles were isolated by distillation-extraction and analysed by GC and GC-MS. Greater growth was attained in darkness with 10:90 (control, SH medium), 50:50 and 25:75 NH(4) (+):NO(3) (-) ratios, and also with SH control medium under the photoperiod condition, with a 10, 14, 12.5 and 12.5 fold increase of biomass in terms of dry weight, respectively, at the end of 42 days of growth. UPGMA cluster analysis of the mixtures of volatiles isolated from the hairy roots grown with different NH(4) (+):NO(3) (-) ratios confirmed their chemical variability. Although no particular grouping was detected in relation to the NH(4) (+):NO(3) (-) ratios or light conditions studied, most of the mixtures of volatiles isolated from the hairy roots were either dominated by n-octanal, (Z)-falcarinol or both components in about the same relative amounts.


Subject(s)
Darkness , Levisticum/metabolism , Nitrogen/metabolism , Oils, Volatile/metabolism , Photoperiod , Plant Roots/metabolism , Ammonia/pharmacology , Levisticum/chemistry , Levisticum/cytology , Nitrates/pharmacology , Oils, Volatile/analysis , Plant Roots/chemistry , Plant Roots/cytology
19.
J Med Food ; 9(1): 128-30, 2006.
Article in English | MEDLINE | ID: mdl-16579741

ABSTRACT

The essential oils isolated by hydrodistillation from freshly obtained aerial parts of sea fennel (Crithmum maritimum L.) were found to be a yellow liquid, obtained in a yield of 0.2% (vol/wt) based on wet weight. The essential oils obtained from young leaves and branches of C. maritimum, collected at two different locations in Turkey (Sipahili and Yesilovacik), were analyzed by gas chromatography-mass spectrometry. Twenty-three components were identified accounting for more than 99% of the total oils. The oils contained mainly monoterpenes, amounting to 89.0% and 99.6%, respectively, of the oils, with gamma-terpinene (36% and 32%), beta-phellandrene (21% and 22%), and sabinene (13% and 9%) as the main components.


Subject(s)
Apiaceae/chemistry , Oils, Volatile/chemistry , Gas Chromatography-Mass Spectrometry , Monoterpenes/analysis , Plant Leaves/chemistry , Turkey
20.
J Agric Food Chem ; 53(21): 8162-8, 2005 Oct 19.
Article in English | MEDLINE | ID: mdl-16218659

ABSTRACT

Antilisterial activities of Thymbra capitata and Origanum vulgare essential oils were tested against 41 strains of Listeria monocytogenes. The oil of T. capitata was mainly constituted by one component, carvacrol (79%), whereas for O. vulgare three components constituted 70% of the oil, namely, thymol (33%), gamma-terpinene (26%), and p-cymene (11%). T. capitata essential oil had a significantly higher antilisterial activity in comparison to O. vulgare oil and chloramphenicol. No significant differences in L. monocytogenes susceptibilities to the essential oils tested were registered. The minimum inhibitory concentration values of T. capitata essential oil and of carvacrol were quite similar, ranging between 0.05 and 0.2 microL/mL. Antioxidant activity was also tested, the essential oil of T. capitata showing significantly higher antioxidant activity than that of O. vulgare. Use of T. capitata and O. vulgare essential oils can constitute a powerful tool in the control of L. monocytogenes in food and other industries.


Subject(s)
Anti-Bacterial Agents/isolation & purification , Antioxidants/isolation & purification , Oils, Volatile/chemistry , Origanum/chemistry , Spices/analysis , Anti-Bacterial Agents/pharmacology , Antioxidants/pharmacology , Listeria monocytogenes/drug effects
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