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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.
Planta 04/2013; · 3.00 Impact Factor
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Maria G Miguel,
Susana Nunes,
Cláudia Cruz,
João Duarte,
Maria D Antunes,
Ana M Cavaco,
Marta D Mendes,
A Sofia Lima,
Luis G Pedro,
José G Barroso, A Cristina Figueiredo
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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.
Natural product research 06/2012; · 1.01 Impact Factor
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ABSTRACT: The scavenging of free radicals and superoxide anion, the inhibition of 5-lipoxygenase and the antiacetylcholinesterase activities of essential oils and decoction waters of eight aromatic plants (Dittrichia viscosa, Foeniculum vulgare, Origanum vulgare, Salvia officinalis, Thymbra capitata, Thymus camphoratus, Thymus carnosus and Thymus mastichina) were studied. The essential oils were dominated by 1,8-cineole in S. officinalis (59%), T. mastichina (49%) and T. camphoratus (21%); borneol (20%) in T. carnosus; carvacrol in Thymbra capitata (68%); gamma-terpinene (49%) in O. vulgare; alpha-pinene (26%) in F. vulgare; and trans-nerolidol (8%) + beta-oplopenone (7%) in D. viscosa. O. vulgare decoction waters had the highest amount of phenols (45 +/- 3mg GAE/mL) while F. vulgare only had 5 +/- 0mg GAE/mL. The decoction waters showed higher radical scavenging activity than the essential oils. O. vulgare decoction water showed the best antioxidant activity (IC(50) = 3 +/- 0 mu g/mL), while the most effective essential oils were those of Thymbra capitata (IC(50) = 61 +/- 2 mu g/mL) and O. vulgare (IC(50) = 156 +/- 5 mu g/mL). Thymbra capitata (IC(50) = 6 +/- 0 mu g/mL) decoction water showed the best superoxide anion scavenging activity. F. vulgare decoction water and essential oil revealed the best 5-lipoxygenase inhibition capacity (IC(50) = 27 +/- 1 mu g/mL and IC(50) = 68 +/- 2 mu/mL, respectively). T. mastichina (IC(50) = 46 +/- 4 mu g/mL), S. officinalis (IC(50) = 51 +/- 4 mu g/mL), Thymbra capitata (IC(50) = 52 +/- 1 mu g/mL) and T. camphoratus (IC(50) = 137 +/- 2 mu g/mL) essential oils showed the best antiacetylcholinesterase activity.
Records of Natural Products 01/2012; 6(1):35-48. · 1.51 Impact Factor
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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.
Flavour and Fragrance Journal 12/2011; 21:1012-1024. · 1.42 Impact Factor
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ABSTRACT: Industrial Crops and Products j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / i n d c r o p ISSR molecular characterization and leaf volatiles analysis of Pittosporum undulatum Vent. naturalized in the Azores archipelago (Portugal) a b s t r a c t Pittosporum undulatum from the Azores archipelago was characterized by both molecular and volatiles analyses. Inter simple sequence repeat (ISSR) evaluation was performed based on a random sampling of 77 individuals from a total of 123 samples collected on all the Azorean islands. Molecular studies grouped the samples mainly according to the geographical collection site, with some exceptions. Leaf volatiles were isolated by distillation–extraction and analyzed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS) from all the 123 samples. Cluster analysis based on the leaf volatiles chemical composition defined three main clusters, not related to sample site collection, and was based mainly on the relative amounts of limonene (3–89%), sabinene (0.1–64%) and terpinen-4-ol (traces-43%). Clusters obtained from both molecular studies and volatiles composition were not super-imposable and no correlation between ISSR markers and volatile oils could be drawn. The results suggest that there is a high genetic variability among individuals of P. undulatum that can explain the invasive ability of this species in the Azores archipelago. The detailed characterization of this alien weed species may assist finding potential commercial uses as well as management strategies to help its eradication and/or control.
Industrial Crops and Products 01/2011; 33:710-719. · 2.47 Impact Factor
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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.
Natural product communications 09/2010; 5(9):1465-76. · 1.24 Impact Factor
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ABSTRACT: The main goal of this study was to isolate and characterize the volatiles from Plicanthus hirtellus and Radula boryana grown in the African Archipelago of São Tomé e Príncipe. The volatiles isolated by distillation–extraction from Plicanthus hirtellus and Radula boryana were analysed by GC and GC–MS. Plicanthus hirtellus volatiles were dominated by anastreptene (13%) and spathulenol (14%). Radula boryana volatiles were characterized by high amounts of p-cymene (17%) along with other monoterpene hydrocarbons and by the unusual presence of the oxygen-containing monoterpenes thymol and carvacrol (1% each). Copyright © 2010 John Wiley & Sons, Ltd.
Flavour and Fragrance Journal 06/2010; 25(4):219 - 222. · 1.42 Impact Factor
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ABSTRACT: Genetic and chemical differences of nine individuals of Chaerophyllum azoricum were studied to determine whether molecular characters and volatile components could be used as taxonomical markers and to examine the correlation between them. Plant material was analysed by random amplified polymorphic DNA (RAPD) and inter simple sequence repeat (ISSR) using 21 and 19 arbitrary primers, respectively, generating 320 RAPD and 310 ISSR markers. The volatiles were isolated from each individual by distillation–extraction and analysed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). Terpinolene (20–67%) was the main component of the volatile fraction isolated from the aerial parts of C. azoricum. Individuals harvested on São Jorge Island also had myristicin (4–23%), -terpinene (5–16%), limonene (3–12%) and -zingiberene (2–12%) as the main components, whereas individuals collected on Flores Island had acorenone B (12–17%), myristicin (8–9%) and sabinene (4–9%) as the other dominant components. Separate cluster analyses based on molecular markers and on the chemical composition of the volatile fraction grouped, in both cases, the nine accessions in two main groups but with some subclustering differences. The correlation between the genetic diversity based on molecular marker patterns and the volatile chemical analysis of the present study was significant (Pearson's r < 0.44, p ∼ 0.01). Copyright © 2009 John Wiley & Sons, Ltd.
Flavour and Fragrance Journal 06/2009; 24(5):259 - 265. · 1.42 Impact Factor
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ABSTRACT: Chemical and genetic differences of 11 individuals of Angelica lignescens and 3 individuals of Melanoselinum decipiens were studied to determine whether volatile components could be used as taxonomical markers and to examine the correlation between molecular and chemical markers. The volatiles were isolated from each individual by distillation–extraction and analyzed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). The same plants were analyzed by Inter Simple Sequence Repeat (ISSR) using 14 arbitrary primers. The main component of volatile fraction isolated from vegetative aerial parts of A. lignescens was limonene (57–86%) while in M. decipiens the main components detected were β-pinene (38–47%) and sabinene (1–33%). Cluster analyses based both on the chemical composition of volatile fraction and on molecular markers grouped the 14 accessions in two main groups, corresponding to each of the two species under study. Considering the species together, a moderate Pearson's correlation of r = 0.61 was obtained between the two analyses.
Biochemical Systematics and Ecology 04/2009; 37(2):98-105. · 0.93 Impact Factor
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Journal of Essential Oil Research 01/2009; 21(4):327-336. · 0.41 Impact Factor
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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.
Biotechnology Letters 08/2008; 30(7):1265-70. · 1.68 Impact Factor
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ABSTRACT: The presence, yield and composition of secondary metabolites in plants, viz. the volatile components and those occurring in essential oils, can be affected in a number of ways, from their formation in the plant to their final isolation. Several of the factors of influence have been studied, in particular for commercially important crops, to optimize the cultivation conditions and time of harvest and to obtain higher yields of high-quality essential oils that fit market requirements. In addition to the commercial importance of the variability in yield and composition, the possible changes are also important when the essential oils and volatiles are used as chemotaxonomic tools. Knowledge of the factors that determine the chemical variability and yield for each species are thus very important. These include: (a) physiological variations; (b) environmental conditions; (c) geographic variations; (d) genetic factors and evolution; (e) political/social conditions; and also (f) amount of plant material/space and manual labour needs. Copyright © 2008 John Wiley & Sons, Ltd.
Flavour and Fragrance Journal 06/2008; 23(4):213 - 226. · 1.42 Impact Factor
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ABSTRACT: The essential oils isolated by hydrodistillation from aerial parts of Teucrium abutilodes L'Hér. and of T. betonicum L'Hér. were obtained in almost similar yields (<0.5%). The oils were complex mixtures consisting mainly of sesquiterpene hydrocarbons, which amounted to 55% of the oil of T. abutiloides and to 45% of that of T. betonicum. However, large differences, both qualitative and quantitative, were observed with regard to the fraction of sesquiterpenes of these oils. Germacrene-D (13%) and δ-cadinene (11%) were the most abundant sesquiterpenes in the oil of T. abutiloides, and β-caryophyllene (12%) in that of T. betonicum. Oct-l-en-3-ol was the main component of both oils (20% of the oil of T. abutiloides and 24% of that of T. betonicum).
Flavour and Fragrance Journal 06/2006; 8(5):277 - 280. · 1.42 Impact Factor
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ABSTRACT: The composition of the essential oils of Thymus capitellatus Hoffmanns. & Link and T. lotocephalus G. López & R Morales was studied by GC and GC–MS. The essential oils of T. capitellatus, isolated either from flowers or from leaves of the plant during its vegetative phase, showed a more or less similar composition, but the corresponding oil from T. lotocephalus showed marked differences. The oils of both species consisted mainly of oxygen-containin monoterpenes (55–69% of the total oils). 1,8-Cineole (50–56%) was the main component of the oils of T. capitellatus both in the oil from its flowers and in that from its leaves.The oil isolated from the flowers of T. lotocephalus was dominated by linalyl acetate (23%); the other major components were linalol (11%) and 1,8-cineole (10%). However, in the oil from the leaves of this species 1,8-cineole (24%) was again the major component, while linalyl acetate and linalol amounted to 5% and 6% respectively Although present in relatively small amounts, sesquiterpenes were more important in the oils of T. lotocephalu (15–17%) than in those of T. capitellatus (3–4%). The presence of 1,8-cineole, in relatively large amounts, in the oil analysed was in agreement with the earlier finding of this compound as major component of other Iberian thyme oils However, the oil isolated from flowers of T. lotocephalus must be considered as being characterized by linalyl acetate, linalol instead of by 1,8-cineole.
Flavour and Fragrance Journal 06/2006; 8(1):53 - 57. · 1.42 Impact Factor
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ABSTRACT: The composition of the essential oils from leaves and from flowers of Achillea millefolium L. ssp. millefolium was analysed by GC and GC-MS. During the flowering period of the plant, both oils consisted mainly of monoterpenes (about 80%). 1,8-Cineole was the dominant component in the oils from the flowers (29%) and from the leaves (25%), while sabinene was the second most important component in the oil from the flowers (15%) and trans-sabinene hydrate in that from the leaves (10%). The sesquiterpene fraction was in both cases dominated by germacrene-D (0.7% in the oil of the flowers and 7% in the leaf oil).In the essential oil isolated from leaves collected during the vegetative phase, the monoterpene fraction was small (<3%), whereas sesquiterpenes amounted to 92%, germacrene-D being the major component (65%) of the oil.
Flavour and Fragrance Journal 04/2006; 7(4):219 - 222. · 1.42 Impact Factor
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ABSTRACT: The seasonal variation in the composition of the essential oil of seafennel, Crithmum maritimum L., was studied by GC and GC-MS. Monoterpenes were found to be the major components of the oil, amounting to 97%. The sesquiterpenes were present in a relatively small amount, constituting up to 2% of the total oil.Although all monoterpenes showed fluctuations in their relative amounts, the most conspicuous ones were recorded for sabinene (7-42%) and γ-terpinene (26-55%). For the sesquiterpenes and for dillapiole, the only substituted phenylpropane derivative identified in this oil, of which the concentration ranged from 0.1% to 7%, no defined pattern of fluctuation was observed.
Flavour and Fragrance Journal 04/2006; 7(3):147 - 150. · 1.42 Impact Factor
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ABSTRACT: The composition of the essential oils from different aerial parts of Lavandula pinnata L. fil. var. pinnata was analysed by GC and GC-MS. The oils were isolated separately from flowering tops, and from leaves and stems collected during the flowering period and the vegetative phase of the plant. The three oil samples consisted mainly of monoterpene hydrocarbons (37-80%), whereas oxygen-containing monoterpenes were hardly present (2-4%). β-Phellandrene (12-32%) was the main component of the oils analysed, and α-phellandrene (6-l6%) the second most important monoterpene. The sesquiterpene fraction of the oils (13-22%) was also characterized by hydrocarbons of which β-caryophyllene (11% of each oil) formed the major part. Phenylacetaldehyde amounted to 6-9% of the leaf oils. Common major components of lavender oils were not found in the oils or were present in very small amounts only.
Flavour and Fragrance Journal 04/2006; 10(2):93 - 96. · 1.42 Impact Factor
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ABSTRACT: The composition of the essential oil isolated from inflorescences of Nepeta tuberosa L. ssp. tuberosa was analysed by GC and GC-MS. The oil consisted mainly of monoterpenes (89%), 5,9-dehydronepetalactone (69%) and geranyl acetate (17%) being the main components. The sesquiterpene fraction amounted to 8% and was dominated by α-caryophyllene (5%).
Flavour and Fragrance Journal 04/2006; 9(2):71 - 73. · 1.42 Impact Factor
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ABSTRACT: The composition of the essential oils isolated from the aerial parts of Micromeria varia Benth. ssp. thymoides (Sol. ex Lowe) Pérez var. thymoides, collected during the vegetative phase and the flowering period of the plant, was analysed by GC and GC-MS. Both oils consisted mainly of monoterpenes (62-69%), α-pinene being the major component (20-35%). Geranial (16%) and trans-nerolidol (15%) were the second and third most important constituents of the oil from the aerial parts collected during the vegetative phase of the plant, and β-caryophyllene epoxide (12%) and β-caryophyllene (10%) during the flowering period. The sesquiterpene fraction amounting to 27% of both oils, was dominated by trans-nerolidol (15%) during the vegetative phase, and by β-caryophyllene epoxide (12%) during the flowering period of the plant.
Flavour and Fragrance Journal 04/2006; 10(3):199 - 202. · 1.42 Impact Factor
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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.
Journal of Medicinal Food 02/2006; 9(1):128-30. · 1.41 Impact Factor
