Teucrium Chamaedrys Research Articles

Antioxidant efficacy of iridoid and phenylethanoid glycosides from the medicinal plant Teucrium chamaedris in cell-free systems

Twelve glycosides, seven iridoids and five phenylethanoids, have been isolated from leaf and root methanolic extracts of Wall Germander ( Teucrium chamaedrys), a Mediterranean species historically used as a medicinal plant. Among them, three iridoid and one phenylethanoid glycosides have been isolated and characterized for the first time. All of the structures have been elucidated on the basis of their spectral data, especially 1D and 2D NMR experiments. The antioxidative properties of pure metabolites, as well as of crude organic extracts of the plant, have been analyzed on the basis of their DPPH radical scavenging capability. The antioxidant capacity in cell-free systems of the isolated metabolites was carried out by measuring their capabilities to inhibit the synthesis of thiobarbituric acid reactive species in assay media using as oxidable substrates a vegetable fat and the pentose sugar 2-deoxyribose and to prevent oxidative damage of the hydrosoluble bovine serum albumin (BSA) protein. Phenylethanoid glycosides resulted efficacious DPPH radical, while iridoid glycosides prevent massively the 2-deoxyribose and BSA oxidations in assay media.

Potential allelopathic effect of neo-clerodane diterpenes from Teucrium chamaedrys (L.) on stenomediterranean and weed cosmopolitan species

The allelopathic effects of neo-clerodane diterpenes, isolated from Teucrium chamaedrys (L.), have been evaluated on the seed germination and seedling growth of four coexisting Mediterranean species ( Dactylis hispanica, Petrorhagia velutina, Phleum subulatum and Petrorhagia saxifraga) and two cosmopolitan weeds ( Amaranthus retroflexus and Avena fatua). All of the structures have been elucidated on the basis of their spectroscopic features. The bioassays data, analyzed by principal component analysis, showed more negative effects on weeds respect to coexisting species. Moreover D. hispanica, P. velutina, P. subulatum showed both stimulating or inhibiting effects depending on the type of metabolite and the concentration used in the test.

Morphological Variation inTeucrium chamaedrysin Serpentine and Non-Serpentine Populations

Abstract - Teucrium chamaedrys is the most variable species in the genus Teucrium, fitting Kruckeberg's category of a bodenvag species. Six populations distributed on serpentine and 3 populations off serpentine were investigated, and 23 morphological features were studied by univariate and multivariate statistical analyses. The variation was higher for the vegetative features and not clearly expressed for the generative ones. In addition, metal concentration in the populations and soil were studied. The species tolerant to the serpentine conditions demonstrated specific morphological differences in stem length, stem length up to the first leave pair, and internode length between second and third leave pairs. Morphological differences, geographical isolation, and preliminary results on the karyology of T. chamaedrys in Bulgaria, suggest that the populations studied were different ecotypes.

Compositions of Essential Oils and Trichomes of Teucrium chamaedrys L. subsp. trapezunticumRech. fil. and subsp. syspirense (C. Koch) Rech. fil.

Teucrium chamaedrys L. is a member of the Lamiaceae family and is represented in the Flora of Turkey by six subspecies. The aerial organs of T. chamaedrys L. subsp. trapezunticum Rech. fil. and subsp. syspirense (C. Koch) Rech. fil. bears numerous eglandular and glandular trichomes. Eglandular trichomes are simple, long-multicellular with cuticular micropapillae, and glandular hairs are of peltate and capitate types. The peltate hairs consist of a basal cell, a short unicellular stalk, and multicellular secretory head, and the capitate ones possess 1-2 stalk cells and one glandular head cell. The aerial parts were subjected to microdistillation for the isolation of volatiles. The analysis was simultaneously performed by using gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The major components were characterized as beta-caryophyllene (18%), nonacosane (12%), germacrene D (11%), caryophyllene oxide (7%), and alpha-pinene (7%) for subsp. trapezunticum, and caryophyllene oxide (23%), alpha-pinene (11%), and caryophyllenol II (5%) for subsp. syspirense.

Ecophysiological adaptations of water relations of Teucrium chamaedrys L. to the hot and dry climate of xeric limestone sites in Franconia (Southern Germany)

Teucrium chamaedrys is a typical plant of dry grassland communities at xeric sites on calcareous soils in Franconia (Southern Germany). The morphological–anatomical appearance of limestone plants in the form of nanism or dwarfing has been interpreted by Gregor Kraus approximately 100 years ago as a consequence of the dry and hot environmental conditions. In the present study the mechanisms of adaptation to drought were evaluated by comparison of water relations of plants growing in the natural habitat at a xeric site in the nature protection area “Grainberg-Kalbenstein und Saupurzel” with plants cultivated at a mesic site in the Botanical Garden of the University of Würzburg. Cuticular water permeances of astomatous leaf sides and minimum conductances of detached leaves were not significantly different between the two growing regimes indicating that there are no intraspecific/phenotypic adaptations in terms of the establishment of a more efficient cuticular transpiration barrier and a more strict regulation of the stomatal aperture as response to the xeric conditions of the limestone site. Pressure–volume analysis of water potential revealed that plants growing at the xeric site exhibited a lower water potential at the turgor loss point and a higher bulk modulus of elasticity. Both parameters emphasise the ability to regain more rapidly a favourable water status at drought by water uptake from the soil and to maintain turgor at lower water potentials. Gas exchange measurements obtained from attached leaves of intact plants under controlled experimental conditions in the laboratory revealed that under drought stress, at water potentials far below the turgor loss point, stomata were only completely closed in the dark. In the light the water loss by stomatal transpiration contributed with values between 60% and 75% to the total water loss. This physiological response was found both for plants grown at the xeric site and plants cultivated at the mesic site. The maintenance of a low but still measurable stomatal conductance under drought stress at maximum light intensity can be interpreted as a mechanism to adjust leaf temperature below the heat resistance limit by transpiration cooling.

Late Neolithic agriculture in eastern Austria: archaeobotanical results from sites of the Baden and Jevišovice cultures (3600–2800 b.c.)

The article presents archaeobotanical results from six late Neolithic excavation sites in eastern Austria. Two of the sites belong to the Jevisovice culture (3200–2800 cal b.c.), the remaining four to the Baden culture (3600–2900 cal b.c.). Results show that farmers around 3000 cal b.c. were relying on the use of Triticum monococcum and Hordeum vulgare as principal cereals, with Triticum dicoccum and Panicum miliaceum as additional crops. Common millet was found in quantity at one of the Jevisovice sites and shows the remarkably early westward spread of this species. Single records of Triticum spelta are discussed in the light of the recently proposed ideas about an independent central European origin of spelt. Another record concerns the “new-type” glume wheat, providing further evidence for the once widespread occurrence of this cultivar. Triticum aestivum (hexaploid naked wheat) and Setaria italica (foxtail millet) were found as rare admixtures at the Jevisovice settlements. Pulses were represented by Pisum sativum and Lens culinaris, oil plants by Papaver somniferum and Linum usitatissimum. One of the Jevisovice sites offered a good opportunity for a study of the undisturbed spatial distribution of charred plant remains within a burnt house. Among wild plants, the occurrence of Stipa sp., Teucrium chamaedrys, Asperula cynanchica and Plantago media point to the presence of dry steppe grassland in the vicinity of the settlements, which was probably used for grazing. Woodland plants were mainly represented by fruit-bearing plants growing in clearings and forest edges, reflecting both the deliberate collection of wild fruits and the growing human impact on the vegetation.

Isolation and characterisation of selected germander diterpenoids from authenticated Teucrium chamaedrys and T. canadense by HPLC, HPLC‐MS and NMR

Teucrium species, such as germander, are rich in neo-clerodane diterpenoids and have been used in traditional folk medicine for their stimulant, diuretic, antipyretic and antiseptic properties. However, the furano neo-clerodane diterpenoids present in germander have been implicated in the in vivo hepatotoxicity of this botanical. In this study, authenticated germander (Teucrium chamaedrys L. and Teucrium canadense L.) was used as the source material. Methanol extracts of powdered plant mate rial were prepared and analysed by HPLC using Synergi Max-RP columns with monitoring at 220 nm. Limited amounts of teucrin A and other diterpenoid standards were analysed on a Synergi Max-RP column in order to determine their retention times and to generate calibration curves. The same standards were subjected to concurrent mass spectral analysis. Teucrin A and diterpenoids such as dihydroteugin, teuflin, teuflidin and teucvidin were tentatively identified in the plant extracts by HPLC-MS and 1H-NMR experiments. For the isolation of teucrium diterpenoids on a semipreparative scale, a solid-phase extraction method was developed for the first time using styrene divinylbenzene and strata-X sorbents for teucrin A and teuflin, respectively. Semi-preparative HPLC of the methanol extract of the powdered aerial parts of Teucrium plants was carried out on a semipreparative Synergi Max-RP column with photodiode array detection in order to confirm the identities of some diterpenoids by HPLC-MS and NMR.

Determination of Teucrium chamaedrys volatiles by using direct thermal desorption–comprehensive two-dimensional gas chromatography–time-of-flight mass spectrometry

The direct qualification and quantification of the volatile components of Teucrium chamaedrys was studied using a direct thermal desorption (DTD) technique with comprehensive two-dimensional (2D) gas chromatography–time-of-flight mass spectrometry (GC × GC–TOF/MS). The GC × GC separation chromatographically resolved hundreds of components within this sample, and with the separation coupled with TOF/MS for detection, high probability identifications were made for 68 compounds. The quantitative results were determined through the use of internal standards and the desorption of differing amounts of raw material in the injector. The highest yield of volatile compounds (0.39%, w/w) was obtained at 150 °C thermal desorption temperature using 1.0 mg of dried sample placed in a glass injector liner when studied over the range 1.0–7.0 mg. Lowest yield of 0.33% (w/w) was found for the largest sample size of 7.0 mg. Relative standard deviation (RSD) for 10 replicates at each size sample were in the range 3.9–21.6%. The major compounds identified were β-pinene, germacrene D, α-pinene, α-farnesene, α-gurjunene, γ-elemene and γ-cadinene. All identified compounds were quantified using total ion chromatogram (TIC) peak areas. DTD is a promising method for quantitative analysis of complex mixtures, and in particular for quantitative analysis of plant samples, which can yield data without the traditional obligation for costly and time-consuming extraction techniques.

Antioxidant Properties of Some Medicinal Lamiaceae (Labiatae) Species

In this study, antioxidant properties of Thymus sipyleus. Boiss. subsp. sipyleus. var. sipyleus., Teucrium chamaedrys L.., Mentha longifolia. (L.) Hudson subsp. longifolia., Salvia limbata. C.A. Meyer, and Thymus fallax. Fisch. & Mey. were investigated. Antioxidant and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities, reducing powers, and the amount of total phenolic compounds of the extracts were studied. The highest antioxidant activity was shown by T. chamaedrys. (decoction, IC50: 9.2 µg/ml), and the lowest one was S. limbata. (decoction, IC50: 619.5 µg/ml). The highest DPPH radical scavenging activity was shown by T. fallax. [decoction, IC50S: 56 µg/ml (IC50S is the extract concentration (µg/ml) required for 50% inhibition of the DPPH solution absorbance at 517 nm)] while the lowest one was S. limbata. (decoction, IC50S: 335.8 µg/ml). The highest reducing power and amount of total phenolic compounds was shown by T. chamaedrys. (decoction, 29.9 µg/ml ascorbic acid equivalent, 27.9 µg/ml gallic acid equivalent, respectively), and the lowest one was S. limbata. (decoction, 5.1 µg/ml ascorbic acid equivalent, 9.9 µg/ml gallic acid equivalent, respectively) at 250 µg/ml extract concentration.

Chemical Composition and Antimicrobial Activities of the Essential Oils of Teucrium chamaedrys. subsp. chamaedrys., T. orientale. var. puberulens., and T. chamaedrys. subsp. lydium.

The composition of the essential oils obtained from the air-dried Teucrium chamaedrys. L. subsp. chamaedrys., Teucrium orientale. L. var. puberulens., and Teucrium chamaedrys. L. subsp. lydium. (Lamiaceae) were analyzed by GC-MS. Thirty-six, 35, and 33 components were identified in the essential oils, and germacrene D (16.7%) was the most abundant constituent in T. chamaedrys. subsp. chamaedrys., and β-caryophyllene was the most abundant component in both T. orientale. var. puberulens. and T. chamaedrys. subsp. lydium. in the ratios 21.7% and 19.7%, respectively. The isolated essential oils of the plants were tested for antimicrobial activity and showed moderate antibacterial activity against Gram-positive and Gram-negative bacteria, but no antifungal activity was observed against two yeast-like fungi.

The essential oil composition ofTeucrium chamaedrys L. from Iran

The composition of the essential oil obtained from the dried flowering aerial parts of Teucrium chamaedrys (Labiatae) was analysed by GC and GC–MS. Forty-nine components were identified in the this oil. The major constituents of the essential oil were germacrene D (16.5%), (Z)-β-farnesene (12.2%), β-caryophyllene (10.5%), α-pinene (9.1%) and δ-cadinene (7.4%). Copyright © 2005 John Wiley & Sons, Ltd.

Analysis by high-performance liquid chromatography of teucrin A in beverages flavoured with an extract of Teucrium chamaedrys L.

Due to its liver toxicity, the medicinal use of germander (Teucrium chamaedrys L.) was banned in some countries. Nevertheless, alcoholic extracts are still permitted as flavour ingredients since they are fundamental in providing a bitter aromatic taste. Teucrin A represents the substance of major concern regarding the potential toxicity of germander. Hence, teucrin A represents the best analytical and toxicological marker of alcoholic extracts of T. chamaedrys. A sensitive high-performance liquid chromatography method to detect teucrin A in beverages is reported. Teucrin A was prepared by isolation from the plant extract using column chromatography and crystallization. The identity and purity (99%) were established by melting point, nuclear magnetic resonance and liquid chromatography-mass spectrometry. The high-performance liquid chromatography procedure was validated and its intra- and interday performance was established (relative standard deviation ≤13% and error ≤10%). In-house validation was carried out by analysing samples of beverages not containing T. chamaedrys spiked with a range of concentrations of teucrin A. The limit of detection was 0.1 ppm and the limit of quantification was 0.3 ppm. Teucrin A accounted for about 70% of the neo-clerodane diterpenoids found in the total extract of a specimen of T. chamaedrys. The content (± standard deviation) in 18 batches of different geographical origin was 2338 ± 740 ppm, per cent coefficient of variation = 32, minimum–maximum = 999−3445 ppm. The mean level of teucrin A in 10 bottles of the same brand was 6.1 ± 0.8 ppm, per cent coefficient of variation = 12. In 10 different brands found on the Italian market, the content of teucrin A ranged from not detectable to 10 ppm.

Would Sacaca, Croton cajucara Benth (Euphorbiaceae) be an hepatotoxic plant like Germander, Teucrium chamaedrys L. (Labiatae)?

Clinical and experimental studies have consistently incriminated the medicinal plant germander (Teucrium chamaedrys L.) in epidemic and sporadic cases of liver diseases. The sacaca (Croton cajucara Benth), a common plant in Brazilian Amazon region also comes being incriminated in similar clinical cases. Of both plants were isolated diterpenoid compounds with similar chemical structures.

Constituents of aromatic plants: teucrin A

Teucrium chamaedrys L. (Labiatae), a herb used to combat obesity, can occasionally cause hepatitis. All mutagenicity tests done were negative. After 13 weeks of administration by oral route in Sprague Dawley rats T. chamaedrys proved to be well tolerated at 0.056 g kg −1 day −1 (i.e. 0.4 mg kg −1 day −1 of teucrin A). At this dose the compound induced minor effects on body weight of both males and females and slight, reversible liver changes, confined to females, which mainly consisted of hepatocellular hypertrophy. This modification, in absence of other morphological findings can be considered an adaptative metabolic, rather than toxic effect.

Neo-clerodane diterpenoids and phenylethanoid glycosides from Teucrium chamaedrys L.

A neo-clerodane type diterpenoid, 12( S)-15,16-epoxy-19-hydroxy- neo-cleroda-13(16),14-dien-18,6α:20,12-diolide, and two phenylethanoid glycosides, teucrioside-3⁗- O-methylether and teucrioside-3⁗,4⁗- O-dimethylether were isolated from the aerial parts of Teucrium chamaedrys. Their structures were identified on the basis of extensive NMR spectra, LC-ESIMS analysis, and molecular modeling studies.

The Effects of Light on Callus Growth and Somatic Embryogenesis from Lavandula vera and Teucrium chamaedrys: A Preliminary Study

SUMMARY In order to investigate the effect of light on the tissue culture of lavender (Lavandula vera L.) and wall germander (Teucrium chamaedrys L.), leaf explants from greenhouse-grown plants were inoculated on a Murashige and Skoog (MS) medium (1) supplemented with 1 mg L−1 2,4-D and 2 mg L−1 kinetin and incubated either (i) continuously in the darkness for 6 weeks or (ii) first in the darkness for 0–5 weeks and then under illumination (150 μmol mr−2 s−1, 16 hour light/8 hour dark photoperiod). Lavender callus growth was improved under increased incubation in darkness while somatic embryogenesis was remarkably reduced under the same conditions. Incubation in darkness did not affect the growth of wall germander cultures, but improved somatic embryogenesis. Moreover, a possible participation of boron in the effect of light on somatic embryogenesis for both species was indicated.

Hepatotoxizität von Arzneimitteln pflanzlichen Ursprungs

Herbal drugs are widely used and often contain highly active pharmacological compounds. Recently, reports have mounted about hepatotoxicity of herbal remedies which ranges from mild liver enzyme alterations to chronic liver disease and liver failure. Hepatotoxicity of Chinese herbs has been recognized, e.g. during treatment of patients with atopic eczema. However, the toxic compounds remain to be determined. Hepatic veno-occlusive disease may result from pyrrolizidine alkaloids which are contained in numerous plants worldwide. Teucrium chamaedrys, commonly referred to as germander, may cause hepatitis and even liver cirrhosis. Significant hepatotoxicity has also been observed after the ingestion of chaparral. Recently, greater celandine, which is widely used for biliary disorders and dyspepsia, was identified as a cause of cholestatic hepatitis. Hepatotoxic reactions have also been observed after the ingestion of Atractylis gummifera, Callilepsis laureola, Senna, Kavapyrone and Pulegium. The aim of this review is to summarize potentially hepatotoxic herbal remedies, to further elucidate their mechanisms of toxicity and thereby underline the likelihood of plants to be the cause of liver damage.

Hepatitis aguda por ingestión de infusiones con Teucrium chamaedrys

Herbal remedies, used for many years for therapeutic purposes, have traditionally been considered safe and effective. Herbal medicine toxicity has been infrequently reported in Spain. We present two cases of acute hepatitis after ingestion of herbal infusions over a period of several months. Among the plants consumed was Teucrium chamaedrys (germander), which has been associated with several cases of hepatotoxicity, mainly in France. After ruling out other causes of hepatitis, we consider that Teucrium chamaedrys provoked the disease. One patient presented acute, cholestatic hepatitis and another presented mixed (hepatocellular and cholestatic) hepatitis. In both patients, the disease was resolved after discontinuing the intake of the herbal teas. We believe that herbal medicine toxicity may be increasing due to the growing consumption of these products. Finally, we emphasize the need to rule out the intake of herbal remedies in patients whose liver tests present abnormalities.

Hepatotoxicity of botanicals.

Hepatic impairment resulting from the use of conventional drugs is widely acknowledged, but there is less awareness of the potential hepatotoxicity of herbal preparations and other botanicals, many of which are believed to be harmless and are commonly used for self-medication without supervision. The aim of this paper is to examine the evidence for hepatotoxicity of botanicals and draw conclusions regarding their pathology, safety and applications. Current literature on the hepatotoxicity of herbal drugs and other botanicals is reviewed. The aetiology, clinical picture and treatment of mushroom (Amanita) poisoning are described. Hepatotoxic effects have been reported for some Chinese herbal medicines (such as Jin Bu Huan, Ma-Huang and Sho-saiko-to), pyrrolizidine alkaloid-containing plants, germander (Teucrium chamaedrys), chaparral (Larrea tridentata), Atractylis gummifera, Callilepsis laureola, and others. The frequency with which botanicals cause hepatic damage is unclear. There is a lack of controlled treatment trials and the few studies published to date do not clarify the incidence of adverse effects. Many plant products do not seem to lead to toxic effects in everyone taking them, and they commonly lack a strict dose-dependency. For some products, such as Sho-saiko-to, the picture is confused further by demonstrations of hepatoprotective properties for some components. Mushroom poisoning is mostly due to the accidental consumption of Amanita species. Treatment with silymarin, thioctic acid, penicillin and liver transplantation have been shown to be effective but require early diagnosis. Severe liver injury, including acute and chronic abnormalities and even cirrhotic transformation and liver failure, has been described after the ingestion of a wide range of herbal products and other botanical ingredients, such as mushrooms. It is concluded that in certain situations herbal products may be just as harmful as conventional drugs.

LIVER INJURY FROM HERBS AND OTHER BOTANICALS

Many prescription medications have well known hepatotoxic potential. The spectrum of drug-related hepatotoxicity can range from subclinical liver disease with mildly abnormal liver chemistry tests to fulminant hepatic failure (FHF) requiring liver transplantation. Less well recognized is the hepatotoxicity associated with certain over-the-counter preparations, herbal remedies, and naturally occurring plants. The major aspects of herbal medicine-induced liver injury will herein be summarized along with the hepatotoxicity seen with mushroom poisoning, aflatoxin and cocaine ingestion. These herbal and botanical hepatotoxins are shown below. Lastly, the potential hepatoprotective effects of certain herbal preparations will be explored. Herbal Preparations, Medicinal Plants and Other Botanicals with Hepatotoxic Potential Crotalaria Heliotropium Mate' (Paraquay) tea Senecio Symphytum officinale (Comfrey) Ackee fruit Atractylis gummifera Azadirachza indica Berberis vulgaris Callillepsis laureola Cassia angustifolia (Senna) Cocaine (Erythroxylon coca) Cycasin Hedeoma pulegoides and Mentha pulegium (Pennyroyal) Larrea tridentata (Chapparal, creosote bush, greasewood) Sassafras albidum (Sassafras) Scutellaria (Skull cap) Teucrium chamaedrys (Germander) Teucrium polium Valeriana officinalis (Valerian) Viscum album (Mistletoe) Lycopodium serratum (Jin Bu Huan) Ma-huang Syo-saiko-to (Xiao-chai-hu-tang)