Biological activities of Teucrium flavum L., Teucrium fruticans L., and Teucrium siculum rafin crude extracts

The genus Teucrium (Lamiaceae) includes 300 species widespread all around the world, which are perennial herbs or shrubs commonly, named germanders. In Italy, Teucrium flavum L., Teucrium fruticans L., and Teucrium siculum Rafin are mostly present in Liguria, Sicily, and Sardegna. Teucrium species are characterized by mono and sesquiterpene hydrocarbons, flavonoids, fatty acid esters, and essential oils. Many species of this genus show antioxidant, antimicrobial, and antifungal activities, rendering them useful as natural preservative ingredients. In view of the interesting biological properties reported for Teucrium spp., in this study we determined the total phenol and flavonoid content of inflorescence extracts of T. flavum L., T. fruticans L., and T. siculum Rafin. In addition, we investigated the in vitro antioxidant and antibacterial activities of inflorescence extracts against pathogenic bacteria. Obtained results demonstrated that extracts had in vitro antioxidant activity and showed antimicrobial ability against Gram-positive and Gram-negative strains albeit with different effectiveness probably due to the different qualitative/quantitative composition of the extract also suggesting that these extracts might be useful in preventing several diseases in which oxidative stress may represent an important pathogenic mechanism.     

A morphological,caryological and morphometrical analysis of Teucrium euganeum Vis. and its allies

The aim of the present study is to clarify the taxonomic position of Teucrium euganeum Vis. vis à vis T.siculum (Rafin.) Guss. and T.scorodonia L. The study is based on an analysis of macro- and micro-morphological characters, type, and distribution of trichomes in different parts of the plant, chromosome counts, and a statistical analysis of such morphometric data. The results of the study allow one to consider the populations of the Euganean Hills (Padua, north-eastern Italy) as a sub-species of T.siculum, and, therefore, a new combination is proposed: Teucrium siculum (Rafin.) Guss. subsp. euganeum (Vis.) Tornadore, comb. et stat.nov.     

Teucrium francoi M. Seq., Capelo, J.C. Costa & R. Jardim, a new species of Teucrium gr. scorodonia (Lamiceae) from Madeira

The species formerly recognized as Teucrium scorodonia in Madeira is here described as new: Teucrium francoi M. Seq., Capelo, J.C. Costa & R. Jardim. Morphologically close to species of Teucrium gr. scorodonia [ T. scorodonia L., T. pseudoscorodonia Desf., T. siculum (Raf.) Guss. and T. kotschyanum Poech], it exhibits, nonetheless, some distinct diagnostic characters. The indumentum density and type of hairs of T. francoi are clearly distinct from those of related species, as are the shape and dimensions of the leaves and bracts, calyx, and corolla, which are all taken as taxonomically significant diagnostic features. A diagnosis and a distribution map are presented for this new species. Morphology, ecology, biogeography, and conservation issues are discussed. Teucrium francoi , which is an endemic from Madeira (Portugal), is to be found mostly in the scope of the association Teucrio francoi–Origanetum virentis J.C. Costa, Capelo, Jardim, Sequeira, Lousã & Rivas-Martínez, but also occurs in somewhat humid habitats, such as open stands of Rosa mandonii Déségl. associated with small streams.  © 2008 The Linnean Society of London, Botanical Journal of the Linnean Society , 2008, 156 , 639–647.     

Micromorphological and phytochemical characters ofTeucrium marum andT. subspinosum (Labiatae) from Sardinia and Balearic Islands

Micromorphology and distribution of trichomes in different plant parts ofTeucrium marum andTeucrium subspinosum from Sardinia and the Balearic Islands are described. The composition of volatile compounds in the same plants has also been studied. The occurrence in Sardinia of two differentT. marum entities is evidenced. One of them, growing in the NW. part of the island, is very similar toT. marum from Minorca.T. subspinosum from Sardinia and Majorca differ for the presence in the last one of short capitate hairs and for a higher ratio of dolichodial/teucrein. While the degree of variability of all the characters is very high, there is a good homogeneity between all the taxa, due to the presence of monoterpene cyclopentanoids not found until now in other species.     

Antimutagenic and Antioxidant Potentials of Teucrium ramosissimum Essential Oil

The mutagenic and antimutagenic effects of the essential oil extracted from the aerial parts of Teucrium ramosissimum were evaluated by the bacterial reverse mutation assay in Salmonella typhimurium TA98, TA100, and TA1535, with and without exogenous metabolic activation (S9 fraction). The T. ramosissimum essential oil showed no mutagenic effect. In contrast, our results established that it possessed antimutagenic effects against sodium azide (SA), aflatoxin B1 (AFB1), benzo[a]pyrene (B[a]P), and 4‐nitro‐o‐phenylenediamine (NOPD). The antioxidant capacity of the tested essential oil was evaluated using enzymatic, i.e., the xanthine/xanthine oxidase (X/XOD) assay, and nonenzymatic systems, i.e., the nitro‐blue tetrazolium (NBT)/riboflavin and the DPPH assays. A moderate free radical‐scavenging activity was observed towards DPPH^. and O$\rm{{_{2}^{{^\cdot} -}}}$ . In contrast, T. ramosissimum essential oil showed no effect for all the tested concentrations in the X/XOD assay.     

Comparative study of genotoxicity and antimutagenicity of methanolic extracts from Teucrium chamaedrys and Teucrium montanum in human lymphocytes using micronucleus assay

Since Teucrium chamaedrys and Teucrium montanum are the most popular plants used in the treatment of many diseases, we evaluated genotoxic potential of their methanolic extracts on cultured human peripheral blood lymphocytes (PBLs) using cytokinesis-block micronucleus (MN) assay. Cultures were treated with four concentrations of both plants (125, 250, 500 and 1,000 μg/ml), both separately and in combination with mitomycin C (MMC). The results revealed that extract of T. chamaedrys administered at the tested concentrations did not significantly affect the mean MN frequency in comparison to untreated cells. Methanolic extract of T. montanum increased the mean MN frequency in PBL at the tested concentrations, but significantly only at the concentration of 1,000 μg/ml. In all tested concentrations, the extract of T. chamaedrys significantly reduced the MMC-induced MN frequency, in a dose dependent manner (r = − 0.687, p < 0.01). The extract of T. montanum decreased the MMC-induced MN frequency at the tested concentrations, but statistically only at 125 μg/ml. Both extracts administered alone did not significantly affect the nuclear division index (NDI) at the tested concentrations. In the combined treatments with MMC, the extract obtained from T. chamaedrys in the concentrations of 500 and 1,000 μg/ml significantly decreased NDI values in comparison to MMC-treated cells alone, while the extract of T. montanum significantly decreased NDI at all tested concentrations. Both extracts nonsignificantly decreased NDI at all tested concentrations in comparison to untreated cells. Our results suggest the important function of T. chamaedrys extract in cancer therapy, this methanolic extract may prevent genotoxic effects of chemotherapy in PBLs.     

Anatomy, palynology and nutlet micromorphology of Turkish endemic Teucrium sandrasicum (Lamiaceae)

In this study, the anatomical features of the leaf and stem, besides the pollen and nutlet characteristics of Teucrium sandrasicum are investigated. T. sandrasicum, belonging to sect. Teucrium, is an endemic perennial herb growing on serpentine around Muğla province. The anatomical studies on T. sandrasicum revealed that the stem shares the general characteristics of the Labiatae family. The leaves clearly exhibit xeromorphy due to features such as the distribution of stomata on the lower surface (hipostomatic), the occurrence of guard cells below the epidermis (xeromorphic type), inrolled margins, thick cuticle layer, thick outer epidermal cell wall, a high density of trichomes and thick palisade layer of the mesophyll. The anatomical studies showed that the upper epidermal cells of the leaf include many spherocrystals. The pollen grains are prolate, medium in size, 3-colpate with verrucate ornamentation. The nutlets are ellipsoid with a reticulate-verrucate surface. The results have proven that T. sandrasicum is different from the other species of the sect. Teucrium because of the branched trichomes on the stem and the lack of eglandular trichomes on the nutlets.     

Structure elucidation and hepatotoxicity evaluation against HepG2 human cells of neo-clerodane diterpenes from Teucrium polium L

Seven neo-clerodanes (teupolins VI–XII) and eleven known compounds were isolated and characterized from leaf extracts of Teucrium polium L., a medicinal plant used in traditional and herbal medicine for its hypolipidemic, hypoglycemic, antioxidant and antiproliferative properties. The structures of these compounds were elucidated by 1D (¹H, ¹³C and DEPT) and 2D (COSY, TOCSY, HSQC, HMBC) NMR experiments and by mass spectrometry analysis. The complete stereostructure of each compound was defined with a NOESY experiment. Because the overexploitation of herbal remedies containing T. polium extracts has resulted in several cases of hepatitis, the hepatotoxic activity of pure metabolites against the human hepatoblastoma cancer cell line HepG2 was assessed by the MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) test. All of the compounds showed low toxicity values at the highest concentration tested (200 μM).     

Chemical Diversity of Volatiles of Teucrium orientale L. var. orientale,var. puberulens,and var. glabrescens Determined by Simultaneous GC‐FID and GC/MS Techniques

In the present work, three varieties of Teucrium orientale, var. orientale, var. puberulens, and var. glabrescens, were collected and investigated for chemical composition of the oils. Subsequent gas chromatography (GC‐FID) and gas chromatography coupled to mass spectrometry (GC/MS) revealed high abundance of sesquiterpenes in the essential oils analyzed. All the oils contained β‐caryophyllene (22.6, 8.5, and 6.3%, resp.) and hexadecanoic acid (7.9, 12.8, and 13.1%). Germacrene D (24.6 and 33.4%) and bicyclogermacrene (6.7 and 8.5%) were found to be the main constituents of var. orientale and var. puberulens, respectively. The high percentages of β‐cubebene (26.9%), α‐cubebene (9.0%), and α‐copaene (7.2%) established the diversity of var. glabrescens. The qualitative difference between the essential oils allowed the differentiation between the varieties in agreement with the morphological observations described in Flora of Turkey for each variety studied. In addition, a cluster analysis of twelve Teucrium taxa based on the essential‐oil composition has been carried out. Hovewer, the analysis did not clearly reflect the infrageneric classification of the genus, it largely confirmed the relationships between the infraspecific taxa of Teucrium orientale and T. chamaedrys.     

香科科属植物化学成分及生物活性研究进展

近年来学术界对香科科属植物的化学成分和生理活性给予了很大关注。从该属植物中分离得封有萜类、黄酮类、苯丙素类化合物,生物活性测试表明该属植物具有抗氧化、抗菌消炎、解热镇痛、利胆利尿、降糖降压等活性,对昆虫具有拒食作用。本文综述了2000年来香科科属20余种植物成分及生物活性研究进展,为该属植物的研究与利用提供理论依据。     

Neo-clerodane diterpenes from Teucrium fruticans

In addition to three out of the four previously reported neo-clerodanes already found in Teucrium fruticans (fruticolone, isofruticolone and 8 beta-hydroxyfruticolone), and 6-acetylteucjaponin B (isolated from T. scordium and T. grisebachii), four new neo-clerodanes, namely 7 beta-hydroxyfruticolone, 11-hydroxyfruticolone, deacetylfruticolone and 6-acetyl-10-hydroxyteucjaponin B were also isolated. The structures were unambiguously elucidated based on extensive NMR spectral studies (one- and two-dimensional experiments). Semi-prep-HPLC proved to be a convenient purification procedure, occasionally being followed by TLC. The new compounds were assayed against Spodoptera littoralis and two of them were shown to have potent antifeedant activity.     

Taxonomic reinstatement of Teucrium andrusi from T. paederotoides based on morphological and anatomical evidences

Teucrium andrusi, described by Post from Mardin province, Turkey, was synonimized with T. paederotoides in the flora of Turkey. According to the records in the flora of Turkey T. paederotoides was a steno‐endemic species, only known from the type locality in Gaziantep and from Mardin province. Specimens of T. paederotoides s.l. were collected from both localities and a detailed comparison of the plants from Gaziantep with those from Mardin revealed that the two populations were sufficiently distinct from each other to be recognised as separate species. Thus, T. andrusi Post is reinstated from the synonymy with T. paederotoides. Teucrium andrusi is morphologically different from T. paederotoides s.s. in terms of its general indumentum, leaf margin, bract and calyx shape, corolla colour and nutlet macro–micromorphology. It can be anatomically distinguished from T. paederotoides s.s. by stoma type, stomatal distribution on the leaf surface, crystal content in the cells and cuticula thickness. Ecological data related with the accompanying species also support species status for T. andrusi. While the two taxa are very similar in pollen and nutlet morphology, trichome density on the nutlets are different.     

Developmental instability in gynodioecious Teucrium lusitanicum

Developmental instability was assessed in two geographical races of Teucrium lusitanicum using morphometric measures of vegetative and reproductive structures. T. lusitanicum is a gynodioecious species. Male sterile (female) individuals showed greater developmental instability at all sites. Plants located inland had higher developmental instability of vegetative characters and lower developmental instability of reproductive characters than coastal plants. These results support the contentions that (1) developmental instability is affected more by the disruption of co-adapted gene complexes than by lower heterozygosity, and (2) different habitat characteristics result in the differential response of vegetative and reproductive structures.     

Teucrium scabrum (Lamiaceae), a new species from Thailand

Summary   Teucrium scabrum (Lamiaceae), a new species from the western part of Thailand, related to T. quadrifarium Buch.-Ham. and T. viscidum Blume is described and illustrated, and a distribution map is provided.     

Chemotaxonomic Importance of the Essential‐Oil Composition in Two Subspecies of Teucrium stocksianum Boiss. from Iran

The hydrodistilled essential oils obtained from aerial flowering parts of Teucrium stocksianum ssp. stocksianum (TSS) and T. stocksianum ssp. gabrielae (TSG) from Iran were analyzed by capillary GC and GC/MS. The oil analysis of two subspecies led to the identification of 65 compounds that accounted for 93.3 and 95.1% of the total oil compositions, respectively. Sesquiterpenoids (52.9%) constituted the main compounds in the essential oil of TSS represented mainly by cis‐sesquisabinene hydrate (12.0%), followed by epi‐β‐bisabolol (6.6%), guaiol (5.4%), and β‐eudesmol (4.4%), whilst monoterpenoids (61.2%) were found to be the major components of the oil of TSG, represented by α‐pinene (23.0%), β‐pinene (13.0%), myrcene (6.3%), and sabinene (6.3%). The principal component in both subspecies, TSS and TSG, was α‐pinene (22.0 and 23.0%, resp.) and β‐pinene (6.5 and 13.0%, resp.). epi‐α‐Cadinol, myrcene, and sabinene, which were detected as principal compounds of TSG, were characterized in lower amounts (<1.5%) in the oil of TSS. Seven components were identified in the oil of TSS corresponding to 25.9% of total oil, which were totally absent in the oil of TSG, of which cis‐sesquisabinene hydrate (12.0%), guaiol (5.4%), and β‐eudesmol (4.4%) were in considerable amounts. Taxonomic position of the subspecies is discussed on the basis of phytochemical data.     

Chemotaxonomy of Serbian Teucrium species inferred from essential oil chemical composition: the case of Teucrium scordium L. ssp. scordioides

The volatile constituents of Teucrium scordium L. ssp. scordioides, T. polium, and T. montanum, obtained by hydrodistillation, were investigated by GC-FID and GC/MS analyses. A total of 296 constituents were identified, representing 89.8-98.4% of the oil compositions. The oils of T. polium and T. montanum consisted mainly of sesquiterpenes (64.3 and 72.7%, resp.), with germacrene D (4; 31.0%) and δ-cadinene (10; 8.1%) as the main constituents, respectively. In contrast, the monoterpene menthofuran (1; 11.9%) predominated in the oil of T. scordium ssp. scordioides, and this clearly distinguished this species from the other Teucrium taxa investigated up to date. The chemistry of the volatiles of eight Teucrium taxa from Serbia and Montenegro were compared using multivariate statistical analysis, and this provided chemotaxonomically important conclusions.     

Biodiversity characteristics of Teucrium polium species in Saudi Arabia

Teucrium (Lamiaceae) is a large and polymorphic genus distributed mainly in Europe, North Africa and in the temperate parts of Asia. In this study, the anatomical features of the leaf and stem of Teucrium polium are investigated. Teucrium has 19 taxa in Iran, which mainly grow in the Irano-Turanian region between 700 and 2000 m above sea level. T. polium belonging to sect. Polium, is a perennial herb growing on Lorestan province. The leaves clearly exhibit xeromorphy due to features such as thick cuticle layer, thick outer epidermal cell wall, high density of trichomes and thick palisade layer of the mesophyll. Anatomical studies on T. polium revealed that the stem shares the general characteristics of the Labiatae family. The aim of our approach was to study the morphological and taxonomical parameters for T. polium in Saudi Arabia. The results of this study showed that there was no influence of environment on the structure of stomata and trichomes as studying species with T.polium. In conclusion our study shows we have studied the geographical distribution of the species in Saudi Arabia and in the world.     

Volatile compounds from some wild growing aromatic herbs of the Lamiaceae from southern France

Abstract

The composition of the volatile fraction in selected aromatic plants of the Lamiaceae from garrigue sites in southern France is described. Calamintha nepeta appeared heterogeneous. The oil was dominated by piperitone oxide, and piperitenone oxide or by pulegone and menthone. In Nepeta nepetella, nepetalactone, almost exclusively the (4a-α, 7α, 7a-β)-isomer, made up more than 85% of the essential oil. Dichloromethane extracts from Teucrium polium contained germacrene D or sabinene as main components, α-pinene, β-pinene and β-caryophyllene in varying proportions as further important constituents, and various minor components depending on the origin.     

Chemical composition and antimicrobial activity of the essential oil of Teucrium ramosissimum (Lamiaceae)

The phytochemical composition of the essential oil of Teucrium ramosissimum (aerial parts), harvested in a mountainous region of Tunisia, was analyzed. A total of 68 compounds, accounting for 99.44% of the essential oil, were identified by GC and GC/MS. The major compounds were beta-eudesmol (61; 44.52%), caryophyllene oxide (56; 9.35%), alpha-thujene (1; 5.51%), sabinene (4; 4.71%), and T-cadinol (59; 3.9%). The essential oil, which is being used in Tunisian folk medicine against infectious diseases, was tested for its antimicrobial properties against five different bacteria, and found to have weak to moderate activity, with minimal-inhibitory-concentration (MIC) and minimal-bactericidal-concentration (MBC) values in the range 0.24-0.36 and 1.3-2.9 mg/ml, resp.     

Enhancement of single cell oil production by Yarrowia lipolytica growing in the presence of Teucrium polium L. aqueous extract

Yarrowia lipolytica, grown in a nitrogen-limited continuous culture (D = 0.032 h^–1), produced 9.3 g dry biomass l^–1, which contained 0.25 g oil g^–1. When an aqueous extract from Teucrium polium L. was added, the biomass concentration remained constant while the oil content increased to 0.33 g oil g^–1 dry weight. The specific rate of oil formation increased from 7.9 to 10.6 mg oil g^–1 biomass h.