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Comparative study on essential oil of some Teucrium species from Cyprus.

A comparative study on the essential oil of Teucrium cyprium ssp. cyprium, T. micropodioides, T. divaricatum ssp. canescens and T. kotschyanum has been carried out. The four specimens are found in Cyprus and were used in the traditional medicine of the island. The first three are endemic to Cyprus. The essential oil was extracted by steam distillation of the dried flowers, leaves and stems and analyzed by GLC and GC-MS. The percentage of the essential oil obtained varies in the different parts of the plants from 0.07 to 1.3%. Forty-eight components have been identified. Some of them were present in all the species which have been investigated, others were characteristic of one species only.

Chromatography, Gas↗

Teucrol, a decarboxyrosmarinic acid and its 4'-O-triglycoside, teucroside from Teucrium pilosum.

Teucrol, a decarboxy rosmarinic acid and its triglycoside, teucroside, 9'-decarboxyrosmarinic acid-4'-O-alpha-rhamnosyl-(1'''-->6''')-O-beta-galactosyl-(1'''-->4'')-O-alpha-rhamnoside, are two new natural phenolics which have been isolated and identified from the aqueous alcohol extract of the whole plant of Teucrium pilosum (Decne) Asch. & Schweinf. (Lamiaceae). Structures were determined by conventional methods of analysis and confirmed by MS and NMR spectral analysis, including 2D-homonuclear COSY experiment.

Caffeic Acids↗

neo-Clerodane diterpenoids from Teucrium oliverianum and structure revision of teucrolin E.

The aerial parts of Teucrium oliverianum yielded two neo-clerodane diterpenoids, teucrolin F and G, together with the known teucrolin E. The previously proposed structure for teucrolin E was revised so that it contains a tetrahydrofuran ring instead of an oxetane ring. This was based on analysis of the NMR spectroscopic data of its diacetate, including its NOE spectra. In addition, the structural assignments of the new diterpenoids were based on 1H and 13C NMR spectroscopic studies, mainly 2D NMR experiments, including homonuclear and heteronuclear correlations.

Diterpenes↗

Hypolipidemic effects of Teucrium polium in rats.

The aqueous extract of Teucrium polium aerial parts, given intraperitoneally at doses from 50 to 150 mg/kg for 10 days, reduced significantly the serum levels of cholesterol and triglycerides in hyperlipidemic rats.

Animals↗

Effects of Teucrium divaricatum Heldr. ssp. divaricatum decoction on experimental ulcer in rats.

The effects of chronic intragastric administration of the aerial parts decoction of Teucrium divaricatum Heldr. ssp. divaricatum (Labiateae) on experimental acetylsalicylic acid (ASA)-induced ulcer were studied in rats. The ulcer index and histological mucosa regeneration were evaluated. The ulcer index significantly decreased (U.I. 1.7+/-1.5; P<0.05) after treatment with a lyophilized decoction of T. divaricatum (500 mg/kg os), once daily for 7 days, compared to the control (U.I. 11.4+/-2.3). The ultrastructure modifications of gastric mucosa were observed by transmission electronic microscopy (TEM) confirming the antisecretory effect exercised by administration of the T. divaricatum decoction. Treatment with T. divaricatum seems to block up parietal cell acid secretion and to stimulate in the chief cells the formation of zymogen granules.

Animals↗

Neoclerodane diterpenoids from Teucrium montbretii subsp. libanoticum and their absolute configuration.

From the aerial parts of Teucrium montbretii subsp. libanoticum 10 neoclerodane diterpenoids were isolated. Three of them are new [3beta-hydroxyteubutilin A (1), 12-epi-montanin G (2), 20-epi-3,20-di-O-deacetylteupyreinidin (3)], whereas the other seven, namely, 6-ketoteuscordin (4), teuscordinon (5), 6beta-hydroxyteuscordin (6), montanin D (7), 3,20-di-O-deacetylteupyreinidin (8), montanin G (9), and 3-O-deacetylteugracilin A (10), are previously known structures. The structures of 1-3 were determined by spectral and chemical methods.

Chromatography, Thin Layer↗

12-epi-teuscordonin and other neoclerodanes from Teucrium bicolor.

A new neoclerodane, (12R)-epi-teuscordonin [1] has been isolated from Teucrium bicolor. The boat conformation of ring B and the configuration at C-12 in 1 were established by nOe experiments. The known diterpenoids montanin C, teucvin, 12-epi-teucvin, teupolin I, 12-epi-teupolin I, and (12S)-teucrin H-2 were also isolated from the extract. Montanin C [2] was found to be moderately toxic in the brine shrimp bioassay.

Animals↗

Neoclerodane diterpenoids from teucrium massiliense

A reinvestigation of the diterpene metabolites of Teucrium massiliense L. allowed the isolation of four new neoclerodane derivatives, teumassilenins A-D, together with all the diterpenoids previously reported as constituents of this plant. The structures of the new compounds (1-4) were established by chemical and spectroscopic means. A plausible biogenetic relationship between several of these substances is briefly discussed, and some unpublished physical and spectroscopic data of the previously known diterpenoid teumassin (5) are now reported.

Journal Article↗

Neoclerodane diterpenoids from Teucrium maghrebinum.

Eight neoclerodane diterpenoids were identified in the extract of the aerial parts of Teucrium maghrebinum. Three of these, 12-epi-teucjaponin A (1), 12-epi-montanin D (2), and 12-epi-montanin B (3), are new natural products, whereas five, teucjaponin A, montanin D, 19-deacetylteuscorodol, teusalvin C (4), and montanin B, are already known. These eight compounds form four pairs of epimers at carbon C-12.

Diterpenes↗

Aqueous extracts of Teucrium polium possess remarkable antioxidant activity in vitro.

Teucrium polium L. (Lamiaceae) (RDC 1117) is a medicinal plant whose species have been used for over 2000 years in traditional medicine due to its diuretic, diaphoretic, tonic, antipyretic, antispasmodic and cholagogic properties. The therapeutic benefit of medicinal plants is often attributed to their antioxidant properties. We previously reported that an aqueous extract of the leaves and stems of this plant could inhibit iron-induced lipid peroxidation in rat liver homogenate at concentrations that were not toxic to cultured hepatic cells. Others have reported that organic extracts of the aerial components of this plant could inhibit oxidative processes. Against this background, we felt further investigation on the antioxidant action of the extract of T. polium prepared according to traditional Arab medicine was warranted. Accordingly, we assessed (i) its ability to inhibit (a) oxidation of beta-carotene, (b) 2,2'-azobis(2-amidinopropan) dihydrochloride (AAPH)-induced plasma oxidation and (c) iron-induced lipid peroxidation in rat liver homogenates; (ii) to scavenge the superoxide (O2*-) radical and the hydroxyl radical (OH(*)); (iii) its effects on the enzyme xanthine oxidase activity; (iv) its capacity to bind iron; and (v) its effect on cell glutathione (GSH) homeostasis in cultured Hep G2 cells. We found that the extract (i) inhibited (a) oxidation of beta-carotene, (b) AAPH-induced plasma oxidation (c) Fe(2+)-induced lipid peroxidation in rat liver homogenates (IC(50) = 7 +/- 2 mug ml(-1)); (ii) scavenged O2*-(IC(50) = 12 +/- 3 mug ml(-1)) and OH(*) (IC(50) = 66 +/- 20 mug ml(-1)); (iii) binds iron (IC(50) = 79 +/- 17 mug ml(-1)); and (iv) tended to increase intracellular GSH levels resulting in a decrease in the GSSG/GSH ratio. These results demonstrate that the extract prepared from the T. polium possesses antioxidant activity in vitro. Further investigations are needed to verify whether this antioxidant effect occurs in vivo.

Journal Article↗

Hepatitis after germander (Teucrium chamaedrys) administration: another instance of herbal medicine hepatotoxicity.

OBJECTIVE: To show that germander (Teucrium chamaedrys), an herbal medicine used to facilitate weight loss, may be hepatotoxic and to delineate the nature of the injury. DESIGN: Retrospective study. SETTING: Liver units of several centers in the French Network of Pharmacovigilance. PATIENTS: Seven patients who developed hepatitis after germander administration and who had no other cause of liver injury. MEASUREMENTS: Clinical examination, liver function tests, various serologic tests, ultrasonography, and histologic study. RESULTS: Hepatitis characterized by jaundice and a marked increase in serum aminotransferase levels occurred 3 to 18 weeks after germander administration. Liver biopsy specimens in three patients showed hepatocyte necrosis. After discontinuing treatment with germander, jaundice disappeared within 8 weeks and recovery was complete in 1.5 to 6 months. In three cases, germander readministration was followed by the prompt recurrence of hepatitis. CONCLUSION: Germander may be hepatotoxic, which supports the view that herbal medicines are not always as safe as generally assumed.

Acute Disease↗

[Chemical constituentes of Teucrium bidentatum Hemsl].

Two diterpenes were isolated from the herb Teucrium bidentatum and identified as teucvin and teupernin A on the basis of chemical properties and spectral data. They were obtained from T. bidentatum for the first time.

Diterpenes↗

Chemical composition and anti-inflammatory activity of an alcoholic extract of Teucrium polium L.

In the Teucrium polium L. were identified, by gaschromatographic and spectroscopic techniques (1H-NMR and MS), beta-sitosterol, stigmasterol, campesterol, brassicasterol and clerosterol. In the aqueous phase of the alcoholic extract were identified glucose, fructose, raffinose and rhamnose by PC on Watmann paper Number 5. Anti-inflammatory activity was tested using male Wistar rats against carrageenin-induced paw oedema. All tested extract shown a sufficient pharmacological activity compared to that of indomethacine.

Animals↗

[Studies on the diterpenoids on Teucrium quadrifarium Buch-Ham].

Six neo-clerodane diterpenoids were isolated from the acetone extract of Teucrium quadrifarium Buch-Ham (I, II, IV, V, VI and VII). Five of them (I, II, IV, V and VII) were identified as known compounds, teucvidin, 12-epi-teucvidin, teuflin, 19-acetyl-teuspinin and teucvidin, respectively. Compound VI was found to be a new neo-clerodane diterpene, named teuquadrin B. Its structure has been determined from the physical and spectral data.

Antineoplastic Agents, Phytogenic↗

Hepatotoxicity of germander (Teucrium chamaedrys L.) and one of its constituent neoclerodane diterpenes teucrin A in the mouse.

The hepatotoxicity of the herbal plant germander and that of one of its major furanoneoclerodane diterpenes, teucrin A, were investigated in mice. Teucrin A was found to cause the same midzonal hepatic necrosis as observed with extracts of the powedered plant material. Evidence that bioactivation of teucrin A by cytochromes P450 (P450) to a reactive metabolite(s) is required for initiation of the hepatocellular damage is provided by results of experiments on the induction and inhibition of P450 and from studies on the effects of glutathione depletion. Pretreatment of mice with the P450 inducer phenobarbital enhanced the hepatotoxic response, as indicated by an increase in plasma alanine aminotransferase (ALT) levels and hepatic necrosis, while pretreatment with the P450 inhibitor piperonyl butoxide markedly attenuated the toxic response. Hepatotoxicity of teucrin A also was increased following pretreatment with the inhibitor of glutathione synthesis buthionine sulfoximine. Most importantly, the tetrahydrofuran analog of teucrin A, obtained by selective chemical reduction of the furan ring, was not hepatotoxic, a result that provides strong evidence that oxidation of the furan ring moiety of the neoclerodane diterpenes is involved in the initiation of hepatocellular injury caused by germander.

Administration, Oral↗

Bioengineered zinc oxide nanoparticles derived from Teucrium polium as a multifunctional platform for anticancer activity, hemocompatibility, larval toxicity and photocatalytic remediation.

In this study, we evaluate the physicochemical properties and the antioxidant, antimicrobial, anticancer, photocatalytic, and larvicidal activities of T. polium-mediated ZnO NPs. The synthesized ZnO NPs were characterized by UV-visible spectroscopy (absorption at 392&#xa0;nm), FTIR, TEM, and XRD, confirming their successful synthesis. The antioxidant activity of ZnO NPs was evaluated using various assays: DPPH scavenging at 54% (100&#xa0;&#xb5;g/mL), ABTS scavenging at 63.3% (100&#xa0;&#xb5;g/mL), FRAP scavenging at 61.2% (100&#xa0;&#xb5;g/mL), and hydrogen peroxide scavenging at 65% (100&#xa0;&#xb5;g/mL), demonstrating concentration-dependent activity. The antibacterial properties were tested against E. coli, P. aeruginosa, K. pneumoniae, and S. aureus, with the largest inhibition zone observed for P. aeruginosa (28.3&#xa0;mm at 100&#xa0;&#xb5;g/mL). Cytotoxicity on MCF-7 cells showed a dose-dependent decrease in cell viability, with values of 75.6%, 44%, 20%, and 8% for concentrations of 25, 50, 75, and 100&#xa0;&#xb5;g/mL, respectively. ROS generation and apoptosis were also observed at higher concentrations. The photocatalytic degradation of Methyl Orange was evaluated under UV irradiation, yielding 85% degradation efficiency at pH 3 with a ZnO NP concentration of 50&#xa0;mg/L. The larvicidal toxicity against Aedes aegypti was significant, with LC50 values of 76.63&#xa0;&#xb5;g/mL for III instar and 82.74&#xa0;&#xb5;g/mL for IV instar larvae. The results suggest that T. polium-mediated ZnO NPs possess significant potential for therapeutic applications, including antioxidant, antimicrobial, anticancer, photocatalytic, and larvicidal activities, making them a promising candidate for biomedical and environmental applications.

Zinc Oxide↗

HPLC analysis of neo-clerodane diterpenoids from Teucrium chamaedrys.

A simple, rapid analytical method for the quantitative determination of nine neo-clerodane diterpenoids was developed. The neo-clerodane diterpenoids present in the plant material and extracts were separated with an acetonitrile-water gradient at a flow rate of 1 mL per minute. The HPLC separation was performed on a Phenomenex Luna C18(2) (150 x 4.6 mm I.D., particle size 5 microm) reversed phase column with detection at 220 nm. The limit of detection was 0.24-0.90 microg/mL. The relative standard deviation (RSD) values for the determination of neo-clerodane diterpenoids in plant extracts were less than 3.20%. This is the first analytical method developed for qualitative and quantitative analysis of nine neo-clerodane diterpenoids by HPLC with PDA detection.

Calibration↗