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At least 19 recordsLinked to original sources
PubMed2005

Labdane diterpenes from Marrubium velutinum and Marrubium cylleneum.

From the aerial parts of Marrubium velutinum and Marrubium cylleneum, seven labdane diterpenes, velutine A, 15-epi-velutine A, velutine B, 15-epi-velutine B, velutine C, cyllenine A and 15-epi-cyllenine A, have been isolated together with five known diterpenes and four known flavones. The structures of the isolated compounds were established by means of NMR [(1)H-(1)H-COSY, (1)H-(13)C-HMQC, HMBC, HMQC-TOCSY, NOESY] and MS spectral analyses. Complete NMR assignments are reported for known compounds.

Diterpenes↗
PubMed2001

Pharmacological evidence of hypotensive activity of Marrubium vulgare and Foeniculum vulgare in spontaneously hypertensive rat.

The hypotensive effects of the water extract of Marrubium vulgare L. and Foeniculum vulgare L. were investigated in spontaneously hypertensive rats (SHR) and in normotensive Wistar-Kyoto rats (WKY). Oral administration of Marrubium or Foeniculum extract lowered the systolic blood pressure of SHR but not of WKY. In SHR, Foeniculum but not Marrubium treatment increased water, sodium and potassium excretion. Ex vivo as well as in vitro, Marrubium extract inhibited the contractile responses of rat aorta to noradrenaline and to KCl (100 mM). Inhibition was greater in aorta from SHR compared to WKY and was not affected by the NO synthase inhibitor N-nitro-L-arginine. Vascular effects of Foeniculum extract were less pronounced than those of Marrubium and were blocked by N-nitro-L-arginine. These results indicate that hypotensive activity of Marrubium and Foeniculum extracts seems to be mediated through different pathways: Foeniculum appeared to act mainly as a diuretic and a natriuretic while Marrubium displayed vascular relaxant activity.

Animals↗
PubMed2004

Comparative study of the antihypertensive activity of Marrubium vulgare and of the dihydropyridine calcium antagonist amlodipine in spontaneously hypertensive rat.

Water extract of Marrubium vulgare is widely used as antihypertensive treatment in folk medicine. We have compared the effect of 10-week-long treatment with amlodipine or Marrubium water extract on systolic blood pressure (SBP), cardiovascular remodeling and vascular relaxation in spontaneously hypertensive rats (SHR). Both treatments produced similar decrease in SBP. Amlodipine treatment reduced left ventricle, aortic and mesenteric artery weight. Marrubium treatment had a significant antihypertrophic effect in aorta only. Relaxation to acetylcholine (ACh) of mesenteric artery was improved by Marrubium but not by amlodipine treatment. These results demonstrate that, in addition to its antihypertensive effect, Marrubium water extract improved the impaired endothelial function in SHR.

Amlodipine↗
PubMed1997

[Chemical tests with Marrubium species. Official data on Marubii herba in Pharmacopoeia Hungarica VII].

About 40 species of the Marrubium genus (Lamiaceae) are known of which 2 species (M. vulgare L. and M. peregrinum L.) and one hybrid (M. x paniculatum Desr.) can be found as native plants in Hungary. The above-ground parts of M. vulgare L. are official in Hungarian Pharmacopoeia VII. Active substances in Marrubii herba are labdane-structured bitter materials. Although the presence of furanic labdane diterpenes in the plant is known, the pharmacopoeia gives only microscopic tests, qualitative tests (for other parts of the plant and foreign organic matter) for the bitter value of Marrubii herba. We have examined the main terpenoid substances isolated with column, gel and preparative layer chromatography. Structure elucidations were performed by means of UV, mass and NMR spectroscopy. We have compared the changes in terpenoid-type compounds (premarrubiin and marrubiin) in plants during the vegetation period; in different Marrubium species and in the different extractions of horehound by means of thin layer chromatography and densitometry. By reason of our results we propose qualitative and quantitative chemical tests for the paragraph of Marrubii herba in Pharmacopoeia Hungarica VII.

Diterpenes↗
PubMed2007

Antibacterial activity of flavonoids and phenylpropanoids from Marrubium globosum ssp. libanoticum.

Marrubium globosum Montbr. et Auch. ex Benth. ssp. libanoticum Boiss. (Lamiaceae) is a medicinal plant used for the treatment of inflammatory diseases, asthma, coughs and other pulmonary and urinary problems. The goal of our study was to assess the biological activity of M. globosum testing the methanol extract of aerial parts for its antibacterial activity against bacteria known to cause respiratory, gastrointestinal, skin and urinary disorders; the extract showed antibacterial effects against all the strains of bacteria used. A purification of this active extract showed the presence, as main constituents, of verbascoside, isorhamnetin 3-O-beta-D-rutinoside, quercetin 3-O-beta-D-rutinoside, naringenin 7-O-beta-D-glucoside, kaempferol 3-O-beta-D-rutinoside, isorhamnetin 3-O-beta-D-glucoside, quercetin 3-O-beta-D-glucoside, apigenin 7-O-(3''-p-coumaryl)-glucoside, p-methoxy-cinnamic acid, kaempferol 3-O-beta-D-glucoside and apigenin 7-O-beta-D-glucoside. The pure compounds were tested for their antibacterial activity; quercetin 3-O-beta-D-rutinoside, verbascoside and naringenin 7-O-beta-D-glucoside showed the greatest activity.

Anti-Infective Agents↗
PubMed2005

Analgesic potential of marrubiin derivatives, a bioactive diterpene present in Marrubium vulgare (Lamiaceae).

Marrubiin, a furane labdane diterpene, is the main analgesic compound present in Marrubium vulgare, a medicinal plant used in Brazil and other countries to treat several ailments. Considering its important pharmacological action, as well as its high yield, some structural modifications were performed in order to obtain more active compounds. Success was obtained in reducing the lactonic function, in the formation of marrubiinic acid and two esterified derivatives, which exhibited significant analgesic effect against the writhing test in mice. Marrubiinic acid showed better activity and excellent yield, and its analgesic effect was confirmed in other experimental models of pain in mice, suggesting its possible use as a model to obtain new and potent analgesic agents.

Analgesics↗
PubMed2006

Antioedematogenic effect of marrubiin obtained from Marrubium vulgare.

This paper describes the antioedematogenic profile of marrubiin (1), the main constituent of Marrubium vulgare, a medicinal plant used in folk medicine of several countries to treat different pathologies. Compound (1) was analyzed in a model of microvascular leakage in mice ears. The results show that it exhibits significant and dose-related antioedematogenic effects. The results obtained for ID50 values (mg/kg, i.p.) and maximal inhibition (%) for the different phlogistic agents used were as follows: histamine (HIS, 13.84 mg/kg and 73.7%); (BK, 18.82 mg/kg and 70.0%); carrageenan (CAR, 13.61 mg/kg and 63.0%). The other phlogistic agonists, such as prostaglandin E2 (PGE2), caused inhibition of less than 50%. In addition, (1) (100 mg/kg) significantly inhibited the OVO-induced allergic edema in actively sensitized animals (maximal inhibition 67.6+/-4%). Our results demonstrate that the systemic administration of marrubiin exerts a non-specific inhibitory effect on pro-inflammatory agent-induced microvascular extravasation of Evans blue in mouse ear.

Animals↗
PubMed2006

Marrubium vulgare extract inhibits human-LDL oxidation and enhances HDL-mediated cholesterol efflux in THP-1 macrophage.

The objective of the present study was to elucidate the beneficial properties of aqueous extracts of Marrubium vulgare (AEM) towards cardiovascular disease by protecting human-LDL against lipid peroxidation and promoting HDL-mediated cholesterol efflux. Human-LDL were oxidised by incubation with CuSO(4) in the presence of increased concentrations of AEM (0-100 microg/ml). LDL lipid peroxidation was evaluated by conjugated diene formation, vitamin E disappearance as well as LDL-electrophoretic mobility. HDL-mediated cholesterol efflux assay was carried out in human THP-1 macrophages. Incubation of LDL with AEM significantly prolonged the lag phase (P=0.014), lowered the progression rate of lipid peroxidation (P=0.004), reduced the disappearance of vitamin E and the electrophoretic mobility in a dose-dependent manner. Also, incubation of HDL with AEM significantly increased HDL-mediated cholesterol efflux from THP-1 macrophages implicating an independent ATP binding cassette A1 (ABCA1) pathways. Our findings suggest that M. vulgare provides a source of natural antioxidants, which inhibit LDL oxidation and enhance reverse cholesterol transport and thus can prevent cardiovascular diseases development. These antioxidant properties increase the anti-atherogenic potential of HDL.

Cell Line↗
PubMed2004

Clinical trial of Cecropia obtusifolia and Marrubium vulgare leaf extracts on blood glucose and serum lipids in type 2 diabetics.

Cecropia obtusifolia and Marrubium vulgare have been widely used in Mexican traditional medicine for the control of type 2 diabetes. In order to evaluate the clinical effect produced by the aqueous extract from these species on type 2 non-controlled diabetes mellitus, a total of 43 outpatients were included. Based on the European NIDDM (policy group) criteria, only patients with poor response to the conventional treatment were selected. All patients maintained their medical treatment and also received a prepared infusion of the dry leaves of the plant treatment for 21 days. In a double-blind manner, the patients were randomly grouped as follows: 22 patients were treated with C. obtusifolia and 21 with M. vulgare. The fasting blood glucose values were reduced by 15.25% on patients treated with C. obtusifolia, while cholesterol and triglycerides were decreased by 14.62% and 42.0%, respectively (ANOVA p< 0.02). In the case of patients treated with M. vulgare, the plasma glucose level was reduced by 0.64% and cholesterol and triglycerides by 4.16% and 5.78%, respectively. When the results were compared between groups, significant differences in glucose and cholesterol diminution were found. The obtained results showed that the infusion prepared with the leaves of C. obtusifolia (containing 2.99+/-0.14mg of chlorogenic acid/g of dried plant) produced beneficial effects on carbohydrate and lipid metabolisms when it was administered as an adjunct on patients with type 2 diabetes with poor response to conventional medical treatment.

Administration, Oral↗
PubMed2003

Acylated flavonoid and phenylethanoid glycosides from Marrubium velutinum.

From the aerial parts of Marrubium velutinum, one acylated flavonoid glycoside, chrysoeriol 7-O-(3",6"-di-O-E-p-coumaroyl)-beta-D-glucopyranoside, and two tetrasaccharidic phenylethanoid glycosides, velutinosides I-II, have been isolated together with ten known flavonoids and seven known phenylethanoid glycosides. The structures of the isolated compounds were established by means of NMR, MS, and UV spectral analyses.

Acylation↗
PubMed2002

Isolation and pharmacological activity of phenylpropanoid esters from Marrubium vulgare.

The isolation and identification of major phenylpropanoid esters from Marrubium vulgare: (+) (E)-caffeoyl-L-malic acid 1, acteoside 2, forsythoside B 3, arenarioside 4, ballotetroside 5, as well as their anti-inflammatory activity are reported for the first time. We evaluated the inhibitory effects of these five compounds on cyclooxygenase (Cox) catalysed prostaglandin biosynthesis activity. Only the glycosidic phenylpropanoid esters showed an inhibitory activity towards the Cox-2 enzyme and three of them: acteoside 2, forsythoside B 3, arenarioside 4, exhibited higher inhibitory potencies on Cox-2 than on Cox-1. These results are of interest, as Cox-2 is mainly associated with inflammation and the Cox-1 inhibition with adverse side effects often observed with non-steroidal anti-inflammatory drugs. The occurrence of these phenylpropanoid esters could also explain some other pharmacological properties of M. vulgare.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed2006

Labdane Diterpenoids from Marrubium globosum ssp. libanoticum.

From the aerial parts of Marrubium globosum ssp. libanoticum, seven labdane diterpenoids were isolated. Three of them are new natural products [(13R)-9alpha,13alpha-epoxylabda-6beta(19),16(15)-diol dilactone (2), deacetylvitexilactone (7), marrulanic acid (8)], whereas the other four, namely, (13S)-9alpha,13alpha-epoxylabda-6beta(19),16(15)-diol dilactone (1), cyllenin A (3), 15-epi-cyllenin A (4), and marrulibanoside, are previously known compounds. The structures of 2, 7, and 8 were determined by spectroscopic and chemical methods.

Diterpenes↗
PubMed2003

Characterisation of marrubenol, a diterpene extracted from Marrubium vulgare, as an L-type calcium channel blocker.

1. The objective of the present study was to investigate the mechanism of the relaxant activity of marrubenol, a diterpenoid extracted from Marrubium vulgare. In rat aorta, marrubenol was a more potent inhibitor of the contraction evoked by 100 mM KCl (IC50: 11.8+/-0.3 microM, maximum relaxation: 93+/-0.6%) than of the contraction evoked by noradrenaline (maximum relaxation: 30+/-1.5%). 2. In fura-2-loaded aorta, marrubenol simultaneously inhibited the Ca2+ signal and the contraction evoked by 100 mM KCl, and decreased the quenching rate of fura-2 fluorescence by Mn2+. 3. Patch-clamp data obtained in aortic smooth muscle cells (A7r5) indicated that marrubenol inhibited Ba2+ inward current in a voltage-dependent manner (KD: 8+/-2 and 40+/-6 microM at holding potentials of -50 and -100 mV, respectively). 4. These results showed that marrubenol inhibits smooth muscle contraction by blocking L-type calcium channels.

Animals↗
PubMed2003

The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgare.

Crude extracts of the aerial parts of Marrubium vulgare show a potent in vitro inhibition of KCl-induced contraction of rat aorta. Bio-guided fractionations, spectroscopic analysis and chemical derivatization revealed the furanic labdane diterpenes marrubenol and marrubiin as the most active compounds.

Animals↗
PubMed2002

Marruboside, a new phenylethanoid glycoside from Marrubium vulgare L.

A new phenylethanoid glycoside, marruboside, has been isolated from the aerial parts of Marrubium vulgare L. Its structure was established as 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-apiofuranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)]-[beta-D-apiofuranosyl-(1-->6)]-4-O-caffeoyl-beta-D-glucopyranoside, on the basis of spectroscopic evidence.

France↗
PubMed1992

Phenylpropanoid glycosides from Marrubium alysson.

From the aerial parts of Marrubium alysson a new phenylpropanoid glycoside, alyssonoside, and five known glycosides, verbascoside (= acteoside), leucosceptoside A, martynoside, forsythoside B and leucosceptoside B were isolated. On the basis of spectral data, the structure of the new compound was elucidated as beta-(3,4-dihydroxyphenyl)ethyl-O-[alpha-L-rhamnopyranosyl-(1-->3)]-O- [beta-D-apiopyranosyl-(1-->6)]-4-O-feruloyl-beta-D-glucopyra noside.

Carbohydrate Sequence↗
PubMed2000

Analysis of the antinociceptive properties of marrubiin isolated from Marrubium vulgare.

We have shown previously that Marrubium vulgare, a medicinal plant employed frequently in folk medicine to treat a variety of ailments, exhibits antispasmodic and antinociceptive effects in different experimental models. This work describes the antinociceptive profile of marrubiin, the main constituent of this plant, which was analysed in some models of nociception in mice. The results showed that marrubiin exhibits potent and dose-related antinociceptive effects, whose calculated ID50 values (micromol/kg, i.p.) were the following: 2.2 in the writhing test, 6.6 (first phase) and 6.3 (second phase) in the formalin-induced pain test and 28.8 when evaluated in the capsaicin test. It was more potent than some well-known analgesic drugs. The antinociception produced by the marrubiin was not reversed by naloxone when analyzed against the writhing test. In the hot-plate test, marrubiin did not increase the latency period of pain induced by the thermal stimuli. Its exact mechanism of action remains to be determined, but the results suggest that marrubiin, like hydroalcoholic extract of M. vulgare, does not interact with opioid systems.

Abdominal Pain↗