Some reactions of the diterpene marrubiin and its congeners

Fulke, J. W. B.; Henderson, M. S.; McCrindle, Robert

doi:10.1039/j39680000807

Cited by 16 publications

(10 citation statements)

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“…It has been identified and characterised as marrubenol (1,4‐naphthalenediol, 1‐[2‐(3‐furanyl)ethyl]decahydro‐5‐(hydroxymethyl)‐2,5,8a‐trimethyl,[1 R ‐(1 α , 2 α , 4 β , 4a α , 5 β , 8a β )] ( El Bardai et al , 2003 ). Marrubenol is a diterpenoid that was first isolated from Marrubium vulgare by Fulke et al (1968) . It relaxes KCl‐contracted artery in a concentration‐dependent manner, with an IC 50 value of 10 μ M ( El Bardai et al , 2003 ).…”

Section: Introductionmentioning

confidence: 99%

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

Bardai

Wibo

Hamaide

et al. 2003

British J Pharmacology

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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 (IC 50 : 11.870.3 mM, maximum relaxation: 9370.6%) than of the contraction evoked by noradrenaline (maximum relaxation: 3071.5%). 2 In fura-2-loaded aorta, marrubenol simultaneously inhibited the Ca 2 þ signal and the contraction evoked by 100 mM KCl, and decreased the quenching rate of fura-2 fluorescence by Mn 2 þ . 3 Patch-clamp data obtained in aortic smooth muscle cells (A7r5) indicated that marrubenol inhibited Ba 2 þ inward current in a voltage-dependent manner (K D : 872 and 4076 mM at holding potentials of À50 and À100 mV, respectively). 4 These results showed that marrubenol inhibits smooth muscle contraction by blocking L-type calcium channels.

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Section: Introductionmentioning

confidence: 99%

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

Bardai

Wibo

Hamaide

et al. 2003

British J Pharmacology

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“…Extensive NMR analysis ( 1 H, 13 C, COSY, HMQC, HMBC) allowed us to identify it as marrubenol, previously isolated from M. vulgare [7]. Table 2 gives, for the first time, the complete NMR assignments of marrubenol.…”

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The Vasorelaxant Activity of Marrubenol and Marrubiin from Marrubium vulgare

Bardai¹,

et al. 2003

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Marrubium vulgare L. (Horehound, Lamiaceae) is a widespread Mediterranean plant used in folk medicine to cure a variety of diseases. Chemically, this genus is best known for its furanic labdane diterpene marrubiin, which has potent antinociceptive [1] and expectorant [2] effects. Other furanic labdane diterpenes including premarrubenol, marrubenol and premarrubiin have been repeatedly reported to occur in this plant [3], [4] but pharmacological information about these components is lacking. In a previous report, we have demonstrated that treatment with an aqueous extract of the aerial parts of M. vulgare significantly lowered the systolic blood pressure in spontaneously hypertensive rats (SHR), related to a vasodilatory effect exhibited by the extract ex vivo as well as in vitro [5]. The present study deals mainly with the isolation and structural elucidation of the compounds responsible for the vasorelaxant activity ascribed to this plant.Preincubation of rat aorta with the cyclohexane fraction of M. vulgare water extract evoked a dose-dependent inhibition of KCl-induced contraction while the aqueous fraction showed no effect ( Table 1). Bio-guided fractionation of this cyclohexane extract by column chromatography gave several fractions, two of which showed a high activity. The first one was further purified using preparative TLC on silica gel (Si 60 F 254 Merck) with hexane-diethyl ether (4 : 6) as mobile phase, yielding 10. C, COSY, HMQC, HMBC) allowed us to identify it as marrubenol, previously isolated from M. vulgare [7]. Table 2 gives, for the first time, the complete NMR assignments of marrubenol. Its structure was further confirmed by comparison with marrubenol obtained by reduction of marrubiin (Fig. 1).The effects of marrubiin and marrubenol on the contractions evoked by high-KCl depolarizing solution in aortic segments were compared to the effect of the calcium channel blocker verapamil, a well known antihypertensive drug which inhibits the contraction evoked by high-KCl solution in arteries [8]. Marrubenol and marrubiin inhibited the aortic contraction in a concentration-dependent manner (Fig. 2) AbstractCrude 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.

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“…(25), and velutine C (26) [56]. From M. cylleneum, three products were isolated: marrubiin (1) [36,39] a natural product, although it had been reported a long time ago [39] as a semisynthetic derivative prepared by chemical transformation of marrubiin. The product, named marrulibanoside, is, therefore, a new natural product; more detailed spectroscopic data of the compound were also reported [58].…”

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confidence: 99%

“…Only from 1952 until 1968 was the problem of the complete structure and stereochemistry solved through extensive studies [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34]. Other papers [35][36][37] reported several reactions, which confirmed the structures 1 for marrubiin and 2 for marrubic acid. The labdane skeleton shown by marrubiin is a typical marker of the genus Marrubium.…”

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confidence: 99%