Menthalactone, a New Analgesic from Mentha cordifolia Opiz. Leaves

Institute of Chemistry, Uiversity of the Philippines, Diliman, Quezon City 11010. Philippines.
Zeitschrift fur Naturforschung C (Impact Factor: 0.55). 01/2009; 64(11-12):809-12. DOI: 10.1515/znc-2009-11-1209
Source: PubMed


* Author for correspondence and reprint requests Z. Naturforsch. 64c, 809-812 (2009); received May 7/July 23, 2009 Menthalactone, a new long-chain alkene with a bicyclic lactone moiety, was isolated as an analgesic constituent from the leaves of Mentha cordifolia Opiz. At a dosage of 100 mg/ kg mouse, it decreased the number of squirms induced by acetic acid by 67.3%. Statistical analysis using Kruskall Wallis one-way analysis of variance by ranks showed that menthalac-tone is different from the solvent control at alpha = 0.01 and approximates the analgesic activity of mefenamic acid at 0.001 level of significance.

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    • "It is known that bioactive properties are mainly associated with the chemical composition of medicinal plants (Gurib- Fakim, 2006). In this context, the genus Mentha can be thought as one of the best candidates for new bioactive compound isolation studies because bicyclic lactones (Villasenor & Sanchez, 2009), triterpenes (Monte et al., 1997), flavonoids (Ko¸sar et al., 2004; Shalaby et al., 2000), phenolic acids (Ko¸sar et al., 2004; Shalaby et al., 2000), monoterpenes (She et al., 2010b), lignans (Zheng et al., 2007), and aliphatic glycosides (Yamamura et al., 1998) were reported from its various species in previous studies. "
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    ABSTRACT: Abstract Context: Mentha L. (Labiatae) species (mint) with their flavoring properties have been used in food industries for centuries. Besides they have a great importance in drug development and medicinal applications due to various bioactive compounds of several members of the genus. Objective: The aim of this study was to isolate bioactive compounds with antimutagenic potential by bio-guided fractionation and determine their structures by spectroscopic methods. Materials and methods: The structural elucidation of the isolated compounds was done based on spectroscopic methods, including MALDI-MS, UV, IR, and 2D NMR experiments, and the bio-guided fractionation process was done by using the Ames/Salmonella test system. Henceforth, solely genotoxic and antigenotoxic potential of the new compounds were also confirmed up to 2 µM/plate by using the same test system. Results: Two new chalcone glycosides: (βR)-β,3,2',6'-tetrahydroxy-4-methoxy-4'-O-rutinosyldihydrochalcone and (βR)-β,4,2',6'-tetrahydroxy-4'-O-rutinosyldihydrochalcone, were isolated from Mentha longifolia (L.) Hudson subsp. longifolia, together with known six flavonoid glycosides and one phenolic acid: apigenin-7-O-glucoside, luteolin-7-O-glucoside, apigenin-7-O-rutinoside, luteolin-7-O-rutinoside, apigenin-7-O-glucuronide, luteolin-7-O-glucuronide, rosmarinic acid. According to the antimutagenicity results, both new test compounds significantly inhibited the mutagenic activity of 9-aminoacridine in a dose-dependent manner at the tested concentrations from 0.8 to 2 µM/plate. (βR)-β,4,2',6'-Tetrahydroxy-4'-O-rutinosyldihydrochalcone showed the maximum inhibition rate as 75.94% at 2 µM/plate concentration. Conclusions: This is the first report that two new chalcone glycosides were isolated from Mentha longifolia subsp. longifolia and their antimutagenic potentials by using mutant bacterial tester strains. In conclusion, the two new chalcone glycosides showed a significant antigenotoxic effect on 9-aminoacridine-induced mutagenesis at tested concentrations.
    Pharmaceutical Biology 11/2014; 53(6):1-9. DOI:10.3109/13880209.2014.948633 · 1.24 Impact Factor
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    • "This mint is generally used in traditional medicine to relieve gastrointestinal problem, asthma, muscle spasm and inflammation. Evidence supporting the biological effect of M. cordifolia has been reported; such as antimutagenicity (Villasenor et al., 2002), analgesic (Villasenor and Sanchez, 2009), anti-nociceptive (Sousa et al., 2009), anti-inflammatory (Moreno et al., 2002) and antioxidant activities (Ka et al., 2005). A vasorelaxing effect of mint leaf extract has been shown in the rat mensenteric bed (Runnie et al., 2004). "
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    ABSTRACT: This study was to test the inhibitory action of Mentha cordifolia (MC) extract on the development of hypertension in N G -nitro-L-arginine methyl ester (L-NAME)-induced hypertensive rats. Male Sprague-Dawley rats received L-NAME (50 mg/kg/day) in drinking water and were either intragastrically administered with MC extract (200 mg/kg/day) or deionized water for 3 weeks. Significant increases in mean arterial blood pressure (MAP; 162.3 ± 2.7 vs 92.9 ± 5.4 mmHg), heart rate (HR; 414.7 ± 13.1 vs 331.7 ± 16.2 beat/min) and hindlimb vascular resistance (HVR; 39.1 ± 3.8 vs 12.6 ± 0.6 mmHg/min/100 g tissue/ml) in L-NAME-treated group compared to that of control group were observed. The MC extract markedly reduced the MAP about 16.7% in L-NAME group which was associated with reductions in HR and HVR. The MC extract alleviated a decrease in vascular responses to acetylcholine in the hypertensive rats. Increased levels of plasma malondialdehyde (MDA) and superoxide production in vascular tissues in hypertensive rats were restored by MC extract. The MC extract contains high level antioxidant in the form of total phenolic compounds. Our results indicated that the MC extract inhibited progress of hypertension in L-NAME group, and this effect might involve the antioxidant capacity of the extract.
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    ABSTRACT: The effect of an aqueous Mentha cordifolia (MC) extract on the haemodynamic status, vascular remodeling, function, and oxidative status in NG-nitro-L-arginine methyl ester (L-NAME)-induced hypertension was investigated. Male Sprague-Dawley rats were given L-NAME [50 mg/(kg body weight (BW) d)] in their drinking water for 5 weeks and were treated by intragastric administration with the MC extract [200 mg/(kgBWd)] for 2 consecutive weeks. Quercetin [25 mg/(kg BW d)] was used as a positive control. The effects of the MC extract on the haemodynamic status, thoracic aortic wall thickness, and oxidative stress markers were determined, and the vasorelaxant activity of the MC extract was tested in isolated mesenteric vascular beds in rats. Significant increases in the mean arterial pressure (MAP), heart rate (HR), hind limb vascular resistance (HVR), wall thickness, and cross-sectional area of the thoracic aorta, as well as oxidative stress markers were found in the L-NAME-treated group compared to the control (P < 0.05). MAP, HVR, wall thickness, cross-sectional area of the thoracic aorta, plasma malondialdehyde (MDA), and vascular superoxide anion production were significantly reduced in L-NAME hypersensitive rats treated with the MC extract or quercetin. Furthermore, the MC extract induced vasorelaxation in the pre-constricted mesenteric vascular bed with intact and denuded endothelium of normotensive and hypertensive rats. Our results suggest that the MC extract exhibits an antihypertensive effect via its antioxidant capacity, vasodilator property, and reduced vascular remodeling.
    Zeitschrift fur Naturforschung C 04/2014; 69(1-2):35-45. DOI:10.5560/ZNC.2012-0212 · 0.55 Impact Factor
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