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: Two new sesquiterpenes, together with 32 known compounds(3-34), were isolated from Artemisia sieversiana Ehrhart ex willd. and the compounds 3-21 were isolated from this plant for the first time. The new compounds were elucidated as 2α,9α-dihydroxymuurol-3(4)-en-12-oic acid (1) and 13α-methyl-(5αH,6αH,7αH,8αH)-austricin 8-O-β-D-glucopyranoside (2), respectively. The structural identification of these compounds was mainly achieved by spectroscopic methods including 1D and 2D NMR techniques, and the structure of compound 1 was confirmed by a single crystal X-ray diffraction experiment. Compounds 1-2 were evaluated for cytotoxic activity in vitro against MCF-7, NCI-H460 and Hep-G2 cell lines, respectively.
    Fitoterapia 05/2014; 97. DOI:10.1016/j.fitote.2014.05.007 · 2.35 Impact Factor
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