Mentha haplocalyx Briq.
5-methyl-2-(propan-2-yl)cyclohexan-1-one/L-MENTHONE/Menthone/MENTHON, ISOMERENGEMISCH/(-)-MENTHONE/MENTHONE MIXTURE OF ISOMERS/MENTHONE/2-ISOPROPYL-5-METHYLCYCLOHEXANONE/MENTHONE(SG)/CYCLOHEXANONE,5-METHYL-2-(1-METHYLETHYL)-/5-Methyl-2-(1-methylethyl)cyclohexanone/Cyclohexanone, 5-methyl-2-(1-methylethyl)-/Menthone, Mixture of Isomers/2-Isopropyl-5-methylcyclohexanone/p-Menthan-3-one/dl-p-Menthan-3-one
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
205.0±0.0 °C at 760 mmHg
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Acyclovir (ACV) is known to be toxic to gonads, inducing apoptosis in the reproductive system. The beneficial effects of vitamin C (Vit C) and menthone, both as antioxidant agents on various organs has been reported.
This study evaluated the potential role of the Vit C and menthone on the DNA damage in rat spermatozoa induced by the ACV.
MATERIALS AND METHODS:
In this experimental study, adult male albino Wistar rats with average weight of 250±10 gr, were divided into six groups (n=18/each), as: ACV (15 mg/kg/day), ACV+Vit C (20 mg/kg/day), ACV+ menthone (100 µl/d), ACV+ menthone (250 µl/d), ACV+ menthone (400 µl/day) and control group without any treatment. At the end of experiment, the animals were sacrificed and sperm samples were collected and isolated in phosphate-buffered saline and examined by TUNEL staining process. The percentage of TUNEL positive spermatozoa was evaluated by fluorescence microscopy. Each experiment was performed in three repeats.
Male rats exposed to ACV had significant increase in DNA damages in comparison to other groups. The percentage of TUNEL positive sperm cells was 90.83 (p<0.001) in ACV group. The protective role of both antioxidants used in high dose, compensate the adverse effects of the ACV. The results showed that the percentage of apoptotic sperm in the ACV+Vit C group was 16.38 (p<0.001) and in the ACV+ menthone (400 µl/d) group was 16.05 (p<0.001). CONCLUSION: The present results showed that Vit C and menthone at higher dose have a good compensatory effect with significant reduction in DNA damages in sperm cells by reversing the adverse effect of ACV on the reproductive system in male rat.
Acyclovir; DNA damage; Menthone; Rat; Vitamin C
The effects of vitamin C and menthone on acyclovir induced DNA damage in rat spermatozoa: An experimental study.
Toghiani S1, Hayati Roudbari N1, Dashti GR2, Rouzbehani S3.
Schistosomiasis is an important parasitic disease caused by Schistosoma mansoni, an intravascular trematode. Schistosomiasis treatment is limited to just one drug, Praziquantel (PZQ). Thus, studies on new antischistosomal compounds are of fundamental importance to disease control. Here we report on the effects of Mentha piperita L. compounds – menthol and menthone – in association with acetylsalicylic acid (ASA) in the regulation of hepatic fibrosis caused by schistosomiasis granulomas. Six different groups of Swiss rats were infected with 80 cercariae. Two groups received only menthol and menthol treatment at different concentrations (30 and 50 mg/kg); two groups received treatment with the same concentration of menthol and menthol, but associated the ASA. All groups received treatment for 14 consecutive days from the 35 days after the parasitic infection. In addition, three other groups were used: uninfected and untreated group, infected and untreated group and infected group treated with the commercial drug (single dose). Parasitological, cytological and histological analyses were performed. Results showed a significant reduction on the number of eosinophils found in the peritoneal cavity lavage (LPC) in all treated groups and on the number of eosinophils found in the blood of PZQ treated group, in the blood of the group treated with 30 mg/kg of Mentaliv® and in the blood of group treated with 50 mg/kg Mentaliv® + ASA when compared to the infected group. All treated groups presented a reduction in the parasite load, represented by the number of S. mansoni eggs, in the experimental group treated with 30 mg/kg of menthol and menthone a 62.80% reduction was observed and in the experimental group treated with 50 mg/kg of menthol and menthone + ASA a reduction of 64.21% was observed. In the liver histological analysis we observed that all Mentaliv® treated groups expressed a unique cytological profile, with diffused cells through the granuloma. In the experimental group treated with 50 mg/kg of Mentaliv® + ASA it was possible to observe the formation of type III collagen fibers, a typical wound healing characteristic. Our data strongly suggest that both the hepatic fibrosis and the inflammatory process were regulated through the schistosomiasis granulomatous process after treatment with menthol and menthone associated with ASA.
Schistosoma mansoni; acetylsalicylic acid; hepatic fibrosis; histology; inflammation
Menthol and Menthone Associated with Acetylsalicylic Acid and Their Relation to the Hepatic Fibrosis in Schistosoma mansoni Infected Mice.
Feitosa KA1, Zaia MG1, Rodrigues V2, Castro CA1,3, Correia RO1, Pinto FG3, Rossi KNZP3, Avo LRS4, Afonso A1,5,6, Anibal FF1.
2018 Jan 18
(−)-Menthone is the predominant monoterpene produced in the essential oil of maturing peppermint (Mentha x piperita) leaves during the filling of epidermal oil glands. This early biosynthetic process is followed by a second, later oil maturation program (approximately coincident with flower initiation) in which the C3-carbonyl of menthone is reduced to yield (−)-(3R)-menthol and (+)-(3S)-neomenthol by two distinct NADPH-dependent ketoreductases. An activity-based in situ screen, by expression in Escherichia coli of 23 putative redox enzymes from an immature peppermint oil gland expressed sequence tag library, was used to isolate a cDNA encoding the latter menthone:(+)-(3S)-neomenthol reductase. Reverse transcription-PCR amplification and RACE were used to acquire the former menthone:(−)-(3R)-menthol reductase directly from mRNA isolated from the oil gland secretory cells of mature leaves. The deduced amino acid sequences of these two reductases share 73% identity, provide no apparent subcellular targeting information, and predict inclusion in the short-chain dehydrogenase/reductase family of enzymes. The menthone:(+)-(3S)-neomenthol reductase cDNA encodes a 35,722-D protein, and the recombinant enzyme yields 94% (+)-(3S)-neomenthol and 6% (−)-(3R)-menthol from (−)-menthone as substrate, and 86% (+)-(3S)-isomenthol and 14% (+)-(3R)-neoisomenthol from (+)-isomenthone as substrate, has a pH optimum of 9.3, and Km values of 674 μm, > 1 mm, and 10 μm for menthone, isomenthone, and NADPH, respectively, with a kcat of 0.06 s−1. The recombinant menthone:(−)-(3R)-menthol reductase has a deduced size of 34,070 D and converts (−)-menthone to 95% (−)-(3R)-menthol and 5% (+)-(3S)-neomenthol, and (+)-isomenthone to 87% (+)-(3R)-neoisomenthol and 13% (+)-(3S)-isomenthol, displays optimum activity at neutral pH, and has Km values of 3.0 μm, 41 μm, and 0.12 μm for menthone, isomenthone, and NADPH, respectively, with a kcat of 0.6 s−1. The respective activities of these menthone reductases account for all of the menthol isomers found in the essential oil of peppermint. Biotechnological exploitation of these genes could lead to improved production yields of (−)-menthol, the principal and characteristic flavor component of peppermint. The essential oil of peppermint (Mentha x piperita) is composed principally of C3-oxygenated p-menthane monoterpenes, and the characteristic organoleptic properties of this oil are derived predominantly from (−)-menthol. The more commonly used p-menthane monoterpene numbering system is utilized here in which the exocyclic methyl (C7) is appended to C1, the oxygen is at C3, and the isopropyl group is attached to C4; thus, (−)-menthol is 1R:3R:4S configured. Menthol biosynthesis (Fig. 1) begins with the diversion of the primary isoprenoid intermediates, isopentenyl diphosphate and its allylic isomer, dimethylallyl diphosphate, to geranyl diphosphate (the precursor of all monoterpenes) by the prenyltransferase geranyl diphosphate synthase (GPPS; Burke et al., 1999), and is followed by ionization and cyclization of this C10 intermediate to limonene by the terpene cyclase (−)-(4S)-limonene synthase (Kjonaas and Croteau, 1983). Regiospecific and stereospecific hydroxylation of this monoterpene olefin intermediate is catalyzed by cytochrome P450 limonene-3-hydroxylase to yield (−)-trans-isopiperitenol and is followed by dehydrogenation of this allylic alcohol (by isopiperitenol dehydrogenase) to afford the α,β-unsaturated ketone (-)-isopiperitenone. The endocyclic double bond of this intermediate is reduced by isopiperitenone reductase to yield (+)-cis-isopulegone, which undergoes enzymatic isomerization of the isopropenyl double bond (Δ8,9) to yield the conjugated ketone (+)-pulegone (Δ4,8). The newly formed isopropylidene double bond is reduced by pulegone reductase to yield (−)-menthone and lesser amounts of (+)-isomenthone. Alternatively, in a cytochrome P450-mediated side-reaction, pulegone undergoes C9 hydroxylation and intramolecular cyclization and dehydration to yield (+)-menthofuran. In the final reductive step of the pathway, (−)-menthone and (+)-isomenthone are reduced to (−)-menthol and (+)-neoisomenthol, respectively, or, by a separate reductase, to (+)-neomenthol and (+)-isomenthol, respectively; the latter three monoterpenol isomers are minor constituents of peppermint oil.Monoterpene biosynthesis in peppermint occurs in the highly specialized secretory cells of epidermal oil glands (McCaskill et al., 1992), and recent evidence suggests this metabolic process is divided into two temporally distinct periods of transcriptional and translational activity. The initial process is characterized by the de novo biosynthesis of the p-menthane monoterpenes (as determined by 14CO2 incorporation) that results in the accumulation of mostly (−)-menthone; once synthesized, only trace levels of monoterpenes are lost to evaporation or catabolism (Gershenzon et al., 2000). In vitro assay of the relevant enzymes of menthone biosynthesis (McConkey et al., 2000) demonstrated that these activities appear coincidentally during leaf expansion and endure for a brief time period (12-20 d post leaf initiation) with peak activity levels correlating with the essential oil secretion (gland filling) phase of gland development (Turner et al., 2000). RNA-blot analysis further showed that maximum transcript accumulation of limonene synthase occurs immediately prior to maximal enzyme activity, suggesting that at least the first committed enzyme of monoterpene biosynthesis is transcriptionally regulated (McConkey et al., 2000). However, the production of (−)-menthol from menthone is not significant until late in leaf development, after de novo monoterpene biosynthesis is essentially complete (Gershenzon et al., 2000); this process occurs in mature oil gland cells during the postsecretory phase (Turner et al., 2000). This second developmental process, termed oil maturation, is characterized by the depletion of the dominant intermediate menthone and is concomitant with increased activity of the menthone reductases and the accumulation of menthol (and lesser amounts of the epimer neomenthol; Croteau and Martinkus, 1979); this process may be accompanied by conjugation of the resulting monoterpenols to acetate esters and glucosides (Martinkus and Croteau, 1981; Croteau and Winters, 1982).
All of the enzymes of menthol biosynthesis have been characterized in cell-free systems, and cDNAs encoding GPPS, limonene synthase, and limonene-3-hydroxylase were isolated using reverse genetic approaches (Colby et al., 1993; Burke et al., 1999; Lupien et al., 1999). The development of a method for isolating intact oil gland secretory cells from peppermint leaf surfaces (Gershenzon et al., 1992) has provided a highly enriched source of terpene biosynthetic enzymes and their corresponding transcripts. These isolated secretory cells were used to prepare a cDNA pool of which 1,250 random clones were partially sequenced to generate an expressed sequence tag (EST) library in which at least 18% of the acquisitions were cDNAs involved in terpene metabolism (Lange et al., 2000). Exploitation of this highly enriched source of cDNAs has led to the cloning and functional expression of isopiperitenone reductase and pulegone reductase (Ringer et al., 2003), menthofuran synthase (Bertea et al., 2001), and, in a companion publication, isopiperitenol dehydrogenase (Ringer et al., 2005).
Because menthol content is paramount to peppermint essential oil quality, considerable interest has focused on the biosynthesis of this compound, the developmental timing of menthone reduction (and its impact on oil yield and composition at harvest), the stereoselectivity of the reduction, and the specificity of the monoterpenol conjugation reactions (Croteau and Hooper, 1979; Croteau and Martinkus, 1979). Clearly, of the remaining pathway genes, the menthone reductases are of principal interest in the context of the oil maturation process, and molecular genetic information about these ketoreductases could provide the tools for understanding, and the means of controlling, menthol production in peppermint. This paper reports the cloning, functional expression, and characterization of the two target menthone reductases, (−)-menthone:(−)-(3R)-menthol reductase (MMR) and (−)-menthone: (+)-(3S)-neomenthol reductase (MNR), and, taken together with previous work (Ringer et al., 2003) and the accompanying publication (Ringer et al., 2005), provides the entire complement of cDNAs encoding the redox enzymes of (−)-menthol biosynthesis in peppermint.
Monoterpene Metabolism. Cloning, Expression, and Characterization of Menthone Reductases from Peppermint1
Edward M. Davis, Kerry L. Ringer, Marie E. McConkey,2 and Rodney Croteau*