Our result about stability of menthol is similar to result that reported by Harlod and coworkers [ ]. Froehlich et al. This case confirmed our molecular orbitals analysis for pulegone.
Also, surfaces for the frontier orbitals were drawn to understand the bonding scheme of present compounds. The features of these molecular orbitals can be seen in Figure 4. Figure 4: The atomic orbital composition of the molecular orbital of peppermint-derived compounds.
The electrostatic potential of a molecule is an established tool in medicinal chemistry, modeling, and computational chemistry [ , ]. The MEP employed abundantly for predicting potentials have been and interpreting the reactive behavior of a wide range of chemical system in both electrophilic and nucleophilic reactions, the study of biological recognition processes and hydrogen bonding interactions [ - ].
To predict reactive sites for electrophilic and nucleophilic attack for the peppermint chemical compounds, MEP was calculated at Hartree-Fock, G basic set optimized geometries. In the most of the MEP, while the maximum negative site which preferred region for electrophilic attack indications as red color, the maximum positive region which preferred site for nucleophilic attack symptoms as blue color [ , ].
In the present study, 3D plot of molecular electrostatic potential of studied compounds has been drawn in Figure 5. In this plot the different values of electrostatic potential at surface are represented by different colors. Figure 5: Molecular electrostatic potential surface of peppermint active compounds. As shown in Figure 5 , the regions having the negative potential are over the electronegative atom oxygen, respectively.
Thus, it would be predicted that an electrophile would preferentially attack peppermint compounds at the oxygen positions. In addition, we found the positive regions over hydrogen atoms of methyl group of peppermint compounds and indicating that these sites can be the most probably involved in nucleophilic processes. Red and blue colors in peppermint compounds map refer to the regions of negative and positive potentials and correspond to electron rich and electron-poor regions, respectively, whereas the green regions signify the neutral electrostatic potential.
The MEP surface map of peppermint compounds provides necessary information about reactive sites. These results can be used for design and development of the stable peppermint-derived drugs.
The importance and application of MEP map in drug development is discussed in many studies [ - ]. Nowadays, the development of phytotherapies aiming at the inhibition of viral diseases [ ], in combination with classical anti-viral therapies, is among the most intensively studied approaches for the treatment of pathogenic viruses [ ].
Infectious viral diseases remain an important worldwide problem, since many viruses have resisted prophylaxis or therapy longer than other microorganisms [ ]. At the moment, only few effective antiviral drugs are available for the treatment of viral diseases [ ]. There is need to find new compounds with not only intracellular but also extracellular antiviral properties [ ]. It seems, peppermint helps to immune system and protect the body from viruses [ - ].
Table 5 presents a comprehensive list of antivirus effect of peppermint extracts. Medicinal plants have been broadly used in common medicine and therefore, plant secondary metabolites are increasingly of interest as antimicrobial agents today [ , ].
Currently, biologically active compounds from peppermint sources have always been a great interest for scientists working on infectious diseases [ ]. Studies showed that the antibacterial activity of peppermint leaves extract against Gram negative bacilli was higher than of its stem extract [ ]. A number of studies demonstrated that essential oil from leaves of peppermint exhibited the highest antibacterial activity with There are differences in the chemical composition of peppermint essential oil from different parts of its structure [ ].
As mentioned above, this differences can be effect on antibacterial activity of peppermint species [ ]. It seems peppermint can become a novel target for synthesis of plant-derived drugs against a large spectrum of multidrug resistance bacteria. In-vitro data suggested that PO and extracts are good fungicidal against Candida albicans, Aspergillus albus and dermatophytic fungi [ ].
Currently, PO has become most considered agent as treatment for a large body of human diseases [ 38 ]. The major health benefits of PO are shown in Figure 6. In addition to medicinal uses, its extract is broadly used as flavoring in food industries [ ]. As mentioned in pervious sections, among all chemical compounds that purified from PO [ 31 ], menthol is common ingredient and widely is used for respiratory congestion [ , ], headache [ ], and skeletal muscle pain [ ]. The best dosage of PO for consumption in adult was reported 0.
Angiogenesis, the formation of new arterioles from preexisting vessels, is a multistep event involving degradation and remodeling of the underlying basement membrane and the surrounding extracellular matrix with subsequent proliferation and migration of vascular endothelial cells into the tissue to be vascularized [ - ].
Inflammation is regarded as an important baseline reaction responsible for manifestations of various chronic diseases such as cancer, septic shock, diabetes, atherosclerosis and obesity [ 18 , ]. Recent data have expanded the concept that inflammation is a critical component of tumor progression [ ].
There are several reports that peppermint compounds have crucial roles in prevention of inflammation and angiogenesis [ - ]. Methanol extract of peppermint has cytotoxic effect on L cancer cells [ ]. Lin and colleagues [ ] showed that apparently menthol, in higher doses, effects on NAT activity in the human liver tumor cell line J5 [ ]. The NAT is responsible for the biotransformation of numerous arylamine drugs and carcinogens [ ]. This enzyme has three critical residues consist of Cys68, His and Asp [ ].
These residues corresponding to active site of NAT enzyme [ ]. Herein, we performed a molecular docking to find the binding mode of peppermint compounds into NAT enzyme as receptor Figure 7. Figure 7: Representation of peppermint compounds docked with NAT enzyme as a receptor. Docking results showed that cineole and menthyl acetate interact with His residue and therefore, they are able to inhibit NAT enzyme activity Figure 7A and 7C.
The docking energies for cineole, menthol, menthyl acetate, isopulegol, menthone and carvone were The His is one of critical residues in the active site of NAT enzyme and it is important for its activity [ ]. Lin and Co-workers [ ] reported that menthol a possible uncompetitive inhibitor to NAT activity in cytosols. Our docking result showed that menthol is able to interact with two residues Tyr 94 and Thr 96 from NAT enzyme with a great probability Figure 7B.
Other docked compounds i. One small study looked at the topical application of a 10 percent menthol solution for migraine treatment. They found that when applied to the forehead and temples, participants had a longer duration of pain relief and less nausea and light sensitivity compared to placebo. Another study investigated the use of a treatment gel for migraines. The gel contained menthol as one of its components and was applied to the skin when a migraine began. Researchers found that there was a significant improvement by at least one severity level two hours after application.
A recent study examined the effect of peppermint oil tablets on people with difficulty swallowing and non-cardiac chest pain. Over half of the participants reported an improvement in their symptoms.
Peppermint oil is often used in cosmetic products. A small study looked at the topical application of peppermint oil and the effect that it had on chronic itching. Researchers found that a one percent solution of peppermint oil led to improvements in how long itchiness lasted and the severity of the itch.
A second small study examined the effect of applying peppermint oil on the skin to reduce itching during pregnancy. Researchers found that applying a 0. Another study in mice compared peppermint oil to minoxidil Rogaine and control compounds. The researchers found that a three percent solution of peppermint oil led to growth of thick, long hair in mice after four weeks of treatment, similar to results obtained using minoxidil.
Peppermint oil also has mild antimicrobial properties. Various studies have been performed to determine its effectiveness against different types of bacteria and fungi. The results have been mixed. One study found that incubating peppermint oil with several strains of Staphylococcus aureus , some of which were antibiotic resistant, inhibited the production of an important bacterial toxin.
This effect was dose-dependent, meaning that the effect increased with rising doses of peppermint oil. While this result is promising, the antimicrobial activity of peppermint oil may depend on the species of bacteria. Another study found that peppermint oil showed no antimicrobial activity against a species of Streptococcus. A study from looked at the activity of several essential oils against different strains of Candida yeast. While peppermint oil did have some antifungal activity, it had the lowest activity out of all the oils that were tested.
Essential oils are not meant to be taken orally. Some possible side effects from taking peppermint extract orally include heartburn, nausea, and vomiting. Aromatherapy or topical use of diluted essential peppermint oil can have significant benefits with little risk.
But be aware that peppermint aromatherapy can be toxic to pets. Always consider children, pets, and pregnant women before using aromatherapy. If taken in very large doses, peppermint oil can be toxic. It contains a known toxic compound called pulegone.
Cosmetic formulations of peppermint oil are supposed to contain one percent or less pulegone, although in some cases they may contain more. Only a few drops are needed for diluting in an ounce of carrier oil. Peppermint oil comes from the peppermint plant. While some of the proposed benefits of peppermint oil come from anecdotal evidence, research suggests peppermint oil may be beneficial for IBS and other digestive conditions, as well as pain relief.
Peppermint has a long history. Ancient Egyptian medical text dating as early as BC includes peppermint. Early history mentions peppermint in Greek mythology, by Roman philosophers, Jesus in the Bible and Monks in the middle ages. Michigan is ninth in the U. Michigan has a rich history cultivating mint.
Peppermint has naturalized and can be found growing wild in North America and Europe. Peppermint plants grow between inches tall and 24 inches wide. Peppermint often becomes invasive in the home garden. Specialized cells produce peppermint oil in the leaves of the peppermint plant. The oil is released once the leaves are crushed or chopped.
The best time to harvest peppermint is on a sunny day when the plant is just beginning to flower. Peppermint is the most extensively used volatile oil, both commercially and medicinally. Ancient Greeks thought it could cure hiccups. Peppermint is the number one flavor for non-chocolate, hard candies.
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