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The Neem Cake Project. Editorial The More Things Change Paul Bond Jr. Maria Luz Fernandez. M, Ogueke C. The most relevant of mint species with commercial or medicinal usage are listed in Table 2. Peppermint grows particularly well in lands with high waterholding capacity soil [ 55 - 70 ]. All commercial mint varieties are seed sterile and are propagated using the underground stolons runners or rootstock produced by existing plants [ 71 ]. In general, mints tolerate a wide range of conditions, and can also be grown in full sun [ 72 ].
Many studies showed that peppermint essential oil is composed of various secondary metabolites [ 27 , 28 , 31 , 33 , 34 , 38 , 53 , 54 , 73 , 74 ]. The mint main chemical compounds consist of limonene, cineole, menthone, menthofuran, isomenthone, menthyl acetate, isopulegol, menthol, pulegone and carvone Figure 2 and Table 3 [ 38 , 74 ]. Other constituents include flavonoid glycoside eg. Narirutin, Luteolino-rutinoside, Isorhoifolin and Hesperidin etc [ 75 ] polyphenols e. The amount of peppermint compounds is different in various species [ 80 ].
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Various factors including physiological variations, environmental conditions, geographic differences and genetic factors cause differences in chemical composition of these plants [ 80 ]. The most abundant chemical compounds that isolated form peppermint are largely classified into monoterpenes [ 81 ]. Currently, peppermint is the best model system for the study of monoterpene metabolism [ 82 ].
The pathway of monoterpene biosynthesis in peppermint has been well characterized by in vivo and systems biology studies Figure 3 [ 83 - 85 ]. According to the traditional view [ 86 , 87 ] monoterpenes are amongst the major constituents of essential oils and common secondary metabolites of plant metabolism, and as such they generally have been regarded as metabolic deadlock [ 83 , 84 , 87 ]. As shown in figure 3 , the peppermint monoterpene-derived compounds separate from primary metabolism by conversion of isopentenyl diphosphate and dimethylallyl diphosphate, via the action of the prenyltransferase geranyl diphosphate synthase EC 2.
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In peppermint a microsomal cytochrome Cyt P limonene- 3-hydroxylase EC 1. In these pathways, - -limonene is the first committed intermediate for biosynthesis of other compounds in the peppermint species. However, production of monoterpenes in peppermint id restricted to developing oil glands of young leaves [ 88 , 90 , 91 ], and the correlation between in vitro activity for the several enzymatic steps of menthol biosynthesis and the rate of biosynthesis measured in vivo suggests that monoterpene production is controlled by the coordinately regulated activity of relevant biosynthetic enzymes [ 82 , 90 , 92 ].
To determine stability and reactivity of peppermint main chemical compounds according to Hartree-Fock model G basis set calculation for water solution, the gap energies were measured Table 4. Based on table 4 data, menthol, cineole and isopulegol have higher stability than other compounds. According to Hartree-Fock, G basic set calculation, the highest and lowest gap energies is related to menthol Our result about stability of menthol is similar to result that reported by Harlod and coworkers [ ].
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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 [ , ].