Identification of zingiber components by gas chromatograph/mass spectrometer and semi-empirical calculations

  • Authors

    • Mamoun Sarhan Mahmoud Abd El kareem Egyptian Atomic Energy Authority
    • Mohamed Abd El fattah Rabbih Egyptian Atomic Energy Authority
    • Ezzat Taha Mohamed Selim Egyptian Atomic Energy Authority
    2016-05-14
    https://doi.org/10.14419/ijpr.v4i1.6052
  • Zingiber, Gas Chromatography-Mass Spectrometry and Semi-Empirical Calculations.
  • The important used of Zingiber in different fields such as medicine and foods, this leads to study the physical and chemical properties of its components. The chemical components in Zingiber officinale Roscoe were identified by gas chromatograph/ mass spectrometer (GC/MS) with electron ionization mode. The major components of Zingiber under investigation namely: (1) Pentadecanoic acid (2) 1,3-Dioxepane, 2-pentadecyl (3) 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl (4) gingerol. Electron ionization mass spectra of these compounds have been obtained and investigated. In addition, the semi-empirical (MNDO) method was used to calculate some physical and thermochemical properties for the structural of these compounds such as total energy, electronic energy, ionization energy, heats of formation, proton affinity and dipole moments which might to predict the activity and behavior of these compounds.

  • References

    1. Bobbarala V, Bramhachari PV, Ravichand J, Reddy YHK, Kotresha D, Chaitanya KV (2011), J Pharm Res 4(1): 252-255.
    2. Park EJ, Pizzuto JM (2002), Botanicals in cancer chemoprevention. Cancer Metast Rev. 21:231–55 http://dx.doi.org/10.1023/A:1021254725842.
    3. Shukla Y, Singh M (2007), Cancer preventive properties of ginger: A brief review. Food Chem Toxicol.45:683–90. http://dx.doi.org/10.1016/j.fct.2006.11.002.
    4. Jiang H, Xie Z, Koo HJ, McLaughlin SP, Timmermann BN, Gang DR (2006), metabolic profiling and phylogenetic analysis of medicinal Zingiber species: Tools for authentication of ginger (Zingiber officinale Rosc.) Phytochemistry. 67:232–44. http://dx.doi.org/10.1016/j.phytochem.2005.08.001.
    5. Ali BH, Blunden G, Tanira MO, Nemmar A (2008), some phytochemical, pharmacological and toxicological properties of ginger (Zingiber officinale Roscoe): A review of recent research. Food Chem Toxicol.46:409–20. http://dx.doi.org/10.1016/j.fct.2007.09.085.
    6. Nicoll R, Henein MY (2009), Ginger (Zingiber officinale Roscoe): A hot remedy for cardiovascular disease. Int. J. Cardiol. 131:408–9. http://dx.doi.org/10.1016/j.ijcard.2007.07.107.
    7. K. Mythili, C. Umamaheswara Reddy, D. Chamundeeswari, P.K. Manna(2013), GC-MS analysis of phytocomponents and in-vitro inhibitory effects ofCalanthe triplicata. Journal of Natural Products, 6:141-146).
    8. V. Lakshmi and G. Viji Stella Bai (2015), Determination of Biologically active compounds in Clerodendrum phlomidis (L.) leaf extract using GC/MS. International Journal of Multidisciplinary Research and Development. 2(1): 294-300.
    9. Jeena K1, Liju VB, Kuttan R(2013), Antioxidant, anti-inflammatory and antinociceptive activities of essential oil from ginger.Indian Journal of Physiology and Pharmacology. 57(1):51-62.
    10. Omnia Ismail Mohamed, Abeer Fekry El-Nahas, Yasser Said El-Sayed & Khaled Mohamed Ashry.(2015). Ginger extract modulates Pb-induced hepatic oxidative stress and expression of antioxidant gene transcripts in rat liver .Pharm Biol, Early Online: 1–9 http://dx.doi.org/10.3109/13880209.2015.1057651.
    11. Catchpole OJ, Grey JB, Perry NB, Burgess EJ, Redmond WA, Porter NG (2003), Extraction of chili, black pepper, and ginger with near-critical CO2, propane, and dimethyl ether: analysis of the extracts by quantitative nuclear magnetic resonance.Journal of Agricultural and Food Chemistry. 51: 4853. http://dx.doi.org/10.1021/jf0301246.
    12. Connell DW, McLachlan R. J. D.W. Connell, R(1972), Journal of Chromatography A, 67( 1),29-35 http://dx.doi.org/10.1016/S0021-9673(01)97144-4.
    13. He X, Bernart M, Lian L, Lin L (1998),High-performance liquid chromatography–electrospray mass spectrometric analysis of pungent constituents of ginger. Journal of Chromatography A, 796, 2,327-334. http://dx.doi.org/10.1016/S0021-9673(97)01013-3.
    14. Huang H, Kuo K, Hsieh Y(1997), Determination of cinnamaldehyde, cinnamic acid, paeoniflorin, glycyrrhizin and [6]-gingerol in the traditional Chinese medicinal preparation Kuei-chih-tang by cyclodextrin-modified micellar electrokinetic chromatography. J. Chromatogr. A, 771, 267-274. http://dx.doi.org/10.1016/S0021-9673(97)00136-2.
    15. Jolad S, Lantz R, Solyom A, Chen G, Bates R, Timmermann B(2004),Fresh organically grown ginger (Zingiber officinale): composition and effects on LPS-induced PGE2production. Phytochemistry. 65: 1937-1954. http://dx.doi.org/10.1016/j.phytochem.2004.06.008.
    16. S.S. Choudhari, B.M. Kareppa(2013), Identification of bioactive compounds of Zingiber Officinale Roscoe Rhizomes through gas chromatography and mass spectrometry . International Journal of Pharmaceutical Research & Development, 5(08), 16 – 20.
    17. A.C.Larry and R.Krishnan; (1998), “Computational Thermochemistry Prediction and Estimation of Molecular Thermodynamicsâ€,(Eds. K.I.Karl and D.J.Frurip), American Chemical Society, pp. 176.
    18. M.J.S. Dewar (1969), “The molecular Orbital Theory of Organic Chemistryâ€, McGrawHill: New York, NY.
    19. D.L.Pople and J.A.Beveridge(1970), “Approximate Molecular Orbital Theory†, Mc Graw-Hill, New York,NY.
    20. J.N.Murrell and A.J.Harget (1972), “Semiempirical Self-Consistent-Field Molecular Orbital Theory of Moleculesâ€, Wiley,New York,NY.
    21. G.A.Segal(1977), “Modern Theoritcal Chemistryâ€; Plenum: New York,NY, 7-8.
    22. Dewar, M.J.S. (1975) Quantum Organic Chemistry. Science, 187, 1037-1044. http://dx.doi.org/10.1126/science.187.4181.1037.
    23. Jug, K. (1980). Quantum Chemical Methods and Their Applications to Chemical Reactions. Theoretica Chimica Acta, 54, 263-300. http://dx.doi.org/10.1007/BF00552463.
    24. Dewar, M.J.S. (1985) Applications of Quantum Mechanical Molecular Models to Chemical Problems. Part 70. Quantum Mechanical Molecular Models. The Journal of Physical Chemistry, 89, 2145-2150. http://dx.doi.org/10.1021/j100257a004.
    25. Thiel, W. (1988), Semiempirical Methods: Current Status and Perspectives. Tetrahedron, 44, 7393-7408. http://dx.doi.org/10.1016/S0040-4020(01)86235-9.
    26. Stewart, J.J.P. (1990), MOPAC: A Semiempirical Molecular Orbital Program. Journal of Computer-Aided Molecular Design, 4, 1-103. http://dx.doi.org/10.1007/BF00128336.
    27. J.J.P.Stewart (1991), “Reviews in Computational Chemistryâ€,(Eds. K.B.Lipkowitz and D.B.Boyd),VCH Publishers, New York,NY,1, pp.45.
    28. M.C.Zamer; “Reviews in Computational Chemistryâ€,(Eds. K.B.Lipkowitz and D.B.Boyd), VCH Publishers; New York,NY, 2, pp.313,(1990).
    29. W.Thiel; “Advances in Chemical Physics: New Methods in Computational Quntum Mechanicsâ€, (Eds. I.Prigogine and A.R.Stuart), 93, 703, (1996).
    30. Luciana A. Fernandez , Marisa R. Santo , Mario Reta , Liliana Giacomelli , Rosa Cattana, Juana J. Silber , Mariela Risso , Hugo Cerecetto , Mercedes Gonzalez and Claudio Olea-Azar. Relationship between Physicochemical Properties and Herbicidal Activity of 1, 2, 5-Oxadiazole N-Oxide Derivatives. Molecules 2005, 10(9), 1197-1208; http://dx.doi.org/10.3390/10091197.
    31. Saskia A. B. E. van Acker , Marcel J. de Groot , Dirk-Jan van den Berg , Michèl N. J. L. Tromp , Gabrielle Donné-Op den Kelder , Wim J. F. van der Vijgh , and Aalt Bast. A Quantum Chemical Explanation of the Antioxidant Activity of Flavonoids. Chemical Research in Toxicology, 1996, 9 (8), pp 1305–1312. http://dx.doi.org/10.1021/tx9600964.
    32. El Hassane Anouar. A Quantum Chemical and Statistical Study of Phenolic Schiff Bases with Antioxidant Activity against DPPH Free Radical. Antioxidants 2014, 3(2), 309-322; http://dx.doi.org/10.3390/antiox3020309.
    33. Abhishek Giri, Bhuwan B. Mishra, Priyanka Tripathi, Prahlad P. Agrawal and Pashupati P. Singh. Quantitative structure-activity relationship of matrix metalloproteinase inhibitors based on quantum chemical descriptors. Journal of Computational methods in Molecular Design, 2011, 1 (4):14-21.
    34. Omer Abdalla Ahmed Hamdi , El Hassane Anouar , Jamil A. Shilpi , Zuhra Bashir Khalifa Al Trabolsy,Sharifuddin Bin Md Zain, Nur Shahidatul Shida Zakaria, Mohd Zulkefeli, Jean-Frédéric F. Weber,Sri Nurestri A. Malek, Syarifah Nur Syed Abdul Rahman and Khalijah Awang. A Quantum Chemical and Statistical Study of Cytotoxic Activity of Compounds Isolated from Curcuma zedoaria. International Journal of Molecular Sciences. 2015, 16(5), 9450-9468; http://dx.doi.org/10.3390/ijms16059450.
    35. Qing Meng1, Ziyin Yang, Guoliang Jie1, Ying Gao, Xinghai Zhang, Wei Li, Bo Li1, Youying Tu1. Evaluation of Antioxidant Activity of Tea Polyphenols by a Quantum Chemistry Calculation Method - PM6. Journal of Food and Nutrition Research, 2014, Vol. 2, No. 12, 965-972. http://dx.doi.org/10.12691/jfnr-2-12-17.
    36. Ammar A. Ibrahim and Eid A.A. alrazaq. Physical Properties of Phenol Compound: Semi-empirical Calculation of Substituent Effects [Part One]. American journal of applied sciences 6(7)1385-1389, 2009. American Journal of Applied Sciences http://dx.doi.org/10.3844/ajassp.2009.1385.1389.
    37. HyperChemTM, Release 7.5 Pro for Windows, “Molecular Modeling Systemâ€, Hypercube, User Evaluation copy, Organization: Evaluation copy, Dealer: Copyright©2002 Hypercube,Inc, Serial No.99-999-9999999999.
    38. G.H. Wannier. The Threshold Law for Single Ionization of Atoms or Ions by Electrons. Physical Review Letters., 90, 817 (1953). http://dx.doi.org/10.1103/physrev.90.817.
    39. Mamoun S.M. Abd El Kareem. Mass Spectrometric Study Of Some FLUOROQUINOLONE Drugs Using Electron Ionization and Chemical Ionization Techniques In Combination with Semi-Empirical Calculations. Physics department, Faculty of Science, Benha University (2013).
  • Downloads

  • How to Cite

    Sarhan Mahmoud Abd El kareem, M., Abd El fattah Rabbih, M., & Taha Mohamed Selim, E. (2016). Identification of zingiber components by gas chromatograph/mass spectrometer and semi-empirical calculations. International Journal of Physical Research, 4(1), 20-26. https://doi.org/10.14419/ijpr.v4i1.6052