Medicinal Plant Using Ground State Stabilization of Natural Antioxidant Curcumin by Keto-Enol Tautomerisation

doi:10.1007/s13659-018-0170-1

应用天然产物 ›› 2018, Vol. 8 ›› Issue (5): 369-390.DOI: 10.1007/s13659-018-0170-1

Medicinal Plant Using Ground State Stabilization of Natural Antioxidant Curcumin by Keto-Enol Tautomerisation

S. Manimaran¹, K. SambathKumar², R. Gayathri³, K. Raja⁴, N. Rajkamal⁵, M. Venkatachalapathy⁵, G. Ravichandran⁶, C. Lourdu EdisonRaj⁶

1 P. G & Research Department of Physics, Thanthai Hans Roever College(Autonomous), Perambalur, Tamil Nadu 621220, India;
2 Post Graduate and Research Department of Physics, (NANO Science Divisions), A. A. Govt. Arts College, Villupuram, Tamil Nadu 605602, India;
3 Post Graduate and Research Department of Physics, Cauvery College for Women, Tiruchirappalli, Tamil Nadu, India;
4 Post Graduate and Research Department of Physics, Dr. R. K. Shanmugam College of Arts & Science, Kallakurichi, Tamil Nadu 606213, India;
5 Post Graduate and Research Department of Physics, Thiru. A. Govindasamy Govt Arts College, Tindivanam, Tamil Nadu 604002, India;
6 Post Graduate and Research Department of Chemistry, A. A. Govt. Arts College, Villupuram, Tamil Nadu 605602, India

收稿日期:2018-03-13 修回日期:2018-05-23 出版日期:2018-10-24 发布日期:2018-09-19
通讯作者: S. Manimaran, K. SambathKumar

Medicinal Plant Using Ground State Stabilization of Natural Antioxidant Curcumin by Keto-Enol Tautomerisation

S. Manimaran¹, K. SambathKumar², R. Gayathri³, K. Raja⁴, N. Rajkamal⁵, M. Venkatachalapathy⁵, G. Ravichandran⁶, C. Lourdu EdisonRaj⁶

1 P. G & Research Department of Physics, Thanthai Hans Roever College(Autonomous), Perambalur, Tamil Nadu 621220, India;
2 Post Graduate and Research Department of Physics, (NANO Science Divisions), A. A. Govt. Arts College, Villupuram, Tamil Nadu 605602, India;
3 Post Graduate and Research Department of Physics, Cauvery College for Women, Tiruchirappalli, Tamil Nadu, India;
4 Post Graduate and Research Department of Physics, Dr. R. K. Shanmugam College of Arts & Science, Kallakurichi, Tamil Nadu 606213, India;
5 Post Graduate and Research Department of Physics, Thiru. A. Govindasamy Govt Arts College, Tindivanam, Tamil Nadu 604002, India;
6 Post Graduate and Research Department of Chemistry, A. A. Govt. Arts College, Villupuram, Tamil Nadu 605602, India

Received:2018-03-13 Revised:2018-05-23 Online:2018-10-24 Published:2018-09-19
Contact: S. Manimaran, K. SambathKumar

摘要/Abstract

摘要： Curcumin is a medicinal agent that exhibits anti-cancer properties and bioactive pigment in Turmeric has a huge therapeutic value. It has a keto-enol moiety that gives rise to many of its chemical properties. A recent study has shown that keto-enol tautomerisation at this moiety is implicated the effect of curcumin. The tautomerisation of curcumin in methanol, acetone and acetonitrile are used in nuclear magnetic resonance (¹H, ¹³C) spectroscopy. It was characterized using UV, IR and Raman spectral values. The molecular electrostatic potential surface of the Curcumin has been visualized in electropositive potential in the region of the CH³⁺ group and most electronegative potential in the two oxygen atom has very strong binding group. In the following, the modality of structural and thermo dynamical parameters, electrophilicity (ω), chemical potential (μ), chemical hardness (η) and electronic charge transfer confirms the local reactivity. The rate constant of tautomerisation of curcumin shows strong temperature dependence. Molecular electrostatic potential and Temperature dependence of various thermodynamic properties like (C_p,m⁰, S_m⁰, and H_m⁰) is increase with increase in temperature for monomer and dimer of various electrical fields.

关键词: Curcumin, NMR, UV, HOMO-LUMO, MEP

Abstract: Curcumin is a medicinal agent that exhibits anti-cancer properties and bioactive pigment in Turmeric has a huge therapeutic value. It has a keto-enol moiety that gives rise to many of its chemical properties. A recent study has shown that keto-enol tautomerisation at this moiety is implicated the effect of curcumin. The tautomerisation of curcumin in methanol, acetone and acetonitrile are used in nuclear magnetic resonance (¹H, ¹³C) spectroscopy. It was characterized using UV, IR and Raman spectral values. The molecular electrostatic potential surface of the Curcumin has been visualized in electropositive potential in the region of the CH³⁺ group and most electronegative potential in the two oxygen atom has very strong binding group. In the following, the modality of structural and thermo dynamical parameters, electrophilicity (ω), chemical potential (μ), chemical hardness (η) and electronic charge transfer confirms the local reactivity. The rate constant of tautomerisation of curcumin shows strong temperature dependence. Molecular electrostatic potential and Temperature dependence of various thermodynamic properties like (C_p,m⁰, S_m⁰, and H_m⁰) is increase with increase in temperature for monomer and dimer of various electrical fields.

Key words: Curcumin, NMR, UV, HOMO-LUMO, MEP

S. Manimaran, K. SambathKumar, R. Gayathri, K. Raja, N. Rajkamal, M. Venkatachalapathy, G. Ravichandran, C. Lourdu EdisonRaj. Medicinal Plant Using Ground State Stabilization of Natural Antioxidant Curcumin by Keto-Enol Tautomerisation[J]. 应用天然产物, 2018, 8(5): 369-390.

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Medicinal Plant Using Ground State Stabilization of Natural Antioxidant Curcumin by Keto-Enol Tautomerisation

Medicinal Plant Using Ground State Stabilization of Natural Antioxidant Curcumin by Keto-Enol Tautomerisation

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