Curcuminoids as antioxidants and theoretical study of stability of curcumin isomers in gaseous state

Jasim Hilo Naama, Ghadah H. Alwan, Hasan R. Obayes, Ahmed A. Al-Amiery, Ali A. Al-Temimi, Abdul Amir H. Kadhum, Abu Bakar Mohamad

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The antioxidant activity of three extracted curcuminods, namely, curcumin [(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5dione] (C), demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC), were studied with the DPPH, hydrogen peroxide and nitric oxide radical methods, and compared with the known antioxidant ascorbic acid. Structures for the extracted curcuminods are proposed on the basis of spectroscopic evidence. Curcumin molecule stability was studied in the gaseous state, and it has two isomers [the diketone form, curcumin(I), and the enol form, curcumin(II)] through the theoretical study by relying on the results of density functions theory (DFT). The results of each of the total energy and the high occupied molecular orbital (HOMO) to curcumin(I) are more stable than to curcumin(II). The increase of the amount of total energy is -0.01301141 a.u., or equivalent, -8,164.783 cal mol-1. The HOMO level is -0.35865 eV, also the thermodynamic values (the change in entropy â̂†S and the change in enthalpy â̂†H) of the isomerization conversion form curcumin(II) to curcumin(I) spontaneous and endothermic reaction, of â̂†S and â̂†H are -3.136 cal mol-1 K-1 and -0.673 kcal mol-1, respectively. The results showed that the wavelength for greatest absorption (λ max) of the enol form curcumin(II) is longer than curcumin(I). This is due to the formation of a new double bond which leads to the association distribution of the electronic density along the molecule in the enol form.

Original languageEnglish
Pages (from-to)4047-4059
Number of pages13
JournalResearch on Chemical Intermediates
Volume39
Issue number9
DOIs
Publication statusPublished - Nov 2013

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Curcumin
Isomers
Antioxidants
Molecular orbitals
Molecules
Isomerization
Probability density function
Hydrogen Peroxide
Ascorbic Acid
Enthalpy
Nitric Oxide
Entropy
demethoxycurcumin
Association reactions
Thermodynamics
Wavelength

Keywords

  • Antioxidant
  • Curcumin
  • DPPH
  • HOMO
  • LUMO

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Curcuminoids as antioxidants and theoretical study of stability of curcumin isomers in gaseous state. / Naama, Jasim Hilo; Alwan, Ghadah H.; Obayes, Hasan R.; Al-Amiery, Ahmed A.; Al-Temimi, Ali A.; Kadhum, Abdul Amir H.; Mohamad, Abu Bakar.

In: Research on Chemical Intermediates, Vol. 39, No. 9, 11.2013, p. 4047-4059.

Research output: Contribution to journalArticle

Naama, Jasim Hilo ; Alwan, Ghadah H. ; Obayes, Hasan R. ; Al-Amiery, Ahmed A. ; Al-Temimi, Ali A. ; Kadhum, Abdul Amir H. ; Mohamad, Abu Bakar. / Curcuminoids as antioxidants and theoretical study of stability of curcumin isomers in gaseous state. In: Research on Chemical Intermediates. 2013 ; Vol. 39, No. 9. pp. 4047-4059.
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AU - Obayes, Hasan R.

AU - Al-Amiery, Ahmed A.

AU - Al-Temimi, Ali A.

AU - Kadhum, Abdul Amir H.

AU - Mohamad, Abu Bakar

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AB - The antioxidant activity of three extracted curcuminods, namely, curcumin [(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5dione] (C), demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC), were studied with the DPPH, hydrogen peroxide and nitric oxide radical methods, and compared with the known antioxidant ascorbic acid. Structures for the extracted curcuminods are proposed on the basis of spectroscopic evidence. Curcumin molecule stability was studied in the gaseous state, and it has two isomers [the diketone form, curcumin(I), and the enol form, curcumin(II)] through the theoretical study by relying on the results of density functions theory (DFT). The results of each of the total energy and the high occupied molecular orbital (HOMO) to curcumin(I) are more stable than to curcumin(II). The increase of the amount of total energy is -0.01301141 a.u., or equivalent, -8,164.783 cal mol-1. The HOMO level is -0.35865 eV, also the thermodynamic values (the change in entropy â̂†S and the change in enthalpy â̂†H) of the isomerization conversion form curcumin(II) to curcumin(I) spontaneous and endothermic reaction, of â̂†S and â̂†H are -3.136 cal mol-1 K-1 and -0.673 kcal mol-1, respectively. The results showed that the wavelength for greatest absorption (λ max) of the enol form curcumin(II) is longer than curcumin(I). This is due to the formation of a new double bond which leads to the association distribution of the electronic density along the molecule in the enol form.

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