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Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey

Phenolic acids and flavonoids exist naturally in Malaysian honey and contribute significantly to antioxidant contents. Antioxidants plays an important role in scavenging free radicals and prevent health deterioration. Total antioxidant content is measured using DPPH (2,2-diphenyl-1-picrylhydrazyl) r...

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Main Authors: Jamaludin, Rosmahaida, Maarop, Nurazean, Siti Fatimah, Siti Fatimah, Mustafa, Zaharah, Maarof, Hasmerya, Usman, Bishir
Format: Article
Published: UKM Press 2019
Subjects:
T Technology (General)
Online Access:http://eprints.utm.my/id/eprint/89492/
http://dx.doi.org/10.17576/jkukm-2019-si2(1)-10
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spelling my.utm.894922021-02-22T01:47:47Z http://eprints.utm.my/id/eprint/89492/ Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey Jamaludin, Rosmahaida Maarop, Nurazean Siti Fatimah, Siti Fatimah Mustafa, Zaharah Maarof, Hasmerya Usman, Bishir T Technology (General) Phenolic acids and flavonoids exist naturally in Malaysian honey and contribute significantly to antioxidant contents. Antioxidants plays an important role in scavenging free radicals and prevent health deterioration. Total antioxidant content is measured using DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity. The phenolic acids such as gallic, caffeic, syringic and hydroxybenzoic acids and flavonoids like naringenin, apigenin, kaempferol, catechin and luteolin previously have been identified in Malaysian honey of tualang, gelam and borneo type using high-performance liquid chromatography (HPLC). In order to investigate the structure-antioxidant activity relationships of these phenolic compounds using hydrogen atom transfer (HAT) mechanism, density functional theory (DFT) calculation at B3LYP/6-311++G(d,p) levels of theory was performed. In this work, optimization of the compounds chemical structure and radical forms in gas-phase has been calculated with computation of bond dissociation enthalpy (BDE) as antioxidant descriptor. The finding showed that abstraction of H at different OH groups in the structure of the compound, led to a different scavenging free radical activity thus contribute to the overall variation in the antioxidant properties. Besides that, B ring of flavonoids and unsaturated bond in pyran ring are proposed factors that could lower the BDE values and consequently influence the antioxidant properties of the antioxidant compounds. Hence, DFT calculation with BDE descriptor had been successfully applied to investigate the relationship between structure of phenolic acids and antioxidant activity of Malaysian honey and the interesting results could contribute in future development of antioxidant compound. UKM Press 2019 Article PeerReviewed Jamaludin, Rosmahaida and Maarop, Nurazean and Siti Fatimah, Siti Fatimah and Mustafa, Zaharah and Maarof, Hasmerya and Usman, Bishir (2019) Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey. Jurnal Kejuruteraan SI, 2 (1). pp. 77-83. ISSN 0012-80198 http://dx.doi.org/10.17576/jkukm-2019-si2(1)-10
institution Universiti Teknologi Malaysia
building UTM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Malaysia
content_source UTM Institutional Repository
url_provider http://eprints.utm.my/
topic T Technology (General)
spellingShingle T Technology (General)
Jamaludin, Rosmahaida
Maarop, Nurazean
Siti Fatimah, Siti Fatimah
Mustafa, Zaharah
Maarof, Hasmerya
Usman, Bishir
Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey
description Phenolic acids and flavonoids exist naturally in Malaysian honey and contribute significantly to antioxidant contents. Antioxidants plays an important role in scavenging free radicals and prevent health deterioration. Total antioxidant content is measured using DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity. The phenolic acids such as gallic, caffeic, syringic and hydroxybenzoic acids and flavonoids like naringenin, apigenin, kaempferol, catechin and luteolin previously have been identified in Malaysian honey of tualang, gelam and borneo type using high-performance liquid chromatography (HPLC). In order to investigate the structure-antioxidant activity relationships of these phenolic compounds using hydrogen atom transfer (HAT) mechanism, density functional theory (DFT) calculation at B3LYP/6-311++G(d,p) levels of theory was performed. In this work, optimization of the compounds chemical structure and radical forms in gas-phase has been calculated with computation of bond dissociation enthalpy (BDE) as antioxidant descriptor. The finding showed that abstraction of H at different OH groups in the structure of the compound, led to a different scavenging free radical activity thus contribute to the overall variation in the antioxidant properties. Besides that, B ring of flavonoids and unsaturated bond in pyran ring are proposed factors that could lower the BDE values and consequently influence the antioxidant properties of the antioxidant compounds. Hence, DFT calculation with BDE descriptor had been successfully applied to investigate the relationship between structure of phenolic acids and antioxidant activity of Malaysian honey and the interesting results could contribute in future development of antioxidant compound.
format Article
author Jamaludin, Rosmahaida
Maarop, Nurazean
Siti Fatimah, Siti Fatimah
Mustafa, Zaharah
Maarof, Hasmerya
Usman, Bishir
author_facet Jamaludin, Rosmahaida
Maarop, Nurazean
Siti Fatimah, Siti Fatimah
Mustafa, Zaharah
Maarof, Hasmerya
Usman, Bishir
author_sort Jamaludin, Rosmahaida
title Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey
title_short Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey
title_full Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey
title_fullStr Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey
title_full_unstemmed Density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in Malaysian honey
title_sort density functional theory calculations of structure-antioxidant activity of selected phenolic acids and flavonoids found in malaysian honey
publisher UKM Press
publishDate 2019
url http://eprints.utm.my/id/eprint/89492/
http://dx.doi.org/10.17576/jkukm-2019-si2(1)-10
_version_ 1692991790039171072
score 13.211869

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