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Synthesis of polyhydroxylated flavonoids

Flavonoids are a group of polyphenolic compounds ubiquitously found in the plant kingdom. Flavonoids have gained recent interest because of their broad pharmacological activities. In the present study, several polyhydroxylated flavonoids namely, 3,4-bis(benzyloxy)-3-hydroxyflavone, 3,4,5,7-tetrahydr...

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Main Authors: Ahmad, Farediah, Mohd. Sirat, Hasnah, Azahar, Muhammad Syamil, Mohamed Adib, Adiana
Format: Monograph
Published: Faculty of Science 2009
Online Access:http://eprints.utm.my/id/eprint/9146/
https://www.researchgate.net/publication/44161112_Synthesis_of_Polyhydroxylated_Flavonoids
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spelling my.utm.91462017-09-02T08:01:34Z http://eprints.utm.my/id/eprint/9146/ Synthesis of polyhydroxylated flavonoids Ahmad, Farediah Mohd. Sirat, Hasnah Azahar, Muhammad Syamil Mohamed Adib, Adiana Flavonoids are a group of polyphenolic compounds ubiquitously found in the plant kingdom. Flavonoids have gained recent interest because of their broad pharmacological activities. In the present study, several polyhydroxylated flavonoids namely, 3,4-bis(benzyloxy)-3-hydroxyflavone, 3,4,5,7-tetrahydroxyflavanone, 4,5,7-trihydroxyflavanone and 4,5,7-trihydroxy-3-prenylflavanone have been synthesised. These target compounds were synthesised via its chalcones as the key precursor. The initial step in the synthesis was to prepare various derivatives of 2- hydroxyacetophenone and benzaldehyde by protection of the phenolic hydroxyl groups. The approach for the synthesis of chalcones is by the Claisen-Schmidt condensation of the respective 2-hydroxyacetophenones and benzaldehydes under basic condition to give the corresponding 2-hydroxychalcones. 3,4-Bisbenzyloxy- 3-hydroxyflavone was synthesised from 3,4-bis(benzyloxy)-2-hydroxychalcone by the Algar-Flynn-Olyamada (AFO) oxidative method. The natural occurring flavanones, 3,4,5,7-tetrahydroxyflavanone and 4,5,7-trihydroxyflavanone were prepared from 2-hydroxy-3,4,4,6-tetrakis (methoxymethyloxy)chalcone and 2- hydroxy-4,4,6-tris(methoxymethyloxy) chalcone respectively, by acid hydrolysis and subsequent treatment with sodium acetate. The last feature in the synthesis was the preparation of 4,5,7-trihydroxy-3-prenylflavanone starting from the prenylation of 4-hydroxybenzaldehyde, protection of the phenolic group, formation of 2- hydroxy-4,4,6-tris(methoxymethyloxy)-3-prenylchalcone and followed by acid hydrolysis and cyclisation of the chalcone led to the production 4,5,7-trihydroxy-3- prenylflavanone in 89.3% yield. The antibacterial activity of the targeted compounds and its chalcone precursor were demonstrated by the filter paper disc diffusion method. The antioxidant activity were evaluated based on the free radical scavenging activity of the flavonoids against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical by using UV and Electron Spin Resonance techniques. Structures were confirmed spectroscopically by UV, IR, NMR (1H and 13C), COSY and MS. Faculty of Science 2009-01-31 Monograph NonPeerReviewed Ahmad, Farediah and Mohd. Sirat, Hasnah and Azahar, Muhammad Syamil and Mohamed Adib, Adiana (2009) Synthesis of polyhydroxylated flavonoids. Project Report. Faculty of Science, Skudai, Johor. (Unpublished) https://www.researchgate.net/publication/44161112_Synthesis_of_Polyhydroxylated_Flavonoids
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/
description Flavonoids are a group of polyphenolic compounds ubiquitously found in the plant kingdom. Flavonoids have gained recent interest because of their broad pharmacological activities. In the present study, several polyhydroxylated flavonoids namely, 3,4-bis(benzyloxy)-3-hydroxyflavone, 3,4,5,7-tetrahydroxyflavanone, 4,5,7-trihydroxyflavanone and 4,5,7-trihydroxy-3-prenylflavanone have been synthesised. These target compounds were synthesised via its chalcones as the key precursor. The initial step in the synthesis was to prepare various derivatives of 2- hydroxyacetophenone and benzaldehyde by protection of the phenolic hydroxyl groups. The approach for the synthesis of chalcones is by the Claisen-Schmidt condensation of the respective 2-hydroxyacetophenones and benzaldehydes under basic condition to give the corresponding 2-hydroxychalcones. 3,4-Bisbenzyloxy- 3-hydroxyflavone was synthesised from 3,4-bis(benzyloxy)-2-hydroxychalcone by the Algar-Flynn-Olyamada (AFO) oxidative method. The natural occurring flavanones, 3,4,5,7-tetrahydroxyflavanone and 4,5,7-trihydroxyflavanone were prepared from 2-hydroxy-3,4,4,6-tetrakis (methoxymethyloxy)chalcone and 2- hydroxy-4,4,6-tris(methoxymethyloxy) chalcone respectively, by acid hydrolysis and subsequent treatment with sodium acetate. The last feature in the synthesis was the preparation of 4,5,7-trihydroxy-3-prenylflavanone starting from the prenylation of 4-hydroxybenzaldehyde, protection of the phenolic group, formation of 2- hydroxy-4,4,6-tris(methoxymethyloxy)-3-prenylchalcone and followed by acid hydrolysis and cyclisation of the chalcone led to the production 4,5,7-trihydroxy-3- prenylflavanone in 89.3% yield. The antibacterial activity of the targeted compounds and its chalcone precursor were demonstrated by the filter paper disc diffusion method. The antioxidant activity were evaluated based on the free radical scavenging activity of the flavonoids against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical by using UV and Electron Spin Resonance techniques. Structures were confirmed spectroscopically by UV, IR, NMR (1H and 13C), COSY and MS.
format Monograph
author Ahmad, Farediah
Mohd. Sirat, Hasnah
Azahar, Muhammad Syamil
Mohamed Adib, Adiana
spellingShingle Ahmad, Farediah
Mohd. Sirat, Hasnah
Azahar, Muhammad Syamil
Mohamed Adib, Adiana
Synthesis of polyhydroxylated flavonoids
author_facet Ahmad, Farediah
Mohd. Sirat, Hasnah
Azahar, Muhammad Syamil
Mohamed Adib, Adiana
author_sort Ahmad, Farediah
title Synthesis of polyhydroxylated flavonoids
title_short Synthesis of polyhydroxylated flavonoids
title_full Synthesis of polyhydroxylated flavonoids
title_fullStr Synthesis of polyhydroxylated flavonoids
title_full_unstemmed Synthesis of polyhydroxylated flavonoids
title_sort synthesis of polyhydroxylated flavonoids
publisher Faculty of Science
publishDate 2009
url http://eprints.utm.my/id/eprint/9146/
https://www.researchgate.net/publication/44161112_Synthesis_of_Polyhydroxylated_Flavonoids
_version_ 1643645127494729728
score 13.211869

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