Chalcones and Aurones

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Chalcones and Aurones :

Chalcones and Aurones Masatu Godfrey Mafuru Alfred Manyanga Herman Masota Nelson

Introduction:

Introduction The flavonoids are polyphenolic compounds possessing 15 carbon atoms; two benzene rings joined by a linear three carbon chain Flavonoids constitute one of the most characteristic classes of compounds in higher plants. Many flavonoids are easily recognised as flower pigments in most angiosperm families (flowering plants). However, their occurence is not restricted to flowers but include all parts of the plant

Classification of Flavonoids:

Classification of Flavonoids Examples of the 6 major subgroups are 1.Chalcones 2. Flavone (generally in herbaceous families, e.g. Labiatae , Umbelliferae , Compositae ) 3. Flavonol (generally in woody angiosperms 4. Flavanone 5. Anthocyanins 6. Isoflavonoids

Sources:

Sources

Chalcones:

Chalcones Chalcone is an aromatic ketone and an enone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones or chalconoids .

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Benzylideneacetophenone is the parent member of the chalcone series. The alternative name given to chalcone are phenyl styryl ketone , benzalacetophenone , β - phenylacrylophenone , ɣ - oxo - α , ɣ - diphenyl - α -propylene and α -phenyl- β - benzoylethylene

Chalcone structure:

Chalcone structure

Biological activities:

Biological activities These properties have been found to include anticancer, antiviral, antioxidant antiinflammatory activities , effects on capillary fragility, and an ability to inhibit human platelet aggregation

AURONES:

AURONES

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Aurone is a heterocyclic chemical compound which is a type of flavonoid . [ There are two isomers of the molecule, with ( E )- and ( Z )-configurations.

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The molecule contains a benzofuran element associated with a benzylidene linked in position 2. In aurone , a chalcone -like group is closed into a 5-membered ring instead of the 6-membered ring more typical of flavonoids .

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Most aurones are in a ( Z )-configuration, which is the more stable configuration according to Austin Model 1computation, but there are also some in the ( E )-configurations

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Skeletal structure of an ( Z )- aurone with numbering scheme used for nomenclature of derivatives

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Aurone forms the core for a family of derivatives which are known collectively as aurones . Aurones are plant flavonoids that provide yellow color to the flowers of some popular ornamental plants, such as snapdragon and cosmos .

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snapdragon Cosmos

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Aurones including 4'-chloro-2-hydroxyaurone (C 15 H 11 O 3 Cl) and 4'-chloroaurone (C 15 H 9 O 2 Cl) can also be found in the brown alga Spatoglossum variabile .

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Analogy with flavonoids suggests that aurones could have interesting biological properties

Biological Activities:

Biological Activities Antioxidant activity – found in almost all Aurone containing species Anti bacterial activity against gram positive and gram negative bacteria eg in Gomphrena agrestis Antifeedant activity.

References:

References ‘ Aurones : interesting natural and synthetic compounds with emerging biological potential.’ Nat Prod Commun 2012 Mar;7(3):389-94 Zwergel C, Gaascht F, Valente S, Diederich M, Bagrel D, Kirsch G. http://en.wikipedia.org/wiki/Aurone

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‘Synthesis and Insect Antifeedant Activity of Aurones against Spodoptera litura Larvae’ Masanori Morimoto,Hiromi Fukumoto , Toki Nozoe , Ai Hagiwara, and Koichiro Komai Department of Applied Biological Chemistry, Faculty of Agriculture, Kinki University, 3327-204 Nakamachi , Nara, Japan J. Agric. Food Chem. , 2007 , 55 (3), pp 700–705 DOI: 10.1021/jf062562t Publication Date (Web): January 10, 2007 (http://pubs.acs.org/doi/abs/10.1021/jf062562t )

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‘ Aurones as Modulators of ABCG2 and ABCB1: Synthesis and Structure–Activity Relationships’ Dr. Hong May Sim,Ker Yun Loh,Wee Kiang Yeo,Dr . Chong Yew Lee,Prof . Mei Lin Go Article first published online: 7 FEB 2011 ( http://onlinelibrary.wiley.com/doi/10.1002/cmdc.201000520/full )