An aurone is a heterocyclic chemical compound which is a type of

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

. There are two isomers of the molecule, with (''E'')- and (''Z'')-configurations. The molecule contains a benzofuran element associated with a benzylidene linked in position 2. In aurone, a

chalcone Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. Chemical properties Chalcones have two absorption maxima a ...

-like group is closed into a 5-membered ring instead of the 6-membered ring more typical of

Aurone derivatives

Aurone forms the core for a family of derivatives which are known collectively as aurones. Aurones are plant flavonoids that provide

yellow color Yellow is the color between green and orange on the spectrum of light. It is evoked by light with a dominant wavelength of roughly 575585 nm. It is a primary color in subtractive color systems, used in painting or color printing. In the R ...

to the flowers of some popular ornamental plants, such as snapdragon and cosmos. Aurones including 4'-chloro-2-hydroxyaurone (C₁₅H₁₁O₃Cl) and 4'-chloroaurone (C₁₅H₉O₂Cl) can also be found in the brown alga '' Spatoglossum variabile''. Most aurones are in a (''Z'')-configuration, which is the more stable configuration according to Austin Model 1 computation, but there are also some in the (''E'')-configurations such as (E)-3'-O-β-d-glucopyranosyl-4,5,6,4'-tetrahydroxy-7,2'-dimethoxyaurone, found in ''

Gomphrena agrestis ''Gomphrena agrestis'' is a plant native to Cerrado vegetation in Brazil. This plant is cited in ''Flora Brasiliensis'' biosynthesized starting from coumaryl-CoA. Aureusidin synthase catalyzes the creation of aurones from chalcones through hydroxylation and oxidative cyclization.

Applications

Some aurone derivatives possess antifungal properties and analogy with flavonoids suggests that aurones could have other biological properties.

Related compound examples

* Aureusidin * Hispidol (6,4'-dihydroxyaurone)Hispidol on metabolomics.jp
/ref> * Leptosidin * Sulfuretin (6,3',4'-trihydroxyaurone) * 4,5,6-Trihydroxyaurone

References

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