An aurone is a

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

, 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 Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the structural nucleus (parent compound) of many related compounds with more complex stru ...

element associated with a

benzylidene Benzylidene compounds are, formally speaking, derivatives of benzylidene, although few are prepared from the carbene. Benzylidene acetal is a protecting group in synthetic organic chemistry of the form PhCH(OR)2. For example, 4,6-O-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. They are widely known bioactive substances, fluorescent materi ...

-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 ''Antirrhinum'' is a genus of plants in the Plantaginaceae family, commonly known as dragon flowers or snapdragons because of the flowers' fancied resemblance to the face of a dragon that opens and closes its mouth when laterally squeezed. They ...

and

cosmos The cosmos (, ; ) is an alternative name for the universe or its nature or order. Usage of the word ''cosmos'' implies viewing the universe as a complex and orderly system or entity. The cosmos is studied in cosmologya broad discipline covering ...

. Aurones including 4'-chloro-2-hydroxyaurone (C₁₅H₁₁O₃Cl) and 4'-chloroaurone (C₁₅H₉O₂Cl) can also be found in the

brown alga Brown algae (: alga) are a large group of multicellular algae comprising the class Phaeophyceae. They include many seaweeds located in colder waters of the Northern Hemisphere. Brown algae are the major seaweeds of the temperate and polar reg ...

Spatoglossum variabile ''Spatoglossum'' is a marine brown algal genus in the family Dictyotaceae, with a worldwide distribution Its first valid description was given by Friedrich Kützing in 1843. Some accepted species According to Algaebase: *'' Spatoglossum asperu ...

''. Most aurones are in a (''Z'')-configuration, which is the more stable configuration according to

Austin Model 1 Austin Model 1, or AM1, is a semi-empirical method for the quantum calculation of molecular electronic structure in computational chemistry. It is based on the Neglect of Differential Diatomic Overlap integral approximation. Specifically, it is ...

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 Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme- catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthesis) serve ...

starting from coumaryl-CoA.

Aureusidin synthase Aureusidin synthase (, ''AmAS1'') is an enzyme with systematic name ''2',4,4',6'-tetrahydroxychalcone 4'-O-beta-D-glucoside:oxygen oxidoreductase''. Aureusidin synthase has two main enzymatic tasks: hydroxylation at the 3-position on the B-ring o ...

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 Aureusidin is an aurone. Metabolism Aureusidin synthase is an enzyme found in ''Antirrhinum majus ''Antirrhinum majus'', the common snapdragon (often – especially in horticulture – simply "snapdragon"), is a species of flowering plant b ...

* Hispidol (6,4'-dihydroxyaurone)Hispidol on metabolomics.jp
/ref> *

Leptosidin Leptosidin was the first aurone to be isolated in ''Coreopsis grandiflora'' by Geissman T.A. and Heaton C.D. in 1943. Leptosidin blocks the active residues of PRKACA The catalytic subunit α of protein kinase A is a key regulatory enzyme that in ...

* Sulfuretin (6,3',4'-trihydroxyaurone) * 4,5,6-Trihydroxyaurone

References

{{aurone