Aurone
Encyclopedia
Aurone is a heterocyclic chemical compound
which is a type of flavonoid
. 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
-like group is closed into a 5-membered ring instead of the 6-membered ring more typical of flavonoid
s.
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. 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
.
Analogy with flavonoids suggests that aurones could have interesting biological properties.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
which is a type of flavonoid
Flavonoid
Flavonoids , are a class of plant secondary metabolites....
. There are two isomers of the molecule, with (E)- and (Z)-configurations. The molecule contains a benzofuran
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 "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several...
element associated with a benzylidene linked in position 2. In aurone, a chalcone
Chalconoid
Chalconoids, also known as chalcones, are natural phenols related to chalcone. They form the central core for a variety of important biological compounds. They show antibacterial, antifungal, antitumor and anti-inflammatory properties...
-like group is closed into a 5-membered ring instead of the 6-membered ring more typical of flavonoid
Flavonoid
Flavonoids , are a class of plant secondary metabolites....
s.
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
SnapDragon
SnapDragon is a contemporary jazz band based in San Antonio, Texas. The group released their debut CD, "Stealing a Moment" on Humbug Records in 2008, and the 10-song CD soon broke the Top 100 in U.S radio airplay...
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
Gomphrena agrestis is a plant native to Cerrado vegetation in Brazil. This plant is cited in Flora Brasiliensis by Carl Friedrich Philipp von Martius....
.
Analogy with flavonoids suggests that aurones could have interesting biological properties.
Related compound examples
- AureusidinAureusidinAureusidin is an aurone, a type of flavonoids.-Metabolism:Aureusidin synthase is an enzyme found in Antirrhinum majus ....
- Hispidol (6,4'-Dihydroxyaurone)
- LeptosidinLeptosidinLeptosidin was the first aurone to be isolated in Coreopsis grandiflora by Geissman T.A. and Heaton C.D. in 1943....
- Sulfuretin (6,3',4'-Trihydroxyaurone)
- 4,5,6-Trihydroxyaurone