Aurone Explained

Aurone should not be confused with Auron (disambiguation).

An aurone is a heterocyclic chemical compound, which is a type of flavonoid.^[1] 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 flavonoids.

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 to the flowers of some popular ornamental plants, such as snapdragon and cosmos.^[2] Aurones including 4'-chloro-2-hydroxyaurone (C₁₅H₁₁O₃Cl) and 4'-chloroaurone (C₁₅H₉O₂Cl) can also be found in the brown alga Spatoglossum variabile.^[3]

Most aurones are in a (Z)-configuration, which is the more stable configuration according to Austin Model 1 computation.^[3] 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.^[4]

Biosynthesis

Aurones are biosynthesized starting from coumaryl-CoA.^[5] Aureusidin synthase catalyzes the creation of aurones from chalcones through hydroxylation and oxidative cyclization.^[2]

Applications

Some aurone derivatives possess antifungal properties^[6] and analogy with flavonoids suggests that aurones could have other biological properties.^[7]

Related compound examples

• Aureusidin
• Hispidol (6,4'-dihydroxyaurone)^[8]
• Leptosidin
• Sulfuretin (6,3',4'-trihydroxyaurone)

Notes and References

1. 10.1016/S1389-1723(02)80184-0 . 16233339 . Enzymology of aurone biosynthesis . 2002 . Nakayama . T . Journal of Bioscience and Bioengineering . 94 . 6 . 487–91.
2. 10.1016/S0014-5793(01)02529-7 . 11418122 . 2001 . Nakayama . T . Sato . T . Fukui . Y . Yonekura-Sakakibara . K . Hayashi . H . Tanaka . Y . Kusumi . T . Nishino . T . Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration . 499 . 1–2 . 107–11 . FEBS Letters .
3. 10.1248/cpb.49.105 . 11201212 . Atta-Ur-Rahman . 2001 . Choudhary . MI . Hayat . S . Khan . AM . Ahmed . A . Two new aurones from marine brown alga Spatoglossum variabile . 49 . 1 . 105–7 . Chemical & Pharmaceutical Bulletin. free .
4. 15813368 . A new heptasubstituted (E)-aurone glucoside and other aromatic compounds of Gomphrena agrestis with biological activity . 2004 . Ferreira . EO . Salvador . MJ . Pral . EM . Alfieri . SC . Ito . IY . Dias . DA . 59 . 7–8 . 499–505 . Zeitschrift für Naturforschung C . 10.1515/znc-2004-7-808 . 15589214 .
5. Molecular Plant . 3 . 2010 . 2–20 . 10.1093/mp/ssp106 . Phenylpropanoid Biosynthesis . Vogt, T. . 20035037. free .
6. Sutton. Caleb L.. Taylor. Zachary E.. Farone. Mary B.. Handy. Scott T.. 2017-02-15. Antifungal activity of substituted aurones. Bioorganic & Medicinal Chemistry Letters. 27. 4. 901–903. 10.1016/j.bmcl.2017.01.012. 28094180.
7. 10.3390/30300088 . Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones . 1998 . Villemin . Didier . Martin . Benoit . Bar . Nathalie . Molecules . 3 . 88 . 8. free .
8. http://metabolomics.jp/wiki/FL1A1ANS0001 Hispidol on metabolomics.jp