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Aurones are chemical compounds belonging to the flavonoids, a type of polyphenolic compounds and derived from the aurone chemical structure. In aurones, chalcone closes into a 5 instead of the 6 atoms ring (C ring), more typical of flavonoids.
Aurones are plant flavonoids that provide yellow color to the flowers of some popular ornamental plants, such as snapdragon and cosmos. Aurones can also be found in the brown alga Spatoglossum variabile (4'-chloro-2-hydroxyaurone, formula C15H11O3Cl and 4'-chloroaurone, formula C15H9O2Cl).
Most of aurones are in Z configuration, which is a more stable conformation according to Austin Model 1 computation, but there are also some in E configurations ((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.
Related compounds examples
- Aureusidin
- Hispidol (6,4'-Dihydroxyaurone)
- Leptosidin
- Sulfuretin (6,3',4'-Trihydroxyaurone)
- 4,5,6-Trihydroxy-aurone
Metabolism
references
- Enzymology of aurone biosynthesis. Toru Nakayama, Journal of Bioscience and Bioengineering, Volume 94, Issue 6, December 2002, Pages 487-491
- ^ Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration. T. Nakayama, 2001
- ^ Two New Aurones from Marine Brown Alga Spatoglossum variabile Atta-Ur-Rahman, Muhammad Iqbal Choudhary, Safdar Hayat, Abdul Majeed Khan, and Aftab Ahmed, 2000
- A New Heptasubstituted (E)-Aurone Glucoside and Other Aromatic Compounds of Gomphrena agrestis with Biological Activity. Eliane O. Ferreira, Marcos J. Salvador, Elizabeth M. F. Pral, Silvia C. Alfieri, Izabel Y. Ito, and Diones A. Dias, 2004
- Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones. Didier Villemin, Benoit Martin and Nathalie Bar, 1998
- Hispidol on metabolomics.jp
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| Flavonoids |
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| Flavonoid biosynthesis | |||||||||||||||||||||||||||||||||||||||||
| Aurones and their glycosides | |
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| Aurones | |
| Glycosides | |
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