|Molar mass||222.24 g·mol−1|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
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 flavonoids.
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.
Related compound examples
- Hispidol (6,4'-Dihydroxyaurone)
- Sulfuretin (6,3',4'-Trihydroxyaurone)
- Nakayama, T (2002). "Enzymology of aurone biosynthesis". Journal of Bioscience and Bioengineering 94 (6): 487–91. doi:10.1016/S1389-1723(02)80184-0. PMID 16233339.
- Nakayama, T; Sato, T; Fukui, Y; Yonekura-Sakakibara, K; Hayashi, H; Tanaka, Y; Kusumi, T; Nishino, T (2001). "Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration". FEBS Letters 499 (1–2): 107–11. doi:10.1016/S0014-5793(01)02529-7. PMID 11418122.
- Atta-Ur-Rahman; Choudhary, MI; Hayat, S; Khan, AM; Ahmed, A (2001). "Two new aurones from marine brown alga Spatoglossum variabile". Chemical & pharmaceutical bulletin 49 (1): 105–7. doi:10.1248/cpb.49.105. PMID 11201212.
- Ferreira, EO; Salvador, MJ; Pral, EM; Alfieri, SC; Ito, IY; Dias, DA (2004). "A new heptasubstituted (E)-aurone glucoside and other aromatic compounds of Gomphrena agrestis with biological activity" (PDF). Zeitschrift fur Naturforschung. C, Journal of biosciences 59 (7–8): 499–505. PMID 15813368.
- Villemin, Didier; Martin, Benoit; Bar, Nathalie (1998). "Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones". Molecules 3 (3): 88. doi:10.3390/30300088.
- Hispidol on metabolomics.jp