Aurone

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Not to be confused with Auron.
Aurone
Aurone Z configuration
Aurone E configuration
Identifiers
CAS number 582-04-7 YesY=, 
[75318-34-2] (E)
[37542-14-6] (Z)
PubChem 613552
ChemSpider 533325 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H10O2
Molar mass 222.24 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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.

Skeletal structure of an (Z)-aurone with numbering scheme used for nomenclature of 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]

Analogy with flavonoids suggests that aurones could have interesting biological properties.[5]

Related compound examples[edit]

Metabolism[edit]

References[edit]

  1. ^ 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. 
  2. ^ a b 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. 
  3. ^ a b 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. 
  4. ^ 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". Zeitschrift fur Naturforschung. C, Journal of biosciences 59 (7–8): 499–505. PMID 15813368. 
  5. ^ 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. 
  6. ^ Hispidol on metabolomics.jp