Aurone

{{distinguish|Auron (disambiguation)}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 455114263 | Name = Aurone | ImageFile = Aurone.svg | ImageSize = 150 | ImageName = Aurone Z configuration | PIN = 2-Benzylidene-1-benzofuran-3(2''H'')-one | OtherNames = 2-Benzylidenebenzofuran-3(2''H'')-one 2-Benzylidene-1-benzofuran-3-one |Section1={{Chembox Identifiers | CASNo = 582-04-7 | CASNo_Ref = {{cascite|correct|??}} | CASNo2_Ref = {{cascite|changed|??}} | CASNo2 = 75318-34-2 | CASNo2_Comment = (''E'') | CASNo3_Ref = {{cascite|changed|??}} | CASNo3 = 37542-14-6 | CASNo3_Comment = (''Z'') | SMILES = C1=CC=C(C=C1)C=C2C(=O)C3=CC=CC=C3O2 | PubChem = 613552 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 533325 | InChI = 1/C15H10O2/c16-15-12-8-4-5-9-13(12)17-14(15)10-11-6-2-1-3-7-11/h1-10H | InChIKey = OMUOMODZGKSORV-UHFFFAOYAF | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C15H10O2/c16-15-12-8-4-5-9-13(12)17-14(15)10-11-6-2-1-3-7-11/h1-10H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OMUOMODZGKSORV-UHFFFAOYSA-N | MeSHName = }} |Section2={{Chembox Properties | C=15 | H=10 | O=2 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} }}

An '''aurone''' is a heterocyclic chemical compound, which is a type of flavonoid.<ref>{{cite journal | doi = 10.1016/S1389-1723(02)80184-0 | pmid = 16233339 | title = Enzymology of aurone biosynthesis | year = 2002 | last1 = Nakayama | first1 = T | journal = Journal of Bioscience and Bioengineering | volume = 94 | issue = 6 | pages = 487–91}}</ref> 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== thumb|right|200px|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.<ref name="Nakayama">{{cite journal | doi = 10.1016/S0014-5793(01)02529-7 | pmid = 11418122 | year = 2001 | last1 = Nakayama | first1 = T | last2 = Sato | first2 = T | last3 = Fukui | first3 = Y | last4 = Yonekura-Sakakibara | first4 = K | last5 = Hayashi | first5 = H | last6 = Tanaka | first6 = Y | last7 = Kusumi | first7 = T | last8 = Nishino | first8 = T | title = Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration | volume = 499 | issue = 1–2 | pages = 107–11 | journal = FEBS Letters | doi-access = }}</ref> Aurones including 4'-chloro-2-hydroxyaurone (C15H11O3Cl) and 4'-chloroaurone (C15H9O2Cl) can also be found in the brown alga ''Spatoglossum variabile''.<ref name="Atta-Ur-Rahman">{{cite journal|doi=10.1248/cpb.49.105 |pmid=11201212 |last1=Atta-Ur-Rahman | year=2001 |last2=Choudhary |first2=MI |last3=Hayat |first3=S |last4=Khan |first4=AM |last5=Ahmed |first5=A |title=Two new aurones from marine brown alga Spatoglossum variabile |volume=49 |issue=1 |pages=105–7 |journal=Chemical & Pharmaceutical Bulletin|doi-access=free }}</ref>

Most aurones are in a (''Z'')-configuration, which is the more stable configuration according to Austin Model 1 computation.<ref name="Atta-Ur-Rahman"/> 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''.<ref>{{cite journal | pmid = 15813368 | url = http://www.znaturforsch.com/ac/v59c/s59c0499.pdf | year = 2004 | last1 = Ferreira | first1 = EO | last2 = Salvador | first2 = MJ | last3 = Pral | first3 = EM | last4 = Alfieri | first4 = SC | last5 = Ito | first5 = IY | last6 = Dias | first6 = DA | title = A new heptasubstituted (E)-aurone glucoside and other aromatic compounds of Gomphrena agrestis with biological activity | volume = 59 | issue = 7–8 | pages = 499–505 | journal = Zeitschrift für Naturforschung C | doi = 10.1515/znc-2004-7-808 | s2cid = 15589214 }}</ref>

==Biosynthesis== Aurones are biosynthesized starting from coumaryl-CoA.<ref>{{cite journal |journal =Molecular Plant |volume=3 |year=2010 |pages=2–20 |doi= 10.1093/mp/ssp106 |title=Phenylpropanoid Biosynthesis |author=Vogt, T. |pmid=20035037|doi-access=free }}</ref> Aureusidin synthase catalyzes the creation of aurones from chalcones through hydroxylation and oxidative cyclization.<ref name="Nakayama"/>

==Applications== Some aurone derivatives possess antifungal properties<ref>{{Cite journal|last1=Sutton|first1=Caleb L.|last2=Taylor|first2=Zachary E.|last3=Farone|first3=Mary B.|last4=Handy|first4=Scott T.|date=2017-02-15|title=Antifungal activity of substituted aurones|journal=Bioorganic & Medicinal Chemistry Letters|volume=27|issue=4|pages=901–903|doi=10.1016/j.bmcl.2017.01.012|pmid=28094180}}</ref> and analogy with flavonoids suggests that aurones could have other biological properties.<ref>{{cite journal | doi = 10.3390/30300088 | title = Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones | year = 1998 | last1 = Villemin | first1 = Didier | last2 = Martin | first2 = Benoit | last3 = Bar | first3 = Nathalie | journal = Molecules | volume = 3 | pages = 88 | issue = 8| doi-access = free }}</ref>

==Related compound examples== * Aureusidin * Hispidol (6,4'-dihydroxyaurone)<ref>[http://metabolomics.jp/wiki/FL1A1ANS0001 Hispidol on metabolomics.jp]</ref> * Leptosidin * Sulfuretin (6,3',4'-trihydroxyaurone) * 4,5,6-Trihydroxyaurone

==References== {{reflist}}

Category:Aurones