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{{distinguish|Auron}} |
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{{distinguish|Auron (disambiguation)}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 455112906 |
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| Watchedfields = changed |
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| Name = Aurone |
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| verifiedrevid = 455114263 |
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| ImageFile = Aurone.svg |
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| ImageSize = 200px |
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| Name = Aurone |
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| ImageName = Aurone Z configuration |
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| ImageFile = Aurone.svg |
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| ImageSize = 150 |
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| ImageFile1 = Aurone.PNG |
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| ImageName = Aurone Z configuration |
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| ImageSize1 = 200px |
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| PIN = 2-Benzylidene-1-benzofuran-3(2''H'')-one |
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| ImageName1 = Aurone E configuration |
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| IUPACName = 2-Benzylidene-1-benzofuran-3-one <!-- 2-benzylbenzofuran-3-one --> |
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| OtherNames = 2-Benzylidenebenzofuran-3(2''H'')-one<br />2-Benzylidene-1-benzofuran-3-one |
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|Section1={{Chembox Identifiers |
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| OtherNames = <!-- <br> --> |
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| CASNo = 582-04-7 |
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|Section1= {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 582-04-7 |
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| CASNo2_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = |
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| CASOther = <br> (''E'')<br> (''Z'') |
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| CASNo2 = 75318-34-2 |
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| CASNo2_Comment = (''E'') |
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| SMILES = C1=CC=C(C=C1)C=C2C(=O)C3=CC=CC=C3O2 |
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| CASNo3_Ref = {{cascite|changed|??}} |
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| PubChem = 613552 |
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| CASNo3 = 37542-14-6 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo3_Comment = (''Z'') |
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| SMILES = C1=CC=C(C=C1)C=C2C(=O)C3=CC=CC=C3O2 |
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| PubChem = 613552 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 533325 |
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| ChemSpiderID = 533325 |
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| 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 |
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| 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 |
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| InChIKey = OMUOMODZGKSORV-UHFFFAOYAF |
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| InChIKey = OMUOMODZGKSORV-UHFFFAOYAF |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = OMUOMODZGKSORV-UHFFFAOYSA-N |
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| StdInChIKey = OMUOMODZGKSORV-UHFFFAOYSA-N |
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| MeSHName = |
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| MeSHName = |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=15|H=10|O=2 |
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| C=15 | H=10 | O=2 |
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| Appearance = |
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| ExactMass = 222.06807954 |
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| Appearance = |
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| Density = |
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| Solubility = |
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}} |
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'''Aurone''' is a ] ] which is a type of ].<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}}</ref> There are two isomers of the molecule, with (''E'')- and (''Z'')-configurations. The molecule contains a ] element associated with a ] linked in position 2. In aurone, a ]-like group is closed into a 5-membered ring instead of the 6-membered ring more typical of ]s. |
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An '''aurone''' is a ] ], which is a type of ].<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 ] element associated with a ] linked in position 2. In aurone, a ]-like group is closed into a 5-membered ring instead of the 6-membered ring more typical of ]s. |
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==Aurone derivatives== |
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Aurone forms the core for a family of derivatives which are known collectively as aurones. Aurones are plant flavonoids that provide ] to the flowers of some popular ornamental plants, such as ] and ].<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 }}</ref> Aurones including ] (C<sub>15</sub>H<sub>11</sub>O<sub>3</sub>Cl) and ] (C<sub>15</sub>H<sub>9</sub>O<sub>2</sub>Cl) can also be found in the ] '']''.<ref name="Atta-Ur-Rahman">{{cite journal | doi = 10.1248/cpb.49.105 | pmid = 11201212 | last1 = Atta-Ur-Rahman | url = http://www.jstage.jst.go.jp/article/cpb/49/1/105/_pdf | 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}}</ref> |
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Aurone forms the core for a family of derivatives which are known collectively as aurones. Aurones are plant flavonoids that provide ] to the flowers of some popular ornamental plants, such as ] and ].<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 ] (C<sub>15</sub>H<sub>11</sub>O<sub>3</sub>Cl) and ] (C<sub>15</sub>H<sub>9</sub>O<sub>2</sub>Cl) can also be found in the ] '']''.<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> |
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Most aurones are in a (''Z'')-configuration, which is the more stable configuration according to ] computation,<ref name="Atta-Ur-Rahman"/> but there are also some in the (''E'')-configurations such as ], found in '']''.<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 fur Naturforschung. C, Journal of biosciences }}</ref> |
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Most aurones are in a (''Z'')-configuration, which is the more stable configuration according to ] computation.<ref name="Atta-Ur-Rahman"/> But there are also some in the (''E'')-configurations such as ], found in '']''.<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> |
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==Biosynthesis== |
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Analogy with flavonoids suggests that aurones could have interesting 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}}</ref> |
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Aurones are ] starting from ].<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> ] catalyzes the creation of aurones from chalcones through hydroxylation and oxidative cyclization.<ref name="Nakayama"/> |
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==Applications== |
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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> |
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==Related compound examples== |
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==Related compound examples== |
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* ] (6,4'-Dihydroxyaurone)<ref></ref> |
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* ] (6,4'-dihydroxyaurone)<ref></ref> |
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* ] |
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* ] |
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* ] (6,3',4'-Trihydroxyaurone) |
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* ] (6,3',4'-trihydroxyaurone) |
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* ] <!-- ].]] --> |
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* ] <!-- ].]] --> |
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==Metabolism== |
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* ]<ref name="Nakayama"/> |
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==References== |
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==References== |
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