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Aurone
Names
Preferred IUPAC name
2-Benzylidene-1-benzofuran-3(2H )-one
Other names
2-Benzylidenebenzofuran-3(2H )-one 2-Benzylidene-1-benzofuran-3-one
Identifiers
ChemSpider
InChI=1S/C15H10O2/c16-15-12-8-4-5-9-13(12)17-14(15)10-11-6-2-1-3-7-11/h1-10H
Y Key: OMUOMODZGKSORV-UHFFFAOYSA-N
Y 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
Key: OMUOMODZGKSORV-UHFFFAOYAF
C1=CC=C(C=C1)C=C2C(=O)C3=CC=CC=C3O2
Properties
C 15 H 10 O 2
Molar mass
222.243 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
An 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 .
Aurone derivatives
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 (C15 H11 O3 Cl) and
4'-chloroaurone (C15 H9 O2 Cl) 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]
Biosynthesis
Aurones are
biosynthesized starting from
coumaryl-CoA .
[5]
Aureusidin synthase catalyzes the creation of aurones from chalcones through hydroxylation and oxidative cyclization.
[2]
Applications
Some aurone derivatives possess antifungal properties
[6] and analogy with flavonoids suggests that aurones could have other biological properties.
[7]
Related compound examples
References
^ 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 .
^
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 .
^
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 .
^ 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 für Naturforschung C . 59 (7–8): 499–505.
doi :
10.1515/znc-2004-7-808 .
PMID
15813368 .
S2CID
15589214 .
^ Vogt, T. (2010).
"Phenylpropanoid Biosynthesis" . Molecular Plant . 3 : 2–20.
doi :
10.1093/mp/ssp106 .
PMID
20035037 .
^ Sutton, Caleb L.; Taylor, Zachary E.; Farone, Mary B.; Handy, Scott T. (2017-02-15). "Antifungal activity of substituted aurones". Bioorganic & Medicinal Chemistry Letters . 27 (4): 901–903.
doi :
10.1016/j.bmcl.2017.01.012 .
PMID
28094180 .
^ Villemin, Didier; Martin, Benoit; Bar, Nathalie (1998).
"Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones" . Molecules . 3 (8): 88.
doi :
10.3390/30300088 .
^
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