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Not to be confused with Auron (disambiguation).
Aurone
Aurone Z configuration
Aurone Z configuration
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
3D model (JSmol)
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 checkY
    Key: OMUOMODZGKSORV-UHFFFAOYSA-N checkY
  • 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
C15H10O2
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).
☒N verify (what is checkY☒N ?)

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

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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]

Biosynthesis

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Aurones are biosynthesized starting from coumaryl-CoA.[5] Aureusidin synthase catalyzes the creation of aurones from chalcones through hydroxylation and oxidative cyclization.[2]

Applications

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Some aurone derivatives possess antifungal properties[6] and analogy with flavonoids suggests that aurones could have other biological properties.[7]

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References

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  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" (PDF). Zeitschrift für Naturforschung C. 59 (7–8): 499–505. doi:10.1515/znc-2004-7-808. PMID 15813368. S2CID 15589214.
  5. ^ Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3: 2–20. doi:10.1093/mp/ssp106. PMID 20035037.
  6. ^ 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.
  7. ^ 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.
  8. ^ Hispidol on metabolomics.jp

📚 Artikel Terkait di Wikipedia

List of phytochemicals in food

The following is a list of phytochemicals present in foods. orange pigments α-Carotene – to vitamin A: carrots, pumpkins, maize, tangerine, orange β-Carotene

Antifungal

Amorolfine – a morpholine derivative used topically in dermatophytosis Aurones – possess antifungal properties Benzoic acid – has antifungal properties

Phenylpropanoid

(precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is

Coumaroyl-CoA

(precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and other phenylpropanoids. It is generated in nature

Cinnamic acid

(precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the

Aureusidin synthase

mechanism can only produce aurones with 3',4'-dihydroxy or 3',4',5'-trihydroxy functionalization, but there have been aurones reported with one or no hydroxyl

Kalanchoe pinnata

steroid, phenanthrene, flavonoid, flavones, chalcones, taraxasterol, aurones, phenolic acid, caffeic acid, syringic acid, malic, oxalic and ferulic

D'Ocon Films

Valdés, Daniel García (2015-02-27). "Entre Fruittis y Aurones: creciendo en la España animada de D'Ocon Productions". La Soga | Revista