Aurones [2-benzylidenebenzofuran-3(2H)-ones] are either natural or synthetic compounds, belonging to the flavonoid family. They are isomeric to flavones and provide a bright yellow color to the plants in which they occur. Today, a literature survey indicates that the related flavonoids have been studied not only for their physiological properties and effects on Nature, but also for their therapeutic potential. Aurones are recently attracting the interest of an increasing number of research groups, and, since the last review, some interesting advances have been made in understanding the aurones.
In this review, we report the recent advances made on the synthetic routes towards aurones. We also highlight their activity in different biological areas, as well as applied genetic plant modifications to produce these colored compounds. Their synthesis, structure–activity relationships and the importance of the substitution pattern will also be mentioned. Finally, some aspects regarding the possible development of aurones will be discussed briefly.
CodyV, MiddletonE. (1986) Plant flavonoids in biology and medicine: biochemical, pharmacological, and structure-activity relationships; Proceedings of a symposium held in Buffalo, New York, July 22 - 26, 1985. In Progress in Clinical and Biological Research. Liss, New York, USA.
2.
OnoE, Fukuchi-MizutaniM. (2006) Yellow flowers generated by expression of the aurone biosynthetic pathway. Proceedings of the National Academy of Sciences of the United States of America, 103, 11075–11080.
MorimotoM, FukumotoH. (2007) Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae. Journal of Agricultural and Food Chemistry, 55, 700–705.
5.
OkombiS, RivalD. (2006) Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes. Journal of Medicinal Chemistry, 49, 329–333.
6.
VenkateswarluS, PanchagnulaGK. (2004) Synthesis and antioxidative activity of 3′,4′,6,7-tetrahydroxyaurone, a metabolite of Bidens frondosa. Bioscience, Biotechnology, and Biochemistry, 68, 2183–2185.
7.
BoumendjelA. (2003) Aurones: a subclass of flavones with promising biological potential. Current Medicinal Chemistry, 10, 2621–2630.
8.
LawrenceNJ, RennisonD. (2003) The total synthesis of an aurone isolated from Uvaria hamiltonii: aurones and flavones as anticancer agents. Bioorganic & Medicinal Chemistry Letters, 13, 3759–3763.
9.
Auf'mkolkM, KoehrleJ. (1986) Inhibition of rat liver iodothyronine deiodinase. Interaction of aurones with the iodothyronine ligand-binding site. The Journal of Biological Chemistry, 261, 11623–11630.
10.
HadjeriM, BarbierM. (2003) Modulation of P-glycoprotein-mediated multidrug resistance by flavonoid derivatives and analogues. Journal of Medicinal Chemistry, 46, 2125–2131.
11.
SchoepferJ, FretzH. (2002) Structure-based design and synthesis of 2-benzylidene-benzofuran-3-ones as flavopiridol mimics. Journal of Medicinal Chemistry, 45, 1741–1747.
12.
ChengH, ZhangL. (2010) Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines. European Journal of Medicinal Chemistry, 45, 5950–5957.
13.
VarmaRS, VarmaM. (1992) Alumina-mediated condensation. A simple synthesis of aurones. Tetrahedron Letters, 33, 5937–5940.
14.
KimD, LiY. (1990) Synthesis of tunichromes mm-l and mm-2, blood pigments of the iron assimilating tunicate, Molgula manhattensis. Tetrahedron Letters, 31, 7119–7122.
15.
KrausGA, GuptaV. (2010) Divergent approach to flavones and aurones via dihaloacrylic acids. Unexpected dependence on the halogen atom. Organic letters, 12, 5278–5280.
HarkatH, BlancA. (2008) Versatile and expeditious synthesis of aurones via Au I-catalyzed cyclization. The Journal of Organic Chemistry, 73, 1620–1623.
18.
RahmanAtta ur, ChoudharyMI. (2001) Two new aurones from marine brown alga Spatoglossum variabile. Chemical & Pharmaceutical Bulletin, 49, 105–107.
19.
AgrawalNN, SoniPA. (2006) A new process for the synthesis of aurones by using mercury (II) acetate in pyridine and cupric bromide in dimethyl sulfoxide. Indian Journal of Chemistry, 45B, 1301–1303.
20.
ThanigaimalaiP, YangHM. (2010) The scope of thallium nitrate oxidative cyclization of chalcones; synthesis and evaluation of isoflavone and aurone analogs for their inhibitory activity against interleukin-5. Bioorganic & Medicinal Chemistry, 18, 4441–4445.
21.
JungSH, ChoSH. (2003) Structural requirement of isoflavonones for the inhibitory activity of interleukin-5. European Journal of Medicinal Chemistry, 38, 537–545.
22.
YangHM, ShinHR. (2007) The role of alkoxy group on the A ring of isoflavones in the inhibition of interleukin-5. Archives of Pharmacal Research, 30, 950–954.
23.
ThakkarK, CushmanM. (1995) A novel oxidative cyclization of 2′-hydroxychalcones to 4,5-dialkoxyaurones by thallium(III) nitrate. The Journal of Organic Chemistry, 60, 6499–6510.
24.
DetsiA, MajdalaniM. (2009) Natural and synthetic 2′-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. Bioorganic & Medicinal Chemistry, 17, 8073–8085.
25.
HenryAM, ManicacciD. (2005) Molecular evolution of the opaque-2 gene in Zea mays L. Journal of Molecular Evolution, 61, 551–558.
26.
NishiharaM, NakatsukaT. (2011) Genetic engineering of flavonoid pigments to modify flower color in floricultural plants. Biotechnology Letters, 33, 433–441.
27.
TanakaY, KatsumotoY. (2005) Genetic engineering in floriculture. Journal of Plant Biotechnology, 80, 1–24.
28.
ShankerN, DilekO. (2011) Aurones: Small molecule visible range fluorescent probes suitable for biomacromolecules. Journal of Fluorescence, 6, 2173–2184.
29.
OrlikovaB, TasdemirD. (2011) The aromatic ketone 4′-hydroxychalcone inhibits TNFalpha-induced NF-kappaB activation via proteasome inhibition. Biochemical Pharmacology, 82, 620–631.
30.
OrlikovaB, TasdemirD. (2011) Dietary chalcones with chemopreventive and chemotherapeutic potential. Genes & Nutrition, 6, 125–147.
31.
SouardF, OkombiS. (2010) 1-Azaaurones derived from the naturally occurring aurones as potential antimalarial drugs. Bioorganic & Medicinal Chemistry, 18, 5724–5731.
32.
BandgarBP, PatilSA. (2010) Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents. European Journal of Medicinal Chemistry, 45, 3223–3227.
33.
LiuAL, WangHD. (2008) Structure-activity relationship of flavonoids as influenza virus neuraminidase inhibitors and their in vitro anti-viral activities. Bioorganic & Medicinal Chemistry, 16, 7141–7147.
34.
HaudecoeurR, Ahmed-BelkacemA. (2011) Discovery of naturally occurring aurones that are potent allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase. Journal of Medicinal Chemistry, 54, 5395–5402.
35.
ShinSY, ShinMC. (2011) Synthesis of aurones and their inhibitory effects on nitric oxide and PGE(2) productions in LPS-induced RAW 264.7 cells. Bioorganic & Medicinal Chemistry Letters, 21, 4520–4523.
36.
SimHM, LeeCY. (2008) Dimethoxyaurones: Potent inhibitors of ABCG2 (breast cancer resistance protein). European Journal of Pharmaceutical Sciences: official Journal of the European Federation for Pharmaceutical Sciences, 35, 293–306.
37.
OnoM, MayaY. (2007) Aurones serve as probes of beta-amyloid plaques in Alzheimer's disease. Biochemical and Biophysical Research Communications, 361, 116–121.
