Design, Synthesis and Biological Activities of Dihydroaurones

To widen aurones applicability in achromatic food and cosmetic applications, a series of dihydroaurones were designed to mimic natural aurones as well as synthetic aurones. Dihydroaurones have been synthesized from the corresponding aurones by hydrogenation. These dihydroaurones and their corresponding aurones were screened for antioxidant, anti-inflammatory and tyrosinase enzyme inhibitory activity. Synthesized dihydroaurones (3b-f) displayed superior antioxidant activity in superoxide free radical scavenging assay than the standard gallic acid. Dihydroaurones (3b-f) also exhibited significant tyrosinase enzyme inhibitory activity and two dihydroaurones (3h, 3j) showed promising 5-lipoxygenase inhibitory activity.

[1]  Bing-Yu Zhang,et al.  Recent advances on synthesis and biological activities of aurones. , 2020, Bioorganic & medicinal chemistry.

[2]  Mahmud Tareq Hassan Khan,et al.  A comprehensive review on tyrosinase inhibitors , 2019, Journal of enzyme inhibition and medicinal chemistry.

[3]  S. Venkateswarlu,et al.  "On water" synthesis of aurones: first synthesis of 4,5,3',4',5'-pentamethoxy-6-hydroxyaurone from Smilax riparia , 2017 .

[4]  V. Namasivayam,et al.  Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors , 2017, Journal of enzyme inhibition and medicinal chemistry.

[5]  K. Chan,et al.  Blood-brain barrier permeable anticholinesterase aurones: synthesis, structure-activity relationship, and drug-like properties. , 2015, European journal of medicinal chemistry.

[6]  P. Qiu,et al.  A novel synthesis of aurones: Their in vitro anticancer activity against breast cancer cell lines and effect on cell cycle, apoptosis and mitochondrial membrane potential , 2014 .

[7]  Ana S. Newton,et al.  Probing the aurone scaffold against Plasmodium falciparum: design, synthesis and antimalarial activity. , 2014, European journal of medicinal chemistry.

[8]  A. Boumendjel,et al.  Recent advances in the medicinal chemistry of aurones. , 2012, Current medicinal chemistry.

[9]  J. Pawlotsky,et al.  Discovery of naturally occurring aurones that are potent allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase. , 2011, Journal of medicinal chemistry.

[10]  Mei-Lin Go,et al.  Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: synthesis, evaluation and SAR. , 2010, European journal of medicinal chemistry.

[11]  D. Hadjipavlou-Litina,et al.  Natural and synthetic 2'-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. , 2009, Bioorganic & medicinal chemistry.

[12]  Bo Yang,et al.  Design, synthesis and AChE inhibitory activity of indanone and aurone derivatives. , 2009, European journal of medicinal chemistry.

[13]  Eun Ha Lee,et al.  Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts. , 2008, Biological & pharmaceutical bulletin.

[14]  K. Park,et al.  Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz , 2008 .

[15]  Aditya L. Gottumukkala,et al.  Synthesis, structural revision, and biological activities of 4′-chloroaurone, a metabolite of marine brown alga Spatoglossum variabile , 2007 .

[16]  K. Komai,et al.  Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae. , 2007, Journal of Agricultural and Food Chemistry.

[17]  G. Subbaraju,et al.  Isoaurones: synthesis and stereochemical assignments of geometrical isomers , 2006 .

[18]  E. Perrier,et al.  Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes. , 2006, Journal of medicinal chemistry.

[19]  G. Subbaraju,et al.  Synthesis and biological evaluation of polyhydroxycurcuminoids. , 2005, Bioorganic & medicinal chemistry.

[20]  Zhen Yang,et al.  Tyrosinase activity in reversed micelles , 2005 .

[21]  G. Subbaraju,et al.  Synthesis and Antioxidative Activity of 3′,4′,6,7-Tetrahydroxyaurone, a Metabolite of Bidens frondosa , 2004, Bioscience, biotechnology, and biochemistry.

[22]  H. Hirota,et al.  Tetrapetalone A, a Novel Lipoxygense Inhibitor from Streptomyces sp. , 2003, Bioscience, biotechnology, and biochemistry.

[23]  Tao Wang,et al.  Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities. , 2003, Bioorganic & medicinal chemistry.

[24]  N. Lawrence,et al.  The total synthesis of an aurone isolated from Uvaria hamiltonii: aurones and flavones as anticancer agents. , 2003, Bioorganic & medicinal chemistry letters.

[25]  A. Mcbride,et al.  A series of 2(Z)-2-benzylidene-6,7-dihydroxybenzofuran-3[2H]-ones as inhibitors of chorismate synthase. , 2003, Bioorganic & Medicinal Chemistry Letters.

[26]  Kenji Matsumoto,et al.  Gnetol as a Potent Tyrosinase Inhibitor from Genus Gnetum , 2003, Bioscience, biotechnology, and biochemistry.

[27]  A. di Pietro,et al.  4-Hydroxy-6-methoxyaurones with high-affinity binding to cytosolic domain of P-glycoprotein. , 2002, Chemical & pharmaceutical bulletin.

[28]  J. Gebicki,et al.  Perchloric acid enhances sensitivity and reproducibility of the ferric-xylenol orange peroxide assay. , 2002, Analytical biochemistry.

[29]  L. Meijer,et al.  Structure-based design and synthesis of 2-benzylidene-benzofuran-3-ones as flavopiridol mimics. , 2002, Journal of medicinal chemistry.

[30]  R. Varma,et al.  Alumina-mediated condensation. A simple synthesis of aurones , 1992 .

[31]  R. Larson.  The antioxidants of higher plants , 1988 .

[32]  B. Halliwell,et al.  Free radicals in biology and medicine , 1985 .

[33]  I. Fridovich,et al.  Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). , 1969, The Journal of biological chemistry.

[34]  T. Swain,et al.  The flavonoid glycosides of Dahlia variabilis. II. Glycosides of yellow varieties Pius IX and Coton. , 1956, Archives of Biochemistry and Biophysics.