Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

Abstract The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized.

[1]  R. Durst,et al.  Polyphenolic composition of raisins. , 2000, Journal of agricultural and food chemistry.

[2]  T. Tseng,et al.  Hibiscus protocatechuic acid protects against oxidative damage induced by tert-butylhydroperoxide in rat primary hepatocytes. , 1996, Chemico-biological interactions.

[3]  P. R. Jefferies,et al.  The chemistry of the euphorbiaceae—XIII , 1965 .

[4]  K. Shinozuka,et al.  Inhibitory effect of flavonoids on DNA-dependent DNA and RNA polymerases , 1988, Experientia.

[5]  R. Bernini,et al.  Aromatic ring hydroxylation of flavanones by dimethyldioxirane , 2000 .

[6]  Á. Ravelo,et al.  Flavonoids from Salvia texana , 1989 .

[7]  R. E. Montgomery.  Catalysis of peroxymonosulfate reactions by ketones , 1974 .

[8]  J. Edwards,et al.  Dioxiranes: a new class of powerful oxidants , 1989 .

[9]  S. Deans,et al.  Phenolic compounds in food and their effects on health. 11, antioxidants and cancer prevention, edited by Mon-Tuan Huang, Chi-Tang Ho, and Chang Y. Lee, American Chemical Society Series, Vol. 507, ACS, 1992. No. of pages: 402, price £55.00. ISBN 0–8412–2476–5 , 1993 .

[10]  M. Yano,et al.  HL-60 differentiating activity and flavonoid content of the readily extractable fraction prepared from citrus juices. , 1999, Journal of agricultural and food chemistry.

[11]  Hitoshi Yamamoto,et al.  Synthesis of 5,8-dihydroxy-6,7-dimethoxyflavones and revised structures for some natural flavones , 1995 .

[12]  C. Mitra,et al.  Flavonoids of Madhuca butyracea Nut-Shell , 1962 .

[13]  M. Piattelli,et al.  Flavonoids, coumarins, and cinnamic acids as antioxidants in a micellar system. Structure-activity relationship , 1996 .

[14]  E. Feskens,et al.  Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study , 1993, The Lancet.

[15]  T. Patonay,et al.  Epoxidation of flavones by dimethyldioxirane , 1991 .

[16]  C. Chen,et al.  New Flavones from Bauhinia championii BENTH. , 1984 .

[17]  R. Murray,et al.  Dioxiranes: synthesis and reactions of methyldioxiranes , 1985 .

[18]  G. Block.  The data support a role for antioxidants in reducing cancer risk. , 2009, Nutrition reviews.

[19]  W. Adam,et al.  The Acid-Catalyzed Oxidation of Methoxybenzenes to p-Benzoquinones by Dimethyldioxirane , 1994 .

[20]  W. Doering,et al.  Mechanism of the Peracid Ketone—Ester Conversion. Analysis of Organic Compounds for Oxygen-181 , 1953 .

[21]  T. Tseng,et al.  Induction of apoptosis by hibiscus protocatechuic acid in human leukemia cells via reduction of retinoblastoma (RB) phosphorylation and Bcl-2 expression. , 2000, Biochemical pharmacology.

[22]  R. Anton,et al.  Comparative Antilipoperoxidant, Antinecrotic and Scavanging Properties of Terpenes and Biflavones from Ginkgo and some Flavonoids , 1995, Planta medica.

[23]  H. Kuo,et al.  Involvement of tumor suppressor protein p53 and p38 MAPK in caffeic acid phenethyl ester-induced apoptosis of C6 glioma cells. , 2003, Biochemical pharmacology.

[24]  T. P. Berezovskaya,et al.  Flavonoids of Siberian-Far-Eastern species of rhododendrons of the subspeciesRhodorastrum , 1998, Chemistry of Natural Compounds.

[25]  M. Iinuma,et al.  ^ C-Nuclear Magnetic Resonance (NMR) Spectral Studies on Polysubstituted Flavonoids. I. 13C-NMR Spectra of Flavones , 1980 .

[26]  W. Rahman,et al.  Flower Pigments. Flavonoids from Argemone mexicana linn. (Papaveraceae) , 1962 .

[27]  Yean-Jang Lee,et al.  Total Synthesis of Kaempferol and Methylated Kaempferol Derivatives , 2001 .

[28]  J. Gauss,et al.  Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations , 1987 .

[29]  B Havsteen,et al.  Flavonoids, a class of natural products of high pharmacological potency. , 1983, Biochemical pharmacology.

[30]  K. Kohn,et al.  Inhibitors of human immunodeficiency virus integrase. , 1993, Proceedings of the National Academy of Sciences of the United States of America.

[31]  Y. Lee,et al.  Cytotoxicity effects of di- and tri-hydroxybenzaldehydes as a chemopreventive potential agent on tumor cells. , 2001, Toxicology.

[32]  B. Das,et al.  Three flavone glycosides from Gelonium multiflorum. , 1993, Phytochemistry.

[33]  S. Tawata,et al.  Antibacterial Activity of Flavonoids against Staphylococcus epidermidis, a Skin Bacterium , 1987 .

[34]  S. Singh,et al.  Free and glucosyloxy acetophenones from Pancratium biflorum , 1989 .

[35]  Y. Lee,et al.  Preferential cytotoxicity of caffeic acid phenethyl ester analogues on oral cancer cells. , 2000, Cancer letters.

[36]  W. Adam,et al.  Dioxirane Epoxidation of α,β‐Unsaturated Ketones , 1991 .

[37]  M. Huffman,et al.  4',5,6,7-OXYGENATED FLAVONES AND FLAVANONES. , 1964, Journal of pharmaceutical sciences.

[38]  R. Berry,et al.  Six new flavonoids from Citrus , 1972 .

[39]  D. Villemin,et al.  SUPPORTED METALATED PHTHALOCYANINE AS CATALYST FOR OXIDATION BY MOLECULAR OXYGEN. SYNTHESIS OF QUINONES AND CARBONYL COMPOUNDS , 2002 .

[40]  Y. Lee,et al.  Synergistic effect of cadmium chloride and acetaldehyde on cytotoxicity and its prevention by quercetin and glycyrrhizin. , 2001, Mutation research.

[41]  Peter C. H. Hollman,et al.  Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands , 1992 .

[42]  G. Thyagarajan,et al.  Flavonoids of Chromolaena odorata , 1978 .

[43]  T. Tseng,et al.  Inhibitory effect of Hibiscus protocatechuic acid on tumor promotion in mouse skin. , 1998, Cancer letters.

[44]  A. Papucci,et al.  A New Flavone Glycoside from Sideritis romana L. , 1977 .

[45]  D. Jerina,et al.  The bacterial degradation of flavonoids. Oxidative fission of the A-ring of dihydrogossypetin by a Pseudomonas sp. , 1972, The Biochemical journal.

[46]  Wilbur W. Widmer,et al.  Two New Polymethoxylated Flavones, a Class of Compounds with Potential Anticancer Activity, Isolated from Cold Pressed Dancy Tangerine Peel Oil Solids , 1997 .

[47]  H. Kourai,et al.  Studies of the selective O-alkylation and dealkylation of flavonoids. VI. Demethylation of 8-hydroxy-5,7-dimethoxyflavones with anhydrous aluminum chloride or bromide in acetonitrile. , 1983 .

[48]  A. Ortuño,et al.  Citrus Polymethoxylated Flavones Can Confer Resistance against Phytophthora citrophthora, Penicillium digitatum, and Geotrichum Species , 1998 .