1176-88-1Relevant articles and documents
CHEMISTRY OF TOXIC RANGE PLANTS. HIGHLY OXYGENATED FLAVONOL METHYL ETHERS FROM GUTIERREZIA MICROCEPHALA
Roitman, James N.,James Lynn F.
, p. 835 - 848 (1985)
Gutierrezia microcephala; Broomweed; Compositae; Astereae; flavonol; oxygenated kaempferol; quercetin and myricetin derivatives; 13C NMR.The perennial American desert shrub, Gutierrezia microcephala, contains 20 flavonol methyl ethers displaying nine different oxygenation patterns.These include 11 new flavonols: 5,7-dihydroxy-3,6,8,3',4',5'-hexamethoxyflavone, 5,7,4'-trihydroxy-3,6,8,3',5'-pentamethoxyflavone, 5,7,3'-trihydroxy-3,6,8,4',5'-pentamethoxyflavone, 5,7,2',4'-tetrahydroxy-3,6,8,5'-tetramethoxyflavone, 5,7,3',4'-tetrahydroxy-3,6,8-trimethoxyflavone, 5,7,8,3',4'-pentahydroxy-3,6-dimethoxyflavone, 3,5,7,3',4'-pentahydroxy-6,8-dimethoxyflavone, 5,7,4'-trihydroxy-3,6,8-trimethoxyflavone, 5,7,8,4'-tetrahydroxy-3,3'-dimethoxyflavone, 5,7,8,3',4'-pentahydroxy-3-methoxyflavone and 5,7,8,4'-tetrahydroxy-3-methoxyflavone.In addition, the following known flavonols were isolated: 5,7-dihydroxy-3,8,3',4',5'-pentamethoxyflavone, 5,7,4'-trihydroxy-3,8-dimethoxyflavone, 5,7,4'-trihydroxy-3,8,3'-trimethoxyflavone, 5,7,3',4'-tetrahydroxy-3,8-dimethoxyflavone, 5,7,4'-trihydroxy-3,6,3'-trimethoxyflavone, 5,7,3',4'-tetrahydroxy-3-methoxyflavone, 5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone, 5,7,4'-trihydroxy-3,6,8,3'-tetramethoxyflavone and 3,5,7,4'-tetrahydroxy-6,8,3'-trimethoxyflavone.
Semisynthesis of polymethoxyflavonoids from naringin and hesperidin
Li, Yue,Cai, Shuanglian,He, Kailin,Wang, Qiuan
, p. 287 - 290 (2014/06/09)
Polymethoxyflavonoids (PMFs) possess important biological activities, notably as anticancer agents. Semisynthesis of a series of PMFs were performed by glycoside hydrolysis, dehydrogenation, bromination, aromatic nucleophilic substitution, O-methylation, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. A new synthetic method for selective methylation using CuBr catalysed and microwave-assisted reaction was developed, and the dimethyl dioxirane oxidation of flavones to flavonols was much improved. The new semisynthetic route has the advantages of easy availability of starting materials, simple operation and good yields.