82616-06-6Relevant articles and documents
Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin bis-C-β-d-glucosides
Sato, Shingo,Akiya, Toshiki,Nishizawa, Hiroaki,Suzuki, Toshiyuki
, p. 964 - 970 (2006)
Three naturally occurring di-C-glycosylflavonoids, phloretin (dihydrochalcone), naringenin (flavanone), and apigenin (flavone) bis-6,8-C-β-d-glucopyranosides (4, 5, and 6), were synthesized in total yields of 52.3%, 53.5%, and 36.4%, respectively, starting from the key compound, di-C-β-d-glucopyranosylphloroacetophenone (1). Benzyl protection of the phenolic hydroxyls in 1 and a subsequent aldol condensation with benzyloxybenzaldehyde led to the production of chalcone 3, which, after hydrogenolysis or acid hydrolysis and deprotection, gave 4 and 5, respectively. The acetylation of 5, followed by DDQ oxidation and deprotection, gave 6.
Oviposition Stimulant of Papilio xunthus, a Citrus-feeding Swallowtail Butterfly
Ohsugi, Takao,Nishida, Ritsuo,Fukami, Hiroshi
, p. 1897 - 1900 (2007/10/02)
Methanol extracts of fresh leaves of Citrus plants induce oviposotion behaviour by females of the Citrus-feeding swallow-tail butterfly, Papilio xuthus L.One of the oviposotion stimulants was isolated from an extract of Citrus unshiu Marc. and identified as 6,8-di-C-β-D-glucopyranosylapigenin.The compound was inactive alone, but elicited oviposition behaviour when mixed with another component which has not yet been identified.
