Regioselective synthesis of di-C-glycosylflavones possessing anti-inflammation activities
Three methods are utilized to synthesize a variety of 6,8-di-C- glycosylflavones bearing identical or distinct glycosyl moieties. Some C-glycosylation compounds are found to have better anti-inflammation activities than the parent flavones. Among them, 6,8-di-C-glucosylapigenin (known as vicenin-2) shows inhibition of TNF-α expression and NO production with IC50 values of 6.8 and 5.2 μM, respectively.
Synthesis of vicenin-1 and 3, 6,8- and 8,6-di-C-β-d-(glucopyranosyl- xylopyranosyl)-4′,5,7-trihydroxyflavones using two direct C-glycosylations of naringenin and phloroacetophenone with unprotected d-glucose and d-xylose in aqueous solution as the key reactions
Vicenin-3 was synthesized from naringenin via a short five-step reaction, which included two regioselective direct C-glycosylations with d-glucose and d-xylose (yields: 22% and 30%, respectively) as the key reactions for a total yield of 4.4%. Vicenin-1 was also synthesized from phloroacetophenone via a 10-step reaction, including the same glycosylation described above, for a total yield of 2.7% with a vicenin-3 yield of 1.7%.
Sato, Shingo,Koide, Tomoyuki
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p. 1825 - 1830
(2010/10/18)
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