Tangeretin, one of the major components of polymethoxyflavones existing in citrus peels, has shown to exhibit many biological properties including anti-inflammatory and anti-carcinogenic activities. Our previous study has also found that 5-desmethylated tangeretin, naturally occurring in citrus peels in a minor amount, showed stronger bioactivity than that of its 'parent compound' tangeretin.  However, it has been observed that the aqueous solubility of 5-desmethylated tangeretin is too low to portray accurate readings from bioactivity tests.   To obtain good bioavailability and effective bioactivity evaluation of 5-desmethylated tangeretin, we have designed its 'pro-drug' form, or bioisosteric compound, 5-acetyloxy-6,7,8,4'-tetramethoxyflavone.  In the presentation, we report the synthesis, purification and biological study of 5-acetyloxy-6,7,8,4'-tetramethoxyflavone.

Synthesis and biological activity of a tangeretin bioisosteric compound

244th National Meeting (2012)

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