Alphitonin is a flavonoid-related metabolite related to quercetin isolated from the heartwood of the Australian red ash, Alphitonia excela in 1922. Alphitonin's structure was reported by Birch and Ritchie in 1960. Alphitonin is thermally and enzymically converted from the flavonoid, taxifolin. Alphitonin has antidiabetic and antioxidant properties, being more active than quercetin. In contrast, alphitonin did not inhibit TNF responses in a murine small intestinal epithelial cell line, suggesting that microbial transformation of quercetin completely abolished the latter’s anti-inflammatory effect.
Guise GB et al (1962) Further constituents of Alphitonia species Aust. J Chem. 15:3S14
Kim TH et al(2017) Plasma-induced degradation of quercetin associated with the enhancement of biological activities J. Agric. Food Chem. 65:6929
Ruiz PA et al (2007) Quercetin inhibits TNF-induced NF-kappaB transcription factor recruitment to proinflammatory gene promoters in murine intestinal epithelial cells. J. Nutr. 137:1208
Smith HG and REad J (1922) The glucoside occurring in the timber of the red ash, Alphitonia excelsa. J. Proc. Roy. Soc NSW 56:253