Identification of Paracentrone in Fucoxanthin-Fed Mice and Anti-Inflammatory Effect against Lipopolysaccharide-Stimulated Macrophages and Adipocytes

Scope Fucoxanthin is converted to fucoxanthinol and amarouciaxanthin A in the mouse body. However, further metabolism such as cleavage products (i.e., apocarotenoids) remains unclear. The fucoxanthin-derived apocarotenoid in vivo is investigated and the anti-inflammatory effect of apocarotenoids with fucoxanthin partial structure such as allenic bond and epoxide residue against activated macrophages and adipocytes in vitro is evaluated. Methods and Results LC-MS analysis indicates the presence of paracentrone, a C-31-allenic-apocarotenoid, in white adipose tissue of diabetic/obese KK-A(y) and normal C57BL/6J mice fed 0.2% fucoxanthin diet for 1 week. In lipopolysaccharide-activated RAW264.7 macrophages, paracentrone as well as C-26- and C-28-allenic-apocarotenoids suppresses the overexpression of inflammatory factors. Further, apo-10 '-fucoxanthinal, a fucoxanthin-derived apocarotenoid which retained epoxide residue, exhibits a most potent anti-inflammatory activity through regulating mitogen-activated protein kinases and nuclear factor-kappa B inflammatory signal pathways. In contrast, beta-apo-8 '-carotenal without allenic bond and epoxide residue lacks suppressed inflammation. In 3T3-L1 adipocytes, paracentrone, and apo-10 '-fucoxanthinal downregulate the mRNA expression of proinflammatory mediators and chemokines induced by co-culture with RAW264.7 cells. Conclusion Dietary fucoxanthin accumulates as paracentrone as well as fucoxanthinol and amarouciaxanthin A in the mouse body. Allenic bond and epoxide residue of fucoxanthin-derived apocarotenoids have pivotal roles for anti-inflammatory action against activated macrophages and adipocytes.

Automated summary

Fucoxanthin is metabolized into fucoxanthinol and amarouciaxanthin A in mice, with further metabolism of apocarotenoids remaining unclear. In vivo studies show that certain fucoxanthin-derived apocarotenoids with allenic bond and epoxide residue exhibit anti-inflammatory effects against activated macrophages and adipocytes.