Nobiletin: a citrus flavonoid displaying potent physiological activity

Nobiletin systematic name: 2‐(3,4‐dimethoxyphenyl)‐5,6,7,8‐tetramethoxy‐4H‐chromen‐4‐one; C₂₁H₂₂O₈] is a flavonoid found in citrus peels, and has been reported to show a wide range of physiological properties, including anti‐inflammatory, anticancer and antidementia activities. We have solved the crystal structure of nobiletin, which revealed that the chromene and arene rings of its flavone moiety, as well as the two methoxy groups bound to its arene ring, were coplanar. In contrast, the C atoms of the four methoxy groups bound to the chromene ring are out of the plane, making the molecule conformationally chiral. A comparison of the crystal structures of nobiletin revealed that it could adopt a variety of different conformations through rotation of the covalent bond between the chromene and arene rings, and the orientations of methoxy groups bound to the chromene ring.