5-O-Demethylnobiletin

5-O-Demethylnobiletin is a flavonoid that has been found in S. tragoriganum and has diverse biological activities.^1,2,3,4 It induces neurite outgrowth and the expression of the genes encoding the neuronal differentiation and synapse formation markers growth-associated protein 43 (GAP43) and synaptophysin in PC12 cells when used at concentrations ranging from 10 to 20 µM.¹ 5-O-Demethylnobiletin (2.5-20 µM) reduces triglyceride levels in 3T3-L1 preadipocytes and decreases body weight, intra-abdominal fat, plasma and liver triglyceride levels, and plasma cholesterol levels in a mouse model of high-fat diet-induced obesity when administered at a dose of 25 mg/kg.² It reduces hepatic fibrosis and malondialdehyde (MDA) levels in a mouse model of carbon tetrachloride-induced liver injury.³ 5-O-Demethylnobiletin also reduces ear edema, inflammatory cell infiltration, and papillar fibrosis in a mouse model of inflammation induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014).⁴

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1. Chiu, S.-P., Wu, M.-J., Chen, P.-Y., et al. Neurotrophic action of 5-hydroxylated polymethoxyflavones: 5-demethylnobiletin and gardenin A stimulate neuritogenesis in PC12 cells. J. Agric. Food Chem 61(39), 9453-9463 (2013).

2. Tung, Y.-C., Li, S., Huang, Q., et al. 5-Demethylnobiletin and 5-Acetoxy-6,7,8,3',4'-pentamethoxyflavone suppress lipid accumulation by activating the LKB1-AMPK pathway in 3T3-L1 preadipocytes and high fat diet-fed C57BL/6 mice. J. Agric. Food Chem 64(16), 3196-3205 (2016).

3. Chang, S.N., Kim, S.H., Dey, D.K., et al. 5-O-Demethylnobiletin alleviates CCL4-induced acute liver injury by equilibrating ROS-mediated apoptosis and autophagy induction. Int. J. Mol. Sci. 22(3), 1083 (2021).

4. Bas, E., Recio, M.C., Giner, R.M., et al. Anti-inflammatory activity of 5-O-demethylnobiletin, a polymethoxyflavone isolated from Sideritis tragoriganum. Planta Med. 72(2), 136-142 (2006).