3,5,6,7,8,3',4'-Heptamethoxyflavone

3,5,6,7,8,3',4'-Heptamethoxyflavone (HMF) is a polymethoxyflavone that has been found in C. reticulata and has diverse biological activities.^1,2,3,4 It inhibits the efflux of Hoechst 33342 (Item No. 15547) by breast cancer resistance protein (BCRP) and rhodamine 123 (Item No. 16672) by P-glycoprotein (P-gp), also known as multidrug resistance protein 1 (MDR1), in MDCK cells expressing the human transporters (IC₅₀s = 1.4 and 31 µM, respectively).¹ HMF (50, 100, and 200 µg/ml) prevents UVB-induced decreases in type I procollagen in primary human dermal fibroblast neonatal (HDFn) cells.² It inhibits the proliferation of B16 melanoma 4A5, CCRF-HSB-2 leukemia, and TGBC11TKB gastric cancer cells (IC₅₀s = 38, 29, and 9 µM, respectively).³ HMF (50 mg/kg) prevents corticosterone-induced increases in immobility time in the forced swim test in mice.⁴

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1. Pick, A., Müller, H., Mayer, R., et al. Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP). Bioorg. Med. Chem. 19(6), 2090-2102 (2011).

2. Kim, H.-I., Jeong, Y.-U., Kim, J.-H., et al. 3,5,6,7,8,3',4'-heptamethoxyflavone, a Citrus flavonoid, inhibits collagenase activity and induces type I procollagen synthesis in HDFn cells. Int. J. Mol. Sci. 19(2), 620 (2018).

3. Kawaii, S., Tomono, Y., Katase, E., et al. Antiproliferative activity of flavonoids on several cancer cell lines. Biosci. Biotechnol. Biochem. 63(5), 896-899 (1999).

4. Sawamoto, A., Okuyama, S., Yamamoto, K., et al. 3,5,6,7,8,3',4'-heptamethoxyflavone, a citrus flavonoid, ameliorates corticosterone-Induced depression-like behavior and restores brain-derived neurotrophic factor expression, neurogenesis, and neuroplasticity in the hippocampus. Molecules 21(4), 541 (2016).