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Structure Database (LMSD)

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Systematic Name

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

Synonyms

LM ID

LMPK12113345

Formula

C₂₂H₂₄O₉

Exact Mass

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432.142035

Status

Curated

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Classification

Biological Context

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 by breast cancer resistance protein (BCRP) and rhodamine 123 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

This information has been provided by Cayman Chemical

References

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. 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).

3. 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).

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).