5,4'-Dihydroxy-6,7,8-trimethoxyflavone

• CAS: 16545-23-6
• Catalog Number: ACM16545236
• Category: Main Products
• Molecular Weight: 344.32
• Molecular Formula: C18H16O7
• Synonyms: 5-Hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxychromen-4-one
• Appearance: solid

Case Study

Disease Chemopreventive Effects and Molecular Mechanisms of Hydroxylated Polymethoxyflavones

Lai, Ching-Shu, et al. BioFactors, 2015, 41(5), 301-313.

The broad spectrum of biological properties exhibited by Citrus polymethoxyflavones (PMFs) has led to growing scientific interest. Hydroxylated PMFs represent a distinct flavonoid group characterized by methoxy groups replacing the hydroxyl groups found in PMFs. The natural occurrence of hydroxylated PMFs is found in citrus peels and other plant sources and they function as the metabolic products of their PMF counterparts. For example, the metabolites of tangeretin include 4'-demethyltangeretin which is 4'-hydroxy 5,6,7,8-tetramethoxyflavone and 5,4'-didemethyltangeretin which is 5,4'-dihydroxy-6,7,8-trimethoxyflavone.
Several in vitro and in vivo studies indicated hydroxylated PMFs show preventive effects against cancer and other diseases through their anti-inflammatory, anti-atherosclerotic, and neuroprotective actions. These compounds control cell death and cell proliferation along with differentiation and repair functions and metabolic processes through the modulation of signaling pathways and gene transcription activities as well as through changes in protein function and enzyme activity. The mechanism of action of hydroxylated PMFs in disease chemoprevention depends on their structure, the number and position of hydroxyl groups.

Toxicity of 5,4'-Dihydroxy-6,7,8-Trimethoxyflavonoids in Breast Cancer Cell Lines

Sotillo, Wendy Soria, et al. BMC Complementary Medicine and Therapies, 2021, 21, 1-11.

Flavonoids are compounds of interest in the search for novel anticancer therapeutics. This work investigated the toxicity of several methoxyflavones, including 5,4'-dihydroxy-6,7,8,3'-tetramethoxyflavone (8-methoxycirsilineol), 5,4'-dihydroxy-6,7,8-trimethoxyflavone (xanthomicrol), and 5,4,'3'-trihydroxy-6,7,8-trimethoxyflavone (sideritoflavone) in human breast-derived cell lines.
Dose Response Experiments
Dose-response experiments were performed using MCF-7, HCC1937, and JIMT-1 breast cancer and MCF-10A normal-like breast cell lines to derive inhibitory concentration 50 (IC50) values to understand the range of toxicity.
Evaluation Results
· Sideritoflavone containing ortho dihydroxy groups at positions C-3' and C-4' displayed cytotoxic effects at low micromolar levels with an IC50 value of 1.9 ± 0.3 μM for JIMT-1 cells.
· Treatment with 8-methoxycirsilineol that contains an OMe group at C-3' and an ortho dihydroxy group at C-4' showed no cytotoxic effects even at concentrations up to 100 μM.
· Similarly, xanthomicrol, which possesses only one hydroxyl group at C-4', exhibited lower cytotoxicity, with an IC50 of 99.6 ± 24.1 μM.
· Sideritoflavone was also toxic to MCF-7 (IC50 4.9 ± 1.7 μM) and HCC1937 (IC50 4.6 μM) breast cancer cells, as well as MCF-10A normal breast epithelial cells (IC50 6.7 ± 0.9 μM), while methoxycirsilineol and xanthomicrol were significantly less toxic (IC50 ≥ 100 μM).