Amentoflavone

Catalogue number C108732
Chemical nameAmentoflavone
CAS Number1617-53-4
Synonyms8-[5-(5,7-dihydroxy-4-oxo-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyran-4-one
Molecular WeightC30H18O10
Formula538.4
Purity98%
Physical DescriptionCryst.
SolventChloroform, Dichloromethane,DMSO
StorageStored at 2-8°C, Protected from air and light, refrigerate or freeze
Applications

Amentoflavone can interact with many other medications by being a potent inhibitor of CYP3A4 and CYP2C9, which are proteins used for drug metabolism in the body. It is also an inhibitor of human cathepsin B.


Amentoflavone has demonstrated some antimalarial activity in trials significant affinities towards the delta-1, kappa opioid receptors (as an antagonist) and binds to benzodiazepine receptors. Using two electrode voltage-clamp methodology, amentoflavone has been shown to be a negative modulator of GABA at GABAA a1b2g2L receptors expressed in Xenopus laevis oocytes. This action appears to be independent of the flumazenil-sensitive benzodiazepine modulatory sites on the GABAA receptor.


Amentoflavone was administered intraperitoneally, it showed a potent anti-inflammatory activity as determined by amelioration of croton-oil induced mouse ear edema. It also showed a potent anti-inflammatory activity in the rat carrageenan paw edema model (ED50=42 mg/kg) compared to the activity of prednisolone (35 mg/kg) and indomethacin (10 mg/kg). However, amentoflavone did not show a significant inhibitory activity against rat adjuvant-induced arthritis, a chronic inflammatory model. In addition, amentoflavone was found to possess a potent analgesic activity in the acetic acid writhing test (ED50=9.6 mg/kg) compared to the activity of indomethacin (3.8 mg/kg). These results suggest that amentoflavone may be a potential lead for a new type of anti-inflammatory agents having dual inhibitory activity of group II phospholipase A2 and cyclooxygenase.


Amentoflavone and quercetin differentially exerted supression of PGE2 biosynthesis via downregulation of COX-2/iNOS expression.
Amentoflavone and the extracts were screened against five cancer cells, including HeLa (human cervical carcinoma cells), BEL-7402 (human hepatoma carcinoma cells), MCF-7 (human breast cancer cells), PANC-1 (human pancreatic cancer cells) and HL-60 (human leukemia cells). The anticancer activity were determined by means of MTT assay and Trypan Blue cytometry. Assays in vitro showed that they were effective to inhibit the proliferation of HL-60, MCF-7, HeLa, BEL-7402, PANC-1 and had reliable activity against HL-60.

References1. Phytochemistry, 1987, 26(12), 3335-3337.
2. Journal of Chromatography A, 2004, 1035(1), 47-51.
3. Bioorganic & Medicinal Chemistry Letters, 2003, 13(14), 2281-2284.
4. Archives of Pharmacal Research, 1998, 21(4), 406-410.
5. Prostaglandins, Leukotrienes and Essential Fatty Acids, 2002, 66(5-6), 485-492.
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Amentoflavone
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