2284-31-3

Usage

Uses

Used in Pharmaceutical Industry:
PRATENSEIN is used as a pharmaceutical compound for its potential therapeutic properties. The specific application reason is not provided in the materials, but the unique structure of PRATENSEIN suggests that it may have biological activities that could be harnessed for medicinal purposes.
Used in Chemical Research:
PRATENSEIN, being a member of the 7-hydroxyisoflavones class, is used as a research compound in the field of chemistry. Its unique structure allows scientists to study its properties and interactions with other molecules, which could lead to the discovery of new applications and uses.

InChI:InChI=1/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3

Upstream product

• 480-23-9 orobol 
• 491-80-5 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 36191-03-4 calycosin-7-O-β-D-glucopyranoside 
• 63240-66-4 3',4',6'-tri-O-benzyl-2'-hydroxy-4-methoxychalcone 
• 70413-06-8 2,3',4,6-tetrahydroxy-4'-methoxy-desoxybenzoin 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 122087-35-8 5,7,3'-trihydroxy-4'-methoxyisoflavanone 

Relevant academic research and scientific papers

THE FIRST IDENTIFICATION OF ISOFLAVONES FROM A BRYOPHYTE

Bryum capillare is shown to accumulate the isoflavones orobol and pratensein as the 7-O-glucosides and predominantly, as the 7-(6''-malonylglucosides).This is the first finding of isoflavonoids in bryophytes.The phylogenetic relevance of this observation is briefly discussed.Key Word Index - Bryum capillare; Bryales; Musci; moss; isoflavones; orobol; pratensein; 7-O-glucosides; 6''-malonyl glucosides; NMR spectra.

Production and anti-melanoma activity of methoxyisoflavones from the biotransformation of genistein by two recombinant Escherichia coli strains

Biotransformation of the soy isoflavone genistein by sequential 3′-hydroxylation using recombinant Escherichia coli expressing tyrosinase from Bacillus megaterium and then methylation using another recombinant E. coli expressing O-methyltransferase from S

Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover)

Biochanin A and formononetin are the predominant isoflavones in red clover. In a previous study (J. Agric. Food Chem. 2002, 50, 4783-4790), it was demonstrated that human liver microsomes converted biochanin A and formononetin to genistein and daidzein. This paper now shows CYP1B1-catalyzed O-demethylation of biochanin A and formononetin to produce genistein and daidzein, respectively, which inhibit CYP1B1. Recombinant human CYP1A1 or CYP1B1 was incubated with biochanin A or formononetin. CYP1A1 catalyzed isoflavone 4′-O-demethylation and hydroxylations with similar efficiency, whereas CYP1B1 favored 4′-O-demethylation over hydroxylations. Three of the biochanin A metabolites (5,7,3′-trihydroxy-4′-methoxyisoflavone, 5,7,8-trihydroxy-4′-methoxyisoflavone, and 5,6,7-trihydroxy-4′- methoxyisoflavone) were characterized by 1H NMR spectroscopy and mass spectrometry. Daidzein (Ki = 3.7 μM) exhibited competitive inhibition of CYP1B1 7-ethoxyresorufin O-deethylase activity, and genistein (Ki = 1.9 μM) exhibited mixed inhibition. Biochanin A and/or formononetin may exert anticarcinogenic effects directly by acting as competitive substrates for CYP1B1 or indirectly through their metabolites daidzein and genistein, which inhibit CYP1B1.

Synthesis of Naturally Occuring Pratensein and 6,8-Di-C-prenylpratensein

Pratensein (4a) has now been synthesized in two ways.The first route involves condensation of phloroacetophenone dibenzyl ether (1) with O-benzylisovanillin (2) and oxidative cyclization of the resulting chalcone (3) with Tl(NO3)3-MeOH followed by boiling with HCl.In the second route 2,4,6,3'-tetrahydroxy-4'-methoxydesoxybenzoin (5) is treated with DMF, CH3SO2Cl and BF3-Et2O.When pratensein is reacted with 3-hydroxy-3-methyl-1-butene in the presence of BF3-Et2O and dioxan, it gives the naturally occuring 6,8-di-C-prenylpratensein (6a).