76735-58-5

Upstream product

• 358-72-5 dimethylallyl diphosphate 
• 491-71-4 chrysoeriol 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 

Relevant academic research and scientific papers

Regioselective synthesis of C-prenylated flavonoids via intramolecular [1,3] or [1,5] shift reaction catalyzed by acidic clays

Prenyl side chain and dihydropyrano skeleton exists in many natural and synthetic biologically active flavonoids. A highly efficient and regioselective method for the synthesis of C-prenylated flavonoids via intramolecular [1,3] or [1,5] shift reaction of

Biosynthesis of cannflavins A and B from Cannabis sativa L

In addition to the psychoactive constituents that are typically associated with Cannabis sativa L., there exist numerous other specialized metabolites in this plant that are believed to contribute to its medicinal versatility. This study focused on two such compounds, known as cannflavin A and cannflavin B. These prenylated flavonoids specifically accumulate in C. sativa and are known to exhibit potent anti-inflammatory activity in various animal cell models. However, almost nothing is known about their biosynthesis. Using a combination of phylogenomic and biochemical approaches, an aromatic prenyltransferase from C. sativa (CsPT3) was identified that catalyzes the regiospecific addition of either geranyl diphosphate (GPP) or dimethylallyl diphosphate (DMAPP) to the methylated flavone, chrysoeriol, to produce cannflavins A and B, respectively. Further evidence is presented for an O-methyltransferase (CsOMT21) encoded within the C. sativa genome that specifically converts the widespread plant flavone known as luteolin to chrysoeriol, both of which accumulate in C. sativa. These results therefore imply the following reaction sequence for cannflavins A and B biosynthesis: luteolin ? chrysoeriol ? cannflavin A and cannflavin B. Taken together, the identification of these two unique enzymes represent a branch point from the general flavonoid pathway in C. sativa and offer a tractable route towards metabolic engineering strategies that are designed to produce these two medicinally relevant Cannabis compounds.

GuA6DT, a regiospecific prenyltransferase from glycyrrhiza uralensis, catalyzes the 6-prenylation of flavones

GuA6DT, a flavonoid prenyltransferase, was identified from Glycyrrhiza uralensis, and it was found that this enzyme regiospecifically transfers a dimethylallyl moiety to apigenin at the C-6 position. A further substrate specificity investigation indicated that the existence of hydroxyls at both the C-5 and C-7 positions of the flavone skeleton is critical for the prenylation. However, substitutions on the B-ring had negligible influence on the prenylation. A comparison of GuA6DT expression in different organs revealed that mRNA is mainly expressed in the aerial parts. Moreover, the GuA6DT mRNA was found to be regulated at the transcriptional level, because methyl jasmonate induced upregulation in cultured cells. GuA6DT is the first identified flavone prenyltransferase to exhibit strict substrate specificity and regiospecificity.

A regiodivergent synthesis of ring A C-prenylflavones

(Chemical Equation Presented) Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same pre