68097-13-2

Usage

Uses

Used in Pharmaceutical Industry:
4',5,7-Trihydroxy-6-prenylflavone is used as a therapeutic agent for its potential anticancer properties, as it has been shown to inhibit the growth of cancer cells. Its unique structure and medicinal properties make it an intriguing molecule for further research and development in the field of oncology.
Used in Nutraceutical Industry:
4',5,7-Trihydroxy-6-prenylflavone is used as a dietary supplement or functional food ingredient due to its antioxidant and anti-inflammatory properties. It can help reduce inflammation and oxidative stress in the body, contributing to overall health and well-being.
Used in Cosmetic Industry:
4',5,7-Trihydroxy-6-prenylflavone is used as an active ingredient in skincare products for its antioxidant and anti-inflammatory effects. It can help protect the skin from environmental stressors, reduce inflammation, and promote a healthy skin appearance.
Used in Research and Development:
4',5,7-Trihydroxy-6-prenylflavone is used as a subject of scientific research to explore its potential applications in various fields, such as medicine, nutrition, and cosmetics. Its unique structure and biological activities make it an interesting molecule for further investigation and potential development of new therapeutic agents or health products.

Upstream product

• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 870-63-3 prenyl bromide 
• 115-18-4 2-methyl-3-buten-2-ol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 249640-50-4 2',4-dihydroxy-4',6'-di(methoxymethoxy)-5'-C-prenylchalcone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 358-72-5 dimethylallyl diphosphate 
• 1186-30-7 3,3-dimethylallyl diphosphate triammonium salt 
• 100-07-2 4-methoxy-benzoyl chloride 
• 76288-41-0 1-(4'-methoxyphenyl)-3-(2''-hydroxy-3'',6''-dimethoxyphenyl)-1,3-propanedione 
• 83171-42-0 4,6-dimethoxy-2-(4'-methoxybenzoyloxy)acetophenone 
• 5631-70-9 4',5,7-trimethoxyflavone 
• 90632-20-5 1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl]ethanone 

Relevant academic research and scientific papers

Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases

Flavonoids are found mainly in plants and exhibit diverse biological and pharmacological activities, which can often be enhanced by prenylations. In plants, such reactions are catalyzed by membrane-bound prenyltransferases. In this study, the prenylation of nine flavonoids from different classes by a soluble fungal prenyltransferase (AnaPT) involved in the biosynthesis of the prenylated indole alkaloid acetylaszonalenin is demonstrated. The behavior of AnaPT toward flavonoids regarding substrate acceptance and prenylation positions clearly differs from that of the indole prenyltransferase 7-DMATS. The two enzymes are therefore complementary in flavonoid prenylations.

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.

Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata

Prenylated flavonoids are attractive specialized metabolites with a wide range of biological activities and are distributed in several plant families. The prenylation catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylated flavonoids and contributes to the structural diversity and biological activities of these compounds. To date, all identified plant flavonoid prenyltransferases (FPTs) have been identified in Leguminosae. In the present study two new FPTs, Morus alba isoliquiritigenin 3′-dimethylallyltransferase (MaIDT) and Cudrania tricuspidata isoliquiritigenin 3′-dimethylallyltransferase (CtIDT), were identified from moraceous plants M. alba and C. tricuspidata, respectively. MaIDT and CtIDT shared low levels of homology with the leguminous FPTs. MaIDT and CtIDT are predicted to be membrane-bound proteins with predicted transit peptides, seven transmembrane regions, and conserved functional domains that are similar to other homogentisate prenyltransferases. Recombinant MaIDT and CtIDT were able to regioselectively introduce dimethylallyl diphosphate into the A ring of three flavonoids with different skeleton types (chalcones, isoflavones, and flavones). Phylogenetic analysis revealed thatMaIDT and CtIDT are distantly related to their homologs in Leguminosae, which suggests that FPTs in Moraceae and Leguminosae might have evolved independently. MaIDT and CtIDT represent the first two non-Leguminosae FPTs to be identified in plants and could thus lead to the identification of additional evolutionarily varied FPTs in other non-Leguminosae plants and could elucidate the biosyntheses of prenylated flavonoids in various plants. Furthermore, MaIDT and CtIDT might be used for regiospecific prenylation of flavonoids to produce bioactive compounds for potential therapeutic applications due to their high efficiency and catalytic promiscuity.

Synthesis of 5,7,4'-trihydroxy-6-C-prenylflavone

5,7,4'-Trihydroxy-6-C-prenylflavone 6 isolated from the fruits of Maclura pomifera has been synthesized by the following route. Phloroacetophenone 1 on treatment with methoxymethyl chloride afford 2- hydroxy-4,6-di(methoxymethoxy) acetophenone 2 which on

Prenylation of Apigenin

Apigenin (I) on prenylation with 2-methylbut-3-ene-2-ol affords two major and four minor products.The major products are characterized as 6-C-prenylapigenin (II) and 5,4'-dihydroxy-6'',6''-dimethyl-4'',5''-dihydropyranoflavone (III) and the minor products as 7-O-prenylapigenin (IV), 5,4'-dihydroxy-6'',6''-dimethyl-5''-C-prenyl-4'',5''-dihydropyranoflavone (V), 5,4'-dihydroxy-6'',6''-dimethyl-4'',5''-dihydropyranoflavone (VI) and 5,4'-dihydroxy-6'',6''-dimethyl-5''-C-prenyl-4'',5''-dihydropyranoflavone (VII).Prenylation of apigenin with prenyl bromide in presence of methanolic sodium methoxide yields two major products, identified as 6,8-di(C-prenyl)apigenin (VIII) and 6-C-prenylapigenin (II), and four minor products, viz. 7,4'-di-O-prenylapigenin (IX), 8-C-prenyl-5,4'-dihydroxy-6'',6''-dimethyl-4'',5''-dihydropyranoflavone (X), 7-O-prenylapigenin (IV) and 5,4'-dihydroxy-6'',6''-dimethyl-4'',5''-dihydropyranoflavone (VI).Apigenin has been synthesized by a new route in a better yield.