68097-13-2

Basic information

• Product Name: 4',5,7-Trihydroxy-6-prenylflavone
• Synonyms: 4',5,7-Trihydroxy-6-prenylflavone;5,7,4'-Trihydroxy-6-[3''-methylbut-2''-enyl]-flavone;6-Prenyl-4',5,7-trihydroxyflavone;6-Prenylapigenin;5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-Methylbut-2-en-1-yl)-4H-chroMen-4-one
• CAS NO: 68097-13-2
• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338
• Mol File: 68097-13-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4',5,7-Trihydroxy-6-prenylflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 4',5,7-Trihydroxy-6-prenylflavone(68097-13-2)
• EPA Substance Registry System: 4',5,7-Trihydroxy-6-prenylflavone(68097-13-2)

Safety Data

• Hazardous Substances Data: 68097-13-2(Hazardous Substances Data)

Usage

General Description

4',5,7-Trihydroxy-6-prenylflavone is a naturally occurring chemical compound found in plants such as Glycyrrhiza glabra L. This flavonoid has an intricate structure with three hydroxyl groups and a prenyl group attached to the flavone backbone. It possesses various biological activities such as antioxidant, anti-inflammatory, and anticancer properties. Studies have shown that 4',5,7-Trihydroxy-6-prenylflavone has the potential to inhibit the growth of cancer cells and reduce inflammation and oxidative stress in the body. Its unique structure and medicinal properties make it an intriguing molecule for further research and potential therapeutic applications.

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Relevant articles and documents

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.

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.

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.