29741-09-1

Basic information

• Product Name: APIGENIN-7-GLUCURONIDE
• Synonyms: APIGENIN-7-GLUCURONIDE;APIGENIN-7-O-GLUCURONIDE;4',5-Dihydroxy-7-[(β-D-glucopyranuronosyl)oxy]flavone;5,4'-Dihydroxy-7-(β-D-glucopyranuronosyloxy)flavone;7-(6-Oxo-β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Apigenin 7-O-β-D-glucuronide;Glucuronyl-7-apigenin;5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranosiduronic acid
• CAS NO: 29741-09-1
• Molecular Formula: C₂₁H₁₈O₁₁
• Molecular Weight: 446.36
• Product Categories: Miscellaneous Natural Products
• Mol File: 29741-09-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: >300℃
• Boiling Point: 841.8°Cat760mmHg
• Flash Point: 299°C
• Appearance: /
• Density: 1.737
• Vapor Pressure: 4.28E-30mmHg at 25°C
• Refractive Index: 1.739
• Storage Temp.: ?20°C
• PKA: 2.73±0.70(Predicted)
• CAS DataBase Reference: APIGENIN-7-GLUCURONIDE(CAS DataBase Reference)
• NIST Chemistry Reference: APIGENIN-7-GLUCURONIDE(29741-09-1)
• EPA Substance Registry System: APIGENIN-7-GLUCURONIDE(29741-09-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 29741-09-1(Hazardous Substances Data)

Usage

Uses

Apigenin 7-Glucuronide is a metabolite of Apigenin, which induces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 uM) by inhibiting MAP kinase activity. Also inhibits the proliferation of malignant tumor cells by G2/M arrest and induces morphological differentiation. Apigenin has also been reported to enhance the gap juntion intracellular communication in liver cells.

InChI:InChI=1/C21H18O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1

Upstream product

• 34340-20-0 5,4'-diacetoxyflavone-7-O-D-triacetoxyglucuronic acid methyl ester 
• 29781-25-7 apigenin 7-O-β-D-glucopyranosiduronic acid methyl ester 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 3316-46-9 apigenin triacetate 
• 2616-64-0 UDP-glucuronic acid 
• 1245697-26-0 UDP-glucuronic acid 

Downstream Products

• 34366-22-8 O¹-[5-acetoxy-2-(4-acetoxy-phenyl)-4-oxo-4H-chromen-7-yl]-O²,O³,O⁴-triacetyl-ξ-D-glucopyranuronic acid 
• 489-91-8 D-glucuronic acid 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 29781-25-7 apigenin 7-O-β-D-glucopyranosiduronic acid methyl ester 
• 6556-12-3 D-glucuronic acid 

Relevant articles and documents

Total synthesis of scutellarin and apigenin 7-O-β-d-glucuronide

A general protocol for direct glucuronic linkages formation featuring Au(I)-catalyzed appropriately protected glucuronyl o-alkynylbenzoate-involved glycosylation reaction, as well as a concise approach for easy access of scutellarein prominent for the mild and efficient hydroxyl group installation via borylation-oxidation sequence from flavanone derivative, has been established, based on which a novel route for scutellarin derivatives preparation has been devised. The developed strategies, among which the stepwise deprotection process was also included, guarantee the high whole synthetic efficiency, and definitely will find broad application in diversity-oriented synthesis of bioactive flavonoid glycosides.

Identification of flavone glucuronide isomers by metal complexation and tandem mass spectrometry: Regioselectivity of uridine 5′-diphosphate- glucuronosyltransferase isozymes in the biotransformation of flavones

Flavone glucuronide isomers of five flavones (chrysin, apigenin, luteolin, baicalein, and scutellarein) were differentiated by collision-induced dissociation of [Co(II) (flavone-H) (4,7-diphenyl-1,10-phenanthroline) 2]+ complexes. The complexes were generated via postcolumn addition of a metal-ligand solution after separation of the glucuronide products generated upon incubation of each flavone with an array of uridine 5′-diphosphate (UDP)-glucuronosyltransferase (UGT) isozymes. Elucidation of the glucuronide isomers allowed a systematic investigation of the regioselectivity of 12 human UGT isozymes, including 8 UGT1A and 4 UGT2B isozymes. Glucuronidation of the 7-OH position was the preferred site for all the flavones except for luteolin, which possessed adjacent hydroxyl groups on the B ring. For all flavones and UGT isozymes, glucuronidation of the 5-OH position was never observed. As confirmed by the metal complexation/MS/MS strategy, glucuronidation of the 6-OH position only occurred for baicalein and scutellarein when incubated with three of the UGT isozymes.

Co-pigmentation and flavonoid glycosyltransferases in blue Veronica persica flowers

Glycosylation is one of the key modification steps for plants to produce a broad spectrum of flavonoids with various structures and colors. A survey of flavonoids in the blue flowers of Veronica persica Poiret (Lamiales, Scrophulariaceae), which is native of Eurasia and now widespread worldwide, led to the identification of highly glycosylated flavonoids, namely delphinidin 3-O-(2-O-(6-O-p-coumaroyl-glucosyl)-6-O-p-coumaroyl-glucoside)-5-O-glucoside (1) and apigenin 7-O-(2-O-glucuronosyl)-glucuronide (2), as two of its main flavonoids. Interestingly, the latter flavone glucuronide (2) caused a bathochromic shift on the anthocyanin (1) toward a blue hue in a dose-dependent manner, showing an intermolecular co-pigment effect. In order to understand the molecular basis for the biosynthesis of this glucuronide, we isolated a cDNA encoding a UDP-dependent glycosyltransferase (UGT88D8), based on the structural similarity to flavonoid 7-O-glucuronosyltransferases (F7GAT) from Lamiales plants. Enzyme assays showed that the recombinant UGT88D8 protein catalyzes the 7-O-glucuronosylation of apigenin and its related flavonoids with preference to UDP-glucuronic acid as a sugar donor. Furthermore, we identified and functionally characterized a cDNA encoding another UGT, UGT94F1, as the anthocyanin 3-O-glucoside-2″-O-glucosyltransferase (A3Glc2″GlcT), according to the structural similarity to sugar-sugar glycosyltransferases classified to the cluster IV of flavonoid UGTs. Preferential expression of UGT88D8 and UGT94F1 genes in the petals supports the idea that these UGTs play an important role in the biosynthesis of key flavonoids responsible for the development of the blue color of V. persica flowers.