480-10-4

Basic information

• Product Name: ASTRAGALIN
• Synonyms: KAEMPFEROL-3-O-BETA-D-GLUCOPYRANOSIDE;KAEMPFEROL-3-O-GLUCOSIDE;KAEMPFEROL-3-GLUCOSIDE;ASTRAGALIN;4h-1-benzopyran-4-one,3-(beta-d-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyp;astragaline;k5;kaempferol-3-beta-glucopyranoside
• CAS NO: 480-10-4
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.38
• Product Categories: Tetra-substituted Flavones;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Flavonoids
• Mol File: 480-10-4.mol
• Article Data: 24

Chemical Properties

• Melting Point: 223-229°C
• Boiling Point: 823.2 °C at 760 mmHg
• Flash Point: 291.5 °C
• Appearance: /
• Density: 1.79 g/cm³
• Vapor Pressure: 1.09E-28mmHg at 25°C
• Refractive Index: 1.774
• Storage Temp.: ?20°C
• PKA: 6.20±0.40(Predicted)
• CAS DataBase Reference: ASTRAGALIN(CAS DataBase Reference)
• NIST Chemistry Reference: ASTRAGALIN(480-10-4)
• EPA Substance Registry System: ASTRAGALIN(480-10-4)

Safety Data

• Safety Statements: 22
• WGK Germany: 3
• RTECS: DJ3080000
• Hazardous Substances Data: 480-10-4(Hazardous Substances Data)

Usage

Description

Astragaline, also known as kaempferol 3-O-glucoside, is a flavonoid compound that can be isolated from various plant sources such as Phytolacca americana (American pokeweed) and the methanolic extract of fronds of the fern Phegopteris connectilis. It is also found in wine and has a glucosyl residue attached at position 3 of kaempferol via a beta-glycosidic linkage.

Uses

Used in Metabolic Syndrome Treatment:
Astragaline is used as a therapeutic agent for mitigating high-fat and high-fructose diet (HFFD)-induced metabolic syndrome. It is found in Erica multiflora leaf extract, which helps in managing the symptoms and complications associated with metabolic syndrome.
Used in Pharmaceutical Industry:
Astragaline is used as a chemical compound in the pharmaceutical industry for its potential medicinal properties. Its flavonoid nature makes it a valuable component in the development of new drugs and therapies.
Used in Wine Industry:
Astragaline is used in the wine industry as a natural component found in wine, contributing to its unique characteristics and potential health benefits.

source

Astragalin belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Astragalin exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, astragalin is primarily located in the cytoplasm. Astragalin can be converted into astragalin heptaacetate and 2''-acetylastragalin. Outside of the human body, astragalin can be found in a number of food items such as tamarind, american cranberry, chickpea, and bilberry. This makes astragalin a potential biomarker for the consumption of these food products.

InChI:InChI=1/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m1/s1

Upstream product

• 74712-68-8 kaempferol 3-O-(3'',6''-di-O-E-p-coumaroyl)-β-D-glucopyranoside 
• 520-18-3 kaempferol 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 121651-61-4 kaempferol 3-O-[2'',6''-di-O-(trans-p-coumaroyl)]-β-D-glucopyranoside 
• 152390-63-1 kaempferol 3-O-[β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside] 
• 22153-44-2 trans-tiliroside 
• 133-89-1 UDP-glucose 
• 2956-16-3 uridine 5'-diphospho-D-galactose 
• 23243-67-6 3-(4-benzyloxyphenyl)-1-(2,4-dibenzyloxy-6-hydroxyphenyl)prop-2-en-1-one 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 30652-27-8 4',7-di-O-benzyl-kaempferol 
• 96333-59-4 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 23405-70-1 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 

Downstream Products

• 520-18-3 kaempferol 
• 50-99-7 D-glucose 
• 59-23-4 D-Galactose 
• 1257529-57-9 benzyl(6-(5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4a,8a-dihydro-4H-chromen-3-yloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl malonate 
• 1030269-14-7 heptamethyltrifolin 
• 99-96-7 4-hydroxy-benzoic acid 
• 108-73-6 3,5-dihydroxyphenol 
• 492-61-5 β-D-glucose 
• 11055-94-0 hepta-O-acetyltrifolin 
• 2636-51-3 Astragalin-acetat 
• 10257-28-0 D-Galactose 
• 2280-44-6 D-Glucose 

Relevant articles and documents

Phlomisflavosides A and B, new flavonol bisglycosides from Phlomis spinidens

From the aerial parts of Phlomis spinidens, two new flavonol bisglycosides, phlomisflavosides A (1) and B (2), were isolated together with the known compounds, astragalin, isoquercitrin, lamiridoside, phlomoside A, shanzhiside methyl ester, 8-O-acetylshanzhiside methyl ester, phlorigidoside C, rodioloside (=salidroside), forsythoside B, citroside A and lariciresinol-4′-O-β-D-glucoside. The structures of the new compounds were elucidated based on spectral and chemical evidence.

STRUCTURES AND ACCUMULATION PATTERNS OF SOLUBLE AND INSOLUBLE PHENOLICS FROM NORWAY SPRUCE NEEDLES

Key Word Index - Picea abies; Pinaceae; Norway spruce; phenolics; identification; seasonal accumulation pattern; turnover; translocation; cell wall localization; flavonol glucosyltransferase. - Abstract - Twenty-two soluble phenolics have been isolated from Norway spruce needles and their structures elucidated on the basis of chromatographic (TLC, HPLC), chemical (hydrolysis), enzymic and spectroscopic (UV, NMR, MS) techniques.These phenolics have been quantified by HPLC during the first year of needle development from a forest near Bad Muenstereifel (F.R.G.) and showed a differential accumulation pattern.Kaempferol 3-O-glucoside showed an interesting metabolism, indicating rapid turnover and/or translocation from a soluble to an insoluble (cell wall bound) pool.The enzyme involved in the formation of this flavonoid, UDP-glucose:flavonol glucosyltransferase, showed a marked transient increase in activity that correlated with the possible kaempferol 3-O-glucoside translocation.

Functional Characterization and Protein Engineering of a Triterpene 3-/6-/2′-O-Glycosyltransferase Reveal a Conserved Residue Critical for the Regiospecificity

Engineering the function of triterpene glucosyltransferases (GTs) is challenging due to the large size of the sugar acceptors. In this work, we identified a multifunctional glycosyltransferase AmGT8 catalyzing triterpene 3-/6-/2′-O-glycosylation from the medicinal plant Astragalus membranaceus. To engineer its regiospecificity, a small mutant library was built based on semi-rational design. Variants A394F, A394D, and T131V were found to catalyze specific 6-O, 3-O, and 2′-O glycosylation, respectively. The origin of regioselectivity of AmGT8 and its A394F variant was studied by molecular dynamics and hydrogen deuterium exchange mass spectrometry. Residue 394 is highly conserved as A/G and is critical for the regiospecificity of the C- and O-GTs TcCGT1 and GuGT10/14. Finally, astragalosides III and IV were synthesized by mutants A394F, T131V and P192E. This work reports biocatalysts for saponin synthesis and gives new insights into protein engineering of regioselectivity in plant GTs.

Methylglucosylation of Phenolic Compounds by Fungal Glycosyltransferase-Methyltransferase Functional Modules

Glycosylation endows both natural and synthetic small molecules with modulated physicochemical and biological properties. Plant and bacterial glycosyltransferases capable of decorating various privileged scaffolds have been extensively studied, but those from kingdom Fungi still remain underexploited. Here, we use a combination of genome mining and heterologous expression techniques to identify four novel glycosyltransferase-methyltransferase (GT-MT) functional modules from Hypocreales fungi. These GT-MT modules display decent substrate promiscuity and regiospecificity, methylglucosylating a panel of natural products such as flavonoids, stilbenoids, anthraquinones, and benzenediol lactones. Native GT-MT modules can be split up and regrouped into hybrid modules with similar or even improved efficacy as compared with native pairs. Methylglucosylation of kaempferol considerably improves its insecticidal activity against the larvae of oriental armyworm Mythimna separata (Walker). Our work provides a set of efficient biocatalysts for the combinatorial biosynthesis of small molecule glycosides that may have significant importance to the pharmaceutical, agricultural, and food industries.