3681-93-4

Basic information

• Product Name: Vitexin
• Synonyms: 8-beta-d-glucopyranosyl-apigenin;8-d-glucosyl-4’,5,7-trihydroxy-flavon;8-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;VITEXIN 98+%;Vitxein;VITEXIN(P);VITEXIN(SH);Apigenin-8-O-glucoside
• CAS NO: 3681-93-4
• Molecular Formula: C21H20O10
• Molecular Weight: 432.38
• EINECS: 222-963-8
• Product Categories: Tetra-substituted Flavones;Alphabetic;Carbohydrates;Food&Beverage Standards;Neat ComponentsAnalytical Standards;V;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 3681-93-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 256-257°C
• Boiling Point: 767.7 °C at 760 mmHg
• Flash Point: 273.1 °C
• Appearance: /
• Density: 1.686 g/cm³
• Vapor Pressure: 8.68E-25mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Pyridine (Slightly)
• PKA: 6.27±0.40(Predicted)
• Stability: Hygroscopic
• BRN: 67796
• CAS DataBase Reference: Vitexin(CAS DataBase Reference)
• NIST Chemistry Reference: Vitexin(3681-93-4)
• EPA Substance Registry System: Vitexin(3681-93-4)

Safety Data

• WGK Germany: 3
• RTECS: DJ2984000
• F: 10-21
• Hazardous Substances Data: 3681-93-4(Hazardous Substances Data)

Usage

Plant sources

Vitexin, also known as the vitex glycoside, is a natural flavonoid glycoside extracted from leaves of vitex, a plant in the family Verbenaceae. Vitexin is widely distributed in the leaves and stems of dozens of plants in nature, such as vitex, fructus viticis, puberulous glochidion, hawthorn, Ficus microcarpa, Lygodium japonicum, Stenoloma chusanum, Alsophila spinulosa leaf, paper mulberry leaf, and indigowoad leaf, among which the main sources are hawthorn and leaves and stems of plants in the genus Vitex of the family Verbenaceae. Vitexin has a variety of physiological activity, such as anti-cancer, anti-tumor, anti-inflammation, spasmolysis, depressurization, promoting blood circulation and dissipating blood stasis, and regulating qi-flowing and invigorating pulse-beat. Clinically, vitexin mainly used for the treatment of cardiovascular diseases, for example, for the treatment of thoracic obstruction caused by blood stasis congesting veins. The syndrome includes chest tightness, suffocation, precordial tingling, heart palpitations, forgetfulness, dizziness, tinnitus, angina pectoris, hyperlipidemia, insufficient blood supply to the heart, and so on. In addition, this product can also enhance the adrenal function and increase the phagocytic activity of monocyte-macrophage system.

Physical and chemical properties

Yellow powder; melting point, 258-259℃ (265℃); optical rotation, [α] D18? (c = 2, pyridine).

Chemical constituents

The vitex leaf contains volatile oil, of which the main constituent is β-caryophyllene, followed by the sabinene. It also contains α-thujene, α-pinene, β-pinene, camphene, α-phellandrene, p-cymene, limonene, 1, 8-cineole as well as some stomachic ingredients with bitter taste such as vitexilactone, agnuside, ,artemisetin, and p-hydroxybenzoic acid.

Determination

TLCS method (1) Chromatographic condition: RP-18F254s efficient reversed-phase TLC plate was used. Impregnate the plate in 70% tetrahydrofuran-water solution (containing 0.1% tetrabutylammonium bromide) for 10 minutes and dried. Tetrahydrofuran-water (46:54, containing 0.1% tetrabutylammonium bromide) was used as developing solvent. The total distance traveled by the mobile phase was 4.5 cm; detected under UV light (254 nm). (2) Prepare reference solution: weigh proper amount of vitexin and p-hydroxybenzoic acid accurately, and add anhydrous ethanol to prepare 0.1 mg/ml vitexin and 0.05 mg/ml p-hydroxybenzoic acid solution as reference solution. (3) Prepare sample solution: weigh accurately 5 g of fructus viticis powder (particles were passing through a 40-mesh sieve and were dried to constant weight) and soak with anhydrous ethanol for eight hours in a Soxhlet extractor. Recover the solvent to a 25 ml volumetric flask and dilute with anhydrous ethanol to volume. Take the final solution as sample solution. (4) Determination: Imbibe accurately 2 μl of each of the sample solutions and the reference solution, and spot onto the same TLC plate, developing under the above chromatographic condition, then take out the plate and dry. The samples were then analyzed according to the TLC-scanning method and the single wavelength reflection sawtooth scanning method. The detection wavelength 350 nm and 258 nm was used respectively for quantification of vitexin and p-hydroxybenzoic acid. The SX value was 7, and the slit dimension was kept at 6 mm × 0.2 mm. The integral value of light absorbance of the samples and the reference were determined and the sample contents were calculated using the external standard method. (5) The chromatogram Figure 1 is a reversed-phase thin-layer chromatogram of fructus viticis extract. S, Fructus viticis of Rongcheng origin; V, Vitexin; P, p-hydroxybenzoic acid (6) Determination results Figure 2 shows the contents of vitexin and p-hydroxybenzoic acid in samples of different origin or harvest date (n=3，%)

Pharmacological effect

The volatile oil contained in the vitex leaf has significant expectorant effect and play a role in relieving cough by inhibiting the cough center. It also has anti-histamine effect, can relieve bronchial smooth muscle spasm, and thus relieves asthma. Emulsion of the vitex leaf oil has a significant and long-lasting antihypertensive effect on rabbit blood pressure. Leaf oil of vitex can improve the phagocytic capacity of macrophages, promote the serum protein synthesis and regulate the function of immunoglobulin, and has certain sedative and hypnotic effects when taken orally. The decoction made by the stems or leaves of vitex has significant antibacterial effect against Staphylococcus aureus and Bacillus anthracis, and it also has inhibitive effect against the E. coli, beta streptococcus, Corynebacterium diphtheriae, typhoid bacillus, Pseudomonas aeruginosa and Shigella. Vitexin has an obvious protective effect on acute myocardial ischemia of rats. The possible mechanism may be due to the activation of antioxidant enzymes which enhances the activity of SOD and GSH-Px, and reduce the tissue damage by excessive oxygen free radicals. In the meanwhile, it may function against the calcium overload by preventing the Ca2+ influx in a Ca2+ antagonist-like meaner, increasing the Ca2+ uptake of sarcoplasmic reticulum and by reducing the concentration of intracellular free Ca2+, which prevents the myocardial cell from further injury caused by Ca2+ overload and reduces the damage in the endothelial cell, and thus reduces the damage of biomembranes, ion pumps and the entire cardiac cells and ultimately shows the protective effect on acute myocardial ischemia. However, the starting and links of its roles needs further study. In summary, Vitexin has a good protective effect on ischemic myocardial injury. The role may relate to reducing the size of ischemic myocardial infarct, decreasing the viscosity of plasma and whole blood, increasing RBC deformability, and inhibiting thrombosis.

Efficacy and application

1. Vitexin Used for treatments of colds and cough. It also can be used with the perilla leaf in cure of common cold due to wind-cold. It has been used presently to cure chronic bronchitis, with good clinical result. 2. Used for treatments of abdominal pain and vomiting and diarrhea due to summer-heat and damp. It also can be used with herba centellae to cure vomiting and diarrhea due to summer-heat and damp. 3. Used for treatments of itching caused by rubella, athlete's foot, athlete's foot swelling, mastitis, insect or snake bites. It is usually smashed into small pieces and covered onto the affected area, or boiled with water and use the decoction to wash the affected area. It also can be used with loofah, perilla, drug sweetflag rhizome or folium artemisiae argyi to cure athlete's foot swelling.

Chemical Properties

Yellow powder

Uses

Vitexin is a phenolic glycoside drug that shows anti-stress activity. It also shows possible application as an anti-diabetic.

Definition

ChEBI: An apigenin flavone glycoside, which is found in the passion flower, bamboo leaves and pearl millet

Hazard

poison

InChI:InChI=1/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1

Upstream product

• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 29702-25-8 isovitexin 
• 133-89-1 UDP-glucose 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 57-50-1 Sucrose 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 1173925-24-0 vitexin 2-O-sulfate 
• 1154756-98-5 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one 

Downstream Products

• 61393-93-9 6-C-β-D-galactopyranosyl-8-C-β-D-glucopyranosylapigenin 
• 108-73-6 3,5-dihydroxyphenol 
• 866737-00-0 chafuroside B 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 29702-25-8 isovitexin 
• 50-99-7 D-glucose 
• 1233717-62-8 C₂₈H₂₄O₁₃S 
• 1233717-61-7 C₂₈H₂₄O₁₀ 
• 1173925-24-0 vitexin 2-O-sulfate 
• 1144076-91-4 8-C-β-glucopyranosylapigeninidin 
• 105106-80-7 5,7-diethoxy-2-(4-ethoxy-phenyl)-8-(tetra-O-acetyl-β-D-glucopyranosyl)-chromen-4-one 
• 163395-88-8 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 
• 20197-48-2 5,7-dimethoxy-2-(4-methoxyphenyl)-8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 
• 18469-71-1 8-β-D-glucopyranosyl-5,7-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 

Relevant articles and documents

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.

Design and Synthesis of CNb-targeted Flavones and Analogues with Neuroprotective Potential Against H2O2- and Aβ1-42-Induced Toxicity in SH-SY5Y Human Neuroblastoma Cells

With the lack of available drugs able to prevent the progression of Alzheimer’s disease (AD), the discovery of new neuroprotective treatments able to rescue neurons from cell injury is presently a matter of extreme importance and urgency. Here, we were inspired by the widely reported potential of natural flavonoids to build a library of novel flavones, chromen-4-ones and their C-glucosyl derivatives, and to explore their ability as neuroprotective agents with suitable pharmacokinetic profiles. All compounds were firstly evaluated in a parallel artificial membrane permeability assay (PAMPA) to assess their effective permeability across biological membranes, namely the blood-brain barrier (BBB). With this test, we aimed not only at assessing if our candidates would be well-distributed, but also at rationalizing the influence of the sugar moiety on the physicochemical properties. To complement our analvsis logD7.4 was determined. From all screened compounds, the p-morpholinyl flavones stood out for their ability to fully rescue SH-SY5Y human neuroblastoma cells against both H2O2 A β1-42-induced cell death. Cholinesterase inhibition was also evaluated, and modest inhibitory activities were found. This work highlights the potential of C-glucosylflavones as neuroprotective agents, and presents the p-morpholinyl C-glucosylflavone 37, which did not show any cytotoxicity towards HepG2 and Caco-2 cells at 100 ΜM, as a new lead structure for further development against AD.

Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins

The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus.