28608-75-5

Basic information

• Product Name: ORIENTIN
• Synonyms: 2-(3,4-dihydroxyphenyl)-8-beta-d-glucopyranosyl-5,7-dihydroxy-4h-1-benzopyra;4h-1-benzopyran-4-one,2-(3,4-dihydroxyphenyl)-8-beta-d-glucopyranosyl-5,7-dihy;luteolin8-glucoside;lutexin;orientin(flavone);ORIENTIN(P);ORIENTIN(SH);ORIENTIN WITH HPLC
• CAS NO: 28608-75-5
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.38
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Aromatics, Glucuronides, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 28608-75-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 260-285°C
• Boiling Point: 816.1 °C at 760 mmHg
• Flash Point: 289.1 °C
• Appearance: yellow/
• Density: 1.759 g/cm³
• Vapor Pressure: 3.63E-28mmHg at 25°C
• Refractive Index: 1.767
• Storage Temp.: 2-8°C(protect from light)
• Solubility: 1 M NaOH: soluble1mg/mL, clear, yellow-orange
• PKA: 6.24±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: ORIENTIN(CAS DataBase Reference)
• NIST Chemistry Reference: ORIENTIN(28608-75-5)
• EPA Substance Registry System: ORIENTIN(28608-75-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: DJ3009300
• Hazardous Substances Data: 28608-75-5(Hazardous Substances Data)

Usage

Description

Orientin, also known as luteolin 8-C-glucoside, is a flavone glycoside originally isolated from P. orientale. It is a yellow powder with diverse biological activities, including antioxidant, antibacterial, and anti-inflammatory properties. Orientin is characterized by its C-glycosyl compound structure, where luteolin is substituted by a beta-D-glucopyranosyl moiety at position 8.

Uses

Used in Pharmaceutical Applications:
Orientin is used as a therapeutic agent for its anti-oxidant, antihypertensive, and antihyperlipidemic effects. It has been investigated for its potential in treating various health conditions by modulating different biological pathways.
Used in Antioxidant Applications:
Orientin is used as an antioxidant, as it effectively scavenges 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radicals with an IC50 value of 316.21 μg/ml. Its antioxidant properties make it a promising candidate for the development of novel antioxidant therapies.
Used in Antiviral Applications:
Orientin is used as an antiviral agent, particularly against parainfluenza type 3 virus. It decreases the cytopathic effects of the virus with an IC50 value of 11.7 μg/ml and a cytotoxic concentration (CC50) value of 375 μg/ml in Hep-2 cells.
Used in Anti-inflammatory Applications:
Orientin is used as an anti-inflammatory agent, as it inhibits LPS-induced barrier disruption, decreases the expression of toll-like receptor 4 (TLR4), phosphorylated p38, and NF-κB, and decreases TNF-α production and IL-6 secretion in a dose-dependent manner in human umbilical vein endothelial cells (HUVECs).
Used in Endotoxemia Treatment:
Orientin is used in the treatment of LPS-induced lethal endotoxemia in a mouse model, where it prolongs survival when administered at a dose of 36 μg/animal 12 hours after LPS administration.

InChI:InChI=1/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1

Upstream product

• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 57-50-1 Sucrose 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 381686-06-2 3,4,4',6'-tetrakis-benzyloxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2'-hydroxychalcone 
• 169566-46-5 1-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)ethanone 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 
• 39548-86-2 1‐(2‐(benzyloxy)‐4,6‐dihydroxyphenyl)ethan‐1‐one 
• 381686-07-3 2-(3,4-bis-benzyloxyphenyl)-7-benzyloxy-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-hydroxy-4H-1-benzopyran-4-one 
• 131507-99-8 2″,6″-O-diacetylorientin 
• 4261-42-1 3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone 

Downstream Products

• 64661-76-3 orientin-2-O-β-D-glucopyranoside 
• 1377947-82-4 orientin-2-O-β-D-galactopyranoside 
• 50-99-7 D-glucose 
• 4261-42-1 3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone 
• 4261-42-1 isoorientin 

Relevant articles and documents

C-Glycosylflavones with acetyl substitution from Rumex acetosa L.

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Efficient Production of Orientin and Vitexin from Luteolin and Apigenin Using Coupled Catalysis of Glycosyltransferase and Sucrose Synthase

Orientin and vitexin are flavone 8-C-glycosides that exhibit many biological characteristics. This study aimed to establish a two-enzyme-coupled catalytic strategy to enhance the biosynthesis of orientin and vitexin from apigenin and luteolin, respectively. The C-glucosyltransferase (TcCGT1) gene from Trollius chinensis was cloned and expressed in Escherichia coli BL21(DE3). The optimal activity of TcCGT1 was achieved at pH 9.0 and 37 °C. TcCGT1 was relatively stable over the pH range of 7.0-10.0 at a temperature lower than 45 °C. The coupled catalytic strategy of TcCGT1 and different sucrose synthases was adopted to enhance the production of orientin and vitexin. By optimizing the coupling reaction conditions, orientin and vitexin production successfully achieved 2324.4 and 5524.1 mg/L with a yield of 91.4 and 89.3% (mol/mol), respectively. The coupled catalytic strategy proposed in this study might serve as a promising candidate for the large-scale production of orientin and vitexin in the future.

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.

Synthesis of 8-C-glucosylflavones

The syntheses of orientin, parkinsonin A, isoswertiajaponin, and parkinsonin B, which are 8-C-β-D-glucopyranosyl-3′,4′,5,7-tetrahydroxyflavone, 5-methyl orientin, 7-methyl orientin, and 5,7-dimethyl orientin, respectively, are reported herein. The C-glucosyl phloroacetophenone derivatives were obtained via a regio- and stereoselective O → C glycosyl rearrangement. Aldol condensation of the C-glucosyl phloroacetophenone derivatives with 3,4-bisbenzyloxybenzaldehyde afforded the corresponding C-glucosylchalcones. Construction of the flavone system by reaction with I2-Me2SO, followed by the elimination of the 5-benzyl protecting group in the flavone structure, yielded an orientin derivative and a isoswertiajaponin derivative. Methylation of the orientin derivatives with dimethyl sulfate afforded the parkinsonin A derivative, the isoswertiajaponin derivative, and the parkinsonin B derivative. Finally, hydrogenolysis of these C-glucosylflavone derivatives led to the four 8-C-glucosylflavones. The NMR spectra of these C-glucosylflavones showed a duplication of signals corresponding to a major rotamer, along with a minor one. Based on NOESY experiments in Me2SO at ambient temperature, they adopted conformations in which the H-2″ and H-4″ protons in the glucose moiety were oriented toward the B-ring in the flavone structure.