632-85-9

Usage

Uses

Used in Pharmaceutical Applications:
Wogonin is used as an anti-inflammatory agent for attenuating ovalbumin antigen-influenced neutrophillic airway inflammation. Its anti-inflammatory properties make it a potential candidate for treating various inflammatory conditions.
Used in Anticancer Applications:
Wogonin is used as an anti-cancer agent, particularly in reversing multi-drug resistance of human myelogenous leukemia. Its ability to modulate cancer-related pathways and enhance the efficacy of conventional chemotherapeutic drugs makes it a promising compound in the fight against cancer.
Used in Drug Delivery Systems:
In the field of drug delivery, Wogonin can be employed to improve the bioavailability and therapeutic outcomes of various medications. Its incorporation into novel drug delivery systems, such as organic and metallic nanoparticles, can enhance the delivery and effectiveness of Wogonin in treating specific conditions.

Biochem/physiol Actions

Wogonin is an anti-inflammatory agent and COX-2 inhibitor, which inhibits the induction of both iNOS and COX-2. Wogonin inhibits COX-2 (IC50 = 46 μM) without affecting COX-1. Wogonin inhibits iNOS induction and thus inhibts activation-induced C6 glial cell death. Specifically, Wogonin inhibits NF-kappaB-mediated iNOS induction.

InChI:InChI=1/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3

Upstream product

• 51059-44-0 oroxindin 
• 642-71-7 3,4,5-trimethoxyphenol 
• 7499-99-2 1-(2,4-dihydroxy-3,6-dimethoxy)phenylethanone 
• 93-97-0 benzoic acid anhydride 
• 110506-85-9 7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 146329-57-9 tetramethylammonium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-8-yl sulfate 
• 4431-41-8 5,7-dihydroxy-8-methoxyflavanone 
• 102-92-1 Cinnamoyl chloride 
• 70185-52-3 6′-hydroxy-2′,3′,4′-trimethoxychalcone 
• 4443-09-8 norwogonin 
• 54299-50-2 2',4'-dihydroxy-3',6'-dimethoxychalcone 
• 20032-42-2 2,5-dimethoxyresorcinol 
• 42528-81-4 2,6-bis-benzyloxy-benzene-1,4-diol 
• 55020-64-9 1,2,3-tris-benzyloxybenzene 

Downstream Products

• 84757-43-7 5,7-dihydroxy-6-formyl-8-methoxyflavone 
• 95480-80-1 5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl acetate 
• 23050-38-6 5,7,8-trimethoxy-2-phenyl-chromen-4-one 
• 4443-09-8 norwogonin 
• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 51059-44-0 oroxindin 
• 1356855-04-3 C₁₆H₁₂O₅*C₄₂H₇₀O₃₅ 
• 23246-80-2 8-methoxy-4-oxo-2-phenyl-4H-chromene-5,7-diyl diacetate 
• 3570-62-5 5-hydroxy-7,8-dimethoxyflavone 

Relevant academic research and scientific papers

A Practical and Efficient Approach to the Preparation of Bioactive Natural Product Wogonin

A scalable and practical route to wogonin, a bioactive natural product with multiple pharmacological activities which is currently under phase I/II clinical studies, is described. Wogonin was obtained via a four-step process starting from commercially ava

Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.

Synthesis, evaluation and quantitative structure–activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents

A novel series of 49 wogonin derivatives were synthesized by introducing group at 7-, 8- or B ring of wogonin. The cytotoxic activities against HepG2, A549 and BCG-823 cancer cell lines were also investigated in vitro. Several of them showed obvious cytotoxic activities and compound 3h possessed the highest potency against HepG2, A549, and BCG-823 with IC50 values of 1.07 μM, 1.74 μM and 0.98 μM, respectively. A quantitative structure-activity relationship (QSAR) study of these synthetic derivatives as well as wogonin indicated that high solubility and low octanol/water partition coefficient are favorable, and excessive electrostatic properties and refractivity are unfavorable for the cytotoxic activities of these wogonin derivatives. These findings and results provide a base for further investigations.

Preparation method and intermediates of flavonoids

The invention discloses a preparation method and intermediates of flavonoids. The preparation method comprises the following steps: in a solvent, in the presence of an acid, performing a ring-opening reaction and an elimination reaction on a compound 8 to obtain a compound 9. Raw materials used in the method are easy to acquire, and the method has high yields and simple post processes, and does not need column chromatography.

Preparation method of flavonoids

The invention discloses a preparation method of flavonoids. The method comprises the following step: in a solvent, in the presence of iodine and a silver salt or in the presence of iodine and a copper salt, performing an iodination reaction on a compound 1 to obtain a compound 2. Raw materials used in the method are easy to acquire, and the method has high yields and simple post processes, and does not need column chromatography.

An efficient, scalable approach to hydrolyze flavonoid glucuronides via activation of glycoside bond

Hydrolyzing flavonoid glucuronides into corresponding aglycones posed some significant challenges. To improve acid-catalyzed hydrolysis process of flavonoid glucuronide, structures of glucuronide, hydrolysis parameters and post-processing were optimized. The optimized condition was performed by hydrolysis flavonoid glycoside methyl ester in a mixed solvent consisting of 2?mol/L H2SO4/EtOH/H2O (1/8/1, v/v/v) at 95?°C for 7?h and resulted in up to 90% aglycone yields, minimal byproduct formations and milder hydrolysis conditions. Furthermore, the optimized method avoids tedious purification steps and is easily conducted on a relatively large-scale using economical and commercially available reagents.

A new domino oxidation—rearrangement of 2,3-dihydrowogonin to negletein

We report an expeditious, iodine-catalysed oxidation of 2,3-dihydrowogonin to negletein which comprises a Wessely–Moser rearrangement (WMR), associated not with an O-demethylation, as usual, but with an oxygen to oxygen methyl shift. In contrast, DDQ in 1

Methods of synthesizing flavonoids and chalcones

Simple and efficient total syntheses of flavonoids including baicalein, oroxylin A and wogonin are described herein. Simultaneous syntheses of oroxylin A and wogonin are also described.

Novel synthesis of flavonoids of Scutellaria baicalensis Georgi.

A concise and efficient total synthesis of the flavonoids baicalein, oroxylin A and wogonin was described. Intramolecular oxidative cyclization followed by demethylation of chalcone 1, readily prepared from trimethoxyphenol, afforded, depending upon the controlled conditions, baicalein or oroxylin A in excellent yields. Demethylation of 1 yielded 3, which, by oxidation with I(2)/dimethyl sulfoxide (DMSO), was readily converted to oroxylin A and wogonin after column chromatography.