CAS 632-85-9 Wogonin - Analytical Products / Alfa Chemistry

CAT	APS632859
CAS	632-85-9
Structure
MDL Number	MFCD00017736
Synonyms	Flavone, 5,7-dihydroxy-8-methoxy- (7CI,8CI), Wogonin (6CI),4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-methoxy-2-phenyl-, 5,7-Dihydroxy-8-methoxy-2-phenyl-4H-1-benzopyran-4-one, 5,7-Dihydroxy-8-methoxyflavone
IUPAC Name	5,7-dihydroxy-8-methoxy-2-phenylchromen-4-one
Molecular Weight	284.26
Molecular Formula	C16H12O5
Canonical SMILES	COc1c(O)cc(O)c2C(=O)C=C(Oc12)c3ccccc3
InChI	InChI=1S/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

Accurate Mass	284.0685
Assay	≥95.0% (HPLC)
Format	Neat
Size	10MG
Subcategory	Food additives, flavours and adulterants
Type	Native/Parent

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Case Study

Wogonin Inhibits Cell Cycle Progression

Hong, Ming, et al. Phytomedicine 68 (2020): 153174.

Wogonin has been reported to possess various biological activities, including anti-inflammatory, antibacterial, and antitumor effects. Previous studies have indicated that Wogonin can downregulate Cyclin D1 activity in various cancers. However, the underlying mechanisms have not been fully elucidated.
The results here demonstrate that non-toxic doses of Wogonin (10, 20 µM) can inhibit cell proliferation and impede cell cycle progression in MHCC97L and HepG2 cells. Furthermore, the results from Western blotting and immunofluorescence assays confirmed the inhibitory effects of Wogonin (10, 20 µM) on Cyclin D1 expression in MHCC97L cells, and pretreatment with Wogonin (10, 20 µM) promoted the ubiquitination and degradation of Cyclin D1 in MHCC97L cells. Additionally, Wogonin facilitated the phosphorylation of Cyclin D1 at the threonine-286 site, and mutating threonine-286 to alanine-286A could block the Wogonin-induced proteolysis of Cyclin D1.
The promotion of Cyclin D1 phosphorylation and subsequent proteolysis by Wogonin may be related to the activation of GSK3beta in cancer cells. After exposure to Wogonin (20 µM), the phosphorylated form of GSK3beta (the active form) showed a significant increase in expression. Molecular docking studies of GSK3beta mutants and Biacore SPR analysis further validated the high-affinity binding site of Wogonin to GSK3beta. In addition, in vivo studies confirmed that following Wogonin treatment, phosphorylated GSK3beta Tyr216 was overexpressed in HCC specimens, while the quantity of Cyclin D1 significantly decreased.

Wogonin Inhibits DLBCL Cell Survival

Lin, Y., Jiang, X., Zhao, M., Li, Y., Jin, L., Xiang, S., ... & Jiang, L. (2024). Toxicology and Applied Pharmacology, 117103.

Diffuse large B-cell lymphoma (DLBCL) is one of the most aggressive hematologic malignancies, with patients typically receiving combination immunochemotherapy such as R-CHOP. To date, prognosis remains variable and unsatisfactory based on molecular subtypes and treatment responses. There is an urgent need to develop effective and well-tolerated new drugs, and compounds derived from natural sources are gaining increasing attention.
Wogonin is an active flavonoid compound extracted from the traditional Chinese herb Huangqin, known for its broad antitumor potential. However, the therapeutic effects of Wogonin on DLBCL remain unknown. Here, the study found that treatment with Wogonin dose- and time-dependently reduced the viability of a panel of established DLBCL cell lines. The cytotoxic effects of Wogonin were achieved through the induction of apoptosis, loss of mitochondrial membrane potential, and downregulation of BCL-2, MCL-1, and BCL-xL. Mechanistically, Wogonin inhibited the PI3K and MAPK pathways, as evidenced by a significant decrease in the phosphorylation of AKT, GSK3β, S6, ERK, and P38.

Wogonin Reduces Acetaminophen-Induced Liver Injury in Mice

Zhao, Wenyingzi, et al. Journal of Ethnopharmacology 332 (2024): 118364.

Wogonin is a major component of the traditional Chinese medicine Huangqin (SBG) and effectively alleviates liver injury caused by acetaminophen (APAP). It achieves this by regulating the PI3K/AKT pathway in mouse and cellular models.
Wogonin pretreatment dose-dependently mitigated AILI in mice. Additionally, Wogonin inhibited oxidative stress and inflammatory responses. Transcriptomic analysis of the liver indicated that Wogonin primarily regulates immune functions and cytokines during AILI. Wogonin suppresses macrophage inflammatory responses by inhibiting the PI3K/AKT signaling pathway. Overall, Wogonin continuously exerts therapeutic effects on AILI in mice through the PI3K/AKT signaling pathway.