57096-02-3

57096-02-3 structure

Name: 4'-Hydroxywogonin
Chemical Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-methoxychromen-4-one
CAS Number: 57096-02-3
Molecular Formula: C₁₆H₁₂O₆
Molecular Weight: 300.263
Catalog: Natural product Flavonoids
Create Date: 2017-01-06 04:05:12
Modify Date: 2024-01-06 18:03:07
4′-Hydroxywogonin (8-Methoxyapigenin), a flavonoid, could be isolated from a variety of plants including Scutellaria barbata and Verbena littoralis. 4′-Hydroxywogonin has anti-inflammatory activity via TAK1/IKK/NF-κB, MAPKs and PI3/AKT signaling pathways. 4′-Hydroxywogonin inhibits angiogenesis by disrupting PI3K/AKT signaling. 4′-Hydroxywogonin inhibits cell proliferation and induces apoptosis[1][2][3].

Name	5,7-dihydroxy-2-(4-hydroxyphenyl)-8-methoxychromen-4-one
Synonyms	4'-Hydroxywogonin isoscutellarein-8-methylether 8-Methoxy-iso-scutellargin 5,7,4'-trihydroxy-8-methoxyflavone 4'-Hydroxywogonine 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-methoxy- 5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-1-benzopyran-4-one 5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one isooscutellarein 8-methyl ether Isoscutellarein 8-methyl ether 8-methoxy-hebacetin

Description	4′-Hydroxywogonin (8-Methoxyapigenin), a flavonoid, could be isolated from a variety of plants including Scutellaria barbata and Verbena littoralis. 4′-Hydroxywogonin has anti-inflammatory activity via TAK1/IKK/NF-κB, MAPKs and PI3/AKT signaling pathways. 4′-Hydroxywogonin inhibits angiogenesis by disrupting PI3K/AKT signaling. 4′-Hydroxywogonin inhibits cell proliferation and induces apoptosis[1][2][3].
Related Catalog	Signaling Pathways >> Apoptosis >> Bcl-2 Family Signaling Pathways >> NF-κB >> IKK Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Cardiovascular Disease Signaling Pathways >> Immunology/Inflammation >> Interleukin Related Signaling Pathways >> PI3K/Akt/mTOR >> PI3K Signaling Pathways >> Apoptosis >> Caspase Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK Signaling Pathways >> PI3K/Akt/mTOR >> Akt Research Areas >> Inflammation/Immunology
In Vitro	4′-Hydroxywogonin (8-Methoxyapigenin; 0.5-15 μM; 0-24 h) has low cytotoxicity and inhibits NO and PGE2 production in LPS-stimulated RAW 264.7 macrophages by suppression of iNOS and COX-2 expression[1]. 4′-Hydroxywogonin (0.5-15 μM; 1 and 12 h) suppresses LPS-induced expression of pro-inflammatory cytokines in RAW 264.7 macrophages and suppresses LPS-induced activation of NF-κB[1]. 4′-Hydroxywogonin (0.5-15 μM; 1 h) suppresses LPS-induced degradation of IκB-α and activation of IKK and TAK and suppresses the phosphorylation of MAPK and AKTin in RAW 264.7 macrophages[1]. 4′-Hydroxywogonin (0.5-15 μM; 24 h) inhibits ROS production in LPS-stimulated RAW 264.7 macrophages[1]. 4′-Hydroxywogonin (0-10 μg/mL; 24 h) reduces the viability of SW620 cells in a concentration- and time-dependent manner and decreases the mRNA and protein expression of vascular endothelial growth factor-A (VEGF-A), the predominant pro-angiogenic cytokine in tumor angiogenesis[2]. 4′-Hydroxywogonin (24 h; SUP-B15 and Jurkat cells) induces apoptosis and decreases the expression of C-MYC, BCL-2 and cleaved caspase 3[3]. Cell Viability Assay[1] Cell Line: RAW 264.7 macrophages Concentration: 0.5, 5 and 15 μM Incubation Time: 24 hours Result: Had low cytotoxicity in RAW 264.7 macrophages. Western Blot Analysis[1] Cell Line: RAW 264.7 macrophages Concentration: 0.5, 5 and 15 μM Incubation Time: 1 hours Result: Attenuated the increase of iNOS and COX-2 mRNA expression induced by LPS in RAW 264.7 cells. Western Blot Analysis[1] Cell Line: RAW 264.7 macrophages Concentration: 0.5, 5 and 15 μM Incubation Time: 1 and 12 hours Result: Reduced TNF-α, IL-6 and IL-1β mRNA expression in a dose-dependent manner. Inhibited LPS-induced p65 phosphorylation and nuclear translocation. Western Blot Analysis[1] Cell Line: RAW 264.7 macrophages Concentration: 0.5, 5 and 15 μM Incubation Time: 1 hours Result: Attenuated LPS induced IκB-α degradation. Attenuated the phosphorylation of ERK1/2 and p38 in a dose-dependent manner. Reduced the intensity of the TAK1/TAB1 band. Western Blot Analysis[2] Cell Line: SW620 cells Concentration: 0.1, 1, and 10 μg/mL Incubation Time: 24 hours Result: Downregulated VEGF-Aexpression in colorectal cancer cells and suppressed angiogenesis.
In Vivo	4′-Hydroxywogonin (10 and 20 mg/kg; i.p.; male C57BL/6 mice) alleviates LPS-induced acute lung injury (ALI) in a mouse model[1]. Animal Model: Male C57BL/6 mice (6-8 weeks old; 20 g) with acute lung injury model[1] Dosage: 10 and 20 mg/kg Administration: Intraperitoneal injection, 12 and 1 h before LPS treatment Result: Had potential protective effects against inflammation in LPS induced ALI mice. Attenuated the degree of leukocyte infiltration.

Density	1.5±0.1 g/cm3
Boiling Point	578.1±50.0 °C at 760 mmHg
Molecular Formula	C₁₆H₁₂O₆
Molecular Weight	300.263
Flash Point	220.9±23.6 °C
Exact Mass	300.063385
PSA	100.13000
LogP	1.37
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.697

Hazard Codes	Xi

41440-05-5

57096-02-3

51876-19-8

Literature: Brunet, Gunter; Ibrahim, Ragai K. Phytochemistry (Elsevier), 1980 , vol. 19, p. 741 - 746

Precursor 1
41440-05-5
DownStream 0

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