Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

Tran, Thanh-Dao; Sook, Yeon; Kim, Jeongsoo; Kim, Hyun Pyo; Kim, Sanghee; Park, Haeil

doi:10.1016/j.bmcl.2003.12.087

Cited by 79 publications

(29 citation statements)

References 13 publications

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“…The synthetic flavones used in this study were prepared based on the previously described synthetic procedures (23,24) and they showed one spot in TLC. These synthetic flavones were added to IL-1β-treated SW1353 cells at 10 μM under the same experimental conditions described above.…”

Section: Effects Of the Synthetic Flavones On Mmp-13 Induction In Chomentioning

confidence: 99%

Effects of Flavonoids on Matrix Metalloproteinase-13 Expression of Interleukin-1β–Treated Articular Chondrocytes and Their Cellular Mechanisms: Inhibition of c-Fos/AP-1 and JAK/STAT Signaling Pathways

2011

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Abstract. To identify the therapeutic potential for cartilage degradation and its action mechanisms, the effects of naturally-occurring flavonoids on matrix metalloproteinase-13 (MMP-13) induction were examined in the human chondrocyte cell line SW1353. Flavones including apigenin and wogonin strongly inhibited MMP-13 induction in interleukin (IL)-1β-treated SW1353 cells, while flavonols such as kaempferol, quercetin, and flavanone (naringenin) did not at 5 -25 μM. Apigenin and wogonin primarily inhibit MMP-13 by blocking the c-Fos / activator protein-1 (AP-1) and Janus kinase 2 (JAK2) / signal transducer and activator of transcription 1/2 (STAT1/2) pathways, but not nuclear factor-κB (NF-κB) signaling. Apigenin was also shown to inhibit extracellular matrix degradation in rabbit cartilage culture. The following study using some synthetic flavones demonstrated that A-ring C-5,7-dihydroxyl and B-ring dihydroxyl substitution at C-2,3, C-2,4, or C-3,4 are important for the suppression of MMP-13 expression. Among these flavones, 2′,3′,5,7-tetrahydroxyflavone also inhibited both the c-Fos/AP-1 and STAT1/2 pathways. Taken together, these results indicate that certain flavonoids, especially flavones, inhibit MMP-13 expression in IL-1β-treated chondrocytes, at least in part, by suppressing the c-Fos/AP-1 and JAK2/ STAT1/2 pathways. Furthermore, these findings suggest that some flavonoids have the potential for protecting against collagen matrix breakdown in the cartilage of diseased tissues such as those found in arthritic disorders.

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Section: Effects Of the Synthetic Flavones On Mmp-13 Induction In Chomentioning

confidence: 99%

Effects of Flavonoids on Matrix Metalloproteinase-13 Expression of Interleukin-1β–Treated Articular Chondrocytes and Their Cellular Mechanisms: Inhibition of c-Fos/AP-1 and JAK/STAT Signaling Pathways

2011

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“…The modification significantly improves the activities of the derivatives in inhibiting COX2. Some of the chrysin derivatives are able to bind to COX2 molecule and selectively inhibit COX2 activity (Cho et al, 2004;Dao et al, 2004). Chrysin has been described as a testosterone-increasing agent that blocks further testosterone metabolism by inhibiting aromatase activity (Dhawan et al, 2002;Kellis & Vickery, 1984).…”

Section: Chrysinmentioning

confidence: 99%

Natural Flavonoids in StAR Gene Expression and Testosterone Biosynthesis in Leydig Cell Aging

Wang¹

2011

Basic and Clinical Endocrinology Up-to-Date

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“…Flavones for the inhibitory activity tests were prepared following the procedure as described in the precedent literatures (Dao et al, 2004a;Jang et al, 2005). Thus, commercially available desired hydroxyacetopheones were selectively protected and were reacted with appropriately substituted aryl aldehydes to yield the corresponding chalcones.…”

Section: Chemicalsmentioning

confidence: 99%

“…Similarly, the Wogonin derivatives modified at the B-ring of Wogonin exhibited much reduced inhibitory activities against COX-2 catalyzed PGE2 production compared to that of wogonin (Jang et al, 2005). In spite of the structural similarity between chrysin and wogonin, wogonin exhibited much stronger inhibitory activity than chrysin against COX-2 catalyzed PGE2 production from LPS-treated RAW 264.7 cells (Dao et al, 2004a) Therefore, these precedent results led us to carry out the structure alteration at the A-ring of wogonin to observe the effect of each substituent. In this study, several flavones were designed ( Fig.…”

Section: Introductionmentioning

confidence: 97%

Structural Alterations of Wogonin Significantly Reduce the Inhibitory Activity against COX-2 Catalyzed PGE₂Production from LPS-Induced RAW 264.7 Cells

Gurung¹,

Lim

Kim³

et al. 2009

Biomolecules and Therapeutics

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-Structural alterations of wogonin were conducted to observe the role of each functional group at the A-ring of wogonin on the inhibitory activities against COX-2 catalyzed PGE 2 production from LPS-induced RAW 264.7 cells. Serial deletion of the functional groups at the A-ring of wogonin exhibited low to comparable bioactivity. The present study validated that all the functional groups at the A-ring of wogonin are important factors to exhibit the optimum inhibitory activities.

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Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

Cited by 79 publications

References 13 publications

Effects of Flavonoids on Matrix Metalloproteinase-13 Expression of Interleukin-1β–Treated Articular Chondrocytes and Their Cellular Mechanisms: Inhibition of c-Fos/AP-1 and JAK/STAT Signaling Pathways

Effects of Flavonoids on Matrix Metalloproteinase-13 Expression of Interleukin-1β–Treated Articular Chondrocytes and Their Cellular Mechanisms: Inhibition of c-Fos/AP-1 and JAK/STAT Signaling Pathways

Natural Flavonoids in StAR Gene Expression and Testosterone Biosynthesis in Leydig Cell Aging

Structural Alterations of Wogonin Significantly Reduce the Inhibitory Activity against COX-2 Catalyzed PGE₂Production from LPS-Induced RAW 264.7 Cells

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Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

Cited by 79 publications

References 13 publications

Effects of Flavonoids on Matrix Metalloproteinase-13 Expression of Interleukin-1β–Treated Articular Chondrocytes and Their Cellular Mechanisms: Inhibition of c-Fos/AP-1 and JAK/STAT Signaling Pathways

Effects of Flavonoids on Matrix Metalloproteinase-13 Expression of Interleukin-1β–Treated Articular Chondrocytes and Their Cellular Mechanisms: Inhibition of c-Fos/AP-1 and JAK/STAT Signaling Pathways

Natural Flavonoids in StAR Gene Expression and Testosterone Biosynthesis in Leydig Cell Aging

Structural Alterations of Wogonin Significantly Reduce the Inhibitory Activity against COX-2 Catalyzed PGE2Production from LPS-Induced RAW 264.7 Cells

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Structural Alterations of Wogonin Significantly Reduce the Inhibitory Activity against COX-2 Catalyzed PGE₂Production from LPS-Induced RAW 264.7 Cells