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Novel synthesis of flavonoids of Scutellaria baicalensis GEORGI

School of Pharmacy, National Defense Medical Center, Taiwan.
CHEMICAL & PHARMACEUTICAL BULLETIN (Impact Factor: 1.38). 04/2003; 51(3):339-40. DOI: 10.1248/cpb.51.339
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ABSTRACT 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.

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    • "In chemical synthesis of baicalein and wogonin, the production method has been proposed (Huang et al., 2003). On the contrary, baicalin is a glucosylated derivative of baicalein and thus highyield production by chemical process is difficult. "
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    ABSTRACT: Production of baicalein, baicalin and wogonin by liquid culture of Scutellaria baicalensis cells derived from the plant root was studied. The maximum production obtained were 119 mg/L of baicalein at two week, 1372 mg/L of baicalin at eight week, and 14 mg/L of wogonin at two week. In addition, the production of baicalin was drastically increased to 1000 mg/L level at 3-week culture, and the extremely high production rate (339 mg/L•week) was obtained. In the comparison of total antioxidative activities among baicalein, baicalin and wogonin, evaluated by thiocyanate method, it was suggested that the location of hydroxyl groups both at 5- and 6-position contributed to enhancement of radical scavenging activity, and/or methoxylation at 8-position diminished the activity. The possibility of utilizing these flavonoids for natural antioxidants and medicine is also discussed.
    Brazilian Archives of Biology and Technology 01/2009; 52(2). DOI:10.1590/S1516-89132009000200005 · 0.45 Impact Factor
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    ABSTRACT: OBJECTIVE To test the effect of wogonin on cellular proliferation and expression of monocyte chemoattractant protein 1 (MCP-1) in cells derived from normal and diseased tunica albuginea (TA), as related to Peyronie's disease (PD). MATERIALS AND METHODS Cells with characteristics of fibroblasts were isolated from three tissue sources. Those from the plaque of patients with PD were designated as P cells, those from the adjacent, normal-appearing tissue as C cells, and those from the TA of patients without PD as N cells. These cells were treated with wogonin at doses of 0, 10, 20 and 40 mumol/L for 24 h or treated at a fixed dose of 40 mumol/L for 1, 8 and 24 h. Cell proliferation was assayed with a commercial kit, MCP-1 mRNA expression by reverse transcription-polymerase chain reaction, and secreted MCP-1 by enzyme-linked immunosorbent assay. RESULTS Wogonin suppressed cell proliferation in a dose-dependent manner; the effect was more pronounced against P cells at 8 and 24 h. Wogonin down-regulated MCP-1 mRNA expression, especially in P cells. Wogonin suppressed the level of secreted MCP-1 by 59-88%. P cells, which secreted far more MCP-1 than N and C cells at 1 h, were suppressed by 88%. C cells were the least suppressed at all three times. CONCLUSIONS Wogonin suppressed the proliferation, the expression of MCP-1 mRNA, and the expression of secreted MCP-1 in TA-derived cells. In most cases, the effect of wogonin was greatest against cells derived from the plaque. Wogonin appears to be a worthy candidate for preclinical trials in men with PD.
    BJU International 10/2003; 92(7):753 - 757. DOI:10.1046/j.1464-410X.2003.04464.x · 3.13 Impact Factor
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    ABSTRACT: To test the effect of wogonin on cellular proliferation and expression of monocyte chemoattractant protein 1 (MCP-1) in cells derived from normal and diseased tunica albuginea (TA), as related to Peyronie's disease (PD). Cells with characteristics of fibroblasts were isolated from three tissue sources. Those from the plaque of patients with PD were designated as P cells, those from the adjacent, normal-appearing tissue as C cells, and those from the TA of patients without PD as N cells. These cells were treated with wogonin at doses of 0, 10, 20 and 40 micromol/L for 24 h or treated at a fixed dose of 40 micromol/L for 1, 8 and 24 h. Cell proliferation was assayed with a commercial kit, MCP-1 mRNA expression by reverse transcription-polymerase chain reaction, and secreted MCP-1 by enzyme-linked immunosorbent assay. Wogonin suppressed cell proliferation in a dose-dependent manner; the effect was more pronounced against P cells at 8 and 24 h. Wogonin down-regulated MCP-1 mRNA expression, especially in P cells. Wogonin suppressed the level of secreted MCP-1 by 59-88%. P cells, which secreted far more MCP-1 than N and C cells at 1 h, were suppressed by 88%. C cells were the least suppressed at all three times. Wogonin suppressed the proliferation, the expression of MCP-1 mRNA, and the expression of secreted MCP-1 in TA-derived cells. In most cases, the effect of wogonin was greatest against cells derived from the plaque. Wogonin appears to be a worthy candidate for preclinical trials in men with PD.
    BJU International 12/2003; 92(7):753-7. · 3.13 Impact Factor
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