Phenolic glucosides from Bidens parviflora and their anti-histamine activities
Susumu Kitanaka
Abstract
Susumu Kitanaka
Abstract
Objective Based on the activities against histamine release of Bidens parviflora to find biological active compounds. Methods The chemical constituents from B. parviflora were isolated by silica gel column chromatography and Sephadex LH-20 column chromatography, then purified by preparative HPLC. Their chemical structures were identified by 1D NMR, 2D NMR methods. Results Five phenolic glucosides were identified as guaiacyl glycerol 8-O-β-D-glucoside (Ⅰ), syringin (Ⅱ), 4-allyl-2-methoxyphenol-O-(6-O-β-D-apiofuranosyl)-β-D-glucoside (Ⅲ), 5, 7-dihydroxy chromone 7-O-β-D-glucoside (Ⅳ), benzyl alcohol-O-β-D-glucoside (Ⅴ). Compounds Ⅰ-Ⅴ could inhibit the histamine releasing and their IC50 were 70, 61, 100, 52, 100 μg/mL, respectively. Conclusion Compounds Ⅰ-Ⅴ are isolated from B. parviflora for the first time, Ⅲ is a new phenolic glucoside named as bidenphenol glucoside. Compounds Ⅰ-Ⅴ exhibit the activities of anti-histamine release from rat mast cell stimulated by antigen-antibody reaction.
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Objective Based on the activities against histamine release of Bidens parviflora to find biological active compounds. Methods The chemical constituents from B. parviflora were isolated by silica gel column chromatography and Sephadex LH-20 column chromatography, then purified by preparative HPLC. Their chemical structures were identified by 1D NMR, 2D NMR methods. Results Five phenolic glucosides were identified as guaiacyl glycerol 8-O-β-D-glucoside (Ⅰ), syringin (Ⅱ), 4-allyl-2-methoxyphenol-O-(6-O-β-D-apiofuranosyl)-β-D-glucoside (Ⅲ), 5, 7-dihydroxy chromone 7-O-β-D-glucoside (Ⅳ), benzyl alcohol-O-β-D-glucoside (Ⅴ). Compounds Ⅰ-Ⅴ could inhibit the histamine releasing and their IC50 were 70, 61, 100, 52, 100 μg/mL, respectively. Conclusion Compounds Ⅰ-Ⅴ are isolated from B. parviflora for the first time, Ⅲ is a new phenolic glucoside named as bidenphenol glucoside. Compounds Ⅰ-Ⅴ exhibit the activities of anti-histamine release from rat mast cell stimulated by antigen-antibody reaction.
Key concepts: Chemistry, Glucoside, Sephadex, Histamine, Column chromatography, Chromatography, High-performance liquid chromatography, Silica gel