110623-73-9 , Epimedin B ,
3-[(6-Deoxy-2-O-b-D-xylopyranosyl-a-L-mannopyranosyl)oxy]-7-(b-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
Cas:110623-73-9
C38H48O19 / 808.78
MFCD04039834
3-[(6-Deoxy-2-O-b-D-xylopyranosyl-a-L-mannopyranosyl)oxy]-7-(b-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
Epimedin B is a flavonoid glycoside that has been found in E. koreanum and has antioxidant, anti-osteoporotic, and anti-inflammatory activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH;) radicals in a cell-free assay (IC50 = 107.9 µM). Epimedin B increases proliferation of UMR-106 osteoblasts by 24.9 and 36.3% when used at concentrations of 10 and 100 µM, respectively. It prevents osteoporosis induced by prednisolone in zebrafish when used at a concentration of 1 µM. Epimedin B inhibits ear edema induced by phorbol 12-myristate 13-acetate (TPA;) in mice (ED50 = 114 nmol/ear).
Epimedin B, a component extracted from Epimedii Folium, is reported to have antiosteoporotic activity. IC50 value:Target:In vitro:In vivo: Prednisolone-induced osteoporosis model using zebrafish was used to evaluate the antiosteoporotic activity of micro amount epimedin B. The result showed that 1 μmol·L- 1epimedin B groups were significantly increased when compared with model group; Epimedin B can prevent zebrafish osteoporosis induced by prednisolone.
Epimedin B is a natural product that has been shown to have antitumor activity. Epimedin B contains a variety of chemical structures that are thought to act on the cell surface and inhibit receptor binding, leading to the inhibition of tumor growth and progression. Epimedin B has been shown to bind to the response element in cervical cancer cells, which leads to an increased expression of transforming growth factor beta-1 (TGF-β1). Epimedin B also exhibits molecular docking with flavonoid glycosides, which may account for its antioxidant properties. The most active component in Epimedin B is phenolic acid. This compound is thought to be responsible for the anti-inflammatory and immunosuppressive activities observed in animal studies. In addition, phenolic acid is a potent inhibitor of nitric oxide synthase (NOS), an enzyme associated with tumor promotion.
CAS Number | 110623-73-9 |
Product Name | Epimedin B |
IUPAC Name | 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one |
Molecular Formula | C38H48O19 |
Molecular Weight | 808.78 g/mol |
InChI | InChI=1S/C38H48O19/c1-14(2)5-10-18-21(53-37-31(49)28(46)26(44)22(12-39)54-37)11-19(40)23-27(45)34(32(55-33(18)23)16-6-8-17(50-4)9-7-16)56-38-35(29(47)24(42)15(3)52-38)57-36-30(48)25(43)20(41)13-51-36/h5-9,11,15,20,22,24-26,28-31,35-44,46-49H,10,12-13H2,1-4H3/t15-,20+,22+,24-,25-,26+,28-,29+,30+,31+,35+,36-,37+,38-/m0/s1 |
InChI Key | OCZZCFAOOWZSRX-LRHLXKJSSA-N |
SMILES | CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)OC6C(C(C(CO6)O)O)O)O)O |
Synonyms | epimedin B |
Canonical SMILES | CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)OC6C(C(C(CO6)O)O)O)O)O |
Isomeric SMILES | C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)O |
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