Biotransformation of prim-O-glucosylcimifugin by human intestinal flora and its inhibition on NO production and DPPH free radical.
prim-O-Glucosylcimifugin (PGCN), a highest content chromone in the roots of Saposhnikovia divaricata, was incubated with human intestinal flora (HIF), and two biotransformation products were obtained from the incubated solution by chromatographic methods. The chemical structures of the two biotransformation products were elucidated as cimifugin (CN) and 5-O-methylvisamminol (MVL), respectively, on the basis of NMR and MS data. The biotransformation product CN was formed through a deglucosylation of PGCN by β-glucosidase secreted from the HIF, and then the hydroxymethyl group of CN was reduced to lead to occurrence of MVL. All of these compounds were evaluated for their effect on the inhibition of nitric oxide production induced by lipopolysaccharide in macrophage cell line RAW 264.7 and for 1,1-diphenyl-2-picrylhydrazyl free-radical scavenging activity in cell-free bioassay system.
State Key Laboratory of Natural and Biomimetic Drugs, Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University, Beijing, China.
Bo
B
Zhao
Xin-Bao
XB
Yang
Xiu-Wei
XW
Yang
Jian-Xun
JX
Liu
D019661:Apiaceae / Q000737:chemistry*; D001711:Biotransformation; D001713:Biphenyl Compounds / Q000494:pharmacology*; D002867:Chromones / Q000737:chemistry*; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D005609:Free Radicals / Q000032:analysis; D006801:Humans; D007422:Intestines / Q000737:chemistry / Q000382:microbiology*; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry / Q000378:metabolism*; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D010851:Picrates / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry; D014966:Xanthenes / Q000737:chemistry / Q000378:metabolism*
D001713:Biphenyl Compounds; D002867:Chromones; D004365:Drugs, Chinese Herbal; D005609:Free Radicals; D009005:Monosaccharides; D010851:Picrates; D014966:Xanthenes; C533198:cimifugin; C498945:prim-O-glucosylcimifugin; D009569:Nitric Oxide; C004931:1,1-diphenyl-2-picrylhydrazyl