- 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 -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.
- Zhao, Bo,Yang, Xiu-Wei,Yang, Xin-Bao,Liu, Jian-Xun
-
p. 886 - 896,11
(2020/08/24)
-
- The Constituents of Ledebouriella seseloides WOLFF. I. Structures of Three New Chromones
-
Three new chromones (8, 9, and 12), named 3'-O-angeloylhamaudol, ledebouriellol, and 4'-O-β-D-glucosyl-5-O-methylvisamminol, respectively, were isolated from the root and rhizoma of Ledebouriella seseloides WOLFF (Umbelliferae), together with five known coumarins (1-5) and six known chromones (6, 7, 10, 11, 13 and 14).The structures of 8, 9, and 12 were elucidated as (3S)-3,4-dihydro-5-hydroxy-3-(2-methyl-2-butenyl)oxy-2,2,8-trimethyl-2H,6H-benzodipyran-6-one, (3S)-3,4-dihydro-2,2-dimethyl-5-hydroxy-8-hydroxymethyl-3-(2-methyl-2-butenyl)oxy-2H,6H-benzodipyran-6-one, and (2S)-2,3-dihydro-2-(1-β-D-glucopyranosyloxy-1-methylethyl)-4-methoxy-7-methyl-5H-furobenzopyran-5-one, respectively, by chemical and spectral studies.Keywords: Ledebouriella seseloides; Umbelliferae; chromones; coumarins; dihydropyranochromones; dihydrofuranochromones
- Sasaki, Hiroshi,Taguchi, Heihachiro,Endo, Tohru,Yosioka, Itiro
-
p. 3555 - 3562
(2007/10/02)
-
- CHEMICAL STUDIES OF ANGELICA JAPONICA A. GRAY. I. ON THE CONSTITUENTS OF THE ETHYL ACETATE EXTRACT OF THE ROOT
-
The dried roots of Angelica japonica A.Gray (Umbelliferae) afforded three new chromones (VI, VIII and IX) together with six known chromones (I-V and VII) and fourteen known coumarins (X-XXIII) which were identified by comparison with authentic samples.The structure of VI, VIII and IX were established as (3S)-2,2-dimethyl-3,5-dihydroxy-8-hydroxymethyl-3,4-dihydro-2H,6H-benzodipyran-6-one, (3S)-2,2-dimethyl-3-β-D-glucosyloxy-5-hydroxy-8-methyl-3,4-dihydro-2H,6H-benzodipyran-6-one (sec-O-glucosylhamaudol) and (2S)-2-(1-hydroxy-1-methylethyl)-4-methoxy-7-β-D-glucosyloxymethyl-2,3-dihydro-5H-furobenzopyran-5-one (prim-O-glucosylcimifugin).Keywords: - Angelica japonica; chromone; coumarin; dihydropyranochromone; dihydrofurochromone; sec-O-glucosylhamaudol; prim-O-glucosylcimifugin
- Baba, Kimiye,Hata, Kiyoshi,Kimura, Yoshiyuki,Matsuyama, Youko,Kozawa, Mitsugi
-
p. 2565 - 2570
(2007/10/02)
-