• Archives of Pharmacal Research
• /
• v.26 no.12
• /
• pp.1009-1013
• /
• 2003

A new pterocarpan, (-)-maackiain 3-sulfate (1) was isolated from the methanol extract of roots of Sophora subprostarata together with (-)-maackiain(2), trifolirhizin (3), lupeol (4), ononin (5),7,4'-dihydroxyflavone (5), and (+)-syringaresinol (7). The structure of 1 was determined by analyses of 2D NMR and HRFABMS. Compounds 5-7 were isolated from this plant for the first time.

• Journal of the Korean Wood Science and Technology
• /
• v.31 no.3
• /
• pp.70-76
• /
• 2003

Five isoflavonoids, biochanin A-7-O-β-D-xylopyranosyl-(1⟶6)-β-D-gluco- pyranoside (1), (-)-maackiain (2), calycosin (3), trifolirhizin (4) and genistein (5), were tested for antifungal activity against nine fungi. These compounds were isolated from the wood (compound 1 and 2) and from the bark (compound 3, 4 and 5) of S. japonica. According to the results of antifungal activity test, (-)-maackiain was evaluated as the best antifungal compound among the isolated compounds. In this regard, it could be mentioned that high antifungal activity of S. japonica wood extracts was originated from (-)-maackiain.

• Archives of Pharmacal Research
• /
• v.27 no.6
• /
• pp.589-593
• /
• 2004

Two pterocarpans ［(6aR,11aR）-maackiain, (6aR,11aR）-medicarpin］, one flavanone ［(2S）-7-hydroxy-G-methoxy-flavanone］, one isoflavan (sativan） and two isoflavones (pseudobaptigenin, genistein） were isolated from the Spatholobus suberectus (Leguminosae）. Their chemical structures were determined by comparison of their spectroscopic parameters of CD, ElMS, 1D-NMR and 2D-NMR with those reported in the literatures. All of these compounds are reported for the first time from this plant through the present study.

• YAKHAK HOEJI
• /
• v.36 no.5
• /
• pp.481-485
• /
• 1992

Five isoflavones were isolated from the root of Caragana microphylla Lam. and the structures have been identified by means of chemical and physical methods. The isoflavones are 7-hydroxy-4'-methoxyisoflavone(formononetin), $form ononetin-7-O-{\beta}-glucoside(ononin)$, 7-hydroxy-3', 4'-methylenedioxyisoflavone(pseudobaptigenin), $7-O-{\beta}-glucuopyranosyloxy-3'- hydroxy-4'-methoxyisoflavone(calycosin-7-O-{\beta}-gluc-oside)$ and maackiain.

• Journal of the Korean Wood Science and Technology
• /
• v.30 no.3
• /
• pp.42-47
• /
• 2002

This study was carried out to investigate the constituents of Sophora japonica(Leguminosae) bark. To isolate compounds, bark was extracted with ethanol and then partitioned with hexane, dichloromethane, ethylacetate and butanol successively. After partitioned, DCM fraction was subjected to column chromatography with various solvent system in silica gel and/or Sephadex LH-20. Structures were elucidated by spectroscopic methods including MS, ¹H, ¹³C and 2D-NMR experiments. Four compounds were isolated from the bark and identified as 3',7-dihydroxy-4'-methoxyisoflavone (cyclosin), puerol A, maackiain-3-O-𝛽-D-glucopyranoside (trifolirhizin), and 4', 5, 7-trihydroxyisoflavone (genistein). Among these compounds, cyclosin and trifolirhzin were first isolated from S. japonica.

• Korean Journal of Pharmacognosy
• /
• v.33 no.2 s.129
• /
• pp.110-115
• /
• 2002

Seven prenylated flavonoids and two pterocarpans together with a saponin were isolated from the roots of Echinosophora koreensis. They were identical with echinoisosophoranone, echinoisoflavanone, isosophoranone, sophoraisoflavanone A, kenusanone C, kenusanone A, sophoraflavanone D, 4-hydroxy-3-methoxy-(6aR,11aR)-8,9-methylenedioxy-pterocarpans, (-)-maackiain, and $3-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}2)-{\beta}-D-galactopyranosyl(1{\rightarrow}2)-{\beta}-D-glucuronopyranosyl$ kuzusapogenol A. Among them, a pterocarpan, 4-hydroxy-3-methoxy-(6aR,11aR)-8,9-methylenedioxypterocarpan, and a saponin, $3-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}2)-{\beta}- D-galactopyranosyl(l{\rightarrow}2)-{\beta}-D-glucuronopyranosyl$ kuzusapogenol A, were isolated for the first time from this plant.

• Archives of Pharmacal Research
• /
• v.28 no.5
• /
• pp.534-540
• /
• 2005

Activity-guided fractionation of the CH$_2Cl_2$-soluble fraction of the roots of Sophora flavescens furnished five 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scaveng ers: trans-hexadecyl ferulic acid (1) cis-octadecyl ferulic acid (2), trans-hexadecyl sinapic acid (3), (-)-4-hydroxy-3-methoxy-(6aR,11aR)-8, 9-methylenedioxypterocarpan (4) and desmethylanhydroicaritin (8), along with nine known inactive compounds: (-)-maackiain (5), xanthohumol (6), formononetin (7), (2S)-2'-methoxykurarinone (9), (2S)-3${\beta}$,7,4'-trihydroxy-5-methoxy-8-(${\gamma},{\gamma}$- imethylallyl )-flavanone (10), (2S)-7,4'-dihydroxy-5-methoxy-8- (${\gamma},{\gamma}$-dimethylallyl ) -flavanone (11), umbelliferone (12), kuraridin (13), and trifolirhizin (14). Compounds 1-4 and 8 exhibited DPPH free radical scavenging effects at IC$_{50}$ values of 33.01 ${\pm}$ 0.20, 57.06 ${\pm}$ 0.16, 39.84 ${\pm}$ 0.36, 35.83 ${\pm}$ 0.47, and 18.11 ${\pm}$ 0.04${\mu}$M, respectively. L-Ascorbic acid, when used as a positive control, exhibited an IC$_{50}$ value of 7.39 ${\pm}$ 0.01 ${\mu}$M. Compounds 1-4 and 8 also appeared to exert significant scavenging effects on authentic ONOO-, with IC$_{50}$ values of 5.76 ${\pm}$ 1.19, 15.06 ${\pm}$ 1.64, 8.17 ${\pm}$ 4.97, 1.95 ${\pm}$ 0.29 and 4.06 ${\pm}$ 2.41 ${\mu}$M, respectively. Penicillamine (IC$_{50}$= 2.36 ${\pm}$ 0.79${\mu}$M) was used as a positive control. In addition, compounds 2,4,6,8, and 10 were isolated from this plant for the first time.