A new compound, rotenoid isoflavone glycoside named, 6'-O-beta-D: -glucopyranosyl-12a-hydroxydalpanol was isolated from the methanolic (MeOH) fruit extract of Amorpha fruticosa LINNE by means of multi-stage column chromatography. Immuno-modulatory activities of this new glycoside were compared with the partitioned fractions of Amorpha fruticosa LINNE. Both of the fractions and purified single compound showed a 19% relatively low cytotoxicity at a maximum concentration of 1.0 g/L in a cultivated normal human lung cell line (HEL299). The purified single compound showed less cytotoxicity than the crude extracts, possibly because residual toxicants were eliminated during purification processes. Cell growth of human T cells was increased by about 15% by adding 0.5 g/L of the fractions compared to the control. Specific production rates of interleukin-6 (IL-6) and tumor necrosis factor (TNF-alpha) from T cell were higher as 1.16 x 10(-4) and 1.86 x 10(-4 )pg/cell, respectively, in the purified compound, compared to 1.38 x 10(-4) and 2.22 x 10(-4 )pg/cell, respectively, by adding 0.5 g/L of the dichloromethane fraction. Natural killer cell-92MI (NK-92MI) growth supplemented with the supernatant of human T cell was up to 19% higher with the dichloromethane fraction compared with a new single compound at a concentration of 0.5 g/L. Overall, the dichloromethane fraction showed relatively higher immuno-modulatory activities compared with a new single compound, probably due to the synergic effect given by other substances existing in the fractions.

Fatsia japonica Decne. (Araliaceae) is used in eastern folk medicine [1]. Various class of compounds such as triterpene saponins [2][3][4][5], squalene, fatty acids and their methyl esters [6], anthocynanins [7], and sterols [6] and their glycosides [8] have been isolated from this plant.Shade air-dried and powdered roots (16.3 kg) and mature fruits (425.0 g) of F. japonica were extracted with 95% ethanol. Dried EtOH extracts of roots (752.2 g) and fruits (58.9 g) were dissolved in water and fractionated with n-hexane, dichloromethane, and ethyl acetate. The dichloromethane-soluble fraction (139.0 g) of F. japonica root produced some precipitate, which was filtered to give two fractions, FRD-1 (precipitate) and FRD-2 (filtrate). FRD-1 on a silica gel column (CHCl 3 -MeOH 7:1) gave compound 1 (415 mg). On the other hand, fraction FRD-2 on a Sephadex LH-20 column (MeOH) gave four fractions, FRD-2-1 to FRD-2-4. Fraction FRD-2-2 (20 g) on a silica gel column (CHCl 3 -MeOH 20:1) gave 15 fractions, FRD-2-2-1 to FRD-2-2-15. Separate column chromatography of FRD-2-2-6, FRD-2-2-9, and FRD-2-2-10 on Sephadex LH-20 columns using acetone as an eluent yielded compounds 4 (90 mg), 3 (350 mg), and 7 (50 mg), respectively. The EtOAcsoluble fraction of F. japonica fruit (6 g) was chromatographed on a Sephadex LH-20 column using MeOH as eluent to give five fractions, FFE-I to FFE-V. Fraction FFE-I was further chromatographed on a silica gel column using CHCl 3 -MeOH (7:1, v/v) as eluent to yield nine fractions, FFE-I to FFE-IX. Separate preparative TLC of fractions FFE-I-II and FFE-I-VIII in CHCl 3 -MeOH (5:1, v/v) and fractions FFE-I-IV in a solvent system of CHCl 3 -MeOH-H 2 O (15:6:0.6, v/v/v) gave compounds 1 (40 mg), 5 (20 mg), and 2 (190 mg), respectively. The shade air-dried and powdered wood (4.7 kg) of F. japonica was extracted with acetone. The dried acetone extract of wood was dissolved in water and fractionated with n-hexane, dichloromethane, and ethyl acetate. The EtOAc-soluble fraction of F. japonica wood (2.12 g) on a Sephadex column (MeOHEtOH, 1:1, v/v) gave four fractions. Fraction 3 (114.5 mg) was further purified on a silica column using benzene-MeOH (5:1, v/v) as eluent to give compound 6 (64.2 mg).

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