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Callus tissue from the stems of Phellodendron amurense (Rutaceae) produced a new indolopyridoquinazoline-type alkaloid, 7, 8-dihydroxyrutaecarpine (2), together with known 7-hydroxyrutaecarpine (1). Their structures were established using spectroscopic methods.
Previously we have isolated the quaternary base alkaloids, magnoflorine and phellodendrine, from Phellodendri Cortex (cortex of Phellodendron amurense Rupr., Rutaceae) as the biologically active principles to suppress local graft-versus-host (GvH) reactions in mice. In this paper, we focus on phellodendrine. Phellodendrine suppressed local semisyngeneic GvH reactions and systemic allogeneic GvH reactions in X-ray irradiated recipient mice. Phellodendrine also suppressed the induction phase of sheep red blood cell (SRBC)-induced delayed type hypersensitivity in mice and tuberculin-induced delayed type hypersensitivity in guinea pigs, but did not suppress the effector phase of these reactions. Surprisingly, phellodendrine, unlike prednisolone and cyclophosphamide, did not affect antibody production in mice to SRBC. Phellodendrine was expected to be a valuable new type of immunosuppressor against the cellular immune response.
We previously reported that Wen-Qing-Yin (Unsei-in), a traditional Chinese blended medicine, inhibited the induction phase of various kinds of delayed type hypersensitivity (DTH) and local graft-versus-host (GvH) reactions, but did not affect humoral immune responses or the effector phase of DTH in experimental animals. In another report, we demonstrated that Phellodendri Cortex (bark of Phellodendron amurense Rupr. Rutaceae) was a component having the most potent suppressive effect on the cellular immune response among the 8 medical plants composing Unsei-in. In the present study, we isolated OB-1 and OB-5 from Phellodendri Cortex as the biologically active principles to suppress local GvH reactions in mice. OB-1 and OB-5 are quaternary base alkaloids known as magnoflorine and phellodendrine, respectively. They suppressed the local GvH reaction, when given i.p. to the host mice at 5-20 mg/kg for 8 consecutive days from the day of spleen cell transfer to cause the reaction. Both OB-1 and OB-5 suppressed picryl chloride-induced delayed type hypersensitivity (PC-DTH) when given i.p. to mice at 10 and 20 mg/kg for 5 consecutive days from the day of the sensitization, but did not suppress it when given at the time of the challenge. These results suggest that OB-1 and OB-5 suppress the induction phase but not the effector phase of the cellular immune response. They are expected to have a value as a new type of immunosuppressor.
From the leaves of Phellodendron japonicum Maxim. (Rutaceae), six new flavonoid glycosides (I-VI) were isolated, together with eight known compounds. The structures of I-VI were shown to be 8-prenyl-3,4',5-trihydroxy-flavone 7-O-beta-D-(6-O-malonyl) glucopyranoside, (2R,3R)-8-prenyl-3,4',5-trihydroxyflavanone 7-O-beta-D-(6-O-malonyl) glucopyranoside, 8-[(S)-2,3-dihydroxy-3-methylbutyl]-3,4',5-trihydroxyflavone 7-O-beta-D-glucopyranoside, 8-[(R)-2,3-dihydroxy-3-methylbutyl]-3,4',5-trihydroxyflavone 7-O-beta-D-glucopyranoside (2R,3R)-8-[(S)-2,3-dihydroxy-3-methylbutyl]-3,4',5-trihydroxyflavanon e 7-O-beta-D-glucopyranoside and (2R,3R)-8-[(R)-2,3-dihydroxy-3-methylbutyl]-3,4',5-trihydroxyflavanon e 7-O-beta-D-glucopyranoside, respectively, on the basis of the chemical and spectral data.
Berberine (1) and palmatine (2) in cortex phellodendron and Chinese patent medicines were determined by HPLC. The optimal composition of mobile phase CH3COOEt-HCOOH-EtOH (15:3:2) for HPLC separation of berberine and palmatine was successfully determined by using window diagram technique. Detection wavelength was 346nm. Flow rate: 1.5 ml/min. Calibration graphs for 1 and 2 were rectilinear for 0.06-0.32 micrograms and 0.12-0.32 micrograms respectively. The average recoveries of the two corresponding components were found to be over 96% and their coefficients of variation were below 5%.
Berberine from crude and processed Phellodendron chinense was determined by UV TLC densitometry. The results indicate that the content of berberine in processed products is 11.8% to 98% less than that of the crude drug. The recovery of berberine is 98% +/- 1.7% and the Standard relative deviation is 1.7%.
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Limonoids and their glucosides in the seeds and barks of Phellondendron amurense (Kihada) were analyzed. The seeds contained limonin (1950 ppm), obakunone (20 ppm), limonin 17-beta-D-glucopyranoside (820 ppm) and obakunone 17-beta-D-glucopyranoside (1360 ppm). The barks contained limonin (6760 ppm), obakunone (1240 ppm) and nomilin (270 ppm).
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Huangbai (cortex Phellodendri, the dried bark of Phellodendron amurense or Phellodendron chinense) is one of the important traditional Chinese medicines. Protoberberine alkaloids were reported to contribute to the biological activity of this species. A highly specific and sensitive method using (1)H NMR has been developed for the quantitative determination of protoberberine alkaloids in Phellodendron species and their commercial traditional Chinese medicine prescriptions. In the region of delta 8.6-8.9, the signals of H-13 of berberine (1) and palmatine (2), were well separated from other signals in methanol-d(4). The quantity of the compounds was calculated by the relative ratio of the integral values of the target peak of each compound to the known amount of internal standard anthracene. This method allows rapid and simple quantization of protoberberine alkaloids from Phellodendron species or the more complex commercial prescriptions in 5 min without any pre-purification steps. The recoveries of berberine and palmatine from P. amurense were in the range of 95-106%. Limit of detection (LOD) and limit of quantitation (LOQ) of them were 1.0 and 1.8 microg/mL, respectively. The advantages of the method were that no reference compounds are required for calibration curves, the quantification could be directly realized on a crude extract, the better selectivity for protoberberine alkaloids and a very significant time-gain could be achieved, in comparison to conventional HPLC methods, for instance.
In order to develop a new apoptosis inducer, we screened 22 crude drugs for their apoptosis-inducing activity. It was found that Glycyrrhiza uralensis, Cynomorium songaricum, Eucommia ulmoides, Phellodendron amurense, Cinnamomum cassia and Paeonia lactiflora induced the death of HL-60 cells. To investigate the mechanism of apoptosis induced by these six crude drugs, the mitochondrial transmembrane potential and the activity of caspase-3 were measured. Reduced mitochondrial transmembrane potentials within 12 hours after the administration of Glycyrrhiza uralensis, Cynomorium songaricum, Phellodendron amurense and Paeonia lactiflora, and within 24 hours after the administration of Eucommia ulmoides and Cinnamomum cassia were observed. All of the six apoptosis-inducing crude drugs increased caspase-3 activity within 12-36 hours after administration. After further examining the apoptosis-inducing activity of berberine, palmatine, panelofuroline and glycyrrhizin, which were the ingredients obtained from Phellodendron amurense, Glycyrrhiza uralensis and Paeonia lactiflora, it was found that only berberine could induce apoptosis. From these results, it was concluded that the apoptosis induced by the six crude drugs (Glycyrrhiza uralensis, Cynomorium songaricum, Eucommia ulmoides, Phellodendron amurense, Cinnamomum cassia and Paeonia lactiflora) occurred via the mitochondrial route and that the apoptosis-conducting mechanism acted through a cascade involving caspase-3.