• 약학회지
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• 제45권1호
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• pp.34-38
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• 2001

The Phellodendri Cortex of Phellodendron amurense (Rutaceae) is known to contain a number of isoquinoline alkaloid, and berberine, palmatine, jateorrhizine, phellodendrine and magnoflorine are the major constituents of protoberberine alkaloids. For the determination of protoberberine alkaloids from Phellodendri Cortex and berberine chloride from the preparation, the new spectrophotometric method was developed with a simple and selective sample clean-up using thiocyanatocobaltate[II] complex ion. Samples were extracted with 0.1 mM hydrochloric acid, potassium biphthalate reagent, thiocyanatocobaltate reagent and 1.2-dichloroethane for 60 min. The absorbance of protoberberine alkaloid complexes in 1.2-dichloroethane solution was measured at 625 nm. Calibration curve for berberine was linear over the concentration range of 0.05~0.30 mg/ml 1.2-dichloroethane. The method proved to be rapid, simple and reliable for the determination of protoberberine alkaloids from Phellodendri Cortex and berberine chloride from the preparation.

• Natural Product Sciences
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• 제5권4호
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• pp.159-161
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• 1999

The effects of bioactive fractions containing protoberberine alkaloids from Coptis japonica on monoamine oxidase (MAO) activity were investigated. The MAO was obtained from the mitochondrial fraction of mouse brain. The butanol fraction from Coptis japonica was fractionated into separate bioactive fraction (Fr I-IV) by silica gel column chromatography. MAO activity was strongly inhibited by Fr III and IV, which mainly contain protoberberine alkaloids such as berberine, palmatine and coptisine. These results indicated that the protoberberine alkaloids from Coptis japonica had an inhibitory effect on MAO activity.

• 생약학회지
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• 제32권1호통권124호
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• pp.49-54
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• 2001

The effects of protoberberine compounds on serotonin biosynthesis in P815 cells were investigated. Protoberberine compounds such as berberine, palmatine and coralyne decreased serotonin content dose-dependently, but coptisine did not. The $IC_{50}$ values of berberine, palmatine and coralyne were $3.0\;{\mu}M,\;16.5\;{\mu}M\;and\;14.5\;{\mu}M$, respectively. Protoberberine compounds at concentrations up to $20\;{\mu}M$ were not cytotoxic towards P815 cells. The activity of tryptophan hydroxylase, a ratelimiting enzyme in serotonin biosynthesis, was inhibited by the exposure of berberine, palmatine and coralyne in P815 cells (14.9-19.3% inhibition at $2-15\;{\mu}M$), but that of aromatic L-amino acid decarboxylase was not. These results suggest that the inhibition of tryptophan hydroxylase activity by berberine, palmatine and coralyne might partially contribute to the decrease in serotonin content in P815 cells.

• 약학회지
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• 제34권5호
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• pp.296-301
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• 1990

Irradiation of the berberinephenolbetaine in a stream of argon produced the 8,14-cycloberberines [1]. On treatment with ethylchloroformate $C_8-N$ bond cleavage of the compound [1] occurred, accompanied with dehydrochlorination to give 7-ethylcarboxyisoquinoline [3], and the product [3] treated with strong alkali solution to give the 13-oxonorotensane [4] in 64% yield. Irradiation of the compound [4] converted easily to dihydro-8H-dibenzo[a, g] quinolizine-8-one [5]. and then the compound [5] was treated with methyliodide to give the 8-oxo-quinolizinium methiode. The intermediate colume chromatography on IRA-400 afforded the benzo[c, g]azecine-5-one[6] in 63% yield. The results of biological activities for these compounds are also presented.

• 약학회지
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• 제39권1호
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• pp.36-40
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• 1995

In order to investigate the biological activity of protoberberine derivatives, they were synthesized four derivatives (1-4) of 7,8 adduct of cycloberberine, two derivatives (5, 6) treated with alkylamine or phenylamine, four compounds (7, 8) and (9, 10) adduct with 1,3-dichloroacetone and oxalychloride. Antibacterial activity of these synthesized compounds was tested.

• Archives of Pharmacal Research
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• 제29권9호
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• pp.757-761
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• 2006

Six protoberberine alkaloids were isolated from the chloroform layer of the rhizome of Coptis japonica Makino (Ranunculaceae). The structures of the isolated compounds were determined to be 6-([1,3]dioxolo[4,5-g]isoquinoline-5-carbonyl)-2,3-dimethoxy-benzoic acid methyl ester (1), oxyberberine (2), 8-oxo-epiberberine (3), 8-oxocoptisine (4), berberine (5) and palmatine (6) by physicochemical and spectroscopic methods. The compound 3 (8-oxo-epiberberine) was first isolated from natural sources. The compounds were tested for cytotoxicity against five tumor cell lines in vitro by SRB method, and also tested for the MDR reversal activities. Compound 4 was of significant P-gp MDR inhibition activity with ED50 value $0.018\;{\mu}g/mL$ in MES-SA/DX5 cell and $0.0005\;{\mu}g/mL$ in HCT15 cell, respectively.

• 약학회지
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• 제47권4호
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• pp.230-233
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• 2003

Previously, protoberberine alkaloids such as berberine and palmatine have been found to lower dopamine content in PC12 cells (Shin et at., 2000). In this study, the effects of berberine and palmatine on L-DOPA-induced increase in dopamine level and cytotoxicity in PC12 cells were investigated. Treatment of PC12 with L-DOPA at concentration ranges of 20∼50 $\mu$M increased dopamine content and the increase in dopamine levels by L-DOPA was inhibited by 10∼40 $\mu$M berberine and 10∼80 $\mu$M palmatine, which the concentration ranges did not show a cytotoxicity. However, berberine and palmatine at concentrations higher than 50 $\mu$M and 100 $\mu$M caused a cytotoxicity, respectively. In addition, berberine (10∼20 $\mu$M) and palmatine (10∼50 $\mu$M) at non-cytotoxic concentration ranges aggravated L-DOPA-induced cytotoxicity in PC12 cells (L-DOPA concentration ranges, 20∼50 $\mu$M). The L-DOPA-induced cytotoxicity was also significantly potentiated by berberine (50 $\mu$M) and palmatine (100 $\mu$M) with cytotoxic ranges. These data demonstrate that berberine and palmatine inhibit L-DOPA-induced increase in dopamine content and stimulate L-DOPA-induced neurotoxicity. Therefore, the possibility that the long-term L-DOPA treated patients with berberine and palmatine could be checked the adverse symptoms.

• Bulletin of the Korean Chemical Society
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• 제25권10호
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• pp.1559-1563
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• 2004

The topoisomerase II poisoning effect of certain protoberberine alkaloids is associated with anti-cancer activity. Structure-activity relationships of protoberberine analogues substituted on the ring protons reveal that substitution at the C19 position is an important determinant of biological activity. In this study, the effects of substituent modification at the C19 position on the interaction of protoberberines with DNA are determined using UV and NMR spectroscopy. The line broadening effect on aliphatic resonances, chemical shift changes of the imino protons of HP14 upon berberine and berberrubine binding to HP14, and the rate of the exchange process between protoberberine analogs bound indicate that berberrubine binds HP14 more specifically than berberine. In addition, the free HP14 is altered by the substituent at the 19-position. UV spectra of berberrubine have shown a hypochromic effect together with a slight red shift, which are usually regarded as characteristics of DNA intercalation. These results are consistent with our previous report that the berberrubine is partially intercalated with HP14 with molar ratio 1 : 1, whereas a non-specific interaction is predominant between the berberine and HP14.

• 약학회지
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• 제38권1호
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• pp.31-37
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• 1994

Active fraction, $P_2$, was Isolated from natural anti-cancer drug, $CP_2$, by HPLC. We confirmed that $P_2$ includes most of the Isoguanosine and minor components, Berberine and other protoberberine alkaloids, by $^1H-NMR$ and $^{13}C-NMR$ and measured tile cytotoxicity of $P_2$ against various tumor cell-lines.' $P_2$ was very effective to all tumor cell-lines, especially to human colon cancer SNU-C2A$(ED_{50};\;24{\mu}g)$ and liver cancer HEP-3B$(ED_{50};\;27{\mu}g)$.

• 약학회지
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• 제36권3호
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• pp.250-254
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• 1992

Benzo[C]phenanthidine alkaloids were found to exhibit considerably strong antileukemic activies. These alkaloids have been shown to be biosynthesized from the corresponding alkaloids throung an oxidative $C_6-N$ bond cleavage followed by recyclization between $C_6\;and\;C_{13}$ position of the protoberberine. Recently we have achieved the biomimetic transformation of protoberberine alkaloid, berberine into benzo[C]phenanthridine alkaloid, chelerythrine.