• Natural Product Sciences
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• v.5 no.4
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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.

• YAKHAK HOEJI
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• v.45 no.1
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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.

• Mass Spectrometry Letters
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• v.4 no.4
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• pp.79-82
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• 2013

Various types of alkaloids observed in several herbal medicines were analyzed by electrospray ionization tandem mass spectrometry in positive ion mode. In the present study, MS/MS spectralpatterns were investigated for eight-types of alkaloids (aporpine, protoberberine, tetrahydroprotoberberine, benzylisoquinoline, protopine, phthalide, morpine, and bisbenzylisoquinoline). For aporpine- and protoberberine-type alkaloids, main fragmentations occurred at substituted groups on rigid ring structures, not showing ring fusion. Interesting fragmentations due to iminolization and retro-Diels-Alder (RDA) reaction were observed in MS/MS spectra of protopine- and tetrahydroprotobereberine-type alkaloids. Also, several types of fragmentations such as inductive cleavage and ${\alpha}$-cleavage, or bond cleavage between two ring structures were observed depending on their structural characteristics. These fragmentation patterns are expected to allow instant classification of the specific alkaloid type in various MS/MS spectra of alkaloids.

• Korean Journal of Pharmacognosy
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• v.33 no.3 s.130
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• pp.182-186
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• 2002

The Coptidis rhizoma is known for containing protoberberine alkaloids. Berberine, coptisine and palmatine are the major constituents of protoberberine alkaloids. The alkaloids were isolated and determined by forming complex compounds from Coptidis rhizoma in preparation I(Sam-Hwang-Sa-Sim-Tang) and II(Hwang-Ryen-Tang). For the determination of these alkaloids, a new spectrophotometric method was developed with a simple and selective sample clean-up using thiocyanatocobaltate[II] complex compound ion. The absorbance of alkaloidal complex compounds in l.2-dichloroethane solution was measured at 625 nm. Calibration curve for the alkaloids isolated from Coptidis rhizoma was linear over the concentration range of 0.2-0.3 mg/ml. The method was proved to be rapid, simple and reliable for the isolation and the determination of the alkaloids in Coptidis rhizoma preparation I and II.

• YAKHAK HOEJI
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• v.36 no.3
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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.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.65.1-65.1
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• 2003

Natural benzo[c]phenanthridine and protoberberine alkaloids which have been attractive to synthetic organic chemists and biochemists over the last 2 decades since such compounds have shown interesting biological properties such as antitumor, antiviral and antimicrobacterial activities. For the systematic research on these alkaloids, several total syntheses of these alkaloids have been reported. However, the bulk of reported benzo[c]phenanthridine synthetic studies to date have involved multistep sequences for assembly of the target molecules as well as lack of generality for synthesizing substituted molecules. (omitted)

• Archives of Pharmacal Research
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• v.29 no.9
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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.

• YAKHAK HOEJI
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• v.47 no.4
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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.

• YAKHAK HOEJI
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• v.38 no.1
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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$(ED_{50};\;27{\mu}g)$.

• Proceedings of the PSK Conference
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• 2001.04a
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• pp.160.2-161
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• 2001