• 약학회지
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• 제40권2호
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• pp.131-134
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• 1996

3,4-Dimethoxyphenethyl amine(1) and 3,4-dimethoxybenzaldehyde were converted to compounds(4) through sucessive condensation and reduction reaction. Compound(4) was treated with methylthioacetyl chloride to give compound(5) then m-chloroperbenzoic acid(m-CPBA) treatment of compound(5) produced S-oxide(6). To obtain isoquinoline derivative(7),(8), compound(6) were treated with p-TsOH. Xylopinine(9) and it's derivatives(10) were produced by Bischler-Napieralski reaction.

• Bulletin of the Korean Chemical Society
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• 제34권3호
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• pp.749-752
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• 2013

Trehalose-tethered monomeric and dimeric berberines were synthesized in 50% and 30% from the reaction of berberrubine with 6-tosyl-${\alpha}$,${\alpha}^{\prime}$-trehalose and 6,6'-ditosyl-${\alpha}$,${\alpha}^{\prime}$-trehalose, respectively, and fully characterized by MS (HR and ESI) and NMR ($^1H$, $^{13}C$, COSY and HSQC). Spectrophotometric and spectrofluorimetric titrations indicated that compared with berberine, trehalose-tethered monomeric berberine had comparable DNA-binding affinity toward calf-thymus DNA, whereas trehalose-spaced dimeric berberine exhibited higher DNA-binding affinity. The potential application of these conjugates is also briefly discussed.

• 생약학회지
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• 제30권1호
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• pp.79-83
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• 1999

The effects of coralyne, a protoberberine isoquinoline compound, on dopamine biosynthesis in PC12 cells were investigated. Coralyne decreased the dopamine content dose-dependently $(46.3%\;inhibition\;at\;20\;{\mu}M\;for\;24 hr).$ Dopamine content was lowered at 6 hr and reached minimal level at 24 hr after exposure to coralyne at $20\;{\mu}M.$ The decreased dopamine level was maintained up to 48 hr and recovered to the control level at about 72 hr. Tyrosine hydroxylase, the rate-limiting enzyme in the catecholamine biosynthesis, was also inhibited at $20\;{\mu}M\;of\;coralyne$ by 16.1% relative to control. These results suggest that the inhibition of tyrosine hydroxylase by coralyne with a single treatment might be partially contributed to the decrease in dopamine content in PC12 cells.

• Bulletin of the Korean Chemical Society
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• 제23권3호
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• pp.391-394
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• 2002

Berberine and berberrubine, which display antitumor activity, have also demonstrated distinct enzyme-poisoning activities by stabilizing topoisomerase Ⅱ-DNA cleavable complexes. The protoberberine berberrubine differs in chemical structure with berberine at only one position, however, it shows a prominent activity difference from berberine. Solution structures of berberine and berberrubine determined by NMR spectroscopy are similar, however, the minor structural rearrangement has been observed near 19 methoxy or hydroxyl group. We suggest that the DNA cleavage activities of topoisomerase Ⅱ poisons could be correlated with both chemical environments and minor structural change together with hydrophobicity of interacting side chains of drugs with DNA molecule.

• 약학회지
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• 제40권5호
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• pp.487-490
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• 1996

The 13-hydroxyberbine(1), derived from berberinephenolbetaine, has been derivatized to furnish a variety of compounds such as 13-oxoberbine(2), 13-thioberbine(3), 13-chloroberbi ne(4), 13-(2-methylaziridine)berbine(5) and 13-carbolactoneberbine(6). Antitumor activity of these compounds was tested.

• 생약학회지
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• 제28권4호
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• pp.257-263
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• 1997

Berberis amurensis Ruprecht(Berberidaceae) is a medicinal plant indigenous to the middle and northern part of Korean peninsula. The woody parts of this plant have been used for the ocular, peptic and intestinal disorders. The stems of this plants were extracted with MeOH and the MeOH extract was partitioned between organic phases and water layer, successively to fractionated quarternary alkaloids. The acetone-soluble part of guarternary alkaloidal fraction had antibacterial activities and it contained four protoberberine alkaloids such as palmatine(I), Berberine(II), Jatrorrhizine(III) and coptisine(IV), and one aporphine alkaloid, magnoflorine(V). Although the isolations of the compounds I, II, IIII, IV and V from different sources were reported, this is the first report that Berberis amurensis contained the compounds. When the contents of compound I(palmatine) and II(berberine) were quantified and compared with those of other plant parts, cortex contained higher palmatine and berberine than any other part of the plant.

• 생약학회지
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• 제31권4호
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• pp.390-393
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• 2000

From the alkaloidal fraction of the fructus of Chelidonium majus, two protoberberine alkaloids and one benzophenanthridine alkaloid were isolated. On the basis of chemical and spectroscopic evidences, the structures of these compounds were identified as chelidonine, coptisine and berberine.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.205.2-205.2
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• 2003

As part of our program to isolate bioactive compounds from korean natural sources, we have screened traditional medicinal plants to cytotoxity on human tumor cells. Of them, the MeOH extract from rhizome of Coptis japonica Makino was found to be active against five cultured human tumor cell lines. So, the MeOH extract was subjected to successive solvent partitioning to give n-hexane, chloroform and BuOH. The activity was concentrated into the chloroform extract. The extract was chromatographied on a silica gel column and resulted in the isolation 5 alkaloids. (omitted)

• 약학회지
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• 제36권1호
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• pp.1-6
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• 1992

Irradiation of phenolbetaine in a stream of nitrogen produced 8,14-cycioberbine[1]. Compound[1] was treated with 10% HCl solution to give the 8-hydroxycycloberbine[2] in 67.7% yield. Subsequently addition of ethylchloroformate to the compound[2] gave rise to the 8-hydroxy-7-ethylcarboxy-9, 10-dimethoxy-2, 3-methylenelioxy-13-oxo-norochotensane[3] in 78% yield. Treatment of the compound[3] with bis-(2-chloroethyl)amine then lead to the 7-bis(2-chloroethyl)carbamyl-norochoteneare[4]. On the other hand the compound[5], which is the 8-methoxynorochotensane, was derived when compound[1] was treated with methanol in a few drops of BF. Treatment of the compound[6], and the compound[7], 7-bis(2-chloroethyl)-carbanyl-8-methoxy-norocheyensane, was then synthesized by reaction of the compound[6] with bis(2-chloroethyl) amine. In the other synthetic pathway when compound[5] was treated with $POCl_3$ in dried benzene, 13-chloro-6-ene-norochetensane[8] with 42% yield was formed. Finally the 13-bis-(2-chloroethyl) amino-8-methoxy-norochotensane[9] was produced when we treated the compound[8] with bis-(2-chloroethyl) amine. In another pathway, reaction between phenolbetaine which is the precursor of the compound[1] and benzoylchloride in dried chloroform gave us the 5,6,7 trihydro-2, 3-methylene-dioxy-9-chloromethyl-10, 11-dimethoxyphenylisoquinoline-8-benzoate[10] in 73% yield. The results of biological activities for these compounds are also presented in Table I and II.

• Bulletin of the Korean Chemical Society
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• 제25권4호
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• pp.539-544
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• 2004

The ability of protoberberine alkaloids, berberine and berberrubine, to act as topoisomerase II poisons is linked to the anti-cancer activity. Minor alterations in structure have a significant effect on their relative activity. Berberine, which has methoxy group at the 19-position, is significantly less potent than berberrubine. Several observations support non-specific binding to HP14 by the berberine: (i) nonspecific upfield changes in $^1H$ chemical shift for protons of the berberine; (ii) the broadening of imino protons of HP14 upon binding of the berberine; (iii) very small increases in duplex melting temperature in the presence of the berberine. Our results reveal that substitution of a hydroxyl group to a methoxy group on the 19-position, thereby converting the berberrubine to the berberine is associated with a non-specific DNA binding affinity and a reduced topoisomerase II poisoning. The presence of a bulky 19-methoxy substituent decreases intercalating properties of berberine and makes it inactive as topoisomerase II poison.