• 약학회지
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• 제40권6호
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• pp.621-624
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• 1996

Betaine was treated with hydrochloric acid and then with sodium borohydride to give a hydroxy compound 2. The reaction of 2 with thionyl chloride followed by thiourea led a comp ound 5. Oxidation of compound 2 with pyridinium dichromate(PDC) and succesive treatment with Lawesson's reagent also afforded the same compound 5. Cleavage of N-C14 bond compound of 7 was carried out via two reaction sequence from the compound 4. Finally, compound 10 was sythesized by a series of transformations from the compound 4.

• Natural Product Sciences
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• 제17권2호
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• pp.108-112
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• 2011

Several isoquinoline alkaloids (1 - 18), which have basic chemical structures as protoberberine and aporphine skeletones, were evaluated for their inhibitory activities on AChE and BuChE. Among them, compounds 3, 4, 6, 8 and 12 showed the potent AchE activity with the $IC_{50}$ values ranging from $10.2{\pm}0.5\;{\mu}M$ to $24.5{\pm}1.6\;{\mu}M$, meanwhile, compound 14 - 17 exhibited strong inhibitory activity with $IC_{50}$ values from $2.1{\pm}0.2$ to $5.5{\pm}0.3\;{\mu}M$. Compounds 14 - 17 exhibited selective inhibition for AChE compared with BuChE. The isoquinoline alkaloid possesses aromatic methylenedioxy groups and quaternary nitrogen atoms are crucial for the anti-cholinesterase inhibitory activity.

• 한국임상약학회지
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• 제7권2호
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• pp.81-85
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• 1997

Berberine, a protoberberine isoquinoline alkaloid, showed inhibitory effects on dopamine content in PC12 cells $(53.8\%\;inhibition\;at\;20\;{\mu}M)$. Tyrosine hydroxylase, the rate-limiting enzyme in the catecholamine biosynthetic pathway, was inhibited at $20\;{\mu}M)$ of berberine by $21.8\%$ relative to control. Thus, we hypothesized that the inhibition of tyrosine hydroxylase by berberine might be partially contributed to the decrease in dopamine content in PC12 cells. Furthermore, we investigated the effects of berberine on catecholamine content of serum after immobilization and cold stress in mice. Adult male mice were either subjected to 30 min of restraint or to 2 hr of cold chamber at $4-6^{\circ}C$. Serum norepinephrine, 16.8 pmol/ml, in control mice was increased to 28.8 pmol/ml by immobilization and the stress-induced rise in serum norepinephrine was partially blocked by the treatment of berberine (10 mg/kg, i.p.) once a day for 6 days. Berberine (10 mg/kg/day for 3 days, i.p.) also inhibited the increase in serum norepinephrine by cold stress in mice. These results suggest that berberine may be developed as the promising antistress agent.

• Bulletin of the Korean Chemical Society
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• 제32권10호
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• pp.3597-3602
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• 2011

A simple and rapid analytical method was developed for the determination of eight isoquinoline alkaloids in Corydalis species. Eight isoquinoline alkaloids, including 2 aporphine alkaloids (isocorydine and glaucine) and 6 protoberberine alkaloids (coptisine, palmatine, berberine, canadine, corydaline, and tetrahydrocoptisine) were used as chemical markers which have a various biological activity and determined for quality control of Corydalis (C.) species (C. ternata, C. yanhusuo, and C. decumbens). To evaluate the quality of these herbal medicines, LC chromatographic separation of alkaloids were preferentially investigated on reversed-phase C18 column with pH variation and composition of mobile phase. In addition, the separation of these alkaloids in herbal extracts was found to be significantly affected on mobile phase composition using gradient elution. Especially for C. yanhusuo extract, berberine was seriously interfered with other alkaloid extracted from sample matrix when mobile phase composition was not optimized. As results, these compounds were successfully separated within 28 min using 10 mM ammonium acetate containing 0.2% triethylamine (adjusted at pH 5.0) as a mobile phase with gradient elution. On the basis of optimized HPLC conditions, 23 different Corydalis species samples were analyzed for the determination of alkaloid levels. In addition, principal component analysis (PCA) combined with the chromatographic data could be successfully classified the different geographic origin samples.