• Korean Journal of Pharmacognosy
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• v.27 no.2
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• pp.123-128
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• 1996

From the leaves of Magnolia sieboldii a new aporphine-type alkaloid named magnoporphine was isolated. The structure of magnoporphine was all assigned by $^1H-^1H$COSY, $^1H-^{13}C$ COSY and $^1H-^{13}C$ long range NMR. In addition, costunolide, syringin, syringenin $4-O-{\beta}-cellobioside$ and echinacoside was isolated.

• Archives of Pharmacal Research
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• v.12 no.4
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• pp.263-268
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• 1989

From the seeds of Zizyphus vulgaris var. spinosus, aporphine alkaloids : nuciferine, N-methylasimilobine, nornuciferine, norisocorydine, caaverine and tetrahydro benzylisoquinoline alkaloid : (+) coclaurine were isolated and identified. Zyzyphusine, a new quaternary aporphinium alkaloid form butanol soluble fraction was isolated and characterized by spectral data.

• Natural Product Sciences
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• v.26 no.2
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• pp.171-175
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• 2020

Liriodendron tulipifera, belonging to the family Magnoliaceae, is commonly called tulip tree. Four N-acetylated aporphine alkaloids, N-acetylnornuciferine (1), N-acetylanonaine (2), N-acetyl-3-methoxynornuciferine (3), and N-acetyl-3-methoxynornantenine (4) were isolated from the roots of L. tulipifera. Although the purity of each compound (1 - 4) was determined to be 97, 96, 99, and 98%, respectively, the ¹H and ¹³C NMR spectroscopic data of the aporphine alkaloids 1 - 4 displayed all signals in duplicate, indicating the presence of two rotamers due to restricted rotation of N-COCH₃ functionality in solution status. The absolute configurations of 1 - 4 w ere established by measuring specific rotation and comparison with the reported data. This is the first report on the ¹H and ¹³C NMR assignments of N-acetyl-3-methoxynornuciferine (3) and N-acetyl-3-methoxynornantenine (4). This study provides advanced NMR spectroscopic data for the structure determination of rotameric aporphine alkaloids.

• YAKHAK HOEJI
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• v.37 no.2
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• pp.143-148
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• 1993

The objective of this study was to evaluate the sedative activity of four aporphine alkaloids (APA) and nine cyclopeptide alkaloids(CPA), which had been isolated from the seeds (sanjoin) of Zizyphus vulgaris var. spinosus, and the fruits and stem bark of Zizyphus jujuba var. inermis. The assessment of sedative activity was carried out, employing a hexobarbital-induced sleeping time method in mice. When the relative sedative potency of sanjoinine-A(CPA) was given as one unit, those of nuciferine (APA), lysicamine (APA), chlorpromazine (positive control), and sanjoinine -Ahl (an epimer of sanjoinine-A) were 13, 6.5, 5, and 3, respectively. The sedatvie activities of other CPAs were much lower than those of sanjoinine-A and -Ahl, and other APAs were not active. On heat treatment, nuciferine and lysicamine were degraded into some artifacts which exhibited no sedative activity, while sanjoinine-A was converted into sanjoinine-Ahl which showed more potent sedative activity. These results suggested that nuciferine and sanjoinine-A were major sedative components of native sanjoin, and that sanjoinine-A and its epimeric artifact, sanjoinineAhl were the active principles of roasted sanjoin. It provides a scientific basis for heat-processing (roasting) of this Oriental medicine.

• Archives of Pharmacal Research
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• v.29 no.8
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• pp.627-632
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• 2006

Chromatographic separation of the MeOH extract from the stems and rhizomes of Sinomemium acutum led to the isolation of nine alkaloids and a lignan. Their structures were determined to be dauriporphine (1), bianfugecine (2), dauriporphinoline (3), menisporphine (4), (-)-syringaresinol (5), N-feruloyltyramine (6), acutumine (7), dauricumine (8), sinomenine (9), and magnoflorine (10) by spectroscopic means. These compounds were examined for their P-gp mediated MDR reversal activity in human cancer cells. Compound 1 showed the most potent P-gp MDR inhibition activity with an $ED_{50}$ value $0.03\;{\mu}g/mL$ and $0.00010\;{\mu}g/mL$ in the MESSA/DX5 and HCT15 cells, respectively.

• Bulletin of the Korean Chemical Society
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• v.33 no.10
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• pp.3455-3457
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• 2012

• Korean Journal of Pharmacognosy
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• v.16 no.4
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• pp.233-238
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• 1985

A number of sedative alkaloids were isolated from Sanjoin(酸棗仁), the seeds of Zizyphus vulgaris Lamark var. spinosus Bunge (Rhamnaceae) which is an important Chinese medicinal material used to treat insomnia and sometimes to treat sleepiness. Those compounds were designated as Sanjoinine-A, B, C, D, etc. depending on the order of increasing polarity. Sanjoinine-A, $C_{31}H_{42}N_4O_4$, $mp\;249^{\circ}$, $[{\alpha}]^{27}_D-316$, Sanjoinine-B, $C_{30}H_{40}N_4O_4$, $mp\;212{\sim}4^{\circ}$, Sanjoinene, $C_{29}H_{35}N_3O_4$, $mp\;281{\sim}2^{\circ}$, $[{\alpha}]^{22}_D-272$, Sanjoinine-D, $C_{32}H_{46}N_4O_5$, $mp\;256{\sim}8^{\circ}$, $[{\alpha}]^{22}_D-53.6$, Sanjoinine-F, $C_{31}H_{42}N_4O_5$, $mp\;228{\sim}9^{\circ}$, $[{\alpha}]^{22}_D-215$, and $Sanjoinine-G_1,\;C_{31}H_{44}N_4O_5,\;mp\;236{\sim}8^{\circ},\;[{\alpha}]^{22}_D-68.6$, were found as 14-membered cyclic peptide alkaloids, $Sanjoinine-G_2,\;C_{30}H_{42}N_4O_4,\;mp\;182^{\circ},\;[{\alpha}]^{22}_D-79.2$, as being open chain peptide alkaloid, and Sanjoinine-E, $C_{19}H_{21}NO_2$, $mp\;166^{\circ}$, $[{\alpha}]^{20}_D-146.2$, N-Methylasimilobine, $C_{18}H_{19}NO_2$, $mp\;193{\sim}5^{\circ}$, $[{\alpha}]^{20}_D-204$, Sanjoinine-Ia, $C_{18}H_{19}NO_2$, $mp\;155{\sim}7^{\circ}$, $[{\alpha}]^{20}_D-140$, Sanjoinine-Ib, $C_{19}H_{21}NO_4$, $mp\;184^{\circ}$, Sanjoinine-K, $C_{16}H_{19}NO_3$, $mp\;159{\sim}61^{\circ}$, $[{\alpha}]^{20}_D+35$, Caaverine, $C_{17}H_{17}NO_2$, $mp\;204^{\circ}$, $[{\alpha}]^{20}_D-80$, and Zizyphusine, $C_{20}H_{24}NO_4$, $mp\;214{\sim}6^{\circ}$, $[{\alpha}]^{20}_D+317$ as being aporphine alkaloids. The heat treatment of the cyclic peptide alkaloids produced their isomeric products which showed enhanced sedative activity. The chemical structure of the isomeric products will be discussed.

• YAKHAK HOEJI
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• v.42 no.2
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• pp.170-174
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• 1998

The effects of bulbocapnine, an aporphine isoquinoline alkaloid, on dopamine content in PC12 cells were investigated. Bulbocapnine decreased the dopamine content dose-dependentl y (39.2% inhibition at 2O${\mu}$M for 24 hr). The $IC_{50}$ value of bulbocapnine was 22.7${\mu}$M. Dopamine content was lowered at 6 hr after exposure to bulbocapnine. And then, the decreased dopamine level was almost maintained at 36 hr and recovered to the control level at about 60 hr. Tyrosine hydroxylase, the rate limiting enzyme in the catecholamine blosynthetic pathway, was also inhibited at 20${\mu}$M of bulbocapnine by 23.1% relative to control. We, therefore, hypothesized that the inhibition of tyrosine hydroxylase by bulbocapnine with a single treatment might be partially contributed to the decrease in dopamine content in PC12 cells.

• Korean Journal of Pharmacognosy
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• v.28 no.4
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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.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.139.1-139.1
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• 2003

The effects of liriodenine, an aporphine isoquinoline alkaloid, on dopamine biosynthesis and L-DOPA-induced neurotoxicity in PC12 cells were investigated. Treatment of PC12 cells with liriodenine at 10 $\mu\textrm{M}$ showed 33.6％ inhibition of dopamine content decreased at 3 h and reached a minimal level at 12 h after the exposure to liriodenine at 10 $\mu\textrm{M}$. (omitted)