• Archives of Pharmacal Research
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• v.10 no.4
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• pp.208-211
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• 1987

Sedative activity of Zizyphi fructus was evaluated by potentiation of hexobarbital-induced hypnosis test and its active principles have been characterized as nornuciferine and lysicamine. A new cyclopeptide alkaloid, daechucyclopeptide-1 was isolated together with zizyphusine.

• Archives of Pharmacal Research
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• v.14 no.2
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• pp.103-104
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• 1991

The ionophore activity of frangufoline (1), a sedative cyclopeptide alkaloid isolated from Zizyphus jujuba, was investigated by UV and CD spectroscopic methods. Frangufoline (1) showed ion binding activity to calcium and magnesium ions.

• Mass Spectrometry Letters
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• v.7 no.2
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• pp.45-49
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• 2016

An UHPLC-ESI-qTOF-MS analytical method was developed for cyclopeptide alkaloids in the seeds of Ziziphus jujuba var. spinosa (Semen Ziziphi Spinosae), which is a commonly used herb in Chinese and Korean traditional medicines. Considering the basicity of cyclopeptide alkaloids, a specific separation method was developed for an UHPLC system. The compounds were detected by DAD and ESI-qTOF-MS, and their fragmentation patterns were also acquired by MS^E technologies. Peak-picking of major compounds was performed with nine previously isolated compounds and two reference standard compounds. Tandem MS fragmentation behaviors of type-Ia and -Ib cyclopeptide alkaloids were investigated with the acquired data to develop a strategy for dereplication of other cyclopeptide alkaloid compounds in Z. jujuba var. spinosa. Two more cyclopeptide alkaloids were tentatively identified with UHPLC-ESI-qTOF-MS using this method.

• 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.10 no.4
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• pp.203-207
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• 1987

Sedative principles of the seeds of Zizyphus vulgaris var. sphinosus have been characterized as sanjoinine-A (frangufoline), nuciferine and their congeners. Also, heat treatment of sanjoinine-A-produced a more active artifact, sanjoinine-Ahl, which provides a scientific basis for heat-processing (roasting) of this Oriental medicine.

• Archives of Pharmacal Research
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• v.14 no.2
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• pp.99-102
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• 1991

A hight performance liquid chromatographic methods was developed for the seperation and determination of seven alkaloids in "sanjoin" (the seeds of Zizyphus jujuba Rhamnaceae), a plant with potent sedative activity. A reverse phase system of Lichrosorb RP-Select B column and 0.05 M potassium phosphate buffer (pH = 3.5)-acetonitrile with gradient elution was employed. Two known alkaloids, juzirine and lysicamine, were newly isolated fom "sanjoin"."sanjoin".oin&".ot;.

• Archives of Pharmacal Research
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• v.16 no.4
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• pp.289-294
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• 1993

A binding protein of radio-labeled sanjoinine-A (fangufoline) in rat brain cytoplasm was investigated, using an equilibrium dialysis technique. The labeled agent was bound to the cytosol fraction with two distinctly different types of sets in calclum ion-dependent manner. The bound protein was identified as calmodulin by dgel filtration of the sanjoinine-A bound cytosol fraction on a Sephadex G-75 column. Calmodulin was bound to sanjoinine-A bound at two sets of binding sites in the calculated as two at high affinity sites $(Kd=1.1\;mu{M)}$ and four at low affinity sites $(Kd=3.1\;\mu{M)}$.

• Archives of Pharmacal Research
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• v.24 no.3
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• pp.202-206
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• 2001

The effects of various sedative cyclopeptides and peptide alkaloids from the Zizyphus species on calmodulin-dependent $Ca^{2+}$ -ATPase and phosphodiesterase were Investigated. Calmodulin-induced activation of $Ca^{2+}$-ATPase was strongly inhibited by sanjoinine-A dialdehyde (IC_{50}$, 2.3$\mu\textrm{m}$), -Ah1 (IC_{50}$, 4.0$\mu\textrm{m}$), -A (IC, 4.6$\mu\textrm{m}$), and -G2 (IC_{50}$, 7.2$\mu\textrm{m}$), while calmodulin-induced activation of phosphodiesterase was strongly inhibited by both deachuine- S10 (IC_{50}$, 4.9$\mu\textrm{m}$) and sanjoinine-D (IC_{50}$, 9.0$\mu\textrm{m}$). The inhibitory activity of the various cyclopeptides and peptide alkaloids on $Ca^{2+}$-ATPase was found to correlate well with their Sedative activity.

• Biomolecules & Therapeutics
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• v.31 no.5
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• pp.566-572
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• 2023

A chiral derivatization strategy with phenylglycine methyl ester (PGME) was employed to develop a straightforward method to determine the absolute configurations of N,N-dimethyl amino acids. The PGME derivatives were analyzed using liquid chromatography-mass spectrometry to identify the absolute configurations of various N,N-dimethyl amino acids based on their elution time and order. The established method was applied to assign the absolute configuration of the N,N-dimethyl phenylalanine in sanjoinine A (4), a cyclopeptide alkaloid isolated from Zizyphi Spinosi Semen widely used as herbal medicine for insomnia. Sanjoinine A displayed production of nitric oxide (NO) in LPS-activated RAW 264.7 cells.