• Title/Summary/Keyword: Cyclopeptide alkaloids

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UHPLC-ESI-qTOF-MS Analysis of Cyclopeptide Alkaloids in the Seeds of Ziziphus jujuba var. spinosa

  • Kang, Kyo Bin;Jang, Dae Sik;Kim, Jinwoong;Sung, Sang Hyun
    • 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 MSE 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.

Anxiolytic-Like Effects of Cyclopeptide Fraction Alkaloids of Zizyphi Spinosi Semen: Possible Involvement of GABAA Receptors

  • Han, Huishan;Ma, Yuan;Eun, Jae-Soon;Hong, Jin-Tae;Oh, Ki-Wan
    • Biomolecules & Therapeutics
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    • v.16 no.3
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    • pp.261-269
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    • 2008
  • This experiment was performed to investigate the anxiolytic-like effects of cyclopeptide fraction alkaloids of Zizyphi Spinosi Semen (CFAZ), by using the experimental paradigms of anxiety, and compared with those of a known anxiolytic, diazepam. CFAZ (8.0 mg/kg, p.o.) increased the percentage of time spent on the open arms and the number of open arms entries in the elevated plus-maze test, increased the number of head dips in the hole-board test, and increased the percentage of center zone ambulatory time in the open-field box. However, CFAZ has no effect on the locomotor activity, while diazepam (2.0 mg/kg, p.o.) significantly reduced locomotor activity. CFAZ did not influence the grip force in the grip strength meter test, either. From the molecular experiments, CFAZ increased chloride influx in cultured cerebellar granule cells. In addition, $GABA_A$ receptors $\gamma$-subunit were over-expressed by CFAZ in cultured cerebellar granule cells. It is concluded that CFAZ may have anxiolytic-like effects, and these effects may be mediated by $GABA_A$ receptors.

Sedative Activity of Aporphine and Cyclopeptide Alkaoids Isolated from the Seeds of Zizyphus Vulgaris var. Spinosus, and the Fruits and Stem Bark of Zizyphus Jujuba var. Inermis in mice (산조인 및 대추, 대추나무로부터 단리한 아포르핀과 환상 펩티드 알칼로이드의 생쥐에 대한 진정작용)

  • 한병훈;박명환;한용남
    • 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.

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Analysis of Alkaloids in the Seeds of Zizyphus jujuba by High Performance Liquid Chromatography

  • Park, Man-Ki;Park, Jeong-Hill;Shin, Young-Geun;Cho, Kyung-Hee;Han, Byung-Hoon;Park, Myung-Hwan
    • 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;.

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Inhibition of Calmodulin-Dependent Calcium-ATPase and Phosphodiesterase by Various Cyclopeptides and Peptide Alkaloids from the Zizyphus Species

  • Hwang, Keum-Hee;Han, Yong-Nam;Han, Byung-Hoon
    • 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.

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Alkaloids are the sedative principles of the seeds of zizyphus vulgaris var spinosus

  • Han, Byung-Hoon;Park, Myung-Hwan
    • 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.

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