• 제목/요약/키워드: caaverine

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Aporphine and Tetrahydrobenzylisoquinoline Alkaloids from the Seeds of Zizyphus vulgaris var. spinosus

  • Hoon, Han-Byung;Park, Myung-Hwan;Han, Yonng-Nam
    • Archives of Pharmacal Research
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    • 제12권4호
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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.

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Studies on the Sedative Alkaloids from Zizyphus spinosus Semen

  • Han, Byung-Hoon;Park, Myung-Hwan;Park, Jeong-Hill
    • 생약학회지
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    • 제16권4호
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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.

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