• 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.

• Archives of Pharmacal Research
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• 제10권4호
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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.

• 약학회지
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• 제37권2호
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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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• 제24권3호
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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.

• 생약학회지
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• 제12권4호
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• pp.203-207
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• 1981

The acute toxicity and sedative activity of flavonoids and saponin isolated from Zizyphus seeds have been evaluated in mice. All the compounds elicited potentiation of hexobarbital-induced hypnosis, inhibition of ladder-climbing and caffeine-induced hyperactivity. Swertisin was the most potent of all flavonoids tested. The potency of saponin in these tests was found to be higher than that of swertisin. The activities in rotarod test and electroshock seizure test, on the other hand, were relatively weak or nil. From these findings it was suggested that flavonoids and saponin from Zizyphus seeds have neuroleptic activity without anticonvulsant or muscle relaxant activity accompanied by neurological deficit.

• 대한약리학회지
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• 제18권1호
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• pp.17-22
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• 1982

Zizyphus seed(Zizyphus vulgaris Lamark var. Spinosus Bunge) has long been used as hypnotics and sedatives in oriental medicine, and it is reported that the Zizyphus seed elicited a variety of pharmacologic actions besides CNS depression. Present study was undertaken to investigate the effects of Zizyphus seed on the central nervous system and on the blood pressure. The effect of Zizyphus seed on the central nervous system was measured by the influence of thiopental sleeping time and by inhibition of chemical convulsion (strychnine and pentylenetetrazol induced). Blood pressure changes by Zizyphus extract and its mode of action were investigated. The ground Zizyphus seed was extracted with hexane and methanol, consecutively and the supernatants were discarded. The precipitate was re-extracted with distilled water and the supernatant was evaporated to a dark-brownish sticky liquid, which was used as Zizyphus seed extract in this study after dissolving in saline prior to experiment. The results are as follows. 1) Zizyphus seed extract caused marked prolongation of the thiopental sleeping time in mice. 2) The chemical convulsion by strychnine and pentylenetetrazol, and the mortality by them in chicks were not affected by pretreatment of Zizyphus seed extract. 3) Zizyphus seed extract produced transient fall of blood pressure in the cat, and this hypotentive effect was blocked partially by atropine but not affected by bilateral vagotomy and/or hexamethonium, nor propranolol and, chlorpheniramine and/or cimetidine. With the above results, it may be suggested that the water extract of Zizyphus seeds contains components producing CNS depression and hypotension. Furthermore it is felt that the cholinergic effect, but not the adrenergic or histaminergic, is partly responsible for the hypotensive effect of Zizyphus seed extract.

• 한국식품영양과학회지
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• 제35권1호
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• pp.7-14
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• 2006

16종의 한약재 및 약용식물류의 열수 추출물에 대한 흡광도, 총페놀화합물 및 플라보노이드 함량과 이들의 항산화 효과를 분석하였다. 추출수율은 단삼이 $35.49\%$로 다른 시료에 비하여 월등히 높았으며 pH는 $4.00\~5.92$의 범위로 산성 pH에 더 가까웠다. 방향족 화합물의 함량을 검색하고자 $250{\mu}g/mL$농도의 시료로 280 nm에서 흡광도를 측정한 결과 꿀풀이 2.872로 가장 높았으며 엉겅퀴와 산사육, 산조인은 0.5이하의 낮은 흡광도를 나타내었다. 갈색화 반응 생성물의 흡광도를 측정한 결과도 유사한 경향을 나타내어 꿀풀의 경우 1.312로 가장 높은 값을 다음은 옥수수수염 (0.917), 금물초(0.725) 순이었다. 총 페놀 화합물의 함량은 꿀풀이 $5.07{\pm}0.05mg/100g$으로 다른 시료에 비하여 월등히 높은 함량이었고 플라보노이드의 함량은 단삼에서 $4.82{\pm}1.16\;mg/100g$으로 다른 시료에 비하여 약 2배 정도 높은 함량이었다. 대부분의 시료에서 농도가 증가함에 따라 전자공여 효과도 높아지는 경향을 보였는데 산조인, 산수유, 단삼은 $1000{\mu}g/mL$의 농도에서 $90\%$ 이상의 전자공여 효과를 나타내었다. 환원력도 전자공여능과 유사한 경향이었으나 BHT와 비교할 때 유의적으로 낮은 환원력을 나타내었다. 아질산염 소거능은 $500{\mu}g/mL$의 농도에서 $50\%$ 이상의 소거효과를 나타낸 시료는 꿀풀과 금물초 2종에 불과하였으며 $1000{\mu}g/mL$의 농도에서는 산조인, 산수유, 감국, 꿀풀, 금물초, 오가피, 단삼, 울금이 $50\%$ 이상의 소거효과를 나타내었다. 꿀풀의 경우 전 농도에서 다른 시료들에 비하여 유의적으로 높은 아질산염 소거효과를 나타내어 $250{\mu}g/mL$에서는 $59.62{\pm}1.573\%,\;1000{\mu}g/mL$에서는 $80.58{\pm}0.300\%$의 소거효과를 보였다.

• 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.

• 생물정신의학
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• 제4권1호
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• pp.54-59
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• 1997

Objects : Sanjoin, the seeds of Zizyphus vulgaris var. spinosus has been used as the most important hypnotic agent in chinese medicine to treat insomnia. This research was performed in order to examine the effect of betulinic acid and sanjoinine-A which are components of Sanjoin. Method : Sleeping time, sleep recordings of EEG, EMG, serum serotonin level, and locomotor activity were measured in rats which received betulinic acid and sanjoinine-A as sleep induction material extracted from Sanjoin. Results : 1) Groups received betulinic acid, sanjoinine-A, and lorazepam showed increased sleep time than control group with saline. 2) Groups with betulinic acid, sanjoinine-A, lorazepam and saline recorded ${\beta}$-wave in sleep recordings of EEG. In EMG, there was no significant difference among all groups. 3) No significant difference in serum serotonin level among all groups was found. 4) In autonomic activity testing, groups of betulinic acid, sanjoinine-A, and lorazepam showed significantly more decreased in activity than saline group. In comparison of groups of betulinic acid and sanjoinine-A with a group of lorazepam, there was no significant difference. Conclusion : These results suggest that betulinic acid and sanjoinine-A have the sedative effect like lorazepam rather than sleep effect.

• 한국약용작물학회지
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• 제10권5호
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• pp.399-402
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• 2002

50가지 식물자원을 대상으로 혈압상승을 주도하는 효소인 angiotensin converting enzyme의 저해활성을 검색하였다. 그결과 추출물농도 1mg/ml에서 50%이상의 높은 저해활성을 보인 식물은 산뽕나무, 머위, 산부추, 돌나물, 꿀풀, 쇠비름, 마가목, 복분자, 속새, 감초, 창포 등 11종으로 나타났다. 또한 1mg/ml농도에서 목단, 곰취, 도인, 길경, 만형자, 참취, 익모초, 산조인, 가래나무, 석곡, 오갈피, 목향 등 12종은 $40{\sim}49%$의 비교적 높은 ACE 억제활성을 보였다. 1mg/ml에서 $30{\sim}39%$의 억제율을 보인 식물은 백부자, 백출, 세신, 당귀, 인삼, 천궁, 치자 등이었으며 현호색, 행인, 단삼, 백작약, 두충 강활 박하, 진피, 방기, 고본, 구기자, 홍화, 포황, 음양곽, 원지등은 $10{\sim}29%$의 낮은 저해활성을 보였다. 앞으로 ACE 억제활성이 높은 식물자원의 유효성분에 대한 물질확인과 동물모델을 이용한 효능검증에 대하여 더 많은 연구가 있어야 할 것으로 사료된다.