Gleditsia saponins.

The chemical structure of gleditsia saponin C (GS-C), a major triterpenoid saponin of the fruit capsule of GLEDITSIA JAPONICA M IQ. (Leguminosae), comprised echinocystic acid, eight sugar units and two monoterpenyl groups ((+)2,6-dimethyl- and (+) 2-hydroxymethyl-6-methyl-6-(S)hydroxy-2- TRANS-2,7-octadienoyl groups). Methylation analysis of GS-C followed by determination with gas-liquid chromatography and mass spectrometry showed that the monoterpenyl moieties attach to the 2 and 3-positions of terminal L-rhamnose of the C-28 oligoside portion.     

Three triterpenoid saponins acylated with monoterpenic acid from Gymnocladus chinensis

A new triterpenoid saponin acylated with monoterpenic acid, together with two known triterpenoid saponins, has been isolated from the fruit of Gymnocladus chinensis Baill. Their structures were elucidated as 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[3-O-(β-D-glucopyranosyl)-4-O-((6S)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoyl)-β-L-arabinopyranosyl]-2,7-octadienoyl}-acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranosyl ester (1), gymnocladus saponin E (2), and gymnocladus saponin F(2) (3).     

In vitro anticomplementary activity of hederagenin saponins isolated from roots ofDipsacus asper

Anticomplementary activity of hederagenin and related saponins isolated from Dipsacus asper was investigated in vitro. HN saponin F (3) was most potent with IC50 value of 3.7x10(-5) M followed by 3-O-beta-D-glucopyranosyl-(1->3)-alpha-L-rhamnopyranosyl-(1->2)-beta-L-+ ++arabi nopyranosyl hederagenin 28-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyrano side (8), 3-O-beta-L-arabinopyranosyl hederagenin 28-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside (5), dipsacus saponin A (4), and hederagenin (1) on the classical pathway (CP) of complement system, while the saponins 3-5 did not show the inhibition of hemolysis and rather increase the hemolysis on the alternative pathway (AP). However, all of C-3 monodesmosides [prosapogenin CP (2), dipsacus saponin B (6), and dipsacus saponin C (7)] evoked hemolysis directly on the erythrocytes.     

Isolation of a new saponin and cytotoxic effect of saponins from the root of Platycodon grandiflorum on human tumor cell lines

A novel triterpenoid saponin, deapioplatycoside E (1) was isolated from the root extract of Platycodon grandiflorum, together with the seven known saponins 2 - 8, i. e., platycoside E (2), deapioplatycodin D3 (3), platycodin D3 (4), polygalacin D2 (5), platycodin D2 (6), deapioplatycodin D (7) and platycodin D (8). The structure of the new saponin 1 was determined on the basis of spectral analysis and chemical evidence. The crude saponin fraction (ED50: ca. 10 - 15 microg/mL) and compounds 6 - 8 (ED50: ca. 4 - 18 microg/mL) exhibited significant inhibition on the proliferation of five kinds of cultured human tumor cell lines, i. e., A549 (non-small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT-15 (colon), in vitro.     

An evaluation of the hemostatic effect of externally applied notoginseng and notoginseng total saponins

No effective hemostatic agents are available for external use. This project was conducted to evaluate the hemostatic effects of notoginseng using a hemorrhagic rat model. Rats (n = 40) were divided into four groups, and their tails were transected 5 mm from the tip. Group 1 received no treatment (control), while the other groups received external powder applied to the wound. Group 2 received placebo (flour), group 3 received ground notoginseng, and group 4 received a saponin extract of notoginseng. The total bleeding time was determined and compared between groups. The notoginseng group had lower bleeding times (9.60 +/- 1.50 min) than the control group (19.23 +/- 4.09 min, p < 0.001) or the placebo group (15.18 +/- 2.24 min, p < 0.001). Likewise, the saponin extract group had significantly lower bleeding times (11.70 +/- 2.53 min) than the control and placebo groups (p < 0.001 for both comparisons). No differences were found between the notoginseng and the saponin extract groups (p = 0.35). Notoginseng and a saponin extract from notoginseng provide hemostatic effects when applied externally.     

Clematomandshurica saponin E, a new triterpenoid saponin from Clematis mandshurica

A new triterpenoid saponin, clematomandshurica saponin E, together with four known saponins were isolated and characterized from the roots and rhizomes of Clematis mandshurica (Ranunculaceae), a commonly used traditional Chinese medicine with anti-inflammatory and antirheumatoid activities. On the basis of spectroscopic analysis, including HR-ESI-MS, IR, 1D, and 2D NMR spectral data and hydrolysis followed by chromatographic analysis, the structure of the new triterpenoid saponin was elucidated as 3-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 4)-β-D-ribopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside.     

Chemical removal of the endothelium by saponin in the isolated dog femoral artery

Chemical removal of the endothelium by saponin in the isolated dog femoral artery was investigated by comparing the relaxant responses to endothelium-dependent and -independent vasodilators of saponin-treated rings with the responses of non-treated rings. Saponin treatment was done by incubating rings with Krebs-Henseleit solution containing 0.1, 0.3 or 1 mg/ml of saponin for 45 min at 37 degrees C. In non-treated rings, acetylcholine (10(-8)-3 X 10(-6) M) caused a concentration-dependent relaxation of rings precontracted with prostaglandin F2 alpha (3 X 10(-6) M). The acetylcholine-induced relaxation was reduced in rings pretreated with 0.1 mg/ml of saponin and almost abolished with 0.3 or 1 mg/ml. Prostaglandin F2 alpha-induced contraction was suppressed weakly by treatment with 0.3 mg/ml and markedly with 1 mg/ml saponin. The treatment with 0.3 mg/ml saponin markedly reduced relaxations caused by substance P (10(-9)-3 X 10(-8) M) and by Ca2+-ionophore A23187 (10(-6) M). Relaxant responses of saponin-treated rings to nitroglycerin and to nitroprusside were almost identical with those of non-treated rings. These results showing selective suppression by saponin of the endothelium-dependent relaxation suggest that saponin removes the endothelial cells from the intimal surface of the artery, and this was confirmed by electron microscopy. The endothelium removing method with saponin seems to be useful as a pharmacological tool for vascular investigations.     

A new triterpenoid saponin from Albizia julibrissin Durazz

A new triterpenoid, saponin hehuanoside A, was isolated together with the known triterpenoid saponins 2, 3, and 4 from the stem bark of Albizia julibrissin. With the help of chemical and spectral analyzes (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new triterpenoid saponin was elucidated as 21-O-[(6S)-2-trans-2,6-dimethyl-6-O-beta-d-quinovopyranosyl-2,7-octadienoyl]-3-O-beta-d-xylopyranosyl-(1 --> 2)-beta-d-fucopyranosyl-(1 --> 6)-beta-d-2-deoxy-2-acetamidoglucopyrasyl acacic acid 28-O-alpha-l-arabinofuranosyl-(1 --> 4)-[-beta-d-glucopyranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-beta-d-glucopyranosyl ester (1). Three known triterpenoid saponins 2-4 were identified on the basis of spectroscopic data.     

A new triterpenoid saponin from Albizia julibrissin Durazz

A new triterpenoid, saponin hehuanoside A, was isolated together with the known triterpenoid saponins 2, 3, and 4 from the stem bark of Albizia julibrissin. With the help of chemical and spectral analyzes (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new triterpenoid saponin was elucidated as 21-O-[(6S)-2-trans-2,6-dimethyl-6-O-beta-d-quinovopyranosyl-2,7-octadienoyl]-3-O-beta-d-xylopyranosyl-(1 --> 2)-beta-d-fucopyranosyl-(1 --> 6)-beta-d-2-deoxy-2-acetamidoglucopyrasyl acacic acid 28-O-alpha-l-arabinofuranosyl-(1 --> 4)-[-beta-d-glucopyranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-beta-d-glucopyranosyl ester (1). Three known triterpenoid saponins 2-4 were identified on the basis of spectroscopic data.     

Quinquenoside L9 from leaves and stems of Panax quinquefolium L.

During additional chemical investigation on the saponin composition of leaves and stems of Panax quinquefolium L, a new minor dammarane saponin, quinquenoside L9 (1) has been obtained. By means of physico-chemical evidences and spectral analysis, its structure was elucidated 6-O-[alpha-L-rhamnopyranosyl-(1-2)-beta-D-glucopyranosyl]-dammara-3beta, 6beta,12beta,20(S),24zeta,25-hexaol (1).     

麻黄碱与总皂苷对豚鼠气管平滑肌松弛的协同作用

目的　探讨麻黄碱与总皂苷在平喘作用方面有无协同作用。方法　将麻黄碱与总皂苷分成麻黄碱 +总皂苷组、总皂苷组和麻黄碱组进行离体豚鼠气管平滑肌松弛作用强度比较。结果　麻黄碱 +总皂苷组直接松弛豚鼠离体气管平滑肌的作用强度是麻黄碱组的 3 5倍 (P <0 0 5 ) ,总皂苷组无作用 (P >0 0 5 )。麻黄碱 +总皂苷组对氨甲酰胆碱(carbamylcholine,CCH)引起气管平滑肌收缩反应的解痉强度与麻黄碱组相同 ,但两者都比总皂苷组强 (P <0 0 5 )。麻黄碱 +总皂苷、麻黄碱和总皂苷组预先处理气管平滑肌均呈浓度依赖抑制CCH收缩反应 ,三者之间的作用强度无差异。结论　总皂苷对麻黄碱在直接松弛气管平滑肌和抑制CCH引起的气管平滑肌收缩方面具有明显的协同作用 ,但在解痉方面的协同作用不明显     

蓣知子皂甙IV的结构

从木通科木通属植物白木通[Akebia trifoliata(Thunb.)Koidz.var.australis(Diels)Rehd]种子的乙醇提取物中以硅胶层析等方法得四种三萜皂甙。其中甙IV是新天然产物,命名为蓣知子皂甙IV(yuzhiziosideIV)。根据化学和光谱分析,确定甙IV的结构为3-O-β-D-吡喃木糖基-(1→2)-a-L-吡喃阿拉伯糖齐墩果酸-28-O-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖酯甙。另外皂甙B(I)、皂甙C(II)和皂甙D(III)为已知物。这些化合物在白木通种子中均是首次得到。     

Triterpenoid saponins from Stauntonia chinensis

A new triterpenoid saponin, named stauntoside A (1) along with four known saponins (2,3,4,5) was isolated from Stauntonia chinensis DC., (Lardizabalaceae). Their structures were elucidated by spectroscopic analysis and chemical methods as 3-O-alpha-L-arabinopyranosyl-30-norhederagenin -28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (1), 3-O-alpha-L-arabinopyranosyl-30- norhederagenin-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (2), 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-30-norhederagenin-28-O-alpha-L- rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (3), 3-O-alpha-L- arabinopyranosyl-hederagenin-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D- glucopyranosyl ester (4), 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-hederagenin -28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (5). The (1)H and (13)C NMR data for Glycoside L-G1 or Sinofoside A are paradox in the reported before. Thus, the structure elucidation of saponin 2, known as Glycoside L-G1 or Sinofoside A, was discussed and the unambiguous assignments were given.     

刺楸根皮中皂甙的化学成分研究

从刺楸Kalopanox septemlobus(Thunb.)Koidz.根皮中,分离到两个皂甙单体。经光谱(IR,NMR,FAB-MS)分析和化学方法鉴定为刺楸皂甙A(kalopanax saponin A,Ⅰ)和一新的三萜皂甙,结构为3-O-(a-L-吡喃鼠李糖(1→2)-α-L-吡喃阿拉伯糖)-常春藤皂甙元-28-O-[α-L-吡喃鼠李糖(1→2)-β-D-吡喃葡萄糖(1→6)-β-D-葡萄糖]酯甙,命名为刺楸皂甙C(kalopanax saponin C,Ⅱ)。     

Triterpenoidal saponins from the leaves ofKalopanax pictum var.chinense

One new triterpenoidal bisdesmoside, saponin C (3) were isolated from the leaves ofKalopanax pictum var.chinense along with two known saponins, saponin B (2, sapindoside C) and saponin A (1, sapindoside B). On the basis of chemical and spectral evidences, the structure of a new triterpenoidal saponin has been elucidated to be 3-O-β-D-glucopyranosyl(1→4)-β-D-xylopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-23-hydroxyolean-12-en-28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester.     

薤中抗凝和抗癌活性成分的结构鉴定

从百合科葱属植物薤(Alium chinense)鳞茎的抗凝和抗癌活性部位中,分离得到了6个化合物。经过化学方法和光谱分析(IR,EI-MS,¹HNMR,¹³HNMR,¹H-¹HCOSY,HMBC,HMQC和NOESY谱),鉴定它们的结构分别为(25R,S)-5α-spirostane-3β-ol 3-O-｛β-D-glucopyranosyl-(1→2)-[β-D-glucopyra-nosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside｝(1),(25R,S)-5α-spirostane-3β-ol 3-O-｛β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)](6-acetyl-β-D-glucopyranosyl)-(1→4)-β-D-galac-topyranoside｝(2),(25R,S)-5α-spirostane-2α,3β-diol3-O-｛β-D-glucopyranosyl-(1→2)-O-β-D-glucopyra-nosyl-(1→4)-β-D-galactopyranoside｝(3),(25S)-24-O-β-D-glucopyranosyl 3β,24β-dihydroxy-5α-spirost-3-O-α-arabinopyranosyl-(1→6)-β-D-glucopyranoside(4),chinenosideI(5)及2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-3-carboxylicacid(6)。化合物4为一新的甾体皂甙,命名为chinenosideVI。化合物1～3为3对甾体皂甙差向异构体。其中,化合物2的25S型异构体为首次报道;25R型异构体和化合物6为首次从本种植物中分得。此外,通过NOESY谱还首次确定了化合物6的相对构型,并对其C和H信号进行了确切归属。     

A triterpenoid saponin from Albizia julibrissin

A triterpenoid saponin (1) was obtained from the stem barks of Albizia julibrissin Durazz. Its structure was elucidated as 3-O-[beta-D-xylopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-beta-D-glucopyranosyl]-21-O-[(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-beta-D-quinovopyranosyl-2, 7-octadienoyl]-16-deoxy-acacic acid 28-O-beta-D-glucopyranosyl-(1 --> 3)-[alpha-L-arabinofuranosyl-(1 --> 4)]-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl ester (1), named as Julibroside J26, based on the chemical and spectral methods.     

Two new prosapogenins from Albizia adianthifolia

Two new triterpenoidal prosapogenins 1 and 2 were obtained from the mild alkaline hydrolysate of the crude saponin fraction of Albizia adianthifolia (Mimosaceae) roots. Their structures were mainly determined by spectral analyses as acacic acid 3-O-beta-D-xylopyranosyl-(1-->2)-beta-D-fucopyranosyl-(1-->6)- 2-acetylamino-2-deoxy-beta-D-glucopyranoside (1) and acacic acid 3-O-(beta-D-xylopyranosyl-(1-->2)-beta-D-fucopyranosyl-(1-->6)- [beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl)-21-O-(6(S)-2- hydroxymethyl-6-methyl-6-O-(beta-D-quinovopyranosyl)-2,7-octadienoyl) ester (2). Furthermore, the known julibroside A3 was isolated from the crude saponin mixture. Compounds 1 and 2 did not show any ability to potentiate in vitro cisplatin cytotoxicity in a human colon cancer cell line.     

Triterpenoidal saponins from the bark ofKalopanax pictum var.typicum

One new triterpenoidal saponin, saponin F(2) has been isolated from the bark of Kalopanax pictum Nakai var. typicum (Araliaceae), together with one known saponin, kizuta saponin K12 (1). On the basis of chemico-spectral evidences, the structure of 2 has been elucidated to be 3-O-beta-D-xylopyranosyl(1-->3)-alpha- L-rhamnopyranosyl(1-->2)-alpha- L-arabinopyranosyl-23-hydroxyolean-12-en-28-O-alpha-L- rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosy l ester.     

A new ergostanol saponin from Dioscorea deltoidea Wall var. orbiculata

From the fresh rhizomes of Dioscorea deltoidea Wall var. orbiculata , a novel ergostanol saponin, orbiculatoside A ( 1 ), was isolated and identified as 3- O - β- d -glucopyranosyl-ergost-5-ene-3 β, 26-diol-26- O - β- d -glucopyranosyl(1 →3)-[ β- d -glucopyranosyl(1 →2)- β- d -glucupyranosyl(1 →6)]- β- d -glucopyranoside by various NMR techniques in combination with chemical methods. The new saponin showed strong activity against Pyricularia oryzae , with a MMDC (minimum morphological deformation concentration) value of 28.04 μmol/l and was cytotoxic to cancer cell line K562, HCT-15, A549, HT1080, and A2780a in vitro .