鲜盾叶薯蓣中原始皂甙的分离与鉴定

从盾叶薯蓣(Dioscorea zingiberensis Wright)新鲜根茎的甲醇提取物分离到薯蓣皂甙元棕榈酸酯(diosgenin palmitate)、β-谷甾醇(β-sitosterol)、纤细皂甙(gracillin)、原纤细皂甙(protogracillin)和原盾叶皂甙(protozingiberemissaponin),后者为一新甾体皂甙,结构推定为3-O-{α-L-鼠李吡喃糖(1→3)-[β-D-葡萄吡喃糖(1→2)]-β-D-葡萄吡喃糖}-26-O-{β-D-葡萄吡喃糖}-薯蓣皂甙元(3-O-{α-L-rhamnopyran0syl(1→3)-[β-D-glucopyranosyl(1→2)]-β-D-glucopyranosyl}-26-O-{β-D-glucopyranosyl}-diosgenin)。     

浙江山萆薢甾体皂甙的研究

从山萆薢根茎分到6个甾体皂甙,通过乙酰化、酸水解,红外、质谱和碳谱等鉴定,分别为约诺皂甙(A),薯蓣皂甙(C),纤细皂甙(D),原薯蓣皂甙(E),原纤细皂甙(F);皂甙 B 因得率极低,未能完成鉴定。     

盾叶薯蓣灭钉螺活性成分的研究

盾叶薯蓣根茎正丁醇提取物呈现显著的灭钉螺活性。由生物活性引导法分离得到两种具有灭钉螺活性的甾体皂甙,经化学和光谱方法分析,确定它们为纤细皂甙和盾叶皂甙Ａ。其中,纤细皂甙７２ｈ灭钉螺率为９８％（５ｍｇ／Ｌ）,盾叶皂甙Ａ７２ｈ灭钉螺率为９６％（５ｍｇ／Ｌ）。首次报道了灭钉螺活性。     

薯蓣皂甙元氨基酸酯的合成及其动物实验--薯蓣皂甙元衍生物的研究Ⅱ

以薯蓣皂甙元为原料,经过与氨基酸缩合,合成了6个新化合物,甘氨酸薯蓣皂甙元酯(1),DL-组氨酸薯蓣皂甙元酯醋酸盐(2),L-赖氨酸薯蓣皂甙元酯(3),N-L-赖氨酰基甘氨酸薯蓣皂甙元酯醋酸盐(4),N-L-精氨酰基甘氨酸薯蓣皂甙元酯醋酸盐(5),N-DL-组氨酰基甘氨酸薯蓣皂甙元酯醋酸盐(6),并对结构进行了鉴定。同时发现这6个化合物具有抗大鼠实验性心肌梗死作用。     

龙血树果实的甾体皂甙成分

从龙血树(Dracaena cambodiana Pierre et Gagn.)的新鲜果实中分离到四个甾体皂甙,分别鉴定为薯蓣皂甙(dioscin)、22-甲基原薯蓣皂甙(22-methy proto-dioscin),纤细薯蓣皂甙(gracillin)和22-甲基原纤细薯蓣皂甙(22-methy proto-gracillin),龙血树中富含薯蓣皂甙元(diosgenin)的配糖体表明龙血树科作为天门冬目的一个成员,在亲缘关系上与龙舌兰科和天门冬科最为接近,与玉簪科、菝葜科以及薯蓣目亦有密切的联系。     

薯蓣皂甙元ELISA定量分析方法的建立Ⅰ-薯蓣皂甙元全抗原的合成

建立薯蓣皂甙元的ELISA定量分析方法必须先合成薯蓣皂甙元的全抗原。试验利用薯蓣皂甙元3位上的-OH,在DMAP的催化下,薯蓣皂甙元与丁二酸酐反应,生成薯蓣皂甙元丁二酸单酯,用MSI、R1、H NMR1、3CNMR等方法对产物结构进行了表征。用混合酸酐法制备薯蓣皂甙元与牛血清白蛋白的结合物(DG-HS-BSA),碳二亚胺法制备薯蓣皂甙元与卵清蛋白的结合物(DG-HS-OVA),经TNBS测定,每分子结合物连接的薯蓣皂甙元分子数分别为28.0和8.8。     

薯蓣皂甙元生产工艺研究进展

薯蓣皂甙元是一种重要的医药原料,本文阐述了薯蓣皂甙元生产过程中发酵时间,温度,酶预处理和水解的酸浓度,压力,时间对薯蓣皂甙元产率的影响,对其中的提取分离工艺废水的处理工艺进行了综述,并对薯蓣皂甙元生产工艺存在的问题和前景进行了分析。     

薯蓣皂甙元丁二酸单酯氨基酸盐的合成及其动物实验——薯蓣皂甙元衍生物的研究I

以薯蓣皂甙元丁二酸单酯为原料,经过与氨基酸缩合,合成了5个新化合物,4—L—(N—丁二酸—2—基)胺基—4—氧代丁酸薯蓣皂甙元酯二钠盐(1),4—(N—乙酸—2—基)胺基—4—氧代丁酸薯蓣皂甙元酯钠盐(2),4—L(N—(5—胍基)戊酸—2—基)胺基—4—氧代丁酸薯蓣皂甙元酯醋酸盐(3),4—(N—(3—咪唑-4—基)丙酸—2—基)胺基—4—氧代丁酸薯蓣皂甙元酯醋酸盐(4),4—(N—戊二酸—2—基)胺基—4—氧代丁酸薯蓣皂甙元酯二钠盐(5),并对其进行了结构鉴定,同时发现这5个化合物对大鼠都具有抗心肌梗死活性。     

盾叶薯蓣中薯蓣皂甙元不同提取方法的比较

为提高盾叶薯蓣(Dioscorea zingiberensis C.H.Wright)中薯蓣皂甙元得率,在实验室条件下,以薯蓣皂甙元含量为评价指标,采用4因素4水平的正交试验,用高效液相色谱法对16种提取方法所得的薯蓣皂甙元含量进行了比较分析.结果表明,硫酸的浓度对薯蓣皂甙元含量有极显著影响,在实验室条件下,可采用10 g样品加2.0mol·L-1硫酸200 mL水解4 h,水解物用石油醚回流提取5 h,能快速准确提取盾叶薯蓣中的薯蓣皂甙元.     

盾叶薯蓣中薯蓣皂甙元提取新工艺的研究

为研究新工艺提取盾叶薯蓣薯蓣中薯蓣皂甙元的最佳实验指标,以薯蓣皂甙元得率为评价参数,采用6因素5水平的正交实验,用分光光度法对25种提取方法所得到的薯蓣皂甙元进行比较分析。结果表明,硫酸浓度对薯蓣皂甙元提取的影响最大,在实验室条件下,可采用20g样品加甲醇回流提取4h,回流速度为10min／次,用2．5mol／L的硫酸水解6h,120号溶剂汽油回流提取2h,回流速度为15min／次,能清洁快速提取盾叶薯蓣中的薯蓣皂甙元。     

The Identification and Isolation of Steroidal Saponin from Dioscorea gracillima Miq.

Two trisaecharides of diosgenin (A, B) had been isolated from the rhizome of Dioseorea gracillima Maq. (collected from Jiangsi, Lu Shan). By means of acetylafion, acid hydrolysis, IR, MS and 13C-NMR etc. saponin A and saponin B were identifieated as dioscin and gracillin, respectively. Its yieldingratio is 3:1 (A:B).     

Identification and Isolation of Steroidal Saponins of Dioscorea zingiberensis Wright

Two diosgenin trisaccharides (A,B) and two furostanolic tetrasacharides of diosgenin (C, D) had been isolated from Dioscorea zingiberensis wright. By means of acetylation, acid hydrolysis, enzymolysis, IR, MS, 1H-NMR and 13C-NMR, saponin A was proved to be a new compound of structure: diosgenin-3-O- [ β-D-glucopyranosyl (1 → 2) ]-O- [ α-L-rhamnopyra- nosyl (1→3)]-O-β-D-glucopyranoside was provisionally named zingiberenin A; saponin B may be suggested as the steric isomer of gracillin; saponin C was identified as 26-O-β-D- glucopyranoside of A and saponin D as 26-O-β-D-glucopyranoside of B. The last two components named proto-zingiberenin A and proto-zingiberenin B respectively.     

Study on the Structure of a New Triterpene Saponin B from Polygala japoniea Houtt

A new triterpene saponin B has been isolated from the earial parts of Polygala japonica Houtt in folk-lore medicine. Its molecular: C48H78O20, m.p. 199–202℃, [α]D23+30.0 (C, 0.5, CH3OH). Acidic hydrolysis of this saponin gave a sapogenin (2α, 3α, 24-tri-hydroxyolean-12-ene-28-oic acid) and D-glucose. The structure of saponin B was elucidated as 28-O- [β-D-glucopyranosyl (1→2) -β-D-glucopyranosyl (1→2) -β-D-glucopy- ranosyl] 2α, 3α, 24-trihydroxyolean-12-ene-28-oic acid mainly by 13C-NMR, MS and some chemical transfomations.     

Two new triterpene saponins from the anti-inflammatory saponin fraction of Ilex pubescens root

The saponin fraction from the ethanolic extracts of the root of Ilex pubescens Hook. et Arn. (Ilexaceae) was found to exhibit potent anti-inflammatory effects on carrageenan-induced paw edema in rats. Two novel triterpene saponins, pubescenosides C and D (1 and 2, resp.), together with five known saponins were isolated from this saponin fraction. The structures of 1 and 2 were elucidated as (20beta)-3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa-12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, and (20beta)-3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa- 12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, respectively, on the basis of chemical and spectroscopic data. Five known saponins isolated from the saponin fraction were identified as ilexsaponin B(1), B(2), B(3), A(1), and chikusetsusaponin IV(a).     

Molluscicidal saponins from Gundelia tournefortii

From the roots of Gundelia tournefortii seven saponins have been isolated mainly by DCCC. The main saponins (A and B) were characterized, mainly by ¹³C and ¹H NMR spectroscopy, as oleanolic acid 3-O-(2-[α-l-arabinopyranosyl(1 → 3) -β-d-gentiotriosyl(1 → 6) -β-d-glucopyranosyl]gb-d-xylopyranoside) (saponin A) and oleanolic acid 3-O-(2-[α-l-arabinopyranosyl] (1 → 3)-β-d-gentiobiosyl (1 → 6)-β-d-glucopyranosyl β-d-xylopyranoside) (saponin B). The other saponins are also derived from oleanolic acid and contain more sugar units. The saponin mixture and the saponins A and B possess strong molluscicidal activity against the schistosomiasis transmitting snail Biomphalaria glabrata.     

Comparative studies of acidic and enzymatic hydrolysis for production of soyasapogenols from soybean saponin

Abstract

Soyasapogenols, aglycones of soyasaponins, can be produced from crude soybean saponin extract by acid or enzymatic hydrolysis. Soyasapogenol B is known to have hepatoprotective, antimutagenic, antivirus, and anti-inflammatory activities. Hydrolysis of soyabean saponin extract for 72 h with 2 M HCl in methanol gave three soyasapogenols, namely: soyasapogenol D, soyasapogenol B₁ and soyasapogenol A. However, the microbial hydrolysis of soybean saponin extract by Aspergillus terreus led to isolation of soyasapogenol B as a major product. A systematic evaluation of the effect of key operational parameters on the microbial transformation was performed. Maximum production of soyasapogenol B (about 152.3 mg/50ml) was observed using 1.5% (w/v) soybean saponin and 1.5% (w/v) glucose, 32°C after 72 h at pH 7 using phosphate buffer. Under these optimal conditions, the cells’ bioconversion efficiency increased from 20.5 to 85.3%. The isolation of soyasapogenols was performed using chromatographic methods and their structures identified on the basis of spectroscopic tools.     

Optimization of cell permeabilization for multiparametric flow cytometric analysis with lectin staining

BACKGROUND: This study was undertaken in mice to develop a reproducible procedure of cell permeabilization, allowing intracellular protein staining by immunofluorescence (i.e., Bcl-2) without losing surface labeling especially for lectins (i.e., B220 and peanut agglutinin [PNA]). This article reports results obtained with different permeabilization protocols. METHODS: Lymphoid cells were extracted and prepared from Peyer's patches and spleen. After surface labeling using anti-B220-Cy-chrome and PNA-biotin/streptavidin-phycoerythrin, we comparatively tested three permeabilization protocols: saponin 0.3%, methanol 70%, and the commercial kit Dako Intrastain. Final Bcl-2 staining was performed and cells were analyzed by flow cytometry. RESULTS: With 0.3% saponin as the permeabilization reagent, a significant loss of lectin labeling was observed when comparing mono PNA and triple (i.e. , B220-PNA-Bcl-2) staining (74.8% and 22.5% positive cells, respectively). Quality of PNA staining was conserved with Intrastain when comparing multiparametric versus monoparametric stainings (82. 4% of positive cells versus 78.3%, respectively). Intrastain preserved scatter characteristics (69.9% of total cells in the lymphocyte gate with Intrastain versus 13.7% with saponin 0.3% and 20.9% with methanol 70%). This protocol has been used for a preliminary multiparametric analysis in order to quantify Bcl-2 expression in PNA/B220-positive cells. CONCLUSION: This protocol may be useful to assess simultaneously lectin cell surface labeling and intracellular target staining.     

Fungicidal properties of two saponins from Capsicum frutescens and the relationship of structure and fungicidal activity

Two steroidal saponins have been purified from cayenne pepper (Capsicum frutescens). Both have the same steroidal moiety but differ in the number of glucose moieties: the first saponin has four glucose moieties (molecular mass 1081 Da) and the second contains three glucose moieties (molecular mass 919 Da). Solubility in aqueous solution is less for the saponin containing three glucose moieties than for the one containing four glucose moieties. The larger saponin was slightly fungicidal against the nongerminated and germinating conidia of Aspergillus flavus, A. niger, A. parasiticus, A. fumigatus, Fusarium oxysporum, F. moniliforme, and F. graminearum, whereas, the second saponin (molecular mass 919 Da) was inactive against these fungi. Results indicate that the absence of one glucose molecule affects the fungicidal and aqueous solubility properties of these similar molecules.     

异柱五加叶中齐墩果烷型皂苷的研究(英文)

利用柱色谱从异柱五加 (Acanthopanax sieboldianus forma albeofolium Yook) 叶的甲醇提取液中分离出四个齐墩果烷型皂苷类化合物.通过波谱方法(1H NMR、13C NMR、2D NMR和FAB-MS)鉴定它们分别为kalopanax-saponin B (1)、acanthopanax saponin CP3(2)、kalopanax-saponin A (3) 和sieboldianoside A (4).     

Comparison of saponin composition and content in wild soybean (Glycine soja Sieb. and Zucc.) before and after germination

Eight wild soybean accessions with different saponin phenotypes were used to examine saponin composition and relative saponin quantity in various tissues of mature seeds and two-week-old seedlings by LC–PDA/MS/MS. Saponin composition and content were varied according to tissues and accessions. The average total saponin concentration in 1?g mature dry seeds of wild soybean was 16.08?±?3.13?μmol. In two-week-old seedlings, produced from 1?g mature seeds, it was 27.94?±?6.52?μmol. Group A saponins were highly concentrated in seed hypocotyl (4.04?±?0.71?μmol). High concentration of DDMP saponins (7.37?±?5.22?μmol) and Sg-6 saponins (2.19?±?0.59?μmol) was found in cotyledonary leaf. In seedlings, the amounts of group A and Sg-6 saponins reduced 2.3- and 1.3-folds, respectively, while DDMP?+?B?+?E saponins increased 2.5-fold than those of mature seeds. Our findings show that the group A and Sg-6 saponins in mature seeds were degraded and/or translocated by germination whereas DDMP saponins were newly synthesized.