Two new furostanol saponins from Tribulus terrestris L.

Two new furostanol saponins, tribufurosides B (1) and C (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D NMR and 2D NMR), the structures of two new furostanol saponins were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-20(22)-en-2α,3β,26-triol-3-O-β-d-galactopyranosyl(1 → 2)-β-d-glucopyranosyl(1 → 2)-β-d-galactopyranoside (1) and (25S)-5α-furost-20(22)-en-12-one-3β, 26-diol-26-O-β-d-glucopyranoside (2).     

Two new steroidal glucosides from Tribulus terrestris L.

Two new furostanol saponins, tribufurosides D (1) and E (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D, and 2D NMR), the structures of the two new furostanol saponins were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-12-one-2α,3β,22α,26-tetraol-3-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-(25R)-5α-furost-12-one-2α,3β,22α,26-tetraol-3-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (2).     

Two new steroidal saponins from Tribulus terrestris L.

Two new steroidal saponins were isolated from the fruits of Tribulus terrestris L. Their structures were elucidated by spectroscopic and chemical analysis as (23S,24R,25R)-5α-spirostane-3β,23,24-triol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (1) and (23S,24R,25S)-5α-spirostane-3β,23,24-triol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (2).     

Two new steroidal saponins from Tribulus terrestris

Two new steroidal saponins and two known flavonoid glycosides were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic analysis and chemical reaction as 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-12-one-3β,22α,26-triol-3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (1), 26-O-β-d-glucopyranosyl-(25S)-5α-furostan-22-methoxy-2α,3β,26-triol-3-O-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (2), kaempferol-3-gentiobioside (3), and isorhamnetin-3-gentiobioside (4).     

Two new furostanol saponins from Tribulus terrestris L

Two new furostanol saponins, tribufurosides B (1) and C (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D NMR and 2D NMR), the structures of two new furostanol saponins were established as 26-O-beta-d-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-2alpha,3beta,26-triol-3-O-beta-d-galactopyranosyl(1 --> 2)-beta-d-glucopyranosyl(1 --> 2)-beta-d-galactopyranoside (1) and (25S)-5alpha-furost-20(22)-en-12-one-3beta, 26-diol-26-O-beta-d-glucopyranoside (2).     

Two new furostanol saponins from the fibrous root of Ophiopogon japonicus

Two new furostanol saponins ophiopogonins J (1) and K (2) were isolated from the fibrous roots of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-14-hydroxy-furost-5,20(22)-diene 3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (1), and (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-furost-5,20(22)-diene 3-O-α-l-rhamnopyranosyl-(1 → 2)[(β-d-xylopyranosyl-(1 → 4)-β-d-glucopyranoside)] (2) on the basis of spectroscopic means including HRESIMS, 1D, and 2D NMR experiments.     

HPLC测定刺蒺藜总皂苷中的薯蓣皂苷元

目的测定刺蒺藜总皂苷水解后薯蓣皂苷元的含量。方法采用ELSD-HPLC法,并考察其方法学。结果薯蓣皂苷元39.68~942μg.ml-1与峰面积的线性关系良好,方法具有较好的精密度、稳定性、重复性和较高的回收率。结论所建方法准确、简便、易行,可作为刺蒺藜总皂苷的质量控制指标。     

18个不同产地蒺藜药材中蒺藜皂苷元的HPLC含量测定

目的采用HPLC法测定蒺藜中蒺藜皂苷元(25R-Spirostan-4-ene-3,12-dione)的含量。方法采用色谱柱Welch Ultimate LP-C18(250 mm×4.6 mm,5μm);流动相:甲醇-水(80∶20);检测波长:203 nm;柱温:30℃;流速:1.0 m L/min;进样量:20μL。结果蒺藜皂苷元对照品在0.82~7.38μg与峰面积呈良好的线性关系(r=0.999 7),平均回收率为99.3%,RSD=1.67%(n=6)。结论所建立的方法灵敏、准确、重复性好,可用于蒺藜药材的含量测定。18个产地的蒺藜样品中以内蒙产的蒺藜皂苷元含量最高。     

蒺藜果实化学成分研究

目的 对蒺藜果实化学成分进行研究。方法 聚酰胺柱及硅胶柱色谱分离，光谱分析鉴定结构。结果 分离得到了5个化合物，鉴定为支脱皂苷元（Ⅰ）、海柯皂苷元（Ⅱ）、25R-螺甾-4-烯-3，12-二酮（Ⅲ）、酵母甾醇（Ⅳ）、7α-羟基谷甾醇-3-O-β-D葡萄糖苷（Ⅴ）。结论 化合物Ⅳ、Ⅴ在本植物中首次分离获得。     

Potential nephrotoxic effects produced by steroidal saponins from hydro alcoholic extract of Tribulus terrestris in STZ-induced diabetic rats

Abstract

Chronic hyperglycemia leads to the development of microvascular complications like diabetic nephropathy. The present study investigated the potential effects of the hydroalcoholic extract of Tribulus terrestris, a plant of Zygophyllaceae family, on the renal complications in streptozotocin (STZ)-induced diabetic rats. Diabetes was induced by administering STZ (90?mg/kg) to the 2-days old neonates. After 6 weeks of induction, diabetic rats were treated with 50?mg/kg hydroalcoholic extract of T. terrestris for 8 weeks. The anti-hyperglycaemic nature was confirmed by reduction in blood glucose and improvement in insulin levels. Diabetic renal injury associated with decrease in total proteins and albumin levels was observed to be improved by T. terrestris extract. Glomerular filtration rate along with inflammatory and growth factors, adiponectin and erythropoietin were also improved by the treatment, though the findings were not significant. However, the beneficial antidiabetic effects of T. terrestris extract in plasma were not observed in kidney histopathology. This was confirmed by the quantitative estimation of unhydrolyzed fraction of saponins (major component: protodioscin) in plasma and kidney samples of normal and diabetic rats. Hence, it can be concluded that 8 weeks treatment with T. terrestris extract produces potential toxic effects in kidney, which are independent of its anti-diabetic action.     

高效液相色谱法-蒸发光散射检测器测定蒺藜中蒺藜新苷的含量

目的:建立蒺藜中蒺藜新苷的含量测定方法。方法:应用高效液相色谱法-蒸发光散射检测器,Supelco C18色谱柱(250mm×4.6mm,10μm),乙腈-甲醇-水(30:10:60)为流动相,流速为1.0 mL·min-1,Sedex蒸发光散射检测器参数:漂移管温度41℃,压力2.2×105 Pa。测定了蒺藜中蒺藜新苷的含量。结果:蒺藜新苷在3.988-13.96μg范围内有良好线性关系,r=0.9995(n=6)。蒺藜新苷的平均回收率为97.5％(n=6)。结论:该方法快速简便,灵敏、准确,可用于蒺藜药材中蒺藜新苷的含量测定。     

蒺藜果实中甾体皂苷类成分研究

目的研究蒺藜（Tribulus terrestrisL.）果实的皂苷类化合物。方法利用硅胶柱色谱、凝胶柱色谱、中低压色谱、高效液相色谱等手段进行分离,根据理化性质及波谱数据鉴定结构。结果从蒺藜果实中得到4个已知化合物,分别鉴定为（25R）-2α,3β-二醇-5α-螺甾烷-12-酮（门诺皂苷元）-3-O-{β-D-吡喃葡萄糖基-（1→2）-[β-D-吡喃木糖基-（1→3）]-β-D-吡喃葡萄糖基-（1→4）-β-D-吡喃半乳糖苷}（1）、26-O-β-D-吡喃葡萄糖基-（25R）-5α-呋甾-22-甲氧基-2α,3β,26-三醇-3-O-β-D-吡喃葡萄糖基-（1→2）-β-D-吡喃葡萄糖基-（1→4）-β-D-吡喃半乳糖苷（2）、海柯皂苷元-3-O-{β-D-吡喃葡萄糖基-（1→2）-[β-D-吡喃木糖基-（1→3）]-β-D-吡喃葡萄糖基-（1→4）-β-D-吡喃半乳糖苷}（3）、26-O-β-D-吡喃葡萄糖基-（25R）-5α-呋甾-12-羰基-20（22）-烯-3β,26-二醇-3-O-β-D-吡喃葡萄糖基-（1→4）-β-D-吡喃半乳糖苷（4）。结论化合物1和2为首次从该属植物中分离得到,化合物4为首次得到的25位R构型的甾体皂苷类单体化合物。     

蒺藜果实的化学成分研究

目的研究蒺藜果实中的化学成分。方法利用硅胶柱色谱、凝胶柱色谱、高效液相色谱等手段进行分离,根据理化性质及波谱数据鉴定结构。结果与结论从蒺藜果实的乙酸乙酯萃取液中分离得到7个已知成分,分别鉴定为棕榈酸单甘油酯（1）、琥珀酸（2）、香草酸（3）、3-羟基-豆甾-5-烯-7-酮（4）、4-ketopinoresinol（5）、蒺藜酰胺（6）、N-反式咖啡酰基对羟基苯乙胺（7）。化合物1-5为从该植物中首次分离得到。     

蒺藜挥发性成分的GC-MS分析

目的:为蒺藜的开发利用提供试验依据。方法:利用水蒸气蒸馏法提取蒺藜的挥发性成分,采用气相色谱-质谱(GC-MS)联用技术对挥发性成分进行分析,用峰面积归一化法测定各化学成分的质量分数。结果:共分离出64个化学成分,鉴别出其中54个,占挥发油总量的96.920%。主要成分有(E,E)-2,4-癸二烯醛(9.156%)、香芹烯(7.951%)、反式-茴香烯(7.625%)、肉桂酸乙酯(6.687%)、己醛(5.846%)、α-松油醇(4.457%)、科绕魏素(4.050%)、2-戊烷基-呋喃(3.529%)、(E)-2-庚烯醛(3.507%)、芳樟醇(3.312%)、2,4-癸二烯醛(3.058%)。结论:该试验可为蒺藜的综合利用提供科学依据。     

蒺藜皂苷对阿霉素损伤心肌细胞的保护作用

 观察蒺藜皂苷 (gross saponins of Tribulus terrestris, GSTT) 对阿霉素 (adriamycin, ADR) 诱导大鼠乳鼠心肌细胞损伤的保护作用, 并初步探讨其作用机制。分离出生1～3 d大鼠心肌细胞, 培养72 h后随机分为正常对照组、ADR (终浓度为2.0 mg·L⁻¹) 模型组和GSTT (100、30及10 mg·L⁻¹) 组, 继续培养24 h后, 应用MTT比色法检测细胞存活率, 测定培养基中肌酸激酶 (CK)、乳酸脱氢酶 (LDH)、天门冬氨酸氨基转移酶 (AST) 释放量, 超氧化物歧化酶 (SOD) 活性, 丙二醛 (MDA)、一氧化氮 (NO) 含量, 并采用流式细胞仪检测细胞凋亡及应用Western blotting检测GSTT对凋亡相关蛋白caspase-3的作用。结果表明, 与正常对照组比较, ADR模型组心肌细胞存活数明显减少, 心肌细胞培养液中CK、LDH、AST释放量增加 (P < 0.01, P < 0.001), 同时SOD活力下降 (P < 0.01) 而MDA、NO含量升高 (P < 0.001); 与ADR模型组比较, GSTT (100和30 mg·L⁻¹) 组存活心肌细胞数增多 (P < 0.05, P < 0.001), 心肌细胞培养液中CK、LDH、AST含量明显降低, SOD活力增加、MDA和NO含量降低 (P < 0.05, P < 0.01, P < 0.001)。流式细胞仪检测GSTT (100和30 mg·L⁻¹) 组心肌细胞凋亡数明显减少 (P < 0.05, P < 0.01), caspase-3含量下降 (P < 0.05, P < 0.001)。GSTT对ADR损伤的心肌细胞具有保护作用, 可减轻心肌细胞损伤, 抑制心肌细胞凋亡, 其机制与抗自由基作用有关。     

Two new furostanol saponins from the seeds of Trigonella foenum-graecum

Two new furostanol saponins, together with two known steroidal saponins, were isolated from the seeds of Trigonella foenum-graecum L. The structures of the new compounds were determined by detailed analysis of 1D NMR, 2D NMR, MS spectra and chemical evidences as 26-O-β-d-glucopyranosyl-(25S)-5-en-furost-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranosyl-(1 → 4)]-β-d-glucopyranoside (1) and 26-O-β-d-glucopyranosyl-(25R)-5-en-furost-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranosyl-(1 → 4)]-β-d-glucopyranoside (2).     

蒺藜总皂苷抗动脉血栓形成的作用

目的:研究蒺藜总皂苷对小鼠颈总动脉血栓形成的影响。方法:以120,240,480 mg·kg^-1剂量的蒺藜总皂苷连续灌胃小鼠10 d,利用三氯化铁诱导的小鼠颈总动脉血栓模型,采用激光多普勒血流仪监测血栓形成时间和血流变异性,应用小室灌流法和比浊法检测血小板黏附和聚集功能。结果:蒺藜总皂苷可以显著延长血栓形成时间,降低血流变异性,减少血小板在胶原蛋白表面上的黏附面积,降低二磷酸腺苷诱导的血小板最大聚集率。结论:蒺藜总皂苷具有抗动脉血栓形成的作用,机制可能与其抑制血小板黏附和聚集功能有关。     

HPLC法测定蒺藜中总黄酮的含量

目的建立测定蒺藜中总黄酮含量的高效液相色谱法。方法以槲皮素、山柰素、异鼠李素为对照品,色谱条件:ODS柱(150 mm×4.6 mm,5μm),流动相为甲醇:0.4磷酸(v/v)45∶55,检测波长为360 nm。结果槲皮素、山柰素、异鼠李素回收率试验的RSD分别为1.59%、0.98%、1.42%。结论本方法简便易行,适用于蒺藜总黄酮的含量测定。     

Two novel furostanol saponins from Ophiopogon japonicus

Two novel furostanol saponins were isolated from the fresh tubers of Ophiopogon japonicus. Comprehensive spectroscopic analysis allowed the chemical structures of the compounds to be assigned as (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-β-d-xylopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (1, ophiopogonin F) and (25R)-26-[(O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-β-d-xylopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (2, ophiopogonin G). The rare furostanol saponins with two glucosyl residues at C-26 position were isolated from the natural source for the first time.     

蒺藜药材HPLC指纹图谱研究

目的采用高效液相法建立蒺藜药材的指纹图谱,以控制其质量。方法用反相高效液相色谱(RP-HPLC)-ELSD法测定蒺藜的指纹图谱,并根据向量夹角法计算相似度,进行比较分析。结果初步建立了蒺藜药材的指纹图谱。结论HPLC指纹图谱法重现性好,可作为控制蒺藜药材内在质量的标准。