Physiological functions of solanaceous and tomato steroidal glycosides

Solanaceous plants are widely distributed. They are used as food and in folk medicine. Our studies focused on these plants, starting with Solanum lyratum and S. nigrum, which are used as anti-cancer and anti-herpes agents. Extensive investigations in 45 Solanum plant species revealed that a considerable amount of glycosides such as spirosolane, solanidane, spirostane and furostane is in these plants, and some of the isolated glycosides showed strong anti-proliferative activity against various cancer cell lines and anti-herpes activity. Furthermore, we have discovered a few new hypothetical biosynthetic routes in which the pathways for the biosynthesis of 16-acyl-pregnane and pregnane glycosides were the most interesting. The occurrence of these pregnane compounds indicates that they might be internally biosynthesized in the plant from furostanol glycosides by a reaction that is similar to Marker degradation. Furthermore, this may imply that the administration of steroidal glycosides may result in their metabolization into pregnane derivatives possessing various activities. In order to perform metabolic experiments using the steroidal glycosides, we recently isolated tomato glycosides from ripe tomato fruits for the first time. For this experiment, we examined the metabolites in urine obtained from persons that consumed tomatoes. We obtained androstane derivatives that were probably metabolized via pregnane derivatives from tomato glycoside. Hence, when a steroidal glycoside is administered, it may be metabolized into a type of steroidal hormone with various physiological activities.     

Chromone and flavonol glycosides from <Emphasis Type="Italic">Delphinium hybridum</Emphasis> cv. “Belladonna Casablanca”

One new chromone and six known flavonol glycosides were isolated from the stems and leaves of Delphinium hybridum cv. “Belladonna Casablanca” (Ranunculaceae). The new chromone glycoside was elucidated as 2-methyl-chromone-5,7-diol 7-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (1). The six known flavonol glycosides were designated as compounds 2–5, being kaempferol-type glycosides, and compounds 6 and 7, being quercetin-type glycosides. The structures of these glycosides were determined by two-dimensional nuclear magnetic resonance (2D NMR) spectroscopic analysis and chemical evidence.     

大黄总甙、大黄素、番泻甙对不全梗阻后小鼠离体小肠葡萄糖-钠转运电位的影响

本实验采用记录翻转小鼠离体小肠囊葡萄糖－钠转运电位的方法，观察大黄总甙、大黄素、番泻甙对在全梗阻后小肠葡萄糖－钠吸收的影响。结果发现大黄有效成分对葡萄糖－钠转运电位产生明显抑制作用。表明这些成分可阻止不全梗阻后小肠葡萄糖－钠的吸收，并伴随水的吸收减少，使肠腔容积增大，进而使肠蠕动增强，亦可产生通里攻下的作用。这一结果可为进一步阐明大黄治疗不完全性肠梗阻的机理提供新的理论依据。     

6种黄酮化合物对大鼠肝星状细胞胶原合成的抑制作用

目的：研究黄颜木素、槲皮素、芹菜素、根皮素、橙皮素和查尔酮对血清、巨噬细胞培养上清液和转化生长因子β1刺激的大鼠肝星状细胞HSC—T6胶原合成的影响。方法：^3H-脯氨酸掺入法测定细胞胶原合成。结果：黄颜木素、槲皮素、芹菜素、根皮素、橙皮素和查尔酮（12．5～50μmol／L）以浓度依赖方式抑制血清、巨噬细胞上清和转化生长因子β1诱导的胶原合成。结论：黄颜木素、槲皮素、芹菜素、根皮素、橙皮素和查尔酮具有抑制肝星状细胞胶原合成的作用，可能具有潜在的肝纤维化治疗作用。     

银杏黄酮甙治疗肺间质纤维化疗效与免疫细胞因子相关性研究

目的观察银杏黄酮甙(银杏叶提取物)治疗肺间质纤维化的临床疗效及与免疫细胞因子的相关性.方法将所收治的45例肺间质纤维化患者随机分为2组,治疗组口服银杏叶胶囊,对照组口服强的松,治疗3个月,观察各组治疗前后在症状、肺功能等方面的改善情况及白细胞介素-6(IL-6)、白细胞介素-8(IL-8)、肿瘤坏死因子α(TNF-α)情况的变化.结果总有效率治疗组为80.00%,对照组为66.67%;2组治疗前后肺总量(TLC)、肺活量(VC)、肺弥散功能(DLco)、IL-6、IL-8、TNF-α自身对照,有显著差异(P＜0.05).结论银杏黄酮甙治疗肺间质纤维化有一定疗效并与免疫细胞因子有一定相关性.     

蔬菜中类黄酮物质的高效液相色谱测定法

目的:建立蔬菜中类黄酮的高效液相色谱测定方法。方法:摸索优化水解、萃取条件,建立高效液相色谱测定方法,并对天津市售30种蔬菜中槲皮素、杨梅黄酮、玉米黄酮、坎二菲醇、芹菜配基的含量进行测定。结果:所建立的高效液相色谱法变异系数范围为2.8%～6.5%,回收率范围为90.2%～108.4%,槲皮素、玉米黄酮、坎二菲醇检测下限为0.4mg/L,杨梅黄酮、芹菜配基为0.8mg/L。30种蔬菜中29种检测出了槲皮素,含量在7.55～0.60mg/100g鲜重范围,5种检测出芹菜配基,7种检测出玉米黄酮,8种检测出杨梅黄酮,而坎二菲醇在30种蔬菜中均未检出;藕、洋葱、豆角、西红柿、芹菜等蔬菜的类黄酮含量较高。结论:本研究建立的方法可靠,并具有较高的准确度和精密度。所测定的蔬菜中类黄酮物质的组成和含量差异较大,槲皮素为主要的类黄酮。     

胡颓子科植物化学成分研究概况

胡颓子科植物共有3属80余种,主要分布于亚洲东南地区和亚洲其他地区。该科植物含有挥发油、脂肪酸、生物碱、萜类等多种化学成分,许多植物还是珍贵的药食两用植物。为推动我国胡颓子科植物资源的更深层次利用和开发,对我国拥有资源的胡颓子科沙棘属(H ipp ophae L.)和胡颓子属(E laeagnus L.)植物的化学成分研究概况做一综述,为本科植物资源的研究和开发提供参考。     

竹叶提取物大鼠代谢试验研究

目的:研究竹叶提取物在SD大鼠体内的生物转运,为其应用提供安全性毒理学评价依据。方法:选用为4.0 g/kg体重剂量进行代谢试验研究。结果:竹叶提取物灌胃后各个时相血浆、肝脏、肾脏、脑、肌肉组织及尿液中4种碳苷黄酮原形物均无检出;灌胃给予竹叶提取物,只有在12~24 h时段从粪便中检出的原形物占摄入量的27.6%。竹叶提取物中一种羟基香豆素类化合物灌胃后各个时相在大鼠肝脏、脑、肌肉组织及粪便中均无检出,在血液及肾脏中有检出,24 h后该组分在在尿液中检出1.9%。结论:4种碳苷黄酮在大鼠胃肠道内均无直接吸收,其中一部分被直接排出体外,另一部分在胃肠道逐渐分解成小分子而被吸收入血液。其中的一种羟基香豆素类化合物主要经胃肠道直接吸收入血液,在肾脏中代谢后从尿液排出体外。     

DNA stability and lipid peroxidation in vitamin E–deficient rats in vivo and colon cells in vitro

Summary Background Fruit and vegetable consumption protects against cancer. This is attributed in part to antioxidants such as vitamin E combating oxidative DNA damage. Anthocyanins are found in significant concentrations in the human diet. However, it remains to be established whether they are bioactive in vivo. Aim To investigate the consequence both of vitamin E deficiency on oxidative damage to DNA and lipids and the cytoprotective effect of nutritionally relevant levels of cyanidin–3–glycoside both in vivo in rats and in vitro in human colonocytes. Methods Male Rowett Hooded Lister rats were fed a diet containing less than 0.5 mg/kg vitamin E or a vitamin E supplemented control diet containing 100 mg d–tocopherol acetate/kg. Half of the controls and vitamin E–deficient rats received cyanidin–3–glycoside (100 mg/kg). After 12 weeks endogenous DNA stability in rat lymphocytes (strand breaks and oxidised bases) and response to oxidative stress ex vivo (H₂O₂; 200 µM) was measured by single cell gel electrophoresis (SCGE). Tissue levels of 8–oxo–7,8–dihydro–2–deoxyguanosine (8–Oxo–dG) were measured by HPLC with EC detection. D–tocopherol and lipid peroxidation products (thiobarbituric acid reactive substances; TBARS) were measured by HPLC. Rat plasma pyruvate kinase and the production of reactive oxygen by phagocytes were detected spectrophotometrically and by flow cytometry respectively. Immortalised human colon epithelial cells (HCEC) were preincubated in vitro with the anthocyanins cyanidin and cyanidin–3–glycoside and the flavonol quercetin (all 50 µM) before exposure to H₂O₂ (200 µM). DNA damage was measured by SCGE as above. Results Plasma and liver d–tocopherol declined progressively over 12 weeks in rats made vitamin E deficient. Lipid peroxidation was increased significantly in plasma, liver and red cells. Reactive oxygen levels in phagocytes and plasma pyruvate kinase were increased. Vitamin E deficiency did not affect DNA stability in rat lymphocytes, liver or colon. Cyanidin–3–glycoside did not alter lipid peroxidation or DNA damage in rats. However, it was chemoprotective against DNA damage in human colonocytes.DNA strand breakage was decreased 38.8 ± 2.2 % after pretreatment with anthocyanin. Conclusion while it is accepted that vitamin E alters lipid oxidation in vivo, its role in maintaining DNA stability remains unclear. Moreover, whereas cyanidin–3–glycoside protects against oxidative DNA damage in vitro, at nutritionally relevant concentrations it is ineffective against oxidative stress in vivo.     

Tissue factor inhibitory sesquiterpene glycoside from<Emphasis Type="Italic">Eriobotrya japonica</Emphasis>

Tissue factor (TF, tissue thromboplastin) is a membrane bound glycoprotein, which accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor for activated factor VII (Vlla). The TF-factor Vlla complex (TF/Vlla) proteolytically activates factors IX and X, which leads to the generation of thrombin and fibrin clots. In order to isolate TF inhibitors, by means of a bioassay-directed chromatographic separation technique, from the leaves ofEriobotrya japonica Lindley (Rosaceae), a known sesquiterpene glycoside (2) and ferulic acid (3) were isolated as inhibitors that were evaluated using a single-clotting assay method for determining TF activity. Another sesquiterpene glycoside (1) was also isolated but was inactive in the assay system. Compound3 was yielded by alkaline hydrolysis of compound2. The structures of compounds1, 2, and3 were identified by means of spectral analysis as 3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranosyl nerolidol (1), 3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyr-anosyl-(1→2)-[α-L-(4-trans-feruloyl)-rhamnopyranosyl-(1→6)]-β-D-glucopyranosyl nerolidol (2) and ferulic acid (3), respectively. Compounds2 and3 inhibited 50% of the TF activity at concentrations of 2 and 369 μM/TF units, respectively.