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贵州冬凌草的对映-贝壳杉烷二萜化合物 总被引:3,自引:0,他引:3
从贵州产冬凌草[Isodon rubescens (Hemsl.) Hera]中分离得到12个6,7-断 裂-7,20-内酯-对映-贝壳杉烷二萜化合物,经波谱分析鉴定了它们的结构, 其中有7个新化合物,分别命名为贵州冬凌草乙素~辛素(guidongnins B~H, 1~ 7),以及卢氏冬凌草甲素(8)、卢氏冬凌草乙素(9)、贵州冬凌草素(10)、狭 叶香茶菜素(angustifolin, 11)和6-表香茶菜素(6-epiangustifolin, 12)等5个 已知化合物。另外,将作者原命名的贵州冬凌草素(guidongnin, 10)更名为贵州 冬凌草甲素(guidongnin A, 10),并利用二维核磁区振波谱技术修订了卢氏冬凌草 乙素的结构。 相似文献
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从贵州产冬凌草[Isodon rubescens (Hemsl.) Hera]中分离得到12个6,7-断 裂-7,20-内酯-对映-贝壳杉烷二萜化合物,经波谱分析鉴定了它们的结构, 其中有7个新化合物,分别命名为贵州冬凌草乙素~辛素(guidongnins B~H, 1~ 7),以及卢氏冬凌草甲素(8)、卢氏冬凌草乙素(9)、贵州冬凌草素(10)、狭 叶香茶菜素(angustifolin, 11)和6-表香茶菜素(6-epiangustifolin, 12)等5个 已知化合物。另外,将作者原命名的贵州冬凌草素(guidongnin, 10)更名为贵州 冬凌草甲素(guidongnin A, 10),并利用二维核磁区振波谱技术修订了卢氏冬凌草 乙素的结构。 相似文献
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采用紫外光谱动力学方法测定了抗肿瘤对映贝壳杉烯二萜冬凌草甲素和冬凌草乙素与谷胱苷肽迈克尔加成反应的级数、速率常数和平衡常数.结果表明,冬凌草甲素和冬凌草乙素与与谷胱苷肽迈克尔加成反应符合二级动力学方程,25℃下的速率常数分别为16.196 0L·(mol·s)-1和7.480 5L·(mol·s)-1,平衡常数分别为177.98L/mol和85.60L/mol.冬凌草甲素与谷胱苷肽迈克尔加成反应速率和反应程度均比冬凌草乙素的大得多,反应活性更好.对映贝壳杉烯二萜通过与机体发生迈克尔加成反应而产生抗肿瘤作用;因此,冬凌草甲素可能比冬凌草乙素具有更好的抗肿瘤活性. 相似文献
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冬凌草中的新对映-贝壳杉烷二萜化合物 总被引:10,自引:0,他引:10
对河南省济源地区产冬凌草[Isodon rubescens(Hemsl.)Hara]再次进行了深入 的研究,从其叶的乙酸乙酯提取物中分离得到了16个化合物,其中1和2为两个新的 7,20-环氧-对映-贝壳杉烷类二萜化合物,其结构通过波谱分析确定为16(S)-羟 甲基-1α,6β,7β,11β-甲羟基-7α,20-环氧-对映-贝壳杉烷-15-酮(1)和 16(R)-羟甲基-1α,6β,7β,14β-四羟基-7α,20-环氧-对映-贝壳杉烷-15- 酮(2),分别命名为冬凌草已素(1)和庚素(2);其余的已知化合物分别鉴定 为lasiodonin(3),冬凌草甲素(oridonin,4),乙素(ponicidin),丙素( rubescensin C),丁素(rubescensin D),牛尾草丙素(rabdoternin C),荛 花香茶菜乙素(wikstroemioidin B),enmenol-1α-O-β-D-glucoside, enmenol,胡麻素(pedalitin),水杨酸,乌索酸,β-谷甾醇和胡萝卜甙。 相似文献
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A preparative counter-current chromatography (CCC) method for isolation and purification of oridonin, a new cancer chemoprevention agent, from the Chinese medicinal plant Rabdosia rubescens was successfully established. The crude oridonin was obtained by elution with a light petroleum/acetone solvent mixture from ethanol extracts of R. rubescens using column chromatography on silica gel. With a two-phase solvent system composed of n-hexane/ethyl acetate/methanol/water (1:2:1:2, v/v), 120 mg of oridonin at the purity of 97.8% was obtained from 200 mg of the crude sample in a single-step CCC separation. The structure of oridonin was identified by ESI-MS, 1H NMR, and 13C NMR. 相似文献
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Wei Liu Bing Zhao Yin‐Chao Li Hong‐Min Liu 《Magnetic resonance in chemistry : MRC》2011,49(9):611-615
Complexations between three oridonin derivatives and β‐cyclodextrin (βCD) were studied by nuclear magnetic resonance (NMR) method. Job's plots for complexes were depicted by 1H NMR spectra chemical shifts, which proved the 1:1 stoichiometry inclusion complex formation between each derivative and βCD. Two‐dimensional rotating frame overhauser effect spectroscopy (2D ROESY) support the above conclusion and also proved that ring A of each oridonin derivative deeply enters into hydrophobic cavity from the wider rim and the other parts are outside the cavity. Apparent formation constants (Ka) of complexes between three oridonin derivatives and two CDs are calculated according to Scott's equation. Copyright © 2011 John Wiley & Sons, Ltd. 相似文献
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Nurul Akmaryanti Abdullah Nur Fariesha Md Hashim Aula Ammar Noraina Muhamad Zakuan 《Molecules (Basel, Switzerland)》2021,26(4)
Cancer is one of the leading causes of death worldwide, with a mortality rate of more than 9 million deaths reported in 2018. Conventional anti-cancer therapy can greatly improve survival however treatment resistance is still a major problem especially in metastatic disease. Targeted anti-cancer therapy is increasingly used with conventional therapy to improve patients’ outcomes in advanced and metastatic tumors. However, due to the complexity of cancer biology and metastasis, it is urgent to develop new agents and evaluate the anti-cancer efficacy of available treatments. Many phytochemicals from medicinal plants have been reported to possess anti-cancer properties. One such compound is known as oridonin, a bioactive component of Rabdosia rubescens. Several studies have demonstrated that oridonin inhibits angiogenesis in various types of cancer, including breast, pancreatic, lung, colon and skin cancer. Oridonin’s anti-cancer effects are mediated through the modulation of several signaling pathways which include upregulation of oncogenes and pro-angiogenic growth factors. Furthermore, oridonin also inhibits cell migration, invasion and metastasis via suppressing epithelial-to-mesenchymal transition and blocking downstream signaling targets in the cancer metastasis process. This review summarizes the recent applications of oridonin as an anti-angiogenic and anti-metastatic drug both in vitro and in vivo, and its potential mechanisms of action. 相似文献
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Semi-preparative high-speed counter-current chromatography (HSCCC) was successfully used for isolation and purification of oridonin from Isodon rubescens by using a two-phase-solvent system composed of n-hexane-ethyl acetate-methanol-water (2.8:5:2.8:5, v/v/v/v). The targeted compound isolated, collected and purified by HSCCC was analyzed by high performance liquid chromatography (HPLC). A total of 40.6 mg of oridonin with the purity of 73.5% was obtained in less than 100 min from 100 mg of crude Isodon rubescens extract. The chemical structure of the compound was identified by IR, 1H-NMR and 13C-NMR. 相似文献
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W S Zhou Y X Cheng 《Science in China. Series B, Chemistry, life sciences & earth sciences》1992,35(2):194-199
In this paper, we report the first stereo-, regio-, and chemo-selective conversion of oridonin from kamebakaurin. The overall yield in 7 steps is 9%. 相似文献
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In this paper, we report the first stereo-, regio-, and chemo-selective conversion of oridonin (1) from kamebakaurin (3). The overall yield in 7 steps is 9%. 相似文献
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A formal synthesis of semiaquilegin A is achieved starting from readily available oridonin in 19 linear steps. The absolute configuration of the natural product has been established. A variety of useful analogues were prepared through this synthetic route. 相似文献
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A preparative two-dimensional counter-current chromatographic system (2D-CCC) for simultaneous separation and purification of oridonin and ponicidin from the crude extract of Rabdosia rubescens was presented. It was based on the use of a high-speed CCC (HSCCC, total column volume V(c)=146ml) instrument in the first dimension (1st-D) and a preparative upright CCC (UCCC, V(c)=1500ml) column in the second dimension (2nd-D). The interface was a homemade column-switching system with a 50-ml sample loop. In this way, almost the whole interested region from the first dimension was transferred on-line to the second dimension for further separation. The use of a pair of two-phase solvent systems composed of n-hexane-ethyl acetate-methanol-water (1:5:1:5 and 3:5:3:5, v/v) in the two dimensions permitted the simultaneous separation of oridonin and ponicidin, making this 2D-CCC system with satisfactory resolution and peak capacity. During about 9h separation, two injections with about a 250mg amount of the crude extract for each, was accomplished using this 2D-CCC system, yielding 60mg of oridonin (1) and 10mg of ponicidin (2) all at a purity of over 95% as determined by HPLC analysis. Their chemical structures were identified by electrospray ionization (ESI) MS, (1)H NMR and (13)C NMR. 相似文献