A new neolignan glycoside from Dolomiaea souliei

Abstract

One new neolignan glycoside, dolomiside A (1), together with 11 known phenylpropanoid glycosides were isolated from Dolomiaea souliei (Franch.) Shih. The structures of these isolates were determined by UV, CD, HR-ESI-TOFMS, 1D and 2D NMR analysis.     

Targeted Synthesis of 3,3′-, 3,4′- and 3,6′-Phenylpropanoid Sucrose Esters

In this study, we report on an orthogonal strategy for the precise synthesis of 3,3′-, 3,4′-, and 3,6′-phenylpropanoid sucrose esters (PSEs). The strategy relies on carefully selected protecting groups and deprotecting agents, taking into consideration the reactivity of the four free hydroxyl groups of the key starting material: di-isopropylidene sucrose 2. The synthetic strategy is general, and potentially applies to the preparation of many natural and unnatural PSEs, especially those substituted at 3-, 3′-, 4′- and 6′-positions of PSEs.     

Calceolarioside A,a Phenylpropanoid Glycoside from Calceolaria spp., Displays Antinociceptive and Anti-Inflammatory Properties

Phenylpropanoid glycosides are a class of natural substances of plant origin with interesting biological activities and pharmacological properties. This study reports the antinociceptive and anti-inflammatory effects of calceolarioside A, a phenylpropanoid glycoside previously isolated from various Calceolaria species. In models of acute nociception induced by thermal stimuli, such as the hot plate and tail flick test, calceolarioside administered at doses of 1, 5, and 10 μg in the left cerebral ventricles did not modify the behavioral response of mice. In an inflammatory based persistent pain model as the formalin test, calceolarioside A at the high dose tested (100 μg/paw) reduced the licking activity induced by formalin by 35% in the first phase and by 75% in the second phase of the test. In carrageenan-induced thermal hyperalgesia, calceolarioside A (50 and 100 μg/paw) was able to significantly reverse thermal hyperalgesia induced by carrageenan. The anti-inflammatory activity of calceolarioside A was then assessed using the zymosan-induced paw edema model. Calceolarioside A (50 and 100 μg/paw) induced a significant reduction in the edema from 1 to 4 h after zymosan administration. Measuring IL-6, TNFα, and IL-1β pro-inflammatory cytokines released from LPS-stimulated THP-1 cells, calceolarioside A in a concentration-dependent manner reduced the release of these cytokines from THP-1 cells. Taken together, our results highlight, for the first time, the potential and selective anti-inflammatory properties of this natural-derived compound, prompting its rationale use for further investigations.     

利用在线加压溶剂提取-超高效液相色谱-离子肼-飞行时间-质谱法直接分析中药草苁蓉的化学成分组

构建了在线加压溶剂提取-超高效液相色谱-离子肼-飞行时间质谱(online PLE-UHPLC-IT-TOF-MS)系统,并将其应用于草苁蓉化学组的快速、直接分析。将微量草苁蓉粉末(0.5 mg)置于空预柱芯中,空隙用正相硅胶填充,作为提取池;提取池置于预柱套内,将其放入柱温箱(70℃),预柱套通过金属管线连接至UHPLC-IT-TOF-MS系统。通过引入一个二位六通阀将整个分析过程分为提取和洗脱两个阶段。以0.1%(v/v)甲酸水为溶剂,提取3 min。在洗脱阶段,以0.1%(v/v)甲酸水-0.1%(v/v)甲酸乙腈为流动相,梯度洗脱,将色谱柱前端所富集的提取物洗脱至IT-TOF-MS中进行检测。从草苁蓉中检测到48个化合物,结合对照品、文献、数据库以及质谱裂解规律,初步鉴定了其中的45个,包括10个苯乙醇苷类、14个环烯醚萜苷类以及21个苯丙醇苷类化合物。该研究为草苁蓉化学成分组成的阐明以及质量评价提供了可靠信息。同时,构建的online PLE-UHPLC-IT-TOF-MS系统为中药化学成分的快速、直接表征提供了有效方案。     

两种诱导因子对新疆甜瓜愈伤组织某些抗病相关酶系的诱导

用两种诱导因子对新疆甜瓜愈伤组织继代培养物进行诱导的结果表明；９１）苯丙烷类代谢关键酶系的活性和木质素含量在诱导扣均有不同程度的增高，与整体诱导相似，且理炙迅速；（２）可溶性蛋白电泳分析表明，两种诱导因子和对照三者之间都有谱带差异；（３）可以初步认为，这两种诱导因子对整体抗性的诱导是与苯丙烷类系活性增高，木质素含量增加密切相连的，并且这些生理生化变化在愈伤组织水平是这两种性质不同的诱导因子直接作用     

Antiangiogenic phenylpropanoid glycosides from Gynura cusimbua

A new phenylpropanoid glycoside, named α-L-rhamnopyranosyl-(1?2)-β-D-[4″-(8E)-7-(3,4-dihydroxyphenyl)-8-propenoate, 1″-O-(7S)-7-(3,4-dihydroxyphenyl)-7-methoxy-ethyl]-glucopyranoside (1), together with nine known compounds (2–10) were isolated from the active fraction (n-Butanol fraction) of Gynura cusimbua for the first time. The known compounds (2–10) were identified as phenylpropanoid glycosides on the basis of extensive spectral data and references. The antiangiogenic activities of compounds (1–10) were evaluated by MTT assay on HUVECs and wild-type zebrafish in vivo model assay. As a result, compounds 1, 6, 7, 8 and 10 exhibited certain antiangiogenic activities.     

基于分子对接的苯丙素甙（PPGs）类化合物的虚拟筛选和合理设计

采用虚拟化合物生成法对抗肿瘤的苯丙素甙(PPGs)类化合物进行了配体受体对 接研究。以三种不同的骨架结构为基础分别生成了五十个虚拟苯丙素甙(PPGs)类化 合物，并将它们与端粒DNA受体进行分子对接，分析已知结构的对接结果，通过虚 拟筛选的方法得到了一批与受体相互作用能较高并且复合物能量较低的新的有潜力 的活性化合物。该方法可以弥补分子对接研究中，只能计算药物与受体的相互作用 ，无法有效设计新化合物的不足。这种方法在基于结构的药物分子设计中具有重要 的意义。     

Chemical constituents from the bark of bauhinia purpurea and their NO inhibitory activities

Abstract

Phytochemical studies led to the isolation of a new phenylpropanoid glucoside, named purpuroside (1), along with eight known compounds (2–9) from the bark of Bauhinia purpurea. The structure of the new compound was elucidated on the basis of its spectroscopic data. The absolute configuration of compound 2 was verified by X-ray diffraction analysis. Compounds 1, 2, 7, 8, and 9 inhibited NO production in mouse peritoneal macrophages with IC₅₀ values from 35.5 to 63.0?μM.