Stevioside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Stevioside
• 英文别名: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,9S,10R,13R)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• 化学式: C₃₈H₆₀O₁₈
• 分子量: 804.884
• InChiKey: UEDUENGHJMELGK-VCZLYINISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  295
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  Stevioside 在 硫酸 、 水 作用下， 生成 异甜菊醇
  参考文献：
  名称：

  合成，细胞毒性活性以及19-羧基修饰的新型异戊烯醇衍生物作为潜在抗癌药的2D和3D-QSAR研究。

  摘要：

  基于19-羧基修饰，合成了两个系列的新型酰基硫代氨基脲和恶二唑稠合的异甜菊醇衍生物。使用MTT分析评估目标化合物对三种癌细胞系（HCT-116，HGC-27和JEKO-1）的细胞毒性。来自酰基硫代氨基脲的铅化合物（4）的IC50值在较低的微摩尔范围内。例如，化合物（4i，4l，4m，4r和4s）对三种细胞系均表现出显着的抑制活性，IC50值为0.95-3.36微米。此外，建立了2D-HQSAR和3D-拓扑CoMFA分析，可用于开发第二代异雌酚衍生物作为抗癌药。

  DOI：

  10.1111/cbdd.12910

文献信息

• 聚醚脲桥连手性分子钳及其制备和应用
  申请人：浙江工业大学

  公开号：CN108727227B

  公开（公告）日：2019-11-29

  本发明公开了聚醚脲桥连手性分子钳及其制备和应用。所述聚醚脲桥连手性分子钳的结构如式(I)或式(II)所示。本发明提供了所述的聚醚脲桥连手性分子钳在识别手性分子客体中的应用，所述的手性分子客体为D/L‑氨基酸酯盐酸盐。本发明合成的分子钳对D/L‑氨基酸酯盐酸盐具有一定的手性识别性能，可用于手性识别分离对映异构体。
• Synthesis, cytotoxic activity, and 2D- and 3D-QSAR studies of 19-carboxyl-modified novel isosteviol derivatives as potential anticancer agents
  作者：Cong-Jun Liu、Tao Zhang、Shu-Ling Yu、Xing-Jie Dai、Ya Wu、Jing-Chao Tao

  DOI：10.1111/cbdd.12910

  日期：2017.6

  novel acylthiosemicarbazide and oxadiazole fused-isosteviol derivatives were synthesized based on the 19-carboxyl modification. The target compounds were evaluated for their cytotoxicities against three cancer cell lines (HCT-116, HGC-27, and JEKO-1) using an MTT assay. Lead compounds from the acylthiosemicarbazides (4) showed IC50 values in the lower micromolar range. For example, compounds (4i, 4l

  基于19-羧基修饰，合成了两个系列的新型酰基硫代氨基脲和恶二唑稠合的异甜菊醇衍生物。使用MTT分析评估目标化合物对三种癌细胞系（HCT-116，HGC-27和JEKO-1）的细胞毒性。来自酰基硫代氨基脲的铅化合物（4）的IC50值在较低的微摩尔范围内。例如，化合物（4i，4l，4m，4r和4s）对三种细胞系均表现出显着的抑制活性，IC50值为0.95-3.36微米。此外，建立了2D-HQSAR和3D-拓扑CoMFA分析，可用于开发第二代异雌酚衍生物作为抗癌药。
• Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids
  作者：Jilmar A. Murillo、Juan F. Gil、Yulieth A. Upegui、Adriana M. Restrepo、Sara M. Robledo、Winston Quiñones、Fernando Echeverri、Aurelio San Martin、Horacio F. Olivo、Gustavo Escobar

  DOI：10.1016/j.bmc.2018.11.030

  日期：2019.1

  We describe the in vitro activity of two natural isomeric ent-beyerene diterpenes, several derivatives and synthetic intermediates. Beyerenols 1 and 2 showed EC50 of 4.6 ± 9.4 and 5.3 ± 9.4 μg/mL against amastigotes of L. (V) brazilensis, with SI of 5.1 and 7.7, respectively. Beyerenol 1 was synthesized from stevioside. In vivo experiments with bereyenols showed cure in 50% of hamsters infected with

  我们描述了两种天然异构对映体-拜仁二萜，几种衍生物和合成中间体的体外活性。Beyerenols 1和2对巴西L.（V）的吻合动物的EC 50分别为4.6±9.4和5.3±9.4μg/ mL ，SI分别为5.1和7.7。从甜菊糖合成了苯二酚1。体内与bereyenols实验表明治愈感染仓鼠的50％L.（V）brazilensis局部施加如乳霜I（beyerenol 1，0.81％，重量/重量）和霜III（beyerenol 2，1.96％，w / w）。这些结果表明，通过局部应用，拜仁醇是皮肤利什曼病化学疗法的潜在候选者。巴西L.（V）变形虫的体外分析显示，EC中间体10和11的EC 50为1.1±0.1和1.3± 0.04μg / mL，SI分别为3.1和3.5 。
• (-)-Isosteviol as a Versatile Ex-Chiral-Pool Building Block for Organic Chemistry
  作者：Christina Lohoelter、Magdalena Weckbecker、Siegfried R. Waldvogel

  DOI：10.1002/ejoc.201300447

  日期：2013.9

  mutual C–C distance of about 7 A. Their unique concave arrangement experiences a strong asymmetric environment due to an adjacent methyl group. Consequently, this building block has found several applications in supramolecular chemistry and organocatalysis. These areas and the chemical modification of this scaffold as well as its biological activity are surveyed.

  (–)-异甜菊醇可通过对常见替代甜味剂进行酸性处理而大量获得。(-)-异甜菊醇的两个官能团出现在对映-拜尔烷支架的同一侧，相互的 C-C 距离约为 7 A。由于相邻的甲基，它们独特的凹面排列经历了强烈的不对称环境。因此，这种构建块已在超分子化学和有机催化中得到了多种应用。调查了这些区域和该支架的化学修饰及其生物活性。
• Synthesis and anti-hepatitis B virus activity of C4 amide-substituted isosteviol derivatives
  作者：Tsurng-Juhn Huang、Cheng-Lin Yang、Yu-Cheng Kuo、Yi-Chih Chang、Li-Ming Yang、Bo-Hon Chou、Shwu-Jiuan Lin

  DOI：10.1016/j.bmc.2014.12.064

  日期：2015.2

  A series of novel isosteviol derivatives having C4-amide substituents were synthesized in order to test for antiviral effects against the hepatitis B virus (HBV) in vitro. Among them, IN-4 [N-(propylcarbonyl)-4 alpha-amino- 19-nor-ent-16-ketobeyeran] (5) exhibited inhibitory activity against secretion of HBsAg and HBeAg as well as inhibition of HBV DNA replication. Therefore, the mechanism of its antiviral activity was further analyzed using HBV-transfected Huh7 cells. Exposure to IN-4 produced minimal inhibitory effects on viral precore/pregenomic RNA expression. However, expression levels of the 2.4/2.1-kb preS/major S RNA of the viral surface gene significantly decreased, along with intracellular levels of HBV DNA. A promoter activity analysis demonstrated that IN-4 significantly inhibited viral X, S, and preS expression levels but not viral core promoter activities. In particular, IN-4 was observed to significantly inhibit HBV gene regulation by disrupting nuclear factor (NF)-kappa B-associated promoter activity. In addition, the nuclear expression of p65/p50 NF-kappa B member proteins was attenuated following IN-4 treatment, while cytoplasmic I kappa B alpha protein levels were enhanced. Meanwhile, IN-4 was observed to inhibit the binding activity of NF-kappa B to putative DNA elements. Furthermore, transfection of a p65 expression plasmid into Huh7 cells significantly reversed the inhibitory effect of IN-4 on HBV DNA levels, providing further evidence of the central role of NF-kappa B in its antiviral mechanism. It is therefore suggested that IN-4 inhibits HBV by interfering with the NF-kappa B signaling pathway, resulting in downregulation of viral gene expression and DNA replication. (c) 2014 Elsevier Ltd. All rights reserved.