rostratamin

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: rostratamin
• 英文别名: 12-O-nicotinyldeacetylmetaplexigenin；[(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-3,8,14,17-tetrahydroxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] pyridine-3-carboxylate
• 化学式: C₂₇H₃₅NO₇
• 分子量: 485.577
• InChiKey: GQDQWQRPCUUAFD-LLFZLOFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-叔丁氧羰基-4-哌啶乙酸 、 rostratamin 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以49 %的产率得到3β-O-(1-tert-butyloxycarbonylpiperidyl-4-acetyl)rostratamin
  参考文献：
  名称：

  天然存在的C21-甾体苷元3β-含氮杂环酯衍生物的设计、合成及抗癌活性

  摘要：

  为了研究引入含氮杂环酯基团对天然存在的C 21 -甾体糖苷配基抗肿瘤活性的影响，合成了一系列新的3 β-含氮杂环酯衍生物，包括牛尾草素、kidjoranin、青羊神根素和rostratamin。结果表明，大多数合成衍生物对四种人类癌细胞（MCF-7、HCT-116、HeLa 和 HepG2）表现出中等至显着的细胞毒活性，其中具有 piperidine-4-acetyl 取代基的化合物 1s 和 2c 表现出最高的细胞毒活性对四种人类癌细胞的细胞毒活性，IC 50值范围分别为 3.30 至 6.73 μM 和 3.07 至 6.37 μM。进一步的抗肿瘤机制研究表明，化合物2c在体外以剂量依赖的方式有效诱导细胞凋亡，使细胞周期停滞在S期。总的来说，这些目前的研究表明，将含氮杂环酯基团引入 C-3 位是提高天然存在的 C 21 -甾体糖苷配基抗癌活性的有效策略之一，值得进一步研究。

  DOI：

  10.1016/j.molstruc.2023.135778
• 作为产物：
  描述：

  stemucronatoside F 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以8.5 mg的产率得到rostratamin
  参考文献：
  名称：

  Four new C-21 steroidal glycosides from the roots of and their immunological activities

  摘要：

  Four new C-21 steroidal glycoside, stemucronatosides D (1), E (2), F (3), and G (4) were isolated from the roots of Stephanotis mucronata. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods including one-dimensional and two-dimensional NMR. These isolated compounds were assayed for their immunological activities in vitro against concanavalin A (Con A)and lipopolysaccharide (LPS)-induced proliferation of mice splenocytes. Compounds 1, 2, and 4 showed inummosuppressive activities in a dose-dependent manner, while compound 3 showed immunomodulating activities. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.05.001

文献信息

• Steroidal glycosides from the aerial part of Asclepias incarnata
  作者：Tsutomu Warashina、Tadataka Noro

  DOI：10.1016/s0031-9422(99)00560-9

  日期：2000.2

  The aerial part of Asclepias incarnata afforded 34 pregnane glycosides. These were confirmed to have lineolon, isolineolon, ikemagenin, 12-O-nicotinoyllineolon, deacylmetaplexigenin, metaplexigenin, rostratamine, 12-O-acetyllineolon, 15beta-hydroxylineolon and 15beta-hydroxyisolineolon moieties as their aglycones, and 2.6-dideoxyhexopyranose, glucopyranose and allopyranose as the corresponding sugar

  Asclepias incarnata 的地上部分提供了 34 种孕烷苷。这些被证实含有亚麻油酸、异亚麻油酸、ikemagenin、12-O-烟酰亚油酸碱油、脱酰基金属油菜精、金属油菜精、罗斯特拉明、12-O-乙酰油油龙、15β-羟基亚油油龙和15β-羟基异油油龙油部分作为它们的苷元，和2-2-氨基己糖异戊二糖异戊二糖苷。相应的糖成分。它们的结构是使用光谱和化学方法确定的。
• Design, synthesis and anticancer activity of naturally occurring C21-steroidal aglycone 3β-nitrogenous heterocyclic ester derivatives
  作者：Xiao-San Li、Rui Xing、Ming-Shang Liu、Xiao-Yan Liang、Mei-Fang Chen、Zhen-Dong Liang、Jing-Fen Nie、Hui Luo、Yong-Mei Huang、Xue-Mei Yang

  DOI：10.1016/j.molstruc.2023.135778

  日期：2023.9

  To investigate the effect of introduction of the nitrogenous heterocyclic ester group on the antitumor activities of naturally occurring C21-steroidal aglycone, a series of novel 3β-nitrogenous heterocyclic ester derivatives of caudatin, kidjoranin, qingyangshengenin, and rostratamin were synthesized. The results showed that most of synthetic derivatives showed moderate to significant cytotoxic activities

  为了研究引入含氮杂环酯基团对天然存在的C 21 -甾体糖苷配基抗肿瘤活性的影响，合成了一系列新的3 β-含氮杂环酯衍生物，包括牛尾草素、kidjoranin、青羊神根素和rostratamin。结果表明，大多数合成衍生物对四种人类癌细胞（MCF-7、HCT-116、HeLa 和 HepG2）表现出中等至显着的细胞毒活性，其中具有 piperidine-4-acetyl 取代基的化合物 1s 和 2c 表现出最高的细胞毒活性对四种人类癌细胞的细胞毒活性，IC 50值范围分别为 3.30 至 6.73 μM 和 3.07 至 6.37 μM。进一步的抗肿瘤机制研究表明，化合物2c在体外以剂量依赖的方式有效诱导细胞凋亡，使细胞周期停滞在S期。总的来说，这些目前的研究表明，将含氮杂环酯基团引入 C-3 位是提高天然存在的 C 21 -甾体糖苷配基抗癌活性的有效策略之一，值得进一步研究。
• Four new C-21 steroidal glycosides from the roots of and their immunological activities
  作者：Y YE、H SUN、X LI、F CHEN、F QIN、Y PAN

  DOI：10.1016/j.steroids.2005.05.001

  日期：2005.11

  Four new C-21 steroidal glycoside, stemucronatosides D (1), E (2), F (3), and G (4) were isolated from the roots of Stephanotis mucronata. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods including one-dimensional and two-dimensional NMR. These isolated compounds were assayed for their immunological activities in vitro against concanavalin A (Con A)and lipopolysaccharide (LPS)-induced proliferation of mice splenocytes. Compounds 1, 2, and 4 showed inummosuppressive activities in a dose-dependent manner, while compound 3 showed immunomodulating activities. (c) 2005 Elsevier Inc. All rights reserved.