拉肖皂苷元 | 1177-71-5

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 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
• 中文名称: 拉肖皂苷元
• 中文别名: 拉肖皂甙元
• 英文名称: laxogenin
• 英文别名: (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-one
• CAS: 1177-71-5
• 化学式: C₂₇H₄₂O₄
• 分子量: 430.628
• InChiKey: WOJKRRDDERNLBU-BOYSPROGSA-N

物化性质

• 熔点：
  210-212℃
• 沸点：
  548.9±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  拉肖皂苷元 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以86%的产率得到(25R)-5α-spirostan-3β,6β-diol
  参考文献：
  名称：

  (22R, 25R)-3β,26-Dihydroxy-5α-furostan-6-one#的合成

  摘要：

  摘要 描述了在 A 环和 B 环上具有睾酮特征功能的植物生长促进剂呋甾醇的合成。# 献给 Charles Desccoins 博士 62 岁生日。

  DOI：

  10.1080/00397919808006836
• 作为产物：
  描述：

  绿莲皂苷元 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 jones reagent 、 水 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 丙酮 为溶剂， 10.0 ℃ 、137.9 kPa 条件下， 反应 1.0h， 生成 拉肖皂苷元
  参考文献：
  名称：

  Spirostanic analogues of teasterone. Synthesis, characterisation and biological activity of laxogenin, (23S )-hydroxylaxogenin and 23-ketolaxogenin (23-oxolaxogenin)

  摘要：

  描述了天然存在的甾体皂苷元拉甾醇1及其衍生物23-酮拉甾醇10和（23S）-羟基拉甾醇13的合成与表征。据报道，这些化合物在体外测试和田间试验中显示出促进植物生长的活性。

  DOI：

  10.1039/b007656m

文献信息

• Concise synthesis of two natural steroidal glycosides isolated from Allium schoenoprasum
  作者：Qingchao Liu、Tiantian Guo、Dong Li、Wenhong Li

  DOI：10.1007/s11164-015-2106-2

  日期：2016.3

  Two natural steroidal glycosides, diosgenin 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (1) and laxogenin 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (2) with important cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines have been efficiently synthesized via straightforward sequential glycosylation reaction with the combined use of N-phenyltrifluoroacetimidates and trichloroacetimidates donors at room temperature. All structures of the synthesized new compounds were identified by 1H NMR, 13C NMR and HRMS spectra.

  两种天然甾体糖苷，薯蓣皂苷元 3-O-α-L-鼠李吡喃糖基-(1→2)-[β-D-葡萄吡喃糖基-(1→4)]-β-D-葡萄吡喃糖苷（1）和拉可皂苷元 3-O-α-L-鼠李吡喃糖基-(1→2)-[β-D-葡萄吡喃糖基-(1→4)]-β-D-葡萄吡喃糖苷（2），它们对抗人结肠癌HCT 116和HT-29细胞系具有重要的细胞毒活性，已通过室温下使用N-苯基三氟乙酰亚胺盐和三氯乙酰亚胺盐供体的直接顺序糖基化反应高效合成。所有合成的新化合物结构均通过1H NMR、13C NMR和HRMS光谱鉴定。
• The CuI-catalyzed alkyne–azide cycloaddition as direct conjugation/cyclization method of peptides to steroids
  作者：Radell Echemendía、Odette Concepción、Fidel E. Morales、Márcio W. Paixão、Daniel G. Rivera

  DOI：10.1016/j.tet.2013.10.032

  日期：2014.5

  good to excellent yields. The process comprised the solution-phase synthesis of oligopeptides featuring varied chain length and amino acid sequence as well as the preparation of a small library of azidosteroids bearing the azido group either at the side chain or the steroidal nucleus. An alternative strategy relying on a sequential peptide coupling/CuAAC-based macrocyclization procedure was also developed

  铜我催化的叠氮化物-炔烃1,3-偶极环加成反应是炔基肽与叠氮类固醇的直接缀合方法，从而能够以优异的产率制备新型的三唑连接的肽-类固醇缀合物。该方法包括溶液相合成具有变化链长和氨基酸序列的寡肽，以及制备在侧链或甾体核上带有叠氮基的小叠氮类固醇文库。还开发了一种基于顺序肽偶联/基于CuAAC的大环化程序的替代策略，以提供具有不同大小和拓扑结构的大环肽-类固醇共轭物。两种方法均显示出很高的化学效率和多功能性，
• Steroidal saponins from the rhizomes of Smilax sieboldii
  作者：Tamotsu Nikaido、Taichi Ohmoto、Satoshi Kubo、Yoshihiro Mimaki、Yutaka Sashida

  DOI：10.1016/0031-9422(92)83296-b

  日期：1992.7

  Six new steroidal saponins were isolated from the rhizomes of Smilax sieboldii. Their structures were determined by spectroscopic analysis and hydrolysis to be 3 beta-hydroxy-(25R)-5 alpha-spirostan-6-one (laxogenin) 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl-(1- ---6)]-beta-D-glucopyranoside, laxogenin 3-O-alpha-L-arabinopyranosyl-(1----6)-beta-D-glucopyranoside, 3 beta,27-dihydroxy-(25S)-5

  从 Smilax sieboldii 的根茎中分离出六种新的甾体皂苷。它们的结构通过光谱分析和水解确定为 3β-羟基-(25R)-5 α-spirostan-6-one (laxogenin) 3-O-β-D-glupyranosyl-(1----4)- O-[α-L-阿拉伯吡喃糖基-(1- ---6)]-β-D-吡喃葡萄糖苷，laxogenin 3-O-α-L-阿拉伯吡喃糖基-(1----6)-β-D-吡喃葡萄糖苷, 3 β,27-二羟基-(25S)-5 α-spirostan-6-one 3-O-β-D-吡喃葡萄糖基-(1----4)-O-[α-L-阿拉伯吡喃糖基-(1 - ---6)]- β-D-吡喃葡萄糖苷, 26-O-β-D-吡喃葡萄糖基-3 beta,22 xi,26-trihydroxy-(25R)-5 alpha-furostan-6-one 3-O- α-L-阿拉伯吡喃糖
• Glycosyl Trifluoroacetimidates. 2. Synthesis of Dioscin and Xiebai Saponin I
  作者：Biao Yu、Houchao Tao

  DOI：10.1021/jo026103c

  日期：2002.12.1

  Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin 1 (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.
• Structure–activity relationships of saponin derivatives: A series of entry inhibitors for highly pathogenic H5N1 influenza virus
  作者：Ning Ding、Qing Chen、Wei Zhang、Sumei Ren、Ying Guo、Yingxia Li

  DOI：10.1016/j.ejmech.2012.04.022

  日期：2012.7

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Theoretically, each of steps in influenza viral life cycle can be a target of antiviral therapeutics. However, up to date, no licenced entry inhibitor drug is available for H5N1 or any other influenza viruses. Our strategy for developing new anti-influenza therapeutics is to target the interaction between HA and sialic acid which is influenza viral receptor presented on host cell surface. Here, based on our previously discovered small molecule inhibitor saponin 1, intensive SAR studies around the sugar chain and aglycone were conducted. The results showed that both the chacotriosyl residue and the chlorogenin moiety of active compound 1 are important for the antiviral activity, although several subtle modifications can be made on particular positions. (C) 2012 Elsevier Masson SAS. All rights reserved.