去半乳糖替告皂甙 | 39941-51-0

• 物质功能分类: 分析化学 - 标准品 - 分析标准品
• 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
• 中文名称: 去半乳糖替告皂甙
• 中文别名: 龙葵螺甙A
• 英文名称: desgalactotigonin
• 英文别名: degalactotigonin；tigogenin 3-O-β-D-glucopyranosyl(1->2)-[β-D-xylopyranosyl(1->3)]-β-D-glucopyranosyl(1->4)-β-D-galactopyranoside；(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 39941-51-0；5260-40-2
• 化学式: C₅₀H₈₂O₂₂
• 分子量: 1035.19
• InChiKey: BJNQXJIQCPPOHN-NUKVSUKUSA-N

物化性质

• 熔点：
  284-286℃
• 密度：
  1.49

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  72
• 可旋转键数：
  11
• 环数：
  10.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  335
• 氢给体数：
  12
• 氢受体数：
  22

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  aspidistrin 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 12.0h， 以19 mg的产率得到去半乳糖替告皂甙
  参考文献：
  名称：

  Cytotoxic Activities and Structure-Cytotoxic Relationships of Steroidal Saponins.

  摘要：

  我们系统地研究了主要从百合科植物中分离出来的甾体皂甙对 HL-60 人类早幼粒细胞白血病细胞的细胞毒活性，发现了几种结构-活性关系。检测系统中评估的一些甾体皂苷显示出相当强的细胞毒活性，其效力几乎与作为阳性对照的依托泊苷相当。研究发现，这些活性对构成糖分子的单糖及其序列以及苷元的结构非常敏感。

  DOI：

  10.1248/bpb.24.1286

文献信息

• The steroidal glycosides of the flowers of Yucca gloriosa
  作者：Kimiko Nakano、Emi Matsuda、Kaori Tsurumi、Tokushi Yamasaki、Kotaro Murakami、Yoshihisa Takaishi、Toshiaki Tomimatsu

  DOI：10.1016/0031-9422(88)80033-5

  日期：1988.1

  Abstract Four steroidal compounds were isolated from the fresh flowers of Yucca gloriosa and their structures were elucidated as tigogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, gitogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, gitogenin 3-O-α- l -rhamnopyranosyl-β-lycotetraoside and proto-type of gitogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, on the basis of physical and chemical investigations

  摘要 从兰兰鲜花中分离得到4种甾体化合物，并阐明了其结构为：tigogenin 3-O-β-d-吡喃木糖基-β-lycotetraoside、gitogenin 3-O-β-d-xylopyranosyl-β-lycotetraoside、gitogenin 3-O-α-l -rhamnopyranosyl-β-lycotetraoside 和 gitogenin 3-O-β-d -xylopyranosyl-β-lycotetraoside 的原型，基于物理和化学研究。
• Application of the glycal assembly strategy to the synthesis of a branched oligosaccharide: the first synthesis of a complex saponin
  作者：John T. Randolph、Samuel J. Danishefsky

  DOI：10.1021/ja00071a077

  日期：1993.9
• First Synthesis of a Digitalis Saponin. Demonstration of the Scope and Limitations of a Convergent Scheme for Branched Oligosaccharide Synthesis by the Logic of Glycal Assembly
  作者：John T. Randolph、Samuel J. Danishefsky

  DOI：10.1021/ja00126a010

  日期：1995.5

  The synthesis of complex glycosides, with branching at C-2, is demonstrated. The key element involves the use of a 1,2-oxirane donor. Upon glycosylation, a C-2 hydroxyl is exposed to serve as the acceptor in the next glycosylation. Branching at C-2 with a beta-linked glycoside at C-1 was not achievable with epoxy 23 donor, but was accomplished with fluoro donor 25, in turn derived from 23. (See 19 + 18 --> 20; 20 + 25 --> 26. Compound 26 was deprotected to complete the first total synthesis of a natural saponin, desgalactotigonin (3)). A limitation in stereospecifity in the use of donor 23 and monoprotected galactal acceptor 28 was also encountered.
• Steroidal glycosides from Capsicum annuum
  作者：Shoji Yahara、Takeshi Ura、Chie Sakamoto、Toshihiro Nohara

  DOI：10.1016/s0031-9422(00)90366-2

  日期：1994.11

  Four new steroidal glycosides, named capsicosides A-D together with proto-degalactotigonin, were isolated from the roots and seeds of Capsicum annuum var. conoides and Capsicum annuum var. fasciculatum. On the basis of detailed chemical and spectroscopic evidence, the structures of capsicosides A-D were shown to be furostanol glycosides corresponding to gitogenin and tigogenin oligoglycosides. Capsicoside A was regarded as the same compound as the previously described capsicoside, whose structure now needs to be revised according to the data presented in this report.
• NAKANO, KIMIKO;MATSUDA, EMI;TSURUMI, KAORI;YAMASAKI, TOKUSHI;MURAKAMI, KO+, PHYTOCHEMISTRY, 27,(1988) N 10, C. 3235-3239
  作者：NAKANO, KIMIKO、MATSUDA, EMI、TSURUMI, KAORI、YAMASAKI, TOKUSHI、MURAKAMI, KO+

  DOI：——

  日期：——