capsicoside B1 | 108027-19-6

• 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: capsicoside B1
• 英文别名: gitogenin 3-O-β-D-glucopyranosyl(1->4)-β-D-galactopyranoside；gitogenin 3-O-4)-β-D-galactopyranoside>；(25R)-2α,3β-dihydroxy-5α-spirostane 3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside；(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,15R,16R,18S)-15-hydroxy-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-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 108027-19-6
• 化学式: C₃₉H₆₄O₁₄
• 分子量: 756.929
• InChiKey: BOFSXGGSAUTBNA-YROJOSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  217
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  terrestrosin F 在 β-glucosidase 作用下， 以5 mg的产率得到capsicoside B1
  参考文献：
  名称：

  蒺藜果实中的甾体皂苷

  摘要：

  F-gitonin、desglucolanatigonin、gitonin 和tigogenin 3-O-β-D-吡喃木糖基)1-2)-[β-D-吡喃木糖基)1-3)]-β-D-吡喃葡萄糖基)1-4)-[α -L-吡喃鼠李糖基(1-2)]-β-D-吡喃半乳糖苷。在光谱分析的基础上阐明了新皂苷的结构，包括二维核磁共振技术和化学反应。

  DOI：

  10.1016/s0031-9422(97)00043-5

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。
• Steroidal saponins from Hosta longipes and their inhibitory activity on tumour promoter-induced phospholipid metabolism of HeLa Cells
  作者：Yoshihiro Mimaki、Toshihiro Kanmoto、Minpei Kuroda、Yutaka Sashida、Yoshiko Satomi、Atsuko Nishino、Hoyoku Nishino

  DOI：10.1016/0031-9422(96)00030-1

  日期：1996.7

  3-O-O-alpha-L -rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl -(1-->4)]-beta-D-galactopyranoside}, respectively. The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbor-13-acetate-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.

  从玉簪的地下部分分离出三种新的螺甾醇皂苷和两种新的呋甾醇皂苷。它们的结构被确定为 (25R)-5 alpha-spirostane-2 alpha, 3 beta-diol (gitogenin) 3-O-O-alpha-L -rhamnopyranosyl-(1-->2)-beta-D-吡喃半乳糖苷}，gitogenin 3-O-O-alpha-L-rhamnopyranosyl-(1-->2) -O-[β-D-吡喃葡萄糖基-(1-->4)]-β-D-吡喃半乳糖苷-， (25R)-5 alpha-spirostan-3 beta-ol (tigogenin) 3-O-O-alpha-L-rhamnopyranosyl-(1-->2) -O-[beta-D-glupyranosyl-(1-- >4)]-β-D-吡喃半乳糖苷-, 26-O-β-D-吡喃葡萄糖基-22-O-甲基-(25R)-5
• Total synthesis and cytotoxicity evaluation of the spirostanol saponin gitonin
  作者：Yong Li、Xun Lv、Jun Liu、Yuguo Du

  DOI：10.1039/d3ob02101g

  日期：——

  commercially available isopropyl β-D-1-thiogalactopyranoside (IPTG) and tigogenin. A cascade two-step glycosylation and Schmidt's inverse procedure significantly facilitated the synthesis of gitonin and its derivatives. The cytotoxic activities of gitonin and its structural analogues were evaluated against A549, HepG2, and MCF-7, and most of them exhibited moderate to excellent inhibitory activity. Our study

  由市售的异丙基 β- D -1-硫代半乳糖苷 (IPTG) 和替高配元，通过 12 个步骤（最长的线性序列）有效合成了螺甾烷皂苷 gitonin，总产率为 18.5%。级联两步糖基化和施密特逆过程显着促进了 gtonin 及其衍生物的合成。对A549、HepG2和MCF-7的Gtonin及其结构类似物的细胞毒活性进行了评估，其中大多数表现出中等至优异的抑制活性。我们的研究表明，从 gitonin 中去除 β- D-吡喃半乳糖基残基（连接在葡萄糖单元的 C-2 处）不会降低抑制活性；然而，糖单元的进一步裂解可能会严重降低活性。对这些癌细胞系的生物测定还表明，苷元上 2α-羟基的存在削弱了设计的皂苷的细胞毒性。