(3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->4)-6-deoxy-α-L-mannopyranosyl-(1->3)]-β-D-glucopyranoside | 1206850-20-5

• 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: (3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->4)-6-deoxy-α-L-mannopyranosyl-(1->3)]-β-D-glucopyranoside
• 英文别名: (25R)-spirost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1>2)-O-[O-β-D-glucopyranosyl-(1>4)-α-L-rhamnopyranosyl-(1->3)]-β-D-glucopyranoside；chantrieroside A；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1206850-20-5
• 化学式: C₅₁H₈₂O₂₁
• 分子量: 1031.2
• InChiKey: DSIMBHGLGKGFRL-GUVCCSFUSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  72
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  315
• 氢给体数：
  11
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  (3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->4)-6-deoxy-α-L-mannopyranosyl-(1->3)]-β-D-glucopyranoside 在 水 、 三氟乙酸 作用下， 反应 2.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Chantriolide C, a New Withanolide Glucoside and a New Spirostanol Saponin from the Rhizomes of Tacca chantrieri

  摘要：

  从香茶菜（Tacca chantrieri）的根茎中分离出了一种新的香茶菜内酯--香茶菜内酯 C (1)和一种新的螺甾醇皂甙--香茶菜内酯 A (2)，以及另外五种已知的甾体化合物。它们的结构被确定为 (22R)-1α,12α-二乙酰氧基-2α,3α；6α,7α-diepoxy-27-[(β-D-glucopyranosyl)oxy]-5α-hydroxywith-24-enolide (1) 和 (25R)-spirost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[O-β-D-Glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→3)]-β-D-Glucopyranoside (2)。通过对这些新皂苷的一维（1D）和二维核磁共振光谱以及化学证据的详细分析，确定了它们的结构。

  DOI：

  10.1248/cpb.57.1126

文献信息

• Cytotoxic Steroidal Saponins from the Rhizomes of<i>Tacca integrifolia</i>
  作者：Htay Htay Shwe、Mye Aye、Myint Myint Sein、Khin Than Htay、Peter Kreitmeier、Jürg Gertsch、Oliver Reiser、Jörg Heilmann

  DOI：10.1002/cbdv.200900042

  日期：2010.3

  a-L-mannopyranosyl-(1-->3)]-beta-D-glucopyranosyl]oxy}-20-oxopregn-5-en-16-yl (4R)-5-(beta-D-glucopyranosyloxy)-4-methylpentanoate (6), were isolated from the rhizomes of Tacca integrifolia together with two known (25R) configurated steroid saponins (3beta,25R)-spirost-5-en-3-yl 6-deoxy-alpha-L-mannopyranosyl-(1-->2)-[6-deoxy-alpha-L-mannopyranosyl-(1-->3)]-beta-D-glucopyranoside (2) and (3beta,22R

  3）]-β-D-吡喃葡萄糖基]氧基} -20-氧杂戊烯-5-en-16-基（4R）-5-（β-D-吡喃葡萄糖基氧基）-4-甲基戊酸酯（6），从根茎中分离出来麦草与两种已知的（25R）构型甾体皂苷（3beta，25R）-spirost-5-en-3-yl 6-脱氧-alpha-L-甘露吡喃糖基-（1-> 2）-[6-脱氧-alpha-L-甘露吡喃糖基-（1-> 3）]-β-D-吡喃葡萄糖苷（2）和（3beta，22R，25R）-26-（β-D-吡喃葡糖氧基）-22-甲氧基呋喃-5- -3-yl 6-脱氧-α-L-甘露吡喃糖基-（1-> 2）-[6-6-脱氧-α-L-甘露吡喃糖基-（1-> 3）]-β-D-吡喃葡萄糖苷（4） 。在HeLa细胞中评估了分离出的化合物的细胞毒性活性，并显示了化合物2的最高细胞毒性值，IC（50）为1.2 +/- 0.4μM。有趣的是，虽然化合物1-5在1.2 +/-
• Chantriolide C, a New Withanolide Glucoside and a New Spirostanol Saponin from the Rhizomes of Tacca chantrieri
  作者：Lin Zhang、Jiang-Yun Liu、Li-Zhen Xu、Shi-Lin Yang

  DOI：10.1248/cpb.57.1126

  日期：——

  A new withanolide, chantriolide C (1) and a new spirostanol saponin, chantrieroside A (2) were isolated from the rhizomes of Tacca chantrieri, together with another five known steroidal compounds. Their structures were established as (22R)-1α,12α-diacetoxy-2α,3α;6α,7α-diepoxy-27-[(β-D-glucopyranosyl)oxy]-5α-hydroxywith-24-enolide (1) and (25R)-spirost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (2). The structures of the new saponins were determined by detailed analysis of their 1 dimensional (1D) and 2D NMR spectra, and chemical evidences.

  从香茶菜（Tacca chantrieri）的根茎中分离出了一种新的香茶菜内酯--香茶菜内酯 C (1)和一种新的螺甾醇皂甙--香茶菜内酯 A (2)，以及另外五种已知的甾体化合物。它们的结构被确定为 (22R)-1α,12α-二乙酰氧基-2α,3α；6α,7α-diepoxy-27-[(β-D-glucopyranosyl)oxy]-5α-hydroxywith-24-enolide (1) 和 (25R)-spirost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[O-β-D-Glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→3)]-β-D-Glucopyranoside (2)。通过对这些新皂苷的一维（1D）和二维核磁共振光谱以及化学证据的详细分析，确定了它们的结构。