(25S)-spirost-5-en-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside | 91327-42-3

• 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: (25S)-spirost-5-en-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside
• 英文别名: 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl-yamogenin；(25S)-spirost-5-en-3β-yl O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside；3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galacopyranosylyamogenin；(25S)-3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galacopyranosyl-yamogenin；aspidistrin；(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'S,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-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: 91327-42-3
• 化学式: C₅₀H₈₀O₂₂
• 分子量: 1033.17
• InChiKey: XGYNVBAFYOIJRP-UUHWPCKHSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  72
• 可旋转键数：
  11
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  335
• 氢给体数：
  12
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (25S)-spirost-5-en-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以3 mg的产率得到薯蓣皂素
  参考文献：
  名称：

  Sugiyama, Mari; Nakano, Kimiko; Tomimatsu, Toshiaki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1365 - 1372

  摘要：

  DOI：
• 作为产物：
  描述：

  (25S)-26-[(β-D-glucopyranosyl)oxy]furosta-5,20(22)-dien-3β-yl O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside 在 β-D-glucosidase 、 水 作用下， 以 aq. acetate buffer 为溶剂， 反应 12.0h， 以1 mg的产率得到(25S)-spirost-5-en-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside
  参考文献：
  名称：

  Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

  摘要：

  铃兰（百合科）全草的植物化学研究表明，从中提取出了15种甾体苷类化合物（1-15），其中包括9个含有lycotetrose结构单元的新化合物（4-6，10-15）。新化合物的结构通过二维核磁共振（NMR）分析和化学方法确定。所分离的化合物对HL-60人类早幼粒细胞白血病细胞、A549人类肺腺癌细胞以及HSC-4和HSC-2人类口腔鳞状细胞癌细胞系进行了细胞毒性评估。其中，(25S)-螺甾-5-烯-3β-基 O-β-d-吡喃葡糖基-(1→2)-O-[β-d-吡喃木糖基-(1→3)]-O-β-d-吡喃葡糖基-(1→4)-β-d-吡喃半乳糖苷（1）对HL-60、A549、HSC-4和HSC-2细胞显示出细胞毒性活性，IC50值范围从0.96到3.15 μM。相应的呋喃甾苷类化合物1，即(25S)-26-[（β-d-吡喃葡糖基）氧]-22α-羟基呋喃甾-5-烯-3β-基 O-β-d-吡喃葡糖基-(1→2)-O-[β-d-吡喃木糖基-(1→3)]-O-β-d-吡喃葡糖基-(1→4)-β-d-吡喃半乳糖苷（8），对贴壁细胞系A549、HSC-4和HSC-2细胞显示出细胞毒性，IC50值分别为2.97、11.04和8.25 μM。螺甾烷lycotetroside（1）以剂量依赖性方式引起A549细胞的坏死性细胞死亡。相反，呋喃甾烷lycotetroside（8）以时间依赖性方式诱导A549细胞的凋亡性细胞死亡，这一点通过形态学观察和流式细胞术分析得到了证实。

  DOI：

  10.3390/ijms18112358

文献信息

• Sugiyama, Mari; Nakano, Kimiko; Tomimatsu, Toshiaki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1365 - 1372
  作者：Sugiyama, Mari、Nakano, Kimiko、Tomimatsu, Toshiaki、Nohara, Toshihiro

  DOI：——

  日期：——
• Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity
  作者：Yukiko Matsuo、Daisuke Shinoda、Aina Nakamaru、Kuni Kamohara、Hiroshi Sakagami、Yoshihiro Mimaki

  DOI：10.3390/ijms18112358

  日期：——

  Phytochemical examination of Convallaria majalis (Liliaceae) whole plants yielded 15 steroidal glycosides (1–15), including nine new compounds (4–6, 10–15) with a lycotetrose unit. The structures of the new compounds were determined using two-dimensional Nuclear magnetic resonance (NMR) analyses and chemical methods. The isolated compounds were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and HSC-4 and HSC-2 human oral squamous cell carcinoma cell lines. Of these, (25S)-spirost-5-en-3β-yl O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (1) exhibited cytotoxic activity against HL-60, A549, HSC-4, and HSC-2 cells with IC50 values ranging from 0.96 to 3.15 μM. The corresponding furostanol glycoside of 1, (25S)-26-[(β-d-glucopyranosyl)oxy]-22α-hydroxyfurost-5-en-3β-yl O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (8), was cytotoxic to the adherent cell lines of A549, HSC-4, and HSC-2 cells with IC50 values of 2.97, 11.04, and 8.25 μM, respectively. The spirostanol lycotetroside (1) caused necrotic cell death in A549 cells in a dose-dependent manner. Alternatively, the furostanol lycotetroside (8) induced apoptotic cell death in A549 cells in a time-dependent manner, as was evident by morphological observations and flow cytometry analyses.

  铃兰（百合科）全草的植物化学研究表明，从中提取出了15种甾体苷类化合物（1-15），其中包括9个含有lycotetrose结构单元的新化合物（4-6，10-15）。新化合物的结构通过二维核磁共振（NMR）分析和化学方法确定。所分离的化合物对HL-60人类早幼粒细胞白血病细胞、A549人类肺腺癌细胞以及HSC-4和HSC-2人类口腔鳞状细胞癌细胞系进行了细胞毒性评估。其中，(25S)-螺甾-5-烯-3β-基 O-β-d-吡喃葡糖基-(1→2)-O-[β-d-吡喃木糖基-(1→3)]-O-β-d-吡喃葡糖基-(1→4)-β-d-吡喃半乳糖苷（1）对HL-60、A549、HSC-4和HSC-2细胞显示出细胞毒性活性，IC50值范围从0.96到3.15 μM。相应的呋喃甾苷类化合物1，即(25S)-26-[（β-d-吡喃葡糖基）氧]-22α-羟基呋喃甾-5-烯-3β-基 O-β-d-吡喃葡糖基-(1→2)-O-[β-d-吡喃木糖基-(1→3)]-O-β-d-吡喃葡糖基-(1→4)-β-d-吡喃半乳糖苷（8），对贴壁细胞系A549、HSC-4和HSC-2细胞显示出细胞毒性，IC50值分别为2.97、11.04和8.25 μM。螺甾烷lycotetroside（1）以剂量依赖性方式引起A549细胞的坏死性细胞死亡。相反，呋喃甾烷lycotetroside（8）以时间依赖性方式诱导A549细胞的凋亡性细胞死亡，这一点通过形态学观察和流式细胞术分析得到了证实。