25(R)-5α-spirostan-3β-ol-12-one 3-O-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside | 168960-81-4

• 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: 25(R)-5α-spirostan-3β-ol-12-one 3-O-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
• 英文别名: (25R)-3β-[(β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one；(3β,5α,25R)-12-oxospirostan-3-yl O-β-D-glucopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-3)]-β-D-glucopyranosyl-(1-4)-β-D-galactopyranoside；hecogenin O-{O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside}；hecogenin 3-O-{β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside}；hecogenin 3-O-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside；hecogenin-3-O-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside；Hecogenintetraglucoside；(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-16-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one
• CAS: 168960-81-4
• 化学式: C₅₀H₈₀O₂₃
• 分子量: 1049.17
• InChiKey: IXUNZKARBRITGN-WVTRVWQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  73
• 可旋转键数：
  11
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  352
• 氢给体数：
  12
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  25(R)-5α-spirostan-3β-ol-12-one 3-O-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以4.9 mg的产率得到海柯吉宁
  参考文献：
  名称：

  玉Host地下部分的甾体皂苷及其对肿瘤启动子诱导的磷脂代谢的抑制活性。

  摘要：

  对玉Host的地下部分进行植物化学研究后，发现了六种新的甾体皂苷和一种已知的甾体皂苷。通过对新化合物的1H和13C-NMR光谱进行详细分析（包括二维NMR光谱，酸催化的水解反应以及随后的化学相关性），并与已知化合物的光谱数据进行比较，可以确定新化合物的结构。检查了分离的皂苷及其苷元对12-O-十四烷酰phorbol-13-乙酸盐（TPA）刺激的32P掺入HeLa细胞磷脂的抑制活性，以鉴定新的抗肿瘤促进剂化合物。

  DOI：

  10.1248/cpb.43.1190
• 作为产物：
  描述：

  polianthoside D 在 β-glucosidase 作用下， 以 acetate buffer 为溶剂， 反应 16.0h， 以6 mg的产率得到25(R)-5α-spirostan-3β-ol-12-one 3-O-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
  参考文献：
  名称：

  Spirostanol and Furostanol Glycosides from the Fresh Tubers of Polianthes tuberosa

  摘要：

  Six new steroid glycosides-two spirostanols, polianthosides B and C (1, 2), and four furostanols, polianthosides D-G (3-6)-were isolated from the fresh tubers of Polianthes tuberosa, together with seven known spirostanols (7-13) and a known furostanol (14) saponins. Their structures were elucidated on the basis of spectroscopic analysis and the results of acidic and enzymatic hydrolysis. The cytotoxic activities of 1-14 against HeLa cells are reported.

  DOI：

  10.1021/np034028a

文献信息

• Steroidal saponins from the underground parts of Chlorophytum comosum and their inhibitory activity on tumour promoter-induced phospholipids metabolism of hela cells
  作者：Yoshihiro Mimaki、Toshihiro Kanmoto、Yutaka Sashida、Atsuko Nishino、Yoshiko Satomi、Hoyoku Nishino

  DOI：10.1016/0031-9422(95)00789-x

  日期：1996.3

  apiofuranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)]-O-beta-D-gluc opyranosyl- (1-->4)-beta-D-galactopyranoside], respectively. The isolated saponins were examined for inhibitory activity using 12-O-tetradecanoylphorbor-13-acetate-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to identify new antitumour-promoter compounds.

  从新鲜的 Chlorophytum comosum 地下部分中分离出三种新的包含 β-D-apiofuranose 的螺甾醇五糖苷以及四种已知的皂苷。新化合物的结构由光谱数据确定，包括二维核磁共振和部分酸催化水解为 (25R)-5 alpha-spirostane-2 alpha,3 beta-diol 3-O-[O-beta- D-吡喃葡萄糖基-(1-->2)-O-[O-β-D-吡呋喃糖基-(1-->4)-β-D-吡喃葡萄糖基-(1-->3)]-O-β- D-吡喃葡萄糖基-(1-->4)-β-D-吡喃半乳糖苷], (25R)-3 beta-hydroxy-5 alpha-spirostan-12-one (hecogenin) 3-O-[O-beta-D-吡喃葡萄糖基-(1-->2)-O-[O-β-D-吡呋喃糖基-(1- ->4)-β-D-吡喃木糖基-(1-->3)]-O-β-D-吡喃葡
• Steroidal Saponins from the Underground Parts of Hosta longipes and Their Inhibitory Activity on Tumor Promoter-Induced Phospholipid Metabolism.
  作者：Yoshihiro MIMAKI、Toshihiro KANMOTO、Minpei KURODA、Yutaka SASHIDA、Atsuko NISHINO、Yoshiko SATOMI、Hoyoku NISHINO

  DOI：10.1248/cpb.43.1190

  日期：——

  underground parts of Hosta longipes gave six new steroidal saponins together with a known one. The structures of the new compounds were determined by detailed analysis of their 1H- and 13C-NMR spectra including two-dimensional NMR spectroscopy, acid-catalyzed hydrolysis followed by chemical correlation, and by comparison with spectral data of known compounds. The isolated saponins and their aglycones

  对玉Host的地下部分进行植物化学研究后，发现了六种新的甾体皂苷和一种已知的甾体皂苷。通过对新化合物的1H和13C-NMR光谱进行详细分析（包括二维NMR光谱，酸催化的水解反应以及随后的化学相关性），并与已知化合物的光谱数据进行比较，可以确定新化合物的结构。检查了分离的皂苷及其苷元对12-O-十四烷酰phorbol-13-乙酸盐（TPA）刺激的32P掺入HeLa细胞磷脂的抑制活性，以鉴定新的抗肿瘤促进剂化合物。
• Spirostanol and Furostanol Glycosides from the Fresh Tubers of <i>Polianthes tuberosa</i>
  作者：Jian-Ming Jin、Ying-Jun Zhang、Chong-Ren Yang

  DOI：10.1021/np034028a

  日期：2004.1.1

  Six new steroid glycosides-two spirostanols, polianthosides B and C (1, 2), and four furostanols, polianthosides D-G (3-6)-were isolated from the fresh tubers of Polianthes tuberosa, together with seven known spirostanols (7-13) and a known furostanol (14) saponins. Their structures were elucidated on the basis of spectroscopic analysis and the results of acidic and enzymatic hydrolysis. The cytotoxic activities of 1-14 against HeLa cells are reported.