(25R)-2α,3β-dihydroxy-5α-spirost-9-en-12-one | 3514-48-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25R)-2α,3β-dihydroxy-5α-spirost-9-en-12-one
• 英文别名: 9-dehydromanogenin；(1S,2S,4S,5'R,6R,7S,8R,9S,13S,15R,16R,18S)-15,16-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-11-ene-6,2'-oxane]-10-one
• CAS: 3514-48-5
• 化学式: C₂₇H₄₀O₅
• 分子量: 444.612
• InChiKey: LXLRCWVAWYFQIU-BOJOXNMBSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  583.6±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (25R)-2α,3β-dihydroxy-5α-spirost-9-en-12-one 在 platinum(IV) oxide 吡啶 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 溶剂黄146 为溶剂， 反应 24.25h， 生成 manogenin
  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：

  (25R)-2α-hydroxy-3β-[(O-β-D-xylopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl)oxy]-5α-spirost-9-en-12-one 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以4.7 mg的产率得到(25R)-2α,3β-dihydroxy-5α-spirost-9-en-12-one
  参考文献：
  名称：

  Steroidal saponins from the whole plants of Agave utahensis and their cytotoxic activity

  摘要：

  Phytochemical investigation of the whole plants of Agave utahensis Engelm. (Agavaceae) has resulted in the isolation of 15 steroidal saponins (1-15), including five spirostanol saponins (1-5) and three furostanol saponins (11-13). Structures of compounds 1-5 and 11-13 were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.02.013

文献信息

• Cytotoxic steroidal glycosides from the underground parts of <i>Hosta ventricosa</i>
  作者：Hong-Biao Chu、Rui Li、Yan Gao、Dan Li、Jia-Ping Zhang、Zeng-Lamu Dan

  DOI：10.1080/10286020.2020.1787995

  日期：2021.9.2

  Abstract A phytochemical study on the underground parts of Hosta ventricosa yielded one new spirostanol saponin (1), two new furostanol saponins (2 and 3), and one new pregnane glycoside (4), along with three known compounds (5‒7). Their structures were elucidated on the basis of chemical and spectroscopic analysis. All isolated compounds were evaluated for their cytotoxic effects against five human

  摘要 对Hosta ventricosa地下部分的植物化学研究产生了一种新的螺甾醇皂苷 ( 1 )、两种新的呋甾醇皂苷 ( 2和3 ) 和一种新的孕烷苷 ( 4 )，以及三种已知化合物 ( 5-7 )。在化学和光谱分析的基础上阐明了它们的结构。评估了所有分离的化合物对五种人类癌细胞系（HL-60、A-549、SMMC-7721、MCF-7 和 SW-480）的细胞毒性作用。化合物1，2，和5-7显示出细胞毒活性与IC 50 3.21-17.06μM的值。
• The Conversion of Hecogenin and Manogenin into Derivatives of Allopregnane-12,20-dione
  作者：George P. Mueller、Robert E. Stobaugh、Robert S. Winniford

  DOI：10.1021/ja01116a002

  日期：1953.10
• The Δ⁹-12-Keto Steroidal Sapogenins
  作者：R. B. Wagner、Robert F. Forker、Penn F. Spitzer

  DOI：10.1021/ja01150a025

  日期：1951.6
• 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。
• Steroidal saponins from the whole plants of Agave utahensis and their cytotoxic activity
  作者：Akihito Yokosuka、Yoshihiro Mimaki

  DOI：10.1016/j.phytochem.2009.02.013

  日期：2009.4

  Phytochemical investigation of the whole plants of Agave utahensis Engelm. (Agavaceae) has resulted in the isolation of 15 steroidal saponins (1-15), including five spirostanol saponins (1-5) and three furostanol saponins (11-13). Structures of compounds 1-5 and 11-13 were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells. (C) 2009 Elsevier Ltd. All rights reserved.