Agavogenin | 16822-59-6

• 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: Agavogenin
• 英文别名: (1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13S,15R,16R,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10,15,16-triol
• CAS: 16822-59-6
• 化学式: C₂₇H₄₄O₅
• 分子量: 448.643
• InChiKey: IZSOKVKTMKUCGT-KZJPKIEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Agavogenin 在 吡啶 作用下， 生成 (2aR,4R,5S,5'R,6aS,6bS,8R,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4,5,8-triyl triacetate
  参考文献：
  名称：

  The Δ⁹-12-Keto Steroidal Sapogenins

  摘要：

  DOI：

  10.1021/ja01150a025
• 作为产物：
  描述：

  (25R)-2α,3β-dihydroxy-5α-spirost-9-en-12-one 在 吡啶 、 乙醇 、 sodium 作用下， 生成 Agavogenin
  参考文献：
  名称：

  The Δ⁹-12-Keto Steroidal Sapogenins

  摘要：

  DOI：

  10.1021/ja01150a025

文献信息

• Steroidal Sapogenins^1a
  作者：Russell E. Marker、R. B. Wagner、Paul R. Ulshafer、Emerson L. Wittbecker、Dale P. J. Goldsmith、Clarence H. Ruof

  DOI：10.1021/ja01201a032

  日期：1947.9
• Sterols. CLVII. Sapogenins. LXIX.¹ Isolation and Structures of Thirteen New Steroidal Sapogenins. New Sources for Known Sapogenins
  作者：Russell E. Marker、R. B. Wagner、Paul R. Ulshafer、Emerson L. Wittbecker、Dale P. J. Goldsmith、Clarence H. Ruof

  DOI：10.1021/ja01246a051

  日期：1943.6
• Steroidal Sapogenins. No. 160. The Conversion of Pseudosapogenins to Sapogenins and Neosapogenins
  作者：Russell E. Marker、Josefina Lopez

  DOI：10.1021/ja01202a036

  日期：1947.10
• Sannie; Lapin, Bulletin de la Societe Chimique de France, 1952, p. 1080,1083
  作者：Sannie、Lapin

  DOI：——

  日期：——
• Steroidal saponins from the rhizomes of Hosta sieboldii and their cytostatic activity on HL-60 cells
  作者：Yoshihiro Mimaki、Minpei Kuroda、Aiko Kameyama、Akihito Yokosuka、Yutaka Sashida

  DOI：10.1016/s0031-9422(98)00157-5

  日期：1998.8

  total of eighteen steroidal saponins were isolated from the rhizomes of Hosta sieboldii, one of which appeared to be the first isolation from a plant source and six to be new compounds. The structures of the new saponins were determined by spectral data and a few chemical transformations to be (25R)-2 alpha,3 beta-dihydroxy-5 alpha-spirostan-12-one (manogenin) 3-O-O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(l-->4)-beta-D-galacltopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-5 alpha-spirost-9-en-12-one (9,11-dehydromanogenin) 3-O-O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, 9,11-dehydromanogenin 3-O-O-beta-D-glucopyranosyl-(1-->2)-O-[O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-26-beta-D-glucopyranosyloxy-22-methoxy-5 alpha-furostan-12-one 3-O-O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-26-beta-D-glucopyranosyloxy-22-methoxy-5 alpha-furost-9-en-12-one 3-O-O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} and (25R)-5 alpha-spirostan-2 alpha,3 beta,12 beta-triol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranoside), respectively. Cytostatic activity of the isolated saponins on leukaemia HL-60 cells was examined. (C) 1998 Elsevier Science Ltd. All rights reserved.