9-去氢龙舌兰皂苷 | 3514-26-9

• 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
• 中文名称: 9-去氢龙舌兰皂苷
• 英文名称: Δ⁹⁽¹¹⁾-22-isoallospirosten-3β-ol-12-one
• 英文别名: 3β-hydroxy-9(11)-en-12-oxo-(25R)-5α-spirostane；(25R)-3β-hydroxy-5α-spirost-9-en-12-one；Δ9(11)-hecogenin；9(11)-dehydrohecogenin；9-dehydrohecogenin；(25R)-3β-hydroxy-5α-spirost-9(11)-en-12-one；(1S,2S,4S,5'R,6R,7S,8R,9S,13S,16S,18S)-16-hydroxy-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: 3514-26-9；107242-24-0
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: YLZUMNXGXFXZNQ-SMCBIBCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-去氢龙舌兰皂苷 在 一水合肼 、 乙二醇 作用下， 生成 (3β,5Alpha,25R)3-羟基螺甾-9(11)-烯
  参考文献：
  名称：

  Steroidal Sapogenins. XI. Experiments in the Hecogenin Series (Part 2)

  摘要：

  DOI：

  10.1021/jo50002a015
• 作为产物：
  描述：

  Δ⁹⁽¹¹⁾22-isoallospirosten-3β-ol-12-one-3-acetate 在 氢氧化钾 作用下， 生成 9-去氢龙舌兰皂苷
  参考文献：
  名称：

  STEROIDAL SAPOGENINS. VII.¹ EXPERIMENTS IN THE HECOGENIN SERIES (PART 1)

  摘要：

  DOI：

  10.1021/jo01142a021

文献信息

• Two New Steroidal Saponins with Antifungal Activity from Hosta plantaginea Rhizomes
  作者：Mengyue Wang、Zihan Xu、Ying Peng、Guoyue Zhong、Xiaobo Li

  DOI：10.1007/s10600-016-1858-2

  日期：2016.11

  Two new steroidal saponins, (25R)-3β-hydroxy-5α-spirost-9-en-12-one 3-O-β-D-galactopyranoside (hostasaponin A, 1), and (25R)-2α,3β-dihydroxy-5α-spirost-12-one 3-O-β-D-galactopyranoside (hostasaponin B, 2), together with a new natural product, 2α,3β-dihydroxy-5α-pregn-16-en-20-one (3), were isolated from the rhizomes of Hosta plantaginea, a perennial herb used mainly as an ornamental plant and folk medicine for fungal infection and various inflammations. The active evaluation results showed that 1 and 2 possess potent inhibition activity against Candida albicans, with MIC values less than 20 μg/mL.

  两种新的类固醇皂苷，(25R)-3β-羟基-5α-螺甾烯-12-酮 3-O-β-D-半乳糖吡喃糖苷（宿根皂苷 A，1），和 (25R)-2α,3β-二羟基-5α-螺甾烯-12-酮 3-O-β-D-半乳糖吡喃糖苷（宿根皂苷 B，2），以及一种新的天然产物 2α,3β-二羟基-5α-孕烯-16-酮（3），是从主要作为观赏植物和民间药物用于真菌感染及各种炎症的宿根植物的根茎中分离得到的。活性评估结果显示，1 和 2 对白色念珠菌具有效的抑制活性，最小抑制浓度（MIC）值低于 20 μg/mL。
• Simple and Convenient Method for the Synthesis of Δ⁹⁽¹¹⁾-3-Hydroxy, Δ^1,4- and Δ^1,4,9(11)-3-Ketosteroids by Selective Dehydrogenation of 3-Hydroxy-12-Ketosteroids
  作者：Boonsong Kongkathip、Ngampong Kongkathip、Ponsak Khunnavutimanotum、Uthai Sakee

  DOI：10.1246/cl.1998.1207

  日期：1998.12

  Hecogenin can be selectively dehydrogenated to the corresponding Δ9(11)-3-hydroxysteroid, Δ1,4- and Δ1,4,9(11)-3-ketosteroids by the treatment of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) with a variety of solvents.

  通过用多种溶剂处理 2,3-二氯-5,6-二氰基苯醌 (DDQ)，可选择性地脱氢生成相应的 Δ9(11)-3-羟类固醇、Δ1,4- 和 Δ1,4,9(11)-3-酮类固醇。
• Separation of hecogenin-tigogenin mixtures
  申请人：Omni Research Incorporated

  公开号：US03935194A1

  公开（公告）日：1976-01-27

  A process for separating hecogenin-tigogenin mixtures which involves acetylating the mixed genins, then solvent recrystallization separation of the mixed genin acetates, crystallizing out hecogenin acetate from a non-polar solvent, tigogenin acetate from a polar solvent. A sequential sequence is contemplated to first recover the predominant genin, then the less-predominant genin. Preferred source materials are crude 5-25% sapogenin content acid hydrolyzates of Agave leaf juice. Specifically preferred is the acid hydrolyzate from fresh Agave leaf juice obtained prior to decortication.

  一种分离赫科根因-提戈根因混合物的方法，包括醋酸化混合的基因素，然后通过溶剂重结晶分离混合的基因酯，从非极性溶剂中结晶出赫科根因酯，从极性溶剂中结晶出提戈根因酯。考虑到首先回收主要基因素，然后回收次要基因素的顺序。优选的原料是龙舌兰叶汁粗5-25％皂甙含量的酸水解物。特别优选的是在去皮前获取的新鲜龙舌兰叶汁的酸水解物。
• Steroids. LI.¹ Δ^4,6-Dien-3-ones^2,3
  作者：Franz Sondheimer、C. Amendolla、G. Rosenkranz

  DOI：10.1021/ja01119a044

  日期：1953.12
• Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides
  作者：Karell Pérez-Labrada、Ignacio Brouard、Sara Estévez、María Teresa Marrero、Francisco Estévez、Daniel G. Rivera

  DOI：10.1016/j.bmc.2012.05.018

  日期：2012.7

  Twelve C-ring modified spirostanyl glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). With the aim of assessing the influence of the hydrophobic character, the conformational flexibility and the stereochemistry of the C-ring functionalities on the cytotoxic activity, a variety of spirostanic aglycones incorporating methylene, methoxyl, alpha,beta-unsaturated ketone and lactone groups were subjected to a linear glycosylation strategy leading to glycosides derived from the 3,6-dipivaloylated beta-D-glucoside and the beta-chacotrioside moieties. The 3,6-dipivaloylated spirostanyl beta-D-glucosides showed moderate to good cytotoxic activity against HL-60, but no significant cytotoxicity against benign blood cells. However, the cytotoxicity of spirostanyl beta-chacotriosides was highly dependent on the nature of the C-ring functional groups of the steroidal aglycones. Actually, the chacotrioside-based saponins either with no functionality or bearing a hydrophobic methylene group at C-12 were the most cytotoxic ones against both HL-60 and benign blood cells. On the other hand, the incorporation of very polar functionalities and the opening of the ring C with the consequent loss of rigidity led to a significant drop in the cytotoxicity against HL-60. These results confirm that spirostanyl beta-chacotriosides including very lipophilic aglycones are the most cytotoxic ones among their congeners. (C) 2012 Elsevier Ltd. All rights reserved.