(22S)-cholest-5-ene-1β,3β,16β,22-tetrol | 142735-57-7

• 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: (22S)-cholest-5-ene-1β,3β,16β,22-tetrol
• 英文别名: (22S)-cholest-5-ene-1β,3β,16β,22-tetraol；alliosterol；(22s)-Cholest-5-ene-1beta,3beta,16beta,22-tetrol；(1R,3R,8S,9S,10R,13S,14S,16S,17R)-17-[(2S,3S)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1,3,16-triol
• CAS: 142735-57-7
• 化学式: C₂₇H₄₆O₄
• 分子量: 434.66
• InChiKey: KPXZHYLGRFOLAD-UXKFJXGFSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  580.5±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (22S)-cholest-5-ene-1β,3β,16β,22-tetrol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以6.3 mg的产率得到
  参考文献：
  名称：

  Three New Cholestane Bisdesmosides from Nolina recurvata Stems and Their Inhibitory Activity on cAMP Phosphodiesterase and Na+/K+ ATPase.

  摘要：

  Fresh stems of Nolina recurvata were found to contain three new cholestane bisdesmosides. Their structures were determined on the basis of spectroscopic data and acid-catalyzed hydrolysis to be (22S)-cholest-5-ene-1β, 3β, 16β, 22-tetrol 1-O-β-D-glucopyranoside 16-O-α-L-rhamnopyranoside (1), (22S)-cholest-5-ene-1β, 3β, 16β, 22-tetrol 1, 16-di-O-β-D-glucopyranoside (2) and (22S)-cholest-5-ene-1β, 3β, 16β, 22-tetrol 1-O-{O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside} 16-O-α-L-rhamnopyranoside (3), respectively. The prominent downfield shift of the aglycone 19-Me of 3, compared with that of 1 and 2, is likely caused by the interaction between the 19-Me and 6'''-Me of the rhamnose attached to C-2 of the inner glucose, evidence for which was provided through molecular mechanics and molecular dynamics calculation studies and by the nuclear Overhauser effect (NOE) correlation spectrum. The isolated compounds and their derivatives were evaluated for their inhibitory activity on cAMP phosphodiesterase and Na+/K+ ATPase.

  DOI：

  10.1248/cpb.43.1180
• 作为产物：
  描述：

  (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-3β,22-dihydroxy-cholest-5-en-1β-yl α-L-rhamnopyranoside 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以1.8 mg的产率得到(22S)-cholest-5-ene-1β,3β,16β,22-tetrol
  参考文献：
  名称：

  Steroidal Glycosides from the Bulbs of Ornithogalum thyrsoides

  摘要：

  Phytochemical analyses have been carried out on the fresh bulbs of Ornithogalum thyrsoides with particular attention to the steroidal glycoside constituents, resulting in the isolation of four new spirostanol saponins and seven new cholestane glycosides, together with three known steroidal compounds. The structures of the new glycosides were determined on the basis of their spectroscopic data, including 2D NMR spectroscopy, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.

  DOI：

  10.1021/np040108i

文献信息

• Schubertosides A-D, new (22s)-hydroxycholestane glycosides from Allium schubertii.
  作者：Kazuhiro KAWASHIMA、Yoshihiro MIMAKI、Yutaka SASHIDA

  DOI：10.1248/cpb.39.2761

  日期：——

  Four new (22S)-hydroxycholestane glycosides, schubertosides A - D, have been isolated from the bulbs of Allium schubertii. Their structures were determined by spectroscopic analaysis and hydrolysis. The advanced Mosher's method was applied to determined the C-22 absolute configuration.

  从葱属植物Allium schubertii的鳞茎中分离得到四种新的（22S）-羟基胆甾烷糖苷，即schubertosides A-D。通过光谱分析和酸水解确定了它们的结构，并应用改进的Mosher法确定了C-22位的绝对构型。
• Steroidal Glycosides from the Aerial Parts of <i>Polianthes </i><i>t</i><i>uberosa</i>
  作者：Yoshihiro Mimaki、Akihito Yokosuka、Yutaka Sashida

  DOI：10.1021/np000230r

  日期：2000.11.1

  A chemical investigation of the aerial parts of Polianthes tuberosa resulted in the isolation of a new bisdesmosidic cholestane glycoside (1) and three new spirostanol saponins (2-4), along with a known cholestane glycoside. The structures of new glycosides were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and the results of hydrolytic cleavage. The isolated compounds

  化学分析了aerial菜（Polianthes tuberosa）的地上部分，结果分离出了一种新的双去胆固醇胆甾烷糖苷（1）和三种新的螺固醇皂苷（2-4），以及一种已知的胆甾烷苷。通过光谱分析确定新糖苷的结构，包括2D NMR光谱数据和水解裂解的结果。评价分离的化合物对HL-60人早幼粒细胞白血病细胞的细胞毒性活性。
• Two New Cholestane Bisdesmosides fromReineckia carnea
  作者：Zhong-Quan Zhang、Jian-Chao Chen、Lin Zhou、Ming-Hua Qiu

  DOI：10.1002/hlca.200790063

  日期：2007.3

  Three cholestane bisdesmosides, together with the corresponding aglycone, were isolated from the whole plant of Reineckia carnea. By detailed analysis of the 1D- and 2D-NMR spectra, chemical methods, and comparison with spectral data of known compounds, the structures were determined to be (1β,3β,16β,22S)-cholest-5-ene-1,3,16,22-tetrol (1), (1β,3β,16β,22S)-cholest-5-ene-1,3,16,22-tetrol 1,16-di(β-D-glucopyranoside)

  从Reineckia carnea的整个植物中分离出三种胆甾醇二desmosmosides，以及相应的糖苷配基。由1D-和2D-NMR光谱的详细分析，化学方法，用已知化合物的光谱数据进行比较，确定了结构为（1个β，3 β，16 β，22小号）-cholest -5-烯-1,3,16,22四醇（1），（1个β，3 β，16 β，22小号）-cholest -5-烯1,3,16,22四醇1,16-二（β -D-吡喃葡萄糖苷）（2），（1β，3β，16β，22 S）-cholest -5-烯1,3,16,22四醇1- [ ø - α -L-鼠李糖（12） - β -D-吡喃葡萄糖苷] -16-（β -D-吡喃葡萄糖苷）（3）中，（1个β，3 β，16 β，22小号）-cholest -5-烯1,3,16,22四醇1-（β -D-吡喃葡萄糖苷）16-（3- ö乙酰基β - D-吡喃葡萄糖苷）（4）
• Steroidal glycosides from Allium macleanii and A. senescens, and their inhibitory activity on tumour promoter-induced phospholipid metabolism of hela cells
  作者：Toshihiro Inoue、Yoshihiro Mimaki、Yutaka Sashida、Atsuko Nishino、Yoshiko Satomi、Hoyoku Nishino

  DOI：10.1016/0031-9422(95)00223-t

  日期：1995.9

  with five known spirostanol saponins, were isolated from the bulbs of Allium macleanii, and two known spirostanol saponins were isolated from the bulbs of A. senescens. The identification and structural assignments of the steroidal glycosides were performed by spectroscopic analysis and hydrolysis. Furthermore, the isolated compounds were evaluated for inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate

  一种新的多羟基化胆甾烷三桥苷和一种新的螺甾烷醇五糖，连同五种已知的螺甾醇皂苷，从葱属植物的球茎中分离出来，两种已知的螺甾烷醇皂苷从 A. sensecens 的球茎中分离出来。通过光谱分析和水解进行甾体糖苷的鉴定和结构分配。此外，还评估了分离的化合物对 12-O-十四烷酰佛波醇-13-乙酸酯 (TPA) 刺激的 32P 掺入 HeLa 细胞磷脂的抑制活性，这被认为是鉴定新的抗肿瘤促进剂化合物的绝佳初步筛选试验.
• Steroidal glycosides from the rhizomes of Ruscus hypophyllum
  作者：Yoshihiro Mimaki、Tsukasa Aoki、Maki Jitsuno、Ceyda Sibel Kiliç、Maksut Coşkun

  DOI：10.1016/j.phytochem.2007.09.022

  日期：2008.2

  Seven steroidal glycosides, along with one known glycoside, were isolated from the rhizomes of Ruscus hypophyllum (Liliaceae). Comprehensive spectroscopic analysis, including 2D NMR spectroscopy, and the results of acid hydrolysis allowed the chemical structures of the compounds to be assigned as (23S,25R)-23-hydroxyspirost-5-en-3 beta-yl O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranoside (1), 1 beta-hydroxyspirosta-5,25(27)-dien-3-beta-yl O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranoside (2), (22S)-16 beta,22-dihydroxycholest-5en-3 beta-yl O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranoside (3), (22S)-16 beta-[(beta-D-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3 beta-yl O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranoside (4), (22S)-16 beta-[(beta-D-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3 beta-yl beta-D-glucopyranoside (5), (22S)-16 beta-[(beta-D-glucopyranosyl)oxy]-3 beta,22-dihydroxycholest-5-en-1 beta-yl O-alpha-L-rhamnopyranosyl-(1 -> 2)-(3,4-di-O-acetyl-beta-D-xylopyranoside) (6), and (22S)-16 beta-[(beta-D-glucopyranosyl)oxy]-3 beta,22-dihydroxycholest-5-en-1 beta-yl O-alpha-L-rhamnopyranosyl(1 -> 2)-O-[beta-D-xylopyranosyl-(1 -> 3)]-beta-D-xylopyranoside (7), respectively. This is the first isolation of a series of cholestane glycosides from a Ruscus species. (c) 2007 Elsevier Ltd. All rights reserved.