七鳃鳗醇 | 28979-29-5

• 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
• 中文名称: 七鳃鳗醇
• 中文别名: 5ALPHA-胆烷-3ALPHA,7ALPHA,12ALPHA,24-四醇
• 英文名称: Petromyzonol
• 英文别名: (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
• CAS: 28979-29-5
• 化学式: C₂₄H₄₂O₄
• 分子量: 394.595
• InChiKey: BMSROUVLRAQRBY-JLIFGLSWSA-N

物化性质

• 熔点：
  228-230°C
• 沸点：
  545.1±50.0 °C(Predicted)
• 密度：
  1.134
• 溶解度：
  DMSO（微溶）、乙醇（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  PAPS 、 七鳃鳗醇 生成 3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholan-24-yl sulfate(1-) 、 Adenosine 3',5'-bismonophosphate(4-) 、 氢(+1)阳离子
  参考文献：
  名称：

  Isolation, partial purification, and characterization of a novel petromyzonol sulfotransferase from Petromyzon marinus (lamprey) larval liver

  摘要：

  We have isolated, partially purified, and characterized the 5alpha-petromyzonol (5alpha-PZ), (5alpha-cholan- 3alpha, 7alpha, 12alpha, 24-tetrahydroxy-) sulfotransferase (PZ-SULT) from larval lamprey liver. Crude liver extracts exhibited a PZ-SULT activity of 0.9120 pmol/min/mg in juvenile and 12.62 pmol/min/mg in larvae. Using crude larval liver extracts and various 5 beta-cholan substrates and allocholic acid there was negligible activity, however, with 5alpha-PZ and 3-keto-5alpha-PZ the SULT activity was 231.5 pmol/min/mg and 180.8 pmol/min/mg respectively. This established that the sulfotransferase of lamprey larval liver extracts prefers (5 alpha) substrates and it is selective for hydroxyl at C-24. PZ-SULT was purified through various chromatography procedures. Partially purified PZ-SULT exhibited a pH optimum of 8.0, a temperature optimum of 22degreesC, and activity was linear for 1h. PZ-SULT exhibited a K-m of 2.5 muM for PAPS and a K-m of 8 muM for PZ. The affinity purified peak PZ-SULT exhibited a specific activity of 2,038 pmol/min/mg. The peak protein upon SDS-PAGE, correlated to an Mw 47 kDa. Photoaffinity labeling with PAP(35)S, specifically crosslinked the 47 kDa protein, further confirming the identity of PZ-SULT. Partial amino acid sequencing of the putative 47 kDa PZ-SULT protein yielded a peptide sequence (M)SISQAVDAAFXEI, which possessed an overall (similar to35-40%) homology with mammalian SULT2B1a.-Venkatachalam, K. V., D. E. Llanos, K. J. Karami, and V. A. Malinovskii. Isolation, partial purification, and characterization of a novel petromyzonol sulfotransferase from Petromyzon marinus (lamprey) larval liver.

  DOI：

  10.1194/jlr.m300346-jlr200
• 作为产物：
  描述：

  methyl 3α-hydroxy-7α,12α-bis(formyloxy)-5β-cholan-24-oate 在 甲醇 、 sodium hydroxide 、 Wilkinson's catalyst 、 lithium aluminium tetrahydride 、 meta-iodoxybenzoic acid 、 二苯基二硒醚 、 氢气 、 双氧水 、 sodium carbonate 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 、 苯 为溶剂， 反应 49.0h， 生成 七鳃鳗醇
  参考文献：
  名称：

  Zhu, Xingpei; Amouzou, Etchri; McLean, Stewart, Canadian Journal of Chemistry, 1987, vol. 65, p. 2447 - 2449

  摘要：

  DOI：

文献信息

• BILE ALCOHOL AND DRUG CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：TSUMURA CO., LTD.

  公开号：EP0489933A1

  公开（公告）日：1992-06-17

  A novel bile alcohol of general formula (I), having an efficacious physiological activity and being specified in the configurations of particularly the 20-, 24- and 25-positions; formula (I) wherein one of the groups R₁ and R₂ represents a group of formula (A) or (B) while the other represents -OH or -H; R₃ and R₄ represent each -CH₂OH, -CH₃ or -CH₂OSO₃Na; or alternatively R₂ and R₃ are combined together to represent -OCH₂-, R₂ and R₄ are combined together to represent -OCH₂-, or R₃ and R₄ are combined together to represent -CH₂OCH₂-; provided that R₃ and R₄ do not represent -CH₃ at the same time and that R₁ represents -OH or -H and R₂ represents the group of formula (A) or (B) when R₃ and R₄ represent -CH₂OH at the same time. A drug containing the bile alcohol, including those wherein R₃ and R₄ in the above formula (I) represent each -H, -CH₂OH, -CH₃ or -CH₂OSO₃Na (except for the case where both R₃ and R₄ represent -H at the same time), and 3α 7α, 12α, 24-tetrahydroxy-5α- or -5β-cholane is efficacious as a cerebral function protective agent, cholagogue, cell activator, microcirculation improver, antiarteriosclerotic agent, antihyperlipemia drug, hepatic function improver, anti-inflammatory drug, antithrombotic drug and hypertensive.

  通式（I）的新胆醇具有有效的生理活性，特别是在20、24和25位的构型中进行了指定。其中，R₁和R₂中的一个代表公式（A）或（B）的基团，而另一个代表-OH或-H；R₃和R₄分别代表-CH₂OH、-CH₃或-CH₂OSO₃Na；或者R₂和R₃结合在一起代表-OCH₂-，R₂和R₄结合在一起代表-OCH₂-，或者R₃和R₄结合在一起代表-CH₂OCH₂-；前提是R₃和R₄不能同时表示-CH₃，而且当R₃和R₄同时表示-CH₂OH时，R₁表示-OH或-H，R₂表示公式（A）或（B）的基团。含有胆醇的药物，包括上述公式（I）中R₃和R₄分别表示-H、-CH₂OH、-CH₃或-CH₂OSO₃Na的药物（除了R₃和R₄同时表示-H的情况），以及3α 7α，12α，24-四羟基-5α-或-5β-胆烷作为脑功能保护剂、胆汁促进剂、细胞活化剂、微循环改善剂、抗动脉硬化药、降脂药、肝功能改善剂、抗炎药、抗血栓药和降压药具有有效性。
• Zhu, Xingpei; Amouzou, Etchri; McLean, Stewart, Canadian Journal of Chemistry, 1987, vol. 65, p. 2447 - 2449
  作者：Zhu, Xingpei、Amouzou, Etchri、McLean, Stewart

  DOI：——

  日期：——
• Isolation, partial purification, and characterization of a novel petromyzonol sulfotransferase from Petromyzon marinus (lamprey) larval liver
  作者：K.V. Venkatachalam、Domingo E. Llanos、Kristophe J. Karami、Vladimir A. Malinovskii

  DOI：10.1194/jlr.m300346-jlr200

  日期：2004.3

  We have isolated, partially purified, and characterized the 5alpha-petromyzonol (5alpha-PZ), (5alpha-cholan- 3alpha, 7alpha, 12alpha, 24-tetrahydroxy-) sulfotransferase (PZ-SULT) from larval lamprey liver. Crude liver extracts exhibited a PZ-SULT activity of 0.9120 pmol/min/mg in juvenile and 12.62 pmol/min/mg in larvae. Using crude larval liver extracts and various 5 beta-cholan substrates and allocholic acid there was negligible activity, however, with 5alpha-PZ and 3-keto-5alpha-PZ the SULT activity was 231.5 pmol/min/mg and 180.8 pmol/min/mg respectively. This established that the sulfotransferase of lamprey larval liver extracts prefers (5 alpha) substrates and it is selective for hydroxyl at C-24. PZ-SULT was purified through various chromatography procedures. Partially purified PZ-SULT exhibited a pH optimum of 8.0, a temperature optimum of 22degreesC, and activity was linear for 1h. PZ-SULT exhibited a K-m of 2.5 muM for PAPS and a K-m of 8 muM for PZ. The affinity purified peak PZ-SULT exhibited a specific activity of 2,038 pmol/min/mg. The peak protein upon SDS-PAGE, correlated to an Mw 47 kDa. Photoaffinity labeling with PAP(35)S, specifically crosslinked the 47 kDa protein, further confirming the identity of PZ-SULT. Partial amino acid sequencing of the putative 47 kDa PZ-SULT protein yielded a peptide sequence (M)SISQAVDAAFXEI, which possessed an overall (similar to35-40%) homology with mammalian SULT2B1a.-Venkatachalam, K. V., D. E. Llanos, K. J. Karami, and V. A. Malinovskii. Isolation, partial purification, and characterization of a novel petromyzonol sulfotransferase from Petromyzon marinus (lamprey) larval liver.