黄花菜木脂素B | 76985-93-8

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 香豆素木脂素
• 中文名称: 黄花菜木脂素B
• 英文名称: cleomiscosin B
• 英文别名: 9H-pyrano-(2,3-f)-1,4-benzodioxin-9-one-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-trans-(+/-)；(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• CAS: 76985-93-8；121587-24-4
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: XGADTAYOFHOFIW-NVXWUHKLSA-N

物化性质

• 沸点：
  632.7±55.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 黄花菜木脂素B 在 吡啶 作用下， 生成 cleomiscosin B diacetate
  参考文献：
  名称：

  Lin, Lee-Juian; Cordell, Geoffrey A., Journal of Chemical Research, Miniprint, 1988, # 12, p. 3052 - 3080

  摘要：

  DOI：
• 作为产物：
  描述：

  秦皮素 在 sodium hydroxide 、 锂硼氢 、 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 生成 黄花菜木脂素B
  参考文献：
  名称：

  Tanaka, Hitoshi; Kato, Ichiro; Ito, Kazuo, Heterocycles, 1985, vol. 23, # 8, p. 1991 - 1997

  摘要：

  DOI：

文献信息

• Synthesis of coumarinolignans through chemical and enzymic Oxidation
  作者：Lee-Juian Lin、Geoffrey A. Cordell

  DOI：10.1039/c39840000160

  日期：——

  The first syntheses of coumarinolignans through chemical or enzymic oxidation of a dihydroxycoumarin and a phenylpropene are described.

  描述了通过二羟基香豆素和苯丙烯的化学或酶促氧化来香豆素的第一合成。
• Hyosgerin, a New Optically Active Coumarinolignan, from the Seeds of Hyoscyamus niger
  作者：Begum Sajeli、Mahendra Sahai、Roderich Suessmuth、Teigo Asai、Noriyuki Hara、Yoshinori Fujimoto

  DOI：10.1248/cpb.54.538

  日期：——

  Hyosgerin, a new optically active coumarinolignan, has been isolated and characterized along with three other coumarinolignans, venkatasin, cleomiscosin A and cleomiscosin B, from the seeds of Hyoscyamus niger L. The structure was determined on the basis of spectroscopic analysis and chemical conversion. The optical properties and absolute stereochemistry of these coumarinolignans have also been studied

  Hyosgerin是一种新型的光学活性香豆素，已从Hyoscyamus niger L的种子中与其他三种香豆素，venkatasin，cleomiscosin A和cleomiscosin B分离并进行了表征。该结构是在光谱分析和化学转化的基础上确定的。这些香豆素的光学性质和绝对立体化学也已得到研究和讨论。
• Study of anti-inflammatory, analgesic and antipyretic activities of seeds of Hyoscyamus niger and isolation of a new coumarinolignan
  作者：Sajeli Begum、Bhagawati Saxena、Madhur Goyal、Rakesh Ranjan、Vijaya B. Joshi、Ch V. Rao、Sairam Krishnamurthy、Mahendra Sahai

  DOI：10.1016/j.fitote.2009.08.024

  日期：2010.4

  A chemical and biological validation of the traditional use of Hyoscyamus niger seeds as anti-inflammatory drug has been established The methanolic extract of seeds of H niger (MHN) was evaluated for its analgesic, anti-inflammatory and antipyretic activities in experimental animal models at different doses MHN produced significant increase in hot plate reaction time, while decreasing writhing response in a close-dependent manner indicating its analgesic activity It was also effective in both acute and chronic inflammation evaluated through carrageenin-induced paw oedema and cotton pellet granuloma methods In addition to its analgesic and anti-inflammatory activity, it also exhibited antipyretic activity in yeast-induced pyrexia model Furthermore, the bioactive MHN tinder chemical investigation showed the presence of coumarinolignans as major chemical constituent and yielded a new coumarinolignan, cleomiscosin A methyl ether (1) along with four known coumarinolignans, cleomiscosin A (2), cleomiscosin B (3), cleomiscosin A-9'-acetate (4) and cleomiscosin B-9'-acetate (5) The structure elucidation of 1 was done by spectroscopic data interpretation and comparative HPLC analysis Cleomiscosin A, but not its isomer cleomiscosin B, reduced dry and wet weight of cotton pellet granuloma in mice This suggests that cleomiscosin A is all important constituent of MHN responsible for anti-inflammatory activity (C) 2009 Elsevier B V All rights reserved
• Arnoldi, Anna; Arnone, Alberto; Merlini, Lucio, Heterocycles, 1984, vol. 22, # 7, p. 1537 - 1544
  作者：Arnoldi, Anna、Arnone, Alberto、Merlini, Lucio

  DOI：——

  日期：——
• Lin, Lee-Juian; Cordell, Geoffrey A., Journal of Chemical Research, Miniprint, 1988, # 12, p. 3052 - 3080
  作者：Lin, Lee-Juian、Cordell, Geoffrey A.

  DOI：——

  日期：——