parishin A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: parishin A
• 英文别名: (3aS,6R,6aR,9bS)-6-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,6a,7-hexahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione；(3aS,6R,6aR,9bS)-6-hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-2,8-dione
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: FAESSFVRXUTLPW-FMRSBHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  parishin A 在 硫酸 作用下， 反应 1.0h， 以100%的产率得到(3aS,9bS)-6,9-dimethyl-3-methylene-3,3a,4,5-tetrahydroazuleno[4,5-b]furan-2,8(7H,9bH)-dione
  参考文献：
  名称：

  11,13-脱氢癸二酸-瓜内醇化物的制备及植物毒性评价。

  摘要：

  使用一种涉及高产光化学反应的简便策略，由市售的α-桑顿宁（11）合成11,13-脱氢癸二酚内酯，一种特殊的倍半萜烯内酯。来自蒿的天然产物10和17以高产率合成。具体地，以五个步骤获得化合物10，总产率为17％。倍半萜内酯在黄化的小麦胚芽鞘生物测定中进行了测试，活性最高的化合物在标准目标物种上进行了测定。与已知的除草剂Logran相比，瓜亚胺内酯13具有最高的植物毒性活性。

  DOI：

  10.1021/acs.jnatprod.9b00285
• 作为产物：
  描述：

  山道年 在 nickel(II) sulfate hexahydrate 、 硫酸钴水合物 、 双氧水 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 生成 parishin A
  参考文献：
  名称：

  11,13-脱氢癸二酸-瓜内醇化物的制备及植物毒性评价。

  摘要：

  使用一种涉及高产光化学反应的简便策略，由市售的α-桑顿宁（11）合成11,13-脱氢癸二酚内酯，一种特殊的倍半萜烯内酯。来自蒿的天然产物10和17以高产率合成。具体地，以五个步骤获得化合物10，总产率为17％。倍半萜内酯在黄化的小麦胚芽鞘生物测定中进行了测试，活性最高的化合物在标准目标物种上进行了测定。与已知的除草剂Logran相比，瓜亚胺内酯13具有最高的植物毒性活性。

  DOI：

  10.1021/acs.jnatprod.9b00285

文献信息

• NMR assignments and absolute stereochemistry of two guaianolide sesquiterpenes fromTanacetum densume subsp. amani
  作者：Ayhan Ulubelen、Nezhun Gören、Tian-Yi Jiang、Lincoln Scott、Manoelson Tianasoa-Ramomojy、John M. K. Snyder

  DOI：10.1002/mrc.1260331111

  日期：1995.11

  The guaianolide sesquiterpene pyrethroidinin (1) and the corresponding ketone parishin A (2) wee isolated from Tanacetum densum subsp. amani (Asteraceae). The absolute stereochemistry of 1 was established as (1R, 3R, 6S, 7S, 10R) on the basis of the differential shielfing in the 1H NMR spectra of the (−)‐ and (+)‐O‐methylmandelate esters. The structure, including absolute stereochemistry, of 2 was

  从 Tanacetum densum subsp. 中分离出愈创木酚内酯倍半萜类拟除虫菊酯素 (1) 和相应的酮类物质 A (2)。阿曼尼（菊科）。根据 (-)- 和 (+)-O-甲基扁桃酸酯的 1H NMR 光谱中的差异屏蔽，1 的绝对立体化学确定为 (1R, 3R, 6S, 7S, 10R)。2 的结构，包括绝对立体化学，通过 1 whit Jones' 试剂的氧化得到证实。
• Synthesis of novel α-santonin derivatives as potential cytotoxic agents
  作者：Francisco F.P. Arantes、Luiz C.A. Barbosa、Célia R.A. Maltha、Antônio J. Demuner、Patricia Marçal da Costa、José R.O. Ferreira、Letícia V. Costa-Lotufo、Manoel O. Moraes、Cláudia Pessoa

  DOI：10.1016/j.ejmech.2010.10.003

  日期：2010.12

  Ten novel alpha-santonin derivatives have been synthesized as cytotoxic agents. The in vitro antitumor activity of these compounds has been evaluated against cancer cells lines. Structure-activity relationships indicate that alpha-methylene-gamma-lactone and endoperoxide functionalities play important roles in conferring cytotoxicity. The compounds 2-4, possessing the alpha-methylene-gamma-lactone group showed IC50 values between 5.70 and 16.40 mu M. Mixture of isomers 5 and 6, with the alpha-methylene-gamma-lactone and endoperoxide functionalities, displayed the greatest activity, with IC50 values between 1.45 and 4.35 mu M. The biological assays conducted with normal cells revealed that the compounds 2, 5 and 6 are selective against cancer cells lines tested. Bioactive lactones described herein and in our previous report did not cause disruption of the cell membrane in mouse erythrocytes. (C) 2010 Elsevier Masson SAS. All rights reserved.
• PHARMACEUTICAL COMPOSITION FOR PROMOTING NEUROGENESIS AND METHOD OF UTILIZING GASTRODIA ELATA EXTRACT OR ADENOSINE ANALOG FOR PROMOTING NEUROGENESIS
  申请人：China Medical University

  公开号：US20200054708A1

  公开（公告）日：2020-02-20

  The present invention relates to a composition and a method of utilizing Gastrodia elata extract or an adenosine analog to promote neurogenesis, wherein the G. elata extract includes gastrodin, gastrodigenin, parishins, N 6 -(4-hydroxybenzyl) adenosine (T1-11) and 4-hydroxybenzaldehyde. The G. elata extract of the present invention exhibits anti-aging activity on nerve cells and can induce neurogenesis in mouse hippocampus.
• Pharmaceutical Composition for Promoting Neurogenesis and Method of Utilizing Gastrodia Elata Extract or Adenosine Analog for Promoting Neurogenesis
  申请人：China Medical University

  公开号：US20210205399A1

  公开（公告）日：2021-07-08

  The present invention relates to a composition and a method of utilizing Gastrodia elata extract or an adenosine analog to promote neurogenesis, wherein the G. elata extract includes gastrodin, gastrodigenin, parishins, N 6 -(4-hydroxybenzyl) adenosine (T1-11) and 4-hydroxybenzaldehyde. The G. elata extract of the present invention exhibits anti-aging activity on nerve cells and can induce neurogenesis in mouse hippocampus.
• [EN] RHIZOMA GASTRODIAE PLANT EXTRACT USED TO PREVENT AND TREAT ALZHEIMER DISEASE AND VASCULAR DEMENTIA AND MIXED TYPE DISEASES THEREOF AND PREPARATIVE METHOD THEREOF<br/>[FR] EXTRAIT VÉGÉTAL DE RHIZOMA GASTRODIAE UTILISÉ POUR LA PRÉVENTION ET LE TRAITEMENT DE LA MALADIE D'ALZHEIMER ET DE LA DÉMENCE VASCULAIRE ET DE MALADIES DE TYPE MIXTE DE CELLES-CI ET SON PROCÉDÉ DE PRÉPARATION
  申请人：BEIJING COLLAB PHARMA CO LTD

  公开号：WO2011140676A1

  公开（公告）日：2011-11-17

  The present invention discloses use of Rhizoma Gastrodiae plant extract containing parishin derivative in manufacture of medicaments for preventing and treating Alzheimer disease (AD), vascular dementia (VaD) and mixed type diseases thereof. The present invention also discloses the method for extracting and refining plant extract from Rhizoma Gastrodiae (Gastrodia elata Blume), wherein the effective constituent is parishin derivative, especially parishin A, B, C. The plant extract which is extracted by water or alcohol-water and refined and purified by chromatography contains parishin derivative whose content is more than 35%, especially more than 50%. The dosage forms of the present invention preferably include injection, tablets, capsules, soft capsules, oral liquid or drop pills etc.