3β,8β-dihydroxy-guaia-4(15),10(14),11(13)-trien-1α,5α,6β,7αH-12,6α-olide | 89647-87-0

• 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
• 英文名称: 3β,8β-dihydroxy-guaia-4(15),10(14),11(13)-trien-1α,5α,6β,7αH-12,6α-olide
• 英文别名: 3β,8β-dihydroxy-guaia-4(15),10(14),11(13)-triene-12,6α-olide；8-epi-desacylcynaropicrin；8-epidesacylcinaropicrin；8-epidesacylcynaropicrin；8-epideacylcynaropicrin；integrifolin；(3aR,4R,6aR,8S,9aR,9bR)-4,8-dihydroxy-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• CAS: 89647-87-0；31565-50-1；35932-46-8
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: VPRPYNVJJXOFKZ-BSCCGWMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β,8β-dihydroxy-guaia-4(15),10(14),11(13)-trien-1α,5α,6β,7αH-12,6α-olide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 11βH-11,13-dihydrointegrifolin
  参考文献：
  名称：

  Guaianolides and an ethylcyclohexane lactone from Andriala integrifolia

  摘要：

  The reinvestigation of the aerial parts of Andriala integrifolia afforded three new lactones, a guaianolide, a guaianolide glucopyranoside and an ethylcyclohexane lactonic derivative with a quinol structure, together with five known compounds. Their structures were established by high held H-1 NMR spectroscopy and chemical correlation.

  DOI：

  10.1016/s0031-9422(00)90846-x
• 作为产物：
  描述：

  (3aR,4R,6aR,8S,9aR,9bR)-8-(beta-D-吡喃葡萄糖基氧基)十氢-4-羟基-3,6,9-三(亚甲基)-薁并[4,5-b]呋喃-2(3H)-酮 在 crude hesperidinase 作用下， 以 水 为溶剂， 反应 3.0h， 以23 mg的产率得到3β,8β-dihydroxy-guaia-4(15),10(14),11(13)-trien-1α,5α,6β,7αH-12,6α-olide
  参考文献：
  名称：

  Sesquiterpene lactones from Ixeris stolonifera A. Gray.

  摘要：

  从蹄叶藁本（A. GRAY）（菊科）的甲醇提取物中分离得到8种新的愈创木脂型糖苷——ixerins M、N、O、P、Q、R、S和T，以及8-epidesacylcynaropicrin-葡萄糖苷和大花藁本苷A。这些新化合物的结构是根据化学和光谱数据确定的。

  DOI：

  10.1248/cpb.33.3361

文献信息

• Sesquiterpene lactone glycosides from Crepis capillaris
  作者：Wanda Kisiel

  DOI：10.1016/s0031-9422(00)84949-3

  日期：1984.8

  Abstract Four new sesquiterpene lactone glucosides, in addition to known compounds, have been isolated from the roots of Crepis capillaris and their structures elucidated on the basis of spectral analysis and hydrolytic studies.

  摘要 除了已知化合物外，还从毛细花的根中分离出了四种新的倍半萜内酯糖苷，并在光谱分析和水解研究的基础上阐明了它们的结构。
• Use of tricyclic sesquiterpene lactones in the treatment of obesity and related diseases and non-therapeutic treatable conditions
  申请人：InterMed Discovery GmbH

  公开号：EP2345646A1

  公开（公告）日：2011-07-20

  A compound of the formula I, wherein the symbols are as defined in the remaining specification, or a mixture of two or more compounds of the formula I, for use as active ingredient in the therapeutic - including prophylactic - treatment of a warm-blooded animal for the regulation of body weight (preferred) and/or fat loss (preferred) and/or for the management of obesity and/or for decreasing blood cholesterol; where the compound(s) of the formula I may be present in free form, in the form of a pharmaceutically and/or nutraceutically acceptable salt, in the form of tautomers, in the form of esters and/or in the form of solvates, as well as related invention embodiments.

  式 I 的化合物、 其中符号如其余说明书中所定义，或两种或两种以上式 I 化合物的混合物，作为活性成分用于温血动物的治疗（包括预防性治疗），以调节体重（优选）和/或减脂（优选）和/或控制肥胖和/或降低血液中的胆固醇；式 I 的化合物可以游离形式、药学上和/或营养学上可接受的盐的形式、同分异构体的形式、酯的形式和/或溶解物的形式以及相关的发明实施方案的形式存在。
• Integrifolin, a guaianolide from Andryala integrifolia
  作者：G.M. Massanet、I.González Collado、F.A. Macías、F.Rodríguez Luis、C. Vergara

  DOI：10.1016/s0031-9422(00)85061-x

  日期：1984.4
• Tricyclic sesquiterpene lactones for used in the treatment of obesity and related diseases and non-therapeutic treatable conditions
  申请人：Neem Biotech Ltd.

  公开号：EP2523946B1

  公开（公告）日：2017-09-20
• USE OF TRICYCLIC SESQUITERPENE LACTONES IN THE TREATMENT OF OBESITY AND RELATED DISEASES AND NON-THERAPEUTIC TREATABLE CONDITIONS
  申请人：InterMed Discovery GmbH

  公开号：EP2523946A1

  公开（公告）日：2012-11-21