(1S)-1alpha-(beta-D-吡喃葡萄糖基氧基)-1,4a,5,6,7,7aalpha-六氢-4aalpha,7alpha-二羟基-7-甲基环戊并[c]吡喃-4-羧酸甲酯 | 27934-98-1

• 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
• 中文名称: (1S)-1alpha-(beta-D-吡喃葡萄糖基氧基)-1,4a,5,6,7,7aalpha-六氢-4aalpha,7alpha-二羟基-7-甲基环戊并[c]吡喃-4-羧酸甲酯
• 英文名称: ipolamiide
• 英文别名: methyl (1S,4aR,7S,7aR)-4a,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• CAS: 27934-98-1
• 化学式: C₁₇H₂₆O₁₁
• 分子量: 406.387
• InChiKey: RWMXKBUPLSNIJL-BHBNKKJBSA-N

物化性质

• 熔点：
  140.0-140.5 °C
• 沸点：
  645.8±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  7-deoxy-8-epi-loganin 在 Hebenstreitia dentata L_. (Scrophulariaceae-Selagineae) 作用下， 以 水 为溶剂， 反应 264.0h， 生成 lamiide 、 (1S)-1alpha-(beta-D-吡喃葡萄糖基氧基)-1,4a,5,6,7,7aalpha-六氢-4aalpha,7alpha-二羟基-7-甲基环戊并[c]吡喃-4-羧酸甲酯
  参考文献：
  名称：

  2 H核磁共振波谱研究由8-表位脱氧血凝素合成Lamiide和Ipolamiide

  摘要：

  2 H Nmr光谱显示，在Hebenstreitia dentata中，选择性标记的8- epi- deoxyloganin被有效地掺入了lamiide和ipolamiide中，而选择性标记的deoxyloganin没有提供可观察到的掺入。

  DOI：

  10.1039/c39810000228

文献信息

• PLANT EXTRACTS ENRICHED WITH IPOLAMIIDE DERIVATIVES AS IMMUNOSUPPRESSANTS FOR TREATING IMMUNOLOGICAL DISORDERS AND VITILIGO
  申请人：Aché Laboratórios Farmacêuticos S.A.

  公开号：EP4001270A1

  公开（公告）日：2022-05-25

  The present invention discloses enriched extracts from plants of the genus Stachytarpheta comprising ipolamiide and compounds of the formulae (I), (II) and/or (III): Such extracts could be useful to block activation of CD8+ T cells and reduce secretion of IFNgamma. They could have immunosuppressive activity and could be useful in methods of treatment of immunological disorders and vitiligo. Preferred compounds of formulae (I), (II) and (III) are compounds of the formulae (IV) to (XI): Additionally the extracts preferably contain also compounds of the formulae (XII) to (XVI):

  本发明公开了从 Stachytarpheta 属植物中提取的富集提取物，其中包含异波美度和式 (I)、(II) 和/或 (III) 化合物： 这些提取物可用于阻止 CD8+ T 细胞的活化，减少 IFNgamma 的分泌。它们具有免疫抑制活性，可用于免疫紊乱和白癜风的治疗方法。 式(I)、(II)和(III)化合物中的优选化合物为式(IV)至(XI)化合物： 此外，提取物最好还含有式（XII）至（XVI）的化合物：
• PLANT EXTRACTS ENRICHED WITH IPOLAMIIDE DERIVATIVES AS IMMUNOSUPPRESSANTS FOR TREATING IMMUNOLOGICAL DISORDERS
  申请人：Aché Laboratórios Farmacêuticos S.A.

  公开号：EP3583103B1

  公开（公告）日：2022-01-12
• [EN] COMPOUNDS, PROCESS OF PRODUCTION OF COMPOUNDS, ENRICHED EXTRACT, ENRICHED EXTRACT ACTIVE FRACTIONS, ENRICHED EXTRACT PROCESS OF PRODUCTION, METHOD FOR SELECTING VEGETAL BIOMASS FOR ENRICHED EXTRACT PRODUCTION, COMPOSITION AND USE FOR TREATMENT OF IMMUNOLOGICAL DISORDERS<br/>[FR] COMPOSÉS, PROCÉDÉ DE PRODUCTION DE COMPOSÉS, EXTRAIT ENRICHI, FRACTIONS ACTIVES D'EXTRAIT ENRICHI, PROCÉDÉ DE PRODUCTION D'EXTRAIT ENRICHI, PROCÉDÉ DE SÉLECTION DE BIOMASSE VÉGÉTALE POUR LA PRODUCTION D'EXTRAIT ENRICHI, COMPOSITION ET UTILISATION POUR LE TRAITEMENT DE TROUBLES IMMUNOLOGIQUES
  申请人：ACHE LABORATORIOS FARMACEUTICOS SA

  公开号：WO2018148816A2

  公开（公告）日：2018-08-23

  The invention describes novel and inventive isolated compounds and the process of producing compounds and extracts with immunosuppressive activity, from plants of the genus Stachytarpheta. In this way, the present application also describes novel and inventive compositions and its use for the treatment of immunological disorders. The present invention is in the fields of pharmacy, medicine and chemistry.
• [EN] PLANT EXTRACTS ENRICHED WITH IPOLAMIIDE DERIVATIVES AS IMMUNOSUPPRESSANTS FOR TREATING IMMUNOLOGICAL DISORDERS<br/>[FR] COMPOSÉS, PROCÉDÉ DE PRODUCTION DE COMPOSÉS, EXTRAIT ENRICHI, FRACTIONS ACTIVES D'EXTRAIT ENRICHI, PROCÉDÉ DE PRODUCTION D'EXTRAIT ENRICHI, PROCÉDÉ DE SÉLECTION DE BIOMASSE VÉGÉTALE POUR LA PRODUCTION D'EXTRAIT ENRICHI, COMPOSITION ET UTILISATION POUR LE TRAITEMENT DE TROUBLES IMMUNOLOGIQUES
  申请人：ACHE LABORATORIOS FARMACEUTICOS SA

  公开号：WO2018148816A3

  公开（公告）日：2018-10-18

  [EN] The invention describes extracts from plants of the genus Stachytarpheta enriched with ipolamiide derivatives as immunosuppressants for treating immunological disorders. The isolated active compounds and a process of producing these are also disclosed.
  [FR] L'invention concerne des composés isolés nouveaux et inventifs et le procédé de production de composés et d'extraits présentant une activité immunosuppressive, à partir de plantes du genre Stachytarpheta. De cette manière, la présente invention concerne également des compositions nouvelles et inventives et leur utilisation pour le traitement de troubles immunologiques. La présente invention s'inscrit dans les domaines de la pharmacie, de la médecine, et de la chimie.
• Biosynthesis of lamiide and ipolamiide from 8-epi-deoxyloganin studied by 2H n.m.r. spectroscopy
  作者：S�ren Damtoft

  DOI：10.1039/c39810000228

  日期：——

  2 H N.m.r. spectroscopy shows that selectively labelled 8-epi-deoxyloganin is efficiently incorporated into lamiide and ipolamiide in Hebenstreitia dentata, whereas selectively labelled deoxyloganin provides no obserable incorporation.

  2 H Nmr光谱显示，在Hebenstreitia dentata中，选择性标记的8- epi- deoxyloganin被有效地掺入了lamiide和ipolamiide中，而选择性标记的deoxyloganin没有提供可观察到的掺入。