dimethyl-(E)-labda-8(17),12-diene-15,16-dioate | 1246850-78-1

• 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
• 英文名称: dimethyl-(E)-labda-8(17),12-diene-15,16-dioate
• 英文别名: dimethyl (2E)-2-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]butanedioate
• CAS: 1246850-78-1
• 化学式: C₂₂H₃₄O₄
• 分子量: 362.51
• InChiKey: CVWIJZGTJREBST-OXNXFDESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5S,9S,10S-(+)-(E)-labda-8(17),12-diene-15,16-dioic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 1.0h， 生成 dimethyl-(E)-labda-8(17),12-diene-15,16-dioate
  参考文献：
  名称：

  Phytochemical profiling of Curcuma kwangsiensis rhizome extract, and identification of labdane diterpenoids as positive GABAA receptor modulators

  摘要：

  An ethyl acetate extract of Curcuma kwangsiensis S.G. Lee & C.F. Liang (Zingiberaceae) rhizomes (100 mu g/ml) enhanced the GABA-induced chloride current (I-GABA) through GABA(A) receptors of the alpha(1)beta(2)gamma(2s) subtype by 79.0 +/- 7.0%. Potentiation of I-GABA was measured using the two-microelectrode voltage-clamp technique and Xenopus laevis oocytes. HPLC-based activity profiling of the crude extract led to the identification of 11 structurally related labdane diterpenoids, including four new compounds. Structure elucidation was achieved by comprehensive analysis of on-line (LC-PDA-ESI-TOF-MS) and off-line (microprobe 1D and 2D NMR) spectroscopic data. The absolute configuration of the compounds was established by comparison of experimental and calculated ECD spectra. Labdane diterpenes represent a new class of plant secondary metabolites eliciting positive GABA(A) receptor modulation. The highest efficiency was observed for zerumin A (maximum potentiation of I-GABA by 309.4 +/- 35.6%, and EC50, of 24.9 +/- 8.8 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.004

文献信息

• GLUCAGON-LIKE PEPTIDE 1 (GLP-1) RECEPTOR MODULATORS AND USES THEREOF IN REGULATING BLOOD GLUCOSE LEVELS
  申请人：Liang Chi-Ming

  公开号：US20140350100A1

  公开（公告）日：2014-11-27

  The present disclosure provides novel glucagon-like peptide-1 (GLP-1) receptor modulators such as compounds of Formula (I) or (II), and pharmaceutically acceptable salts thereof. The present disclosure also provides pharmaceutical compositions, kits, and uses that involve the GLP-1 receptor modulators for regulating blood glucose levels and/or treating diabetes via, e.g., modulating the endogenous signaling pathways mediated by the GLP-1 receptor.

  本公开提供了新型胰高血糖素样肽-1（GLP-1）受体调节剂，例如式（I）或（II）的化合物，以及其药学上可接受的盐。本公开还提供了涉及GLP-1受体调节剂用于调节血糖水平和/或治疗糖尿病的药物组合物、试剂盒和用途。例如，通过调节由GLP-1受体介导的内源性信号通路。
• Synthesis and biological evaluation of (+)-labdadienedial, derivatives and precursors from (+)-sclareolide
  作者：Miguel A. González、Juan Mancebo-Aracil、Veronica Tangarife-Castaño、Lee Agudelo-Goméz、Bibiana Zapata、Ana Mesa-Arango、Liliana Betancur-Galvis

  DOI：10.1016/j.ejmech.2010.06.029

  日期：2010.9

  Labdadienedial and a series of C15,C16-functionalized derivatives were synthesized from commercial (+)-sclareolide and evaluated for their cytotoxic, antimycotic, and antiviral activities. Their precursors were similarly evaluated. (C) 2010 Elsevier Masson SAS. All rights reserved.
• [EN] GLUCAGON-LIKE PEPTIDE 1 (GLP-1) RECEPTOR MODULATORS AND USES THEREOF IN REGULATING BLOOD GLUCOSE LEVELS<br/>[FR] MODULATEURS DU RÉCEPTEUR DU GLUCAGON-LIKE PEPTIDE 1 (GLP-1) ET LEURS UTILISATIONS DANS LA RÉGULATION DES TAUX DE GLYCÉMIE
  申请人：ACADEMIA SINICA

  公开号：WO2014193832A2

  公开（公告）日：2014-12-04

  The present disclosure provides novel glucagon-like peptide-1 (GLP-1) receptor modulators such as compounds of Formula (I) or (II), and pharmaceutically acceptable salts thereof. The present disclosure also provides pharmaceutical compositions, kits, and uses that involve the GLP-1 receptor modulators for regulating blood glucose levels and/or treating diabetes via, e.g., modulating the endogenous signaling pathways mediated by the GLP-1 receptor.
• Phytochemical profiling of Curcuma kwangsiensis rhizome extract, and identification of labdane diterpenoids as positive GABAA receptor modulators
  作者：Anja Schramm、Samad Nejad Ebrahimi、Melanie Raith、Janine Zaugg、Diana C. Rueda、Steffen Hering、Matthias Hamburger

  DOI：10.1016/j.phytochem.2013.08.004

  日期：2013.12

  An ethyl acetate extract of Curcuma kwangsiensis S.G. Lee & C.F. Liang (Zingiberaceae) rhizomes (100 mu g/ml) enhanced the GABA-induced chloride current (I-GABA) through GABA(A) receptors of the alpha(1)beta(2)gamma(2s) subtype by 79.0 +/- 7.0%. Potentiation of I-GABA was measured using the two-microelectrode voltage-clamp technique and Xenopus laevis oocytes. HPLC-based activity profiling of the crude extract led to the identification of 11 structurally related labdane diterpenoids, including four new compounds. Structure elucidation was achieved by comprehensive analysis of on-line (LC-PDA-ESI-TOF-MS) and off-line (microprobe 1D and 2D NMR) spectroscopic data. The absolute configuration of the compounds was established by comparison of experimental and calculated ECD spectra. Labdane diterpenes represent a new class of plant secondary metabolites eliciting positive GABA(A) receptor modulation. The highest efficiency was observed for zerumin A (maximum potentiation of I-GABA by 309.4 +/- 35.6%, and EC50, of 24.9 +/- 8.8 mu M). (C) 2013 Elsevier Ltd. All rights reserved.