5S,9S,10S-(+)-(E)-labda-8(17),12-diene-15,16-dioic acid | 1246850-79-2

• 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: 5S,9S,10S-(+)-(E)-labda-8(17),12-diene-15,16-dioic acid
• 英文别名: (E)-labda-8(17),12-diene-15,16-dioic acid；(2E)-2-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]butanedioic acid
• CAS: 1246850-79-2
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: VTLLVHKCLALDAF-QHYHZEAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  dimethyl labda-8(17),12-diene-15,16-dioate 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (Z)-labda-8(17),12-diene-15,16-dioic acid 、 5S,9S,10S-(+)-(E)-labda-8(17),12-diene-15,16-dioic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of (+)-labdadienedial, derivatives and precursors from (+)-sclareolide

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2010.06.029

文献信息

• 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.
• 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.