8(14)-Pimaren-18-oic acid | 5673-40-5

• 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: 8(14)-Pimaren-18-oic acid
• 英文别名: 15,16-Dihydropimaric acid；(13R)-pimaren-(8(14))-oic acid-(18)；(13R)-Pimaren-(8(14))-saeure-(18)；13β-Ethyl-13α-methyl-podocarp-8(14)-en-15-saeure；Dihydro-pimarsaeure；Dihydropimarsaeure；(1R,4aR,4bS,7R,10aR)-7-ethyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• CAS: 5673-40-5
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: BOZVXNYLOGJCKG-APQLOABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8(14)-Pimaren-18-oic acid 在 乙酸酐 作用下， 生成 8(14)-Pimaren-18-oic acid anhydride
  参考文献：
  名称：

  Bardyshev, Russian Journal of Organic Chemistry, 1999, vol. 35, # 1, p. 41 - 55

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 镍 作用下， 生成 8(14)-Pimaren-18-oic acid
  参考文献：
  名称：

  Le-Van-Thoi; Ourgaud, Bulletin de la Societe Chimique de France, 1956, p. 205,206

  摘要：

  DOI：

文献信息

• Molecular Basis of Pimarane Compounds as Novel Activators of Large-Conductance Ca²⁺-Activated K⁺Channel α-Subunit
  作者：Yuji Imaizumi、Kazuho Sakamoto、Aki Yamada、Aya Hotta、Susumu Ohya、Katsuhiko Muraki、Masanobu Uchiyama、Tomohiko Ohwada

  DOI：10.1124/mol.62.4.836

  日期：2002.10.1

  Effects of pimaric acid (PiMA) and eight closely related compounds on large-conductance K+ (BK) channels were examined using human embryonic kidney (HEK) 293 cells, in which either the α subunit of BK channel (HEKBKα) or both α and β1 (HEKBKαβ1) subunits were heterologously expressed. Effects of these compounds (10 μM) on the membrane potential of HEKBKαβ1 were monitored by use of DiBAC4(3), a voltage-sensitive dye. PiMA, isopimaric acid, sandaracoisopimaric acid, dihydropimaric acid, dihydroisopimaric acid, and dihydroisopimarinol induced substantial membrane hyperpolarization. The direct measurement of BKαβ1 opening under whole-cell voltage clamp showed that these six compounds activated BKαβ1 in a very similar concentration range (1–10 μM); in contrast, abietic acid, sclareol, and methyl pimarate had no effect. PiMA did not affect the charybdotoxin-induced block of macroscopic BKαβ1 current. Single channel recordings of BKαβ1 in inside-out patches showed that 10 μM PiMA did not change channel conductance but significantly increased its open probability as a result of increase in sensitivity to Ca2+ and voltage. Because coexpression of the β1 subunit did not affect PiMA-induced potentiation, the site of action for PiMA is suggested to be BKα subunit. PiMA was selective to BK over cloned small and intermediate Ca2+ activated K+ channels. In conclusion, PiMA (>1 μM) increases Ca2+ and voltage-sensitivity of BKα when applied from either side of the cell membrane. The marked difference in potency as BK channel openers between PiMA and abietic acid, despite only very small differences in their chemical structures, may provide insight into the fundamental structure-activity relationship governing BKα activation.

  使用人胚肾（HEK）293细胞研究了皮马酸（PiMA）及八种密切相关化合物对大导电性钾离子（BK）通道的影响，这些细胞中异源表达了BK通道的α亚单位（HEKBKα）或同时表达了α和β1亚单位（HEKBKαβ1）。通过使用电压敏感染料DiBAC4(3)监测这些化合物（10 μM）对HEKBKαβ1膜电位的影响。皮马酸、异皮马酸、沙达卡异皮马酸、二氢皮马酸、二氢异皮马酸和二氢异皮马醇导致了显著的膜超极化。在全细胞电压钳下直接测量BKαβ1开启显示，这六种化合物在相似的浓度范围（1–10 μM）内激活BKαβ1；相比之下，阿比特酸、松香醇和甲基皮马酸没有影响。皮马酸不影响鞘毒素引起的宏观BKαβ1电流的阻断。在内外侧膜片的单通道记录中，10 μM的PiMA没有改变通道导电性，但显著增加了其开放概率，原因是对Ca2+和电压的敏感性增加。由于β1亚单位的共表达并未影响PiMA诱导的增强效果，因此推测PiMA的作用位点为BKα亚单位。PiMA对BK通道相对于克隆的小型和中型Ca2+激活的K+通道具有选择性。总之，PiMA（>1 μM）在从细胞膜任一侧应用时都能增加BKα对Ca2+和电压的敏感性。尽管PiMA和阿比特酸的化学结构仅有微小差异，但作为BK通道开启剂的显著作用差异，可能为理解BKα激活的基础结构-活性关系提供了新的见解。
• Terpenoids of lodgepole pine bark
  作者：J.W. Rowe、R.C. Ronald、B.A. Nagasampagi

  DOI：10.1016/s0031-9422(00)90015-3

  日期：1972.1

  Abstract Additional extractives of lodgepole pine bark include pimaradiene, γ-cadinene, oplopanone (I), and the new natural products, 21-episerratenediol 21-methyl ether (IIa) and 18-norpimara-8(14),15-dien-4-ol (III). The structure of IIa was proved by converting it to 21β-methoxy-14-serraten-3-one (IIc) and to 21-episerratenediol dimethyl ether (IIb). The structure of III was proved by converting

  摘要 黑松树皮的其他提取物包括海松二烯、γ-卡地烯、奥普罗酮 (I) 和新的天然产物 21-表色拉烯二醇 21-甲基醚 (IIa) 和 18-norpimara-8(14),15-dien-4 -ol (III)。通过将其转化为 21β-甲氧基-14-serraten-3-one (IIc) 和 21-episerratenediol 二甲醚 (IIb) 证明了 IIa 的结构。通过将 III 和二氢海松酸 (IVa) 转化为 18-norpimar-8(14)-en-4-ol (IVb) 证明了 III 的结构。还制备了相应的 19-norpimar-8(14)-en-4-ol (IVc)。
• Le-Van-Thoi; Ourgaud, Bulletin de la Societe Chimique de France, 1956, p. 205,206
  作者：Le-Van-Thoi、Ourgaud

  DOI：——

  日期：——
• Lombard, Bulletin de la Societe Chimique de France, 1946, p. 109,112
  作者：Lombard

  DOI：——

  日期：——
• On the Hydration of Dihydropimaric Acid
  作者：Torsten. Hasselstrom、Burt L. Hampton

  DOI：10.1021/ja01873a504

  日期：1939.4