agathic acid | 640-28-8

• 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: agathic acid
• 英文别名: labda-8(17),13-diene-15,19-dioic acid；labda-8(20),13-diene-15,19-dioic acid；Labda-8(20),13-dien-15,19-disaeure；(1S,4aR,5S,8aR)-5-(4-carboxy-3-methylbut-3-enyl)-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 640-28-8；17829-02-6；33123-07-8；37886-48-9；41988-89-0；138125-22-1
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: QYCOHMYDSOZCQD-FIYPYCPBSA-N

物化性质

• 沸点：
  496.5±38.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：

  agathic acid 在 sodium 作用下， 以 正丁醇 为溶剂， 反应 0.5h， 以40 mg的产率得到dihydroagathic acid
  参考文献：
  名称：

  In Vitro Biotransformations of Isocupressic Acid by Cow Rumen Preparations:  Formation of Agathic and Dihydroagathic Acids

  摘要：

  Isocupressic acid [15-hydroxylabda-8(17),13E-dien-19-oic acid] (I) was incubated under anaerobic conditions for 48 h in an in vitro luminal fluid mixture and was transformed into two metabolites. The two metabolites were identified by GC/MS as agathic acid [labda-8(17),13(E)-diene-15,19-dioic acid] (4E) and dihydroagathic acid [labda-8(17)-ene-15,19-dioic acid] (6). Metabolite identities were confirmed by chemical conversions of isocupressic acid (1) and imbricataloic acid (5) into 4E and 6, respectively. Structures of synthetic metabolites were confirmed by H-1 and C-13 NMR, specific rotation, GC/MS, and high-resolution mass spectrometry. Plasma obtained from cows that were fed Ponderosa pine needles contained (13R,S)-dihydroagathic acid (6) but not isocupressic acid (1) or 4E. The results suggest that isocupressic acid (1) is metabolically oxidized to agathic acid (4E), subsequently reduced to (13R,S)-dihydroagathic acid (6) in the rumen, and then absorbed into the bloodstream of cattle.

  DOI：

  10.1021/np970372u

文献信息

• Agathadiol, a labdane diterpenoid from juniper berries, is a positive allosteric modulator of CB1R
  作者：Stefano Salamone、Giovanni Appendino、Adil Khalili、Federica Pollastro、Eduardo Munoz、Juan D. Unciti-Broceta

  DOI：10.1016/j.fitote.2021.105059

  日期：2021.11

  - cannabinoid receptor (CB1R). Bioactivity-directed fractionation identified the labdane diterpenoid agathadiol (4) as a positive allosteric modulator of CB1R, while closely related analogues were inactive. Agathadiol (4) is a minor constituent of juniper, but could be more conveniently obtained by semisynthesis from agathic acid (8), a major constituent of Manila copal.

  杜松 ( Juniperus community L.) 浆果丙酮提取物的中性部分可以积极调节 1 型大麻素受体 (CB 1 R)的活性。以生物活性为导向的分馏鉴定了劳丹丹二萜类agathadiol ( 4 ) 作为CB 1 R的正变构调节剂，而密切相关的类似物是无活性的。Agathadiol ( 4 ) 是杜松的次要成分，但可以更方便地通过从马尼拉柯巴胶的主要成分Agathic acid ( 8 )半合成获得。
• Ruzicka; Hosking, Justus Liebigs Annalen der Chemie, <hi>1929</hi>, vol. 469, p. 188
  作者：Ruzicka、Hosking

  DOI：——

  日期：——
• In Vitro Biotransformations of Isocupressic Acid by Cow Rumen Preparations:  Formation of Agathic and Dihydroagathic Acids
  作者：Shwu-Jiuan Lin、Robert E. Short、Stephen P. Ford、Elaine E. Grings、John P. N. Rosazza

  DOI：10.1021/np970372u

  日期：1998.1.1

  Isocupressic acid [15-hydroxylabda-8(17),13E-dien-19-oic acid] (I) was incubated under anaerobic conditions for 48 h in an in vitro luminal fluid mixture and was transformed into two metabolites. The two metabolites were identified by GC/MS as agathic acid [labda-8(17),13(E)-diene-15,19-dioic acid] (4E) and dihydroagathic acid [labda-8(17)-ene-15,19-dioic acid] (6). Metabolite identities were confirmed by chemical conversions of isocupressic acid (1) and imbricataloic acid (5) into 4E and 6, respectively. Structures of synthetic metabolites were confirmed by H-1 and C-13 NMR, specific rotation, GC/MS, and high-resolution mass spectrometry. Plasma obtained from cows that were fed Ponderosa pine needles contained (13R,S)-dihydroagathic acid (6) but not isocupressic acid (1) or 4E. The results suggest that isocupressic acid (1) is metabolically oxidized to agathic acid (4E), subsequently reduced to (13R,S)-dihydroagathic acid (6) in the rumen, and then absorbed into the bloodstream of cattle.