15-oxolabda-8(17),13E-dien-19-oic acid | 159812-25-6

• 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: 15-oxolabda-8(17),13E-dien-19-oic acid
• 英文别名: (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(E)-3-methyl-5-oxopent-3-enyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 159812-25-6
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: KLAGFFXRUOBTMA-DOEMEAPXSA-N

物化性质

• 沸点：
  454.9±38.0 °C(predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  15-oxolabda-8(17),13E-dien-19-oic acid 在 sodium chlorite 、 potassium dihydrogenphosphate 作用下， 以 叔丁醇 为溶剂， 反应 15.5h， 以100%的产率得到玛瑙酸
  参考文献：
  名称：

  Preparation of Tetrahydroagathic Acid:  A Serum Metabolite of Isocupressic Acid, a Cattle Abortifacient in Ponderosa Pine

  摘要：

  Isocupressic acid (1) was used to synthetically prepare a mixture of (8S,13R,S)-labda-15,19-dioic acid (tetrahydroagathic acid) (5) via a two-step oxidation procedure followed by hydrogenation of the double bonds at C13 and C8. Reduction of the C8,17 double bond was stereospecific producing only the 8S isomer and confirmed by the nOe interaction between the resulting C17 and C20 methyl groups. The 13R and 13S isomers of 5 were separated and analyzed by HPLC/MS, and (13S)tetrahydroagathic acid was isolated and identified by comparison to a standard prepared by hydrogenation of naturally occurring (13S)-dihydroagathic acid (4). (13R,S)-dihydroagathic acid was prepared by selective sodium metal-catalyzed hydrogenation of the C13,14 allylic double bond of agathic acid (3). The prepared compounds were then used as standards to confirm the presence of 4 and 5 and their respective 13R and 13S isomers in bovine serum samples. Tetrahydroagathic acid was shown to be the only metabolite detected in serum samples taken from a suspected cattle abortion case submitted for diagnosis; and, thus, 5 could be a valuable diagnostic marker for pine needle-induced abortions.

  DOI：

  10.1021/jf011501m
• 作为产物：
  描述：

  异柏烯酸 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到15-oxolabda-8(17),13E-dien-19-oic acid
  参考文献：
  名称：

  Preparation of Tetrahydroagathic Acid:  A Serum Metabolite of Isocupressic Acid, a Cattle Abortifacient in Ponderosa Pine

  摘要：

  Isocupressic acid (1) was used to synthetically prepare a mixture of (8S,13R,S)-labda-15,19-dioic acid (tetrahydroagathic acid) (5) via a two-step oxidation procedure followed by hydrogenation of the double bonds at C13 and C8. Reduction of the C8,17 double bond was stereospecific producing only the 8S isomer and confirmed by the nOe interaction between the resulting C17 and C20 methyl groups. The 13R and 13S isomers of 5 were separated and analyzed by HPLC/MS, and (13S)tetrahydroagathic acid was isolated and identified by comparison to a standard prepared by hydrogenation of naturally occurring (13S)-dihydroagathic acid (4). (13R,S)-dihydroagathic acid was prepared by selective sodium metal-catalyzed hydrogenation of the C13,14 allylic double bond of agathic acid (3). The prepared compounds were then used as standards to confirm the presence of 4 and 5 and their respective 13R and 13S isomers in bovine serum samples. Tetrahydroagathic acid was shown to be the only metabolite detected in serum samples taken from a suspected cattle abortion case submitted for diagnosis; and, thus, 5 could be a valuable diagnostic marker for pine needle-induced abortions.

  DOI：

  10.1021/jf011501m

文献信息

• Potential Antitumor Promoting Diterpenoids from the Stem Bark of <i>Thuja standishii</i>
  作者：Manabu Iwamoto、Toshifumi Minami、Harukuni Tokuda、Hironori Ohtsu、Reiko Tanaka

  DOI：10.1055/s-2003-37037

  日期：——

  Six diterpenes, including one new natural product, were isolated from a CHCl 3 extract of the stem bark of Thuja standishii. The new compound has been characterized as 15-oxolabda-8(17),13 Z-dien-19-oic acid. The known compounds were identified as ferruginol (2), sugiol (3), isocupressic acid (4), sandaracopimaric acid (5) and 15-oxolabda-8(17),13 E-dien-19-oic acid (6). Compounds 2-5 and the derivatives

  从侧柏茎皮的 CHCl 3 提取物中分离出六种二萜，包括一种新的天然产物。新化合物已被表征为 15-oxolabda-8(17),13 Z-dien-19-oic 酸。已知的化合物被鉴定为ferruginol (2)、sugiol (3)、isocupressic acid (4)、sandaracopimaric acid (5) 和 15-oxolabda-8(17), 13 E-dien-19-oic acid (6)。测试了化合物 2-5 以及衍生物 4a 和 4b 对 12-O-十四烷酰佛波醇 13-乙酸酯 (TPA) 诱导的 Epstein-Barr 病毒早期抗原 (EBV-EA) 激活的抑制作用。化合物 2、3、4 和 5 对 EBV-EA 诱导显示出强抑制作用（在 1000 摩尔比/TPA 下抑制 100%）。
• 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.
• Preparation of Tetrahydroagathic Acid:  A Serum Metabolite of Isocupressic Acid, a Cattle Abortifacient in Ponderosa Pine
  作者：Massoud Garrossian、Dale R. Gardner、Kip E. Panter、Lynn F. James

  DOI：10.1021/jf011501m

  日期：2002.4.1

  Isocupressic acid (1) was used to synthetically prepare a mixture of (8S,13R,S)-labda-15,19-dioic acid (tetrahydroagathic acid) (5) via a two-step oxidation procedure followed by hydrogenation of the double bonds at C13 and C8. Reduction of the C8,17 double bond was stereospecific producing only the 8S isomer and confirmed by the nOe interaction between the resulting C17 and C20 methyl groups. The 13R and 13S isomers of 5 were separated and analyzed by HPLC/MS, and (13S)tetrahydroagathic acid was isolated and identified by comparison to a standard prepared by hydrogenation of naturally occurring (13S)-dihydroagathic acid (4). (13R,S)-dihydroagathic acid was prepared by selective sodium metal-catalyzed hydrogenation of the C13,14 allylic double bond of agathic acid (3). The prepared compounds were then used as standards to confirm the presence of 4 and 5 and their respective 13R and 13S isomers in bovine serum samples. Tetrahydroagathic acid was shown to be the only metabolite detected in serum samples taken from a suspected cattle abortion case submitted for diagnosis; and, thus, 5 could be a valuable diagnostic marker for pine needle-induced abortions.