南亚松酸 | 41787-69-3

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: 南亚松酸
• 英文名称: (βS,1S,4aR,5S,8aR)-5-carboxy-decahydro-β,5,8a-trimethyl-2-methylenenaphthalene-1-pentanoic acid
• 英文别名: (13S)-dihydroagathic acid；enantio-oliveric acid；junicedric acid；dihydroagathic acid；(1S,4aR,5S,8aR)-5-[(3S)-4-carboxy-3-methylbutyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 41787-69-3
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: HPQKNJHVWUWAOR-BWCMQUJESA-N

物化性质

• 熔点：
  122-128℃
• 沸点：
  486.7±38.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  南亚松酸 在 Wilkinson's catalyst 氢气 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 20.0~55.0 ℃ 、413.68 kPa 条件下， 反应 1.0h， 生成 methyl (8S,13S)-labda-15,19-dioate
  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：

  imbricataloic acid 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以4 mg的产率得到南亚松酸
  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

• Three Labdane-Type Diterpenes from the Bark of Juniperus formosana HAY. var. concolor HAY.
  作者：Yueh-Hsiung KUO、Ming-Tsang YU

  DOI：10.1248/cpb.44.1242

  日期：——

  Three new labdane-type diterpenes, (13S)-15-hydroxylabd-8(17)-en-19-oic acid, (13S)-15-acetoxylabd-8(17)-en-19-oic acid, and (13S)-15-octadecanoyloxylabd-8(17)-en-19-oic acid, together with one known compound, enantio-oliveric acid, were found from the bark of Juniperus formosana HAY. var. concolor HAY. Their structures were elucidated on the basis of spectral data and chemical transformation.

  从杜松（Juniperus formosana HAY.var.concolor HAY）树皮中发现了三种新的拉布丹型二萜，即(13S)-15-羟基拉布丹-8(17)-烯-19-酸、(13S)-15-乙酰氧基拉布丹-8(17)-烯-19-酸和(13S)-15-十八碳酰氧基拉布丹-8(17)-烯-19-酸，以及一种已知化合物对映体奥利韦酸。根据光谱数据和化学变化阐明了它们的结构。
• Labdane diterpenes from Brickellia glomerata☆
  作者：José S. Calderón、Leovigildo Quijano、Federico Gómez-Garibay、Marina Morán、Tirso Ríos

  DOI：10.1016/s0031-9422(00)83897-2

  日期：——

  Abstract The leaves of B. glomerata afforded three new labdane diterpenes. Their structures and stereochemistry were established by spectroscopic methods and chemical transformations.

  摘要 B. glomerata 的叶子提供了三种新的拉丹二萜。它们的结构和立体化学是通过光谱方法和化学转化建立的。