7-oxo-ent-pimara-8(9),15-dien-19-oic acid | 1261121-11-2

• 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: 7-oxo-ent-pimara-8(9),15-dien-19-oic acid
• 英文别名: 7-keto-ent-pimara-8,15-dien-19-oic acid；(1R,4aR,7S,10aS)-7-ethenyl-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthrene-1-carboxylic acid
• CAS: 1261121-11-2
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: MKABKMLRRKPPCP-FRYIKTPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• 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

• 作为产物：
  描述：

  (-)-pimara-8(14),15-diene-19-oic acid 在 ferrous(II) sulfate heptahydrate 、 potassium dihydrogenphosphate 、 一水合硫酸镁 、 potassium chloride 、 sodium nitrite 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 168.0h， 以11.3 mg的产率得到ent-pimara-7,15-dien-19-oic acid
  参考文献：
  名称：

  Anticariogenic Properties of ent-Pimarane Diterpenes Obtained by Microbial Transformation

  摘要：

  在目前的研究中，我们研究了三种通过真菌生物转化获得的pimarane型二萜的抗龋齿活性。在这些代谢物中，ent-8(14),15-pimaradien-19-ol是最活跃的化合物，对导致龋齿的主要微生物（唾液链球菌、索氏链球菌、变形链球菌、米氏链球菌、血链球菌和干酪乳杆菌）的MIC值（从1.5到4.0微克/毫升）非常理想。用ent-8(14),15-pimaradien-19-ol对主要致病菌变形链球菌进行时间杀灭试验，结果表明该

  DOI：

  10.3390/molecules15128553

文献信息

• Anticariogenic Properties of ent-Pimarane Diterpenes Obtained by Microbial Transformation
  作者：Marcela E. Severiano、Marilia R. Simao、Thiago S. Porto、Carlos H. G. Martins、Rodrigo C. S. Veneziani、Niege A. J. C. Furtado、Nilton S. Arakawa、Suraia Said、Dioneia C. R. de Oliveira、Wilson R. Cunha、Luiz E. Gregorio、Sergio R. Ambrosio

  DOI：10.3390/molecules15128553

  日期：——

  In the present work, the anticariogenic activities of three pimarane-type diterpenes obtained by fungal biotransformation were investigated. Among these metabolites, ent-8(14),15-pimaradien-19-ol was the most active compound, displaying very promising MIC values (ranging from 1.5 to 4.0 μg mL-1) against the main microorganisms responsible for dental caries: Streptococcus salivarius, S. sobrinus, S. mutans, S. mitis, S. sanguinis, and Lactobacillus casei. Time kill assays performed with ent-8(14),15-pimaradien-19-ol against the primary causative agent S. mutans revealed that this compound only avoids growth of the inoculum in the first 12 h (bacteriostatic effect). However, its bactericidal effect is clearly noted thereafter (between 12 and 24 h). The curve profile obtained by combining ent-8(14),15-pimaradien-19-ol and chlorhexidine revealed a significant reduction in the time necessary for killing S. mutans compared with each of these two chemicals alone. However, no synergistic effect was observed using the same combination in the checkerboard assays against this microorganism. In conclusion, our results point out that ent-8(14),15-pimaradien-19-ol is an important metabolite in the search for new effective anticariogenic agents.

  在目前的研究中，我们研究了三种通过真菌生物转化获得的pimarane型二萜的抗龋齿活性。在这些代谢物中，ent-8(14),15-pimaradien-19-ol是最活跃的化合物，对导致龋齿的主要微生物（唾液链球菌、索氏链球菌、变形链球菌、米氏链球菌、血链球菌和干酪乳杆菌）的MIC值（从1.5到4.0微克/毫升）非常理想。用ent-8(14),15-pimaradien-19-ol对主要致病菌变形链球菌进行时间杀灭试验，结果表明该