ent-12α,17-dihydroxy-16-ketobeyeran-19-oic acid | 915025-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ent-12α,17-dihydroxy-16-ketobeyeran-19-oic acid
• 英文别名: (1R,4S,5R,9S,10R,12S,13S)-12-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 915025-93-3
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: ZBYFDMJURKQXPY-JNQXFYDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Dihydroisosteviol 在 absidia pseudocylindrospora ATCC 24169 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以29 mg的产率得到ent-16β,17-dihydroxybeyeran-9(11)-en-19-oic acid
  参考文献：
  名称：

  Biotransformation of dihydroisosteviol and the effects of transformed products on steroidogenic gene expressions

  摘要：

  The biotransformation of dihydroisosteviol with Absidia pseudocylindrospora ATCC 24169, Streptomyces griseus ATCC 10137, Mucor recurvatus MR36, and Aspergillus niger BCRC 31130 yielded 15 metabolites, eight of which were previously unknown. Structures of metabolites were established by 2D NMR techniques and HRMS data, two of which were further corroborated by chemical means, and another via single-crystal X-ray diffraction analysis. Subsequently, two steroidogenic cell lines (Y-1 mouse adrenal tumor and MA-10 mouse Leydig tumor cells) were used in a reverse transcription-PCR analysis to assess the effects of all compounds on steroidogenic gene expressions using forskolin as a positive control. The tested gene expressions included steroidogenic factor-1 (SF-1), steroidogenic acute regulatory protein (StAR), and cytochrome P450 side-chain cleavage (P450SCC) enzyme. Gene expression profiles showed that ten of the tested compounds effectively suppressed P450(SCC) mRNA expression in both Y-1 and MA-10 cells. Several induced SF-1 gene expression and two enhanced StAR gene expression in Y-1 cells. By contrast, in MA-10 cells, one compound effectively suppressed StAR mRNA expression, whereas for others effectively suppressed SF-1 gene expression. The results suggest that analogs of dihydroisosteviol can be potential modulators to alter steroidogenic gene expressions and subsequent enzyme activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.07.015