ent-7α,16β-dihydroxybeyeran-19-oic acid

• 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: ent-7α,16β-dihydroxybeyeran-19-oic acid
• 英文别名: (1S,2S,4S,5R,9S,10S,13S,14R)-2,14-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: UAPGBBZPBLMFNI-CPRALFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基戊酰氯 、 ent-7α,16β-dihydroxybeyeran-19-oic acid 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.0h， 以57 mg的产率得到ent-7α,16β-di-O-methyloxalylbeyeran-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
• 作为产物：
  描述：

  Dihydroisosteviol 在 aspergillus niger BCRC 31130 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以20 mg的产率得到ent-7α,16β-dihydroxybeyeran-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

文献信息

• Novel <i>ent-</i>Beyeran-19-oic Acids from Biotransformations of Isosteviol Metabolites by <i>Mortierella isabellina</i>
  作者：Che-Ling Lin、Shwu-Jiuan Lin、Wei-Jan Huang、Yuan-Ling Ku、Tung-Hu Tsai、Feng-Lin Hsu

  DOI：10.1055/s-2007-993756

  日期：2007.12

  Biotransformations of ENT-16beta-hydroxybeyeran-19-oic acid ( 1) by Mortierella isabellina produced hydroxylated metabolites. The isolated metabolites included three new compounds, ent-14beta,16beta-dihydroxybeyeran-19-oic acid ( 3), ent-12beta-hydroxy-16-oxobeyeran-19-oic acid ( 4), and ent-7alpha,12beta-dihydroxy-16-oxobeyeran-19-oic acid ( 5), and one known compound, ent-7alpha,16beta-dihydroxybeyeran-19-oic

  伊莎贝拉莫尔氏菌对ENT-16beta-hydroxybeyeran-19-oic acid（1）的生物转化产生了羟基化的代谢产物。分离出的代谢物包括三种新化合物，ent-14beta，16beta-dihydroxybeyeran-19-oic acid（3），ent-12beta-hydroxy-16-oxobeyeran-19-oic acid（4）和ent-7alpha，12beta-dihydroxy -16-oxobeyeran-19-oic acid（5）和一种已知化合物，ent-7alpha，16beta-dihydroxybeyeran-19-oic acid（2）。通过详细分析LC-MS色谱图以及MS和NMR光谱数据可实现结构解析。在这项研究中，伊莎贝拉球菌在7beta-，12alpha-和14alpha-位羟基化基本骨架beyeran-19-oic酸，并在16-位氧化骨架。用细胞活力测定法评估所有化合物。
• Biotransformation of dihydroisosteviol and the effects of transformed products on steroidogenic gene expressions
  作者：Shwu-Fen Chang、Li-Ming Yang、Tsurng-Juhn Huang、Chin-Yang Chen、Shiow-Yunn Sheu、Pan-Chun Liu、Shwu-Jiuan Lin

  DOI：10.1016/j.phytochem.2013.07.015

  日期：2013.11

  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.