甘肃黄芩素; 2',5,6',7-四羟基二氢黄烷酮 | 80366-15-0

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 甘肃黄芩素; 2',5,6',7-四羟基二氢黄烷酮
• 中文别名: 甲基N-[(1R)-1-[[[(2S,3S)-2-羟基-3-[[(2S)-2-(甲酯基&lt甲氧羰基&gt氨基)-3-甲基-丁酰]氨基]-4-苯基-丁基]-[[4-(1,3-噻唑-5-基)phenyl]甲基]氨基]氨基甲酰]-2-甲基硫烷基-乙基]氨基甲酸酯；甘肃黄芩素;2',5,6',7-四羟基二氢黄烷酮；甘肃黄芩素；2',5,6',7-四羟基二氢黄烷酮
• 英文名称: 3,5,7,2′,6′-pentahydroxyflavanone
• 英文别名: (2R,3R)-2',3,5,6',7-pentahydroxyflavanone；(2R,3R)-3,5,7,2',6'-pentahydroxyflavanone；(2R,3R)2',3,5,6',7-pentahydroxyflavanone；3,5,7,2',6'-pentahydroxyflavanone；(2R,3R)-2',3,5,6',7-pentahydroxy-flavanone；2',3,5,6',7-Pentahydroxyflavanone；(2R,3R)-2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• CAS: 80366-15-0
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: NBQYBZYBTNQEQG-LSDHHAIUSA-N

物化性质

• 沸点：
  713.4±60.0 °C(Predicted)
• 密度：
  1.702±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 甘肃黄芩素; 2',5,6',7-四羟基二氢黄烷酮 以 吡啶 为溶剂， 生成 Acetic acid (2R,3R)-5,7-diacetoxy-2-(2,6-diacetoxy-phenyl)-4-oxo-chroman-3-yl ester
  参考文献：
  名称：

  Studies on scutellariae radix. VI. Effects of flavanone compounds on lipid peroxidation in rat liver.

  摘要：

  从黄芩根中分离出抑制脂质过氧化物形成的化合物（I和II）以及多种黄酮类化合物，并进行了体外实验。根据分析和物理数据，化合物I和II分别被确定为（2S）-2'，5，6'，7-四羟基黄烷酮和（2R，3R）-2'，3，5，6'，7-五羟基黄烷酮。化合物II通过Fe2+和抗坏血酸抑制脂质过氧化物的形成。化合物I和II抑制腺苷二磷酸和还原烟酰胺腺嘌呤二核苷酸磷酸诱导的大鼠肝匀浆中的脂质过氧化物的形成。

  DOI：

  10.1248/cpb.30.1792
• 作为产物：
  描述：

  2,6-bis(methoxymethoxy)benzaldehyde 在 盐酸 、 双氧水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 正己烷 、 水 为溶剂， 反应 6.42h， 生成 trans-5,7,2',6'-Tetrahydroxyflavanonol 、 甘肃黄芩素; 2',5,6',7-四羟基二氢黄烷酮
  参考文献：
  名称：

  Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship

  摘要：

  To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.042

文献信息

• Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship
  作者：Wen-Jun Jiang、Kan’ichiro Ishiuchi、Megumi Furukawa、Tomoko Takamiya、Susumu Kitanaka、Hiroshi Iijima

  DOI：10.1016/j.bmc.2015.09.042

  日期：2015.11

  To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells. (C) 2015 Elsevier Ltd. All rights reserved.
• Studies on scutellariae radix. VI. Effects of flavanone compounds on lipid peroxidation in rat liver.
  作者：YOSHIYUKI KIMURA、HIROMICHI OKUDA、TADATO TANI、SHIGERU ARICHI

  DOI：10.1248/cpb.30.1792

  日期：——

  Compounds (I and II) which inhibited lipid peroxides formation (in in vitro experiments) were isolated together with various flavonoids from the roots of Scutellaria baicalensis GEORGI. From the analytical and physical data, compounds I and II were identified as (2S)-2', 5, 6', 7-tetrahydroxy-flavanone and (2R, 3R)-2', 3, 5, 6', 7-pentahydroxy-flavanone, respectively. Compound II inhibited the lipid peroxide formation by Fe2+ and ascorbic acid. Compounds I and II inhibited the lipid peroxide formation induced by adenosine diphosphate and reduced nicotinamide adenine dinucleotide phosphate in rat liver homogenate.

  从黄芩根中分离出抑制脂质过氧化物形成的化合物（I和II）以及多种黄酮类化合物，并进行了体外实验。根据分析和物理数据，化合物I和II分别被确定为（2S）-2'，5，6'，7-四羟基黄烷酮和（2R，3R）-2'，3，5，6'，7-五羟基黄烷酮。化合物II通过Fe2+和抗坏血酸抑制脂质过氧化物的形成。化合物I和II抑制腺苷二磷酸和还原烟酰胺腺嘌呤二核苷酸磷酸诱导的大鼠肝匀浆中的脂质过氧化物的形成。