trans-dihydromorin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: trans-dihydromorin
• 英文别名: 2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: QIWOFDHUQPJCJF-UHFFFAOYSA-N

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

反应信息

• 作为反应物：
  描述：

  trans-dihydromorin 在 DAICEL CHIRALPAK IA 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 2,3-trans-Dihydromorin 、 二氢桑色素
  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
• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 盐酸 、 双氧水 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 为溶剂， 反应 7.17h， 生成 trans-dihydromorin
  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

• Phenolics from osage orange wood cleavage of oxyresveratrol
  作者：Nancy N. Gerber

  DOI：10.1016/s0031-9422(00)81238-8

  日期：1986.1

  Abstract ‘Dihydromorin pentaacetate,’ mp 192°, was shown to be5,7,2′,4′-tetraacetoxyflavone. Oxyresveratrol with acid or MS (probe) gave resorcinol and 7-(3,5-dihydroxyphenyl)naphthalen-1,3-diol.

  摘要 'Dihydromorin pentaacetate'，mp 192°，显示为 5,7,2',4'-四乙酰氧基黄酮。Oxyresveratrol 与酸或 MS（探针）产生间苯二酚和 7-(3,5-二羟基苯基)萘-1,3-二醇。
• COMPOSITIONS COMPRISING A POLYPEPTIDE HAVING CELLULOLYTIC ENHANCING ACTIVITY AND A BICYCLIC COMPOUND AND USES THEREOF
  申请人：Novozymes, Inc.

  公开号：EP2603594B1

  公开（公告）日：2018-04-25
• COMPOUNDS AND METHODS FOR THE DIAGNOSIS AND TREATMENT OF AMYLOID ASSOCIATED DISEASES
  申请人：YANG Jerry

  公开号：US20100178282A1

  公开（公告）日：2010-07-15

  The invention is in general directed to compounds and methods for diagnosing, preventing or alleviating the symptoms of amyloid-associated diseases, for example, neuronal diseases, such as, for example, Alzheimer's disease, methods of screening for compounds useful in preventing or alleviating the symptoms of amyloid-associated diseases, methods of diagnostic imaging of A-beta fibrils, and compounds and methods useful for studying normal or disease-associated cellular mechanisms relating to amyloid proteins.
• Compositions Comprising A Polypeptide Having Cellulolytic Enhancing Activity And A Bicyclic Compound And Uses Thereof
  申请人：Quinlan Jason

  公开号：US20130217077A1

  公开（公告）日：2013-08-22

  The present invention relates to compositions comprising: a polypeptide having cellulolytic enhancing activity and a bicyclic compound. The present invention also relates to methods of using the compositions.
• USE OF COMPOUNDS ISOLATED FROM MORUS BARK
  申请人：Chang Hwan Bong

  公开号：US20140018552A1

  公开（公告）日：2014-01-16

  The present invention provides an AGE inhibitor and a health functional food for inhibiting an occurrence of diabetic complications. Particularly, the present invention comprises a compound selected from the group consisting of mulberrofuran G, mulberrofuran K, kuwanon G, kuwanon Z, oxyresveratrol, 2′,4′,5,7-tetrahydroxyflavanone, morusignin L and dihydromorin isolated from Morus Bark as an active ingredient. The compounds disclosed above inhibit the production of AGE which is a causative substance of diabetic complications. Thus, the compounds could be used as an AGE inhibitor and a health functional food for inhibiting diabetic nephropathy, diabetic retinopathy and diabetic neuropathy.