(2S,3S)-3,40,5,7-tetrahydroxyflavanone | 118333-31-6

• 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: (2S,3S)-3,40,5,7-tetrahydroxyflavanone
• 英文别名: 5,7,4'-trihydroxy-2,3-dihydroflavonol；(2S,3S)-trans-dihydrokapempferol；5,7,4'-trihydroxydihydroflavonol；(-)-trans-dihydrokaempferol；(2S,3S)-dihydrokaempferol；(2S,3S)-(-)-aromadendrin；(2S,3S)-3,4',5,7-Tetrahydroxyflavanone；(2S,3S)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 118333-31-6
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: PADQINQHPQKXNL-CABCVRRESA-N

物化性质

• 熔点：
  240-241 °C
• 沸点：
  639.0±55.0 °C(Predicted)
• 密度：
  1.599±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3,40,5,7-tetrahydroxyflavanone 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 33.0h， 生成 (2R,3S,4R)-(+)-5,7,4'-trimethoxyflavan-3,4-diol
  参考文献：
  名称：

  Takahashi, Hiroshi; Li, Shaoshun; Harigaya, Yoshihiro, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1877 - 1881

  摘要：

  DOI：
• 作为产物：
  描述：

  tetrakis(O-methoxymethyl)isosalipurpol 在 盐酸 、 叔丁基过氧化氢 、 sodium hydroxide 、 1-benzylquinidinium chloride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.33h， 生成 (2S,3S)-3,40,5,7-tetrahydroxyflavanone
  参考文献：
  名称：

  Takahashi, Hiroshi; Li, Shaoshun; Harigaya, Yoshihiro, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1877 - 1881

  摘要：

  DOI：

文献信息

• Phenolic glycosides from Agrimonia pilosa
  作者：Hiroyoshi Kato、Wei Li、Michihiko Koike、Yinghua Wang、Kazuo Koike

  DOI：10.1016/j.phytochem.2010.08.007

  日期：2010.11

  Phytochemical investigation of the methanolic extract from the aerial parts of Agrimonia pilosa led to the isolation of three compounds, (-)-aromadendrin 3-O-β-D-glucopyranoside, desmethylagrimonolide 6-O-β-D-glucopyranoside, and 5,7-dihydroxy-2-propylchromone 7-O-β-D-glucopyranoside, together with nine known compounds, agrimonolide 6-O-glucoside, takanechromone C, astragalin, afzelin, tiliroside,

  对来自龙牙地上部分的甲醇提取物的植物化学研究导致分离出三种化合物，(-)-aromadendrin 3-O-β-D-吡喃葡萄糖苷、去甲基龙蒿内酯 6-O-β-D-吡喃葡萄糖苷和 5, 7-二羟基-2-丙基色酮 7-O-β-D-吡喃葡萄糖苷，连同九种已知化合物、农杆菌内酯 6-O-葡萄糖苷、takanechromone C、黄芪甲苷、阿夫泽林、tiliroside、木犀草素、槲皮素、异槲皮素和槲皮素。它们的结构是通过各种光谱分析和化学转化确定的。
• Production of flavonoids by recombinant microorganisms
  申请人：Koffas Mattheos

  公开号：US20060019334A1

  公开（公告）日：2006-01-26

  Methods and compositions are provided for production of flavonoids in microbial hosts. The compositions comprises a set of genes which encode for enzymes involved in one or more steps in the biosymthetic pathway for the conversion of phenylpropanoids to various flavonoids. The method comprises the steps of introducing the set of genes into a heterologous host cell, allowing growth of the cells in a suitable medium such that the expression of the genes results in production of enzymes. When specific substrate(s) is/are provided to the transformed cell, the enzymes act on the substrate(s) to produce the desired flavonoids.

  本发明提供了一种在微生物宿主中生产黄酮类化合物的方法和组合物。该组合物包括一组基因，这些基因编码参与苯丙烷类物质转化为各种黄酮类化合物生物合成途径中的酶。该方法包括将该基因组引入异源宿主细胞中，让细胞在适宜培养基中生长，使得基因的表达导致酶的产生。当将特定底物提供给转化后的细胞时，酶作用于底物以产生所需的黄酮类化合物。
• 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.
• In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana
  作者：A Prescott

  DOI：10.1016/s0031-9422(02)00155-3

  日期：2002.7

  cDNA corresponding to a flavonol synthase gene from Arabidopsis thaliana was cloned and expressed in Escherichia coli. The recombinant protein was purified to near-homogeneity and the catalytic properties of the enzyme were studied in vitro. Together with kaempferol and apigenin the recombinant protein synthesised the (2R,3S)-cis- and (2S,3S)-trans-isomers of dihydrokaempferol from the (2S)- and (2R)-isomers of naringenin, respectively. Flavanones and dihydroflavanols differing in degree of A- or B-ring hydroxylation were also accepted as substrates. (C) 2002 Elsevier Science Ltd. All rights reserved.
• TAKAHASHI, HIROSHI;LI, SHAOSHUN;HARIGAYA, YOSHIHIRO;ONDA, MASAYUKI, CHEM. AND PHARM. BULL., 36,(1988) N 5, 1877-1881
  作者：TAKAHASHI, HIROSHI、LI, SHAOSHUN、HARIGAYA, YOSHIHIRO、ONDA, MASAYUKI

  DOI：——

  日期：——