tajixanthone hydrate | 54622-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: tajixanthone hydrate
• 英文别名: Tajixanthonehydrate；(1R,2S)-8-[(2S)-2,3-dihydroxy-3-methylbutyl]-1,11-dihydroxy-5-methyl-2-prop-1-en-2-yl-2,3-dihydro-1H-pyrano[3,2-a]xanthen-12-one
• CAS: 54622-51-4
• 化学式: C₂₅H₂₈O₇
• 分子量: 440.493
• InChiKey: SLCCOTGLZNLRJS-DAESXHAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tajixanthone hydrate 在 hydroxylase 作用下， 生成
  参考文献：
  名称：

  New prenylxanthones, polyketide hemiterpenoid pigments from the endophytic fungus Emericella sp. XL029 and their anti-agricultural pathogenic fungal and antibacterial activities

  摘要：

  从植物内生真菌Emericella sp. XL029中分离出四种新的异戊烯基黄酮和五种已知化合物。生物测定表明，这些化合物对细菌和真菌菌株具有选择性的抑制活性。

  DOI：

  10.1039/c7ra04762b
• 作为产物：
  描述：

  tajixanthone hydrate-15-acetate 在 甲醇 、 potassium hydroxide 作用下， 反应 1.0h， 生成 tajixanthone hydrate
  参考文献：
  名称：

  Development of the Fluorescent Biosensor hCalmodulin (hCaM)L39C-monobromobimane(mBBr)/V91C-mBBr, a Novel Tool for Discovering New Calmodulin Inhibitors and Detecting Calcium

  摘要：

  A novel, sensible, and specific fluorescent biosensor of human calmodulin (hCaM), namely hCaM L39C-mBBr/V91C-mBBr, was constructed. The biosensor was useful for detecting ligands with opposing fluorescent signals, calcium ions (Ca(2+)) and CaM inhibitors in solution. Thus, the device was successfully applied to analyze the allosteric effect of Ca(2+) on trifluoroperazine (TFP) binding to CaM (Ca(2+) K(d) = 0.24 mu M +/- 0.03 with a stoichiometry 4.10 +/- 0.15; TFP K(d) similar to 5.74-0.53 mu M depending on the degree of saturation of Ca(2+), with a stoichiometry of 2:1). In addition, it was suitable for discovering additional xanthones (5, 6, and 8) with anti-CaM properties from the fungus Emericella 25379. The affinity of 1-5, 7, and 8 for the complex (Ca(2+))(4)-CaM was excellent because their experimental K(d)s were in the nM range (4-498 nM). Docking analysis predicted that 1-8 bind to CaM at sites I, III, and IV as does TFP.

  DOI：

  10.1021/jm200167g

文献信息

• Varioxiranols A–G and 19-<i>O</i>-Methyl-22-methoxypre-shamixanthone, PKS and Hybrid PKS-Derived Metabolites from a Sponge-Associated <i>Emericella variecolor</i> Fungus
  作者：Qi Wu、Chongming Wu、Hailin Long、Ran Chen、Dong Liu、Peter Proksch、Peng Guo、Wenhan Lin

  DOI：10.1021/acs.jnatprod.5b00578

  日期：2015.10.23

  Chemical examination of a sponge (Cinachyrella sp.)-associated Emericella variecolor fungus resulted in the isolation of seven new polyketide derivatives, namely, varioxiranols A–G (1–7), and a new hybrid PKS-isoprenoid metabolite, 19-O-methyl-22-methoxypre-shamixanthone (8), together with nine known analogues. Their structures were elucidated on the basis of extensive spectroscopic analyses, including

  海绵的化学检查（Cinachyrella属） -相关联的裸胞壳variecolor真菌，导致七个新聚酮衍生物的分离，即，varioxiranols A-G（1 - 7），以及一种新的混合PKS-类异戊二烯代谢物，19- ö -甲基22-甲氧基预混合蒽酮（8），以及九种已知的类似物。在广泛的光谱分析的基础上阐明了它们的结构，包括ECD效应，Mosher方法，X射线衍射和用于确定绝对构型的化学转化。首次发现瓦瑞拉诺醇F和G通过醚键将黄酮酮部分与苯甲醇连接，而5本质上是不寻常的。基于细胞的降脂试验表明，前混合蒽酮（12）对HepG2细胞中的脂质蓄积具有显着的抑制作用，而没有细胞毒性作用，伴随着总胆固醇和甘油三酯的有效降低。实时定量PCR表明，前混合蒽酮（12）介导脂质积累的减少，这与关键的脂肪生成转录因子SREBP-1c及其下游编码FAS和ACC的基因表达下调有关。
• Prenylxanthones and a Bicyclo[3.3.1]nona-2,6-diene Derivative from the Fungus <i>Emericella rugulosa</i>
  作者：Panawan Moosophon、Somdej Kanokmedhakul、Kwanjai Kanokmedhakul、Kasem Soytong

  DOI：10.1021/np800805f

  日期：2009.8.28

  Five new prenylxanthones, ruguloxanthones A-C (1-3), 14-methoxytajixanthone (4), and tajixanthone ethanoate (5), a new bicyclo[3.3.1]nona-2,6-diene derivative, rugulosone: (6), and seven known compounds, shamixanthone, tajixanthone, 14-methoxytajixanthone-25-acetate, tajixanthone hydrate, tajixanthone methanoate, isoemericellin, and ergosterol, were isolated from the fungus Emericella rugulosa. The structures of 1-6 were established using spectroscopic techniques. Compound 6 exhibited antimalarial and antimycobacterial activities, as well as cytotoxicity against three cancer cell lines.
• Development of the Fluorescent Biosensor <i>h</i>Calmodulin (<i>h</i>CaM)L39C-<i>monobromobimane</i>(<i>mBBr</i>)/V91C-<i>mBBr</i>, a Novel Tool for Discovering New Calmodulin Inhibitors and Detecting Calcium
  作者：Martín González-Andrade、José Rivera-Chávez、Alejandro Sosa-Peinado、Mario Figueroa、Rogelio Rodríguez-Sotres、Rachel Mata

  DOI：10.1021/jm200167g

  日期：2011.6.9

  A novel, sensible, and specific fluorescent biosensor of human calmodulin (hCaM), namely hCaM L39C-mBBr/V91C-mBBr, was constructed. The biosensor was useful for detecting ligands with opposing fluorescent signals, calcium ions (Ca(2+)) and CaM inhibitors in solution. Thus, the device was successfully applied to analyze the allosteric effect of Ca(2+) on trifluoroperazine (TFP) binding to CaM (Ca(2+) K(d) = 0.24 mu M +/- 0.03 with a stoichiometry 4.10 +/- 0.15; TFP K(d) similar to 5.74-0.53 mu M depending on the degree of saturation of Ca(2+), with a stoichiometry of 2:1). In addition, it was suitable for discovering additional xanthones (5, 6, and 8) with anti-CaM properties from the fungus Emericella 25379. The affinity of 1-5, 7, and 8 for the complex (Ca(2+))(4)-CaM was excellent because their experimental K(d)s were in the nM range (4-498 nM). Docking analysis predicted that 1-8 bind to CaM at sites I, III, and IV as does TFP.
• New prenylxanthones, polyketide hemiterpenoid pigments from the endophytic fungus Emericella sp. XL029 and their anti-agricultural pathogenic fungal and antibacterial activities
  作者：Xia Wu、Li-Zhen Fang、Feng-Lou Liu、Xue-Jiao Pang、Hai-Li Qin、Ting Zhao、Lu-Lin Xu、Deng-Feng Yang、Xiao-Long Yang

  DOI：10.1039/c7ra04762b

  日期：——

  Four new prenylxanthones and five known compounds were isolated from the plant endophytic fungusEmericellasp. XL029. Biological assays revealed that the compounds showed selective inhibitory activity against bacterial and fungal strains.

  从植物内生真菌Emericella sp. XL029中分离出四种新的异戊烯基黄酮和五种已知化合物。生物测定表明，这些化合物对细菌和真菌菌株具有选择性的抑制活性。