3,5-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl hydrogen sulfate | 1361317-05-6

• 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: 3,5-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl hydrogen sulfate
• 英文别名: galangin 7-O-sulfate
• CAS: 1361317-05-6
• 化学式: C₁₅H₁₀O₈S
• 分子量: 350.306
• InChiKey: ZACXYGCDMHTOTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134.27
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  高良姜素 在 吡啶 、 四丁基硫酸氢铵 、 N,N'-二环己基碳二亚胺 作用下， 反应 72.0h， 生成 3,5-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl hydrogen sulfate
  参考文献：
  名称：

  欧式蜂胶的代谢产物。葡萄糖醛酸和硫酸盐的合成与分析

  摘要：

  民族药理学相关性 蜂胶是一种源自蜜蜂的产品，自古以来就因其一般的健康特性而被使用，尤其以其抗菌活性而闻名。最近，蜂胶已被用于针对更具体的目标，例如抗增殖作用与癌细胞、伤口愈合和 2 型糖尿病。 研究目的 来自新西兰的欧洲（杨树）型蜂胶含有多种羟基肉桂酸酯和一组苷元黄酮类化合物，主要是白杨素、高良姜素、松香素和松香素。蜂胶通常是口服的，蜂胶代谢物很快就会出现在摄入的血浆中。在这项工作中，我们旨在通过直接分析血浆来鉴定主要的黄酮类血浆代谢物。 材料和方法 单次服用大剂量蜂胶后，采集血液样本并使用 LCMS/MS 进行分析。鉴定出的主要黄酮类代谢物也是使用化学（硫酸盐）或酶促方法（葡萄糖醛酸）合成的。 结果 摄入蜂胶后，四种主要蜂胶黄酮类化合物的硫酸盐和葡萄糖醛酸结合物都可以在人血浆中轻松检测到。四种主要黄酮类化合物的硫酸盐和葡萄糖醛酸化物的制备可以确定各种代谢物的相对比例。尽管硫酸盐在 LCMS/MS

  DOI：

  10.1016/j.jep.2021.114035

文献信息

• SULT1A3-Mediated Regiospecific 7-O-Sulfation of Flavonoids in Caco-2 Cells Can Be Explained by the Relevant Molecular Docking Studies
  作者：Shengnan Meng、Baojian Wu、Rashim Singh、Taijun Yin、John Kenneth Morrow、Shuxing Zhang、Ming Hu

  DOI：10.1021/mp200400s

  日期：2012.4.2

  Flavonoids are polyphenolic compounds with various claimed health benefits, but the extensive metabolism by uridine-S'diphospho-glucuronosyltransferases (UGTs) and sulfotransferases (SULTs) in liver and intestine led to poor oral bioavailabilities. The effects of structural changes on the sulfonation of flavonoids have not been systemically determined, although relevant effects of structural changes on the glucuronidation of flavonoids had. We performed the regiospecific sulfonation of sixteen flavonoids from five different subclasses of flavonoids, which are represented by apigenin (flavone), genistein (isoflavone), naringenin (flavanone), kaempherol (flavonol), and phloretin (chalcone). Additional studies were performed using 4 monohydroxyl flavonoids with a -OH group at the 3, 4', 5 or 7 position, followed by S dihydroxyl flavonoids, and 2 trihydroxyl flavonoids by using expressed human SULT1A3 and Caco-2 cell lysates. We found that these compounds were exclusively sulfated at the 7-OH position by SULT1A3 and primarily sulfated at the 7-OH position in Caco-2 cell lysates with minor amounts of 4'-O-sulfates formed as well. Sulfonation rates measured using SULT1A3 and Caco-2 cell lysates were highly correlated at substrate concentrations of 2.5 and 10 mu M. Molecular docking studies provided structural explanations as to why sulfonation only occurred at the 7-OH position of flavones, flavonols and flavanones. In conclusion, molecular docking studies explain why SULT1A3 exclusively mediates sulfonation at the 7-OH position of flavones/flavonols, and correlation studies indicate that SULT1A3 is the main isoform responsible for flavonoid sulfonation in the Caco-2 cells.
• Metabolic products of European-type propolis. Synthesis and analysis of glucuronides and sulfates
  作者：Stephen J. Bloor、Kevin A. Mitchell

  DOI：10.1016/j.jep.2021.114035

  日期：2021.6

  propolis has been employed against more specific targets such as antiproliferative effects vs cancer cells, wound healing and type-2 diabetes. Aim of the study European (poplar)-type propolis from New Zealand contains a number of hydroxy cinnamic acid esters and a set of aglycone flavonoid compounds, mainly chrysin, galangin, pinocembrin and pinobanksin. Propolis is usually taken orally and propolis metabolites

  民族药理学相关性 蜂胶是一种源自蜜蜂的产品，自古以来就因其一般的健康特性而被使用，尤其以其抗菌活性而闻名。最近，蜂胶已被用于针对更具体的目标，例如抗增殖作用与癌细胞、伤口愈合和 2 型糖尿病。 研究目的 来自新西兰的欧洲（杨树）型蜂胶含有多种羟基肉桂酸酯和一组苷元黄酮类化合物，主要是白杨素、高良姜素、松香素和松香素。蜂胶通常是口服的，蜂胶代谢物很快就会出现在摄入的血浆中。在这项工作中，我们旨在通过直接分析血浆来鉴定主要的黄酮类血浆代谢物。 材料和方法 单次服用大剂量蜂胶后，采集血液样本并使用 LCMS/MS 进行分析。鉴定出的主要黄酮类代谢物也是使用化学（硫酸盐）或酶促方法（葡萄糖醛酸）合成的。 结果 摄入蜂胶后，四种主要蜂胶黄酮类化合物的硫酸盐和葡萄糖醛酸结合物都可以在人血浆中轻松检测到。四种主要黄酮类化合物的硫酸盐和葡萄糖醛酸化物的制备可以确定各种代谢物的相对比例。尽管硫酸盐在 LCMS/MS