apigenin 7-sulfate | 56857-56-8

• 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: apigenin 7-sulfate
• 英文别名: apigenin-7-O-sulfate；[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl] hydrogen sulfate
• CAS: 56857-56-8
• 化学式: C₁₅H₁₀O₈S
• 分子量: 350.306
• InChiKey: UQUHXFINOFUDCC-UHFFFAOYSA-N

物化性质

• 密度：
  1.732±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  347.5°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  apigenin 7-sulfate 生成 apigenin 7-sulfate potassium
  参考文献：
  名称：

  BARRON, D.;IBRAHIM, R. K., TETRAHEDRON, 43,(1987) N 22, 5197-5202

  摘要：

  DOI：
• 作为产物：
  描述：

  白杨素 在 Cunninghamella elegans NRRL 1392 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 504192.0h， 生成 apigenin 7-sulfate
  参考文献：
  名称：

  Biotransformation of Chrysin and Apigenin by Cunninghamella elegans

  摘要：

  Cunninghamella elegans NRRL 1392 对黄酮素的生物转化产生了芹菜素、芹菜素 7-硫酸盐、芹菜素 7,4′-二硫酸盐，以及一种新的代谢物，被鉴定为黄酮素 7-硫酸盐。另一方面，使用相同微生物对芹菜素的发酵则产生了芹菜素 7-硫酸盐和芹菜素 7,4′-二硫酸盐。代谢物的结构通过光谱分析、酸和酶水解以及与参考样品的比较来确定。

  DOI：

  10.1248/cpb.53.671

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.