异鼠李素-3,7-O-二葡萄糖苷 | 6758-51-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 异鼠李素-3,7-O-二葡萄糖苷
• 英文名称: isorhamnetin 3,7-O-di-β-D-glucopyranoside
• 英文别名: isorhamnetin 3,7-di-O-β-D-glucopyranoside；isorhamnetin-3,7-di-O-β-D-glucopyranoside；3,7-di-O-β-D-glucopiranozyd izoramnetyny；isorhamnetin-3,7-O-β-D-diglucopyranoside；isorhamnetin 3,7-di-β-D-glucopyranoside；isorhamnetin-3-O-D-glucoside-7-O-D-glucoside；5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• CAS: 6758-51-6
• 化学式: C₂₈H₃₂O₁₇
• 分子量: 640.552
• InChiKey: ZYYJHXKSQKLEBL-QDYVESOYSA-N

物化性质

• 沸点：
  1016.2±65.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  275
• 氢给体数：
  10
• 氢受体数：
  17

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	isorhamnetin 3-O-(6-O-acetyl-β-D-glucopyranosyl)-7-β-D-glucopyranoside	1187881-48-6	C30H34O18	682.589
  槲皮素	quercetol	117-39-5	C15H10O7	302.24

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  异鼠李素	isorhamnetin	480-19-3	C16H12O7	316.267

反应信息

• 作为反应物：
  描述：

  异鼠李素-3,7-O-二葡萄糖苷 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以220 mg的产率得到异鼠李素
  参考文献：
  名称：

  Antioxidant Effects of Isorhamnetin 3,7-Di-O-β-d-glucopyranoside Isolated from Mustard Leaf (Brassica juncea) in Rats with Streptozotocin-Induced Diabetes

  摘要：

  To investigate the effects of isorhamnetin 3,7-di-O-beta-D-glucopyranoside (isorhamnetin diglucoside), a major flavonoid compound of mustard leaf, on oxidative stress due to diabetes mellitus, in vivo and in vitro studies were carried out. Oral administration of isorhamnetin diglucoside (10 or 20 mg/kg of body weight/day for 10 days) to rats with streptozotocin-induced diabetes significantly reduced serum levels of glucose and 5-(hydroxymethyl)furfural (5-HMF), which is glycosylated with hemoglobin and is an indicator of oxidative stress. After intraperitoneal administration, isorhamnetin diglucoside did not show these activities. In addition, after oral administration, the thiobarbituric acid-reactive substance levels of serum, and liver and kidney mitochondria declined significantly compared with the control group in a dose-dependent manner, whereas after intraperitoneal administration these levels fell only slightly. On the basis of the oral and intraperitoneal results, it was hypothesized that isorhamnetin diglucoside was converted to its metabolite in vivo, and its conversion to its aglycone, isorhamnetin, by beta-glucosidase was confirmed; isorhamnetin acted as an antioxidant. Moreover, it was observed that isorhamnetin diglucoside had no effect on the 1,1-diphenyl-2-picrylhydrazyl radical, whereas isorhamnetin showed a potent antioxidant effect in vitro. In addition, intraperitoneal administration of isorhamnetin reduced serum glucose and 5-HMF levels. Furthermore, lipid peroxidation in blood, liver, and kidney associated with diabetes mellitus declined after the administration of isorhamnetin. These results suggest that isorhamnetin diglucoside is metabolized in vivo by intestinal bacteria to isorhamnetin and that isorhamnetin plays an important role as an antioxidant.

  DOI：

  10.1021/jf0202133
• 作为产物：
  描述：

  isorhamnetin 3-O-(6-O-acetyl-β-D-glucopyranosyl)-7-β-D-glucopyranoside 在 水 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以67%的产率得到异鼠李素-3,7-O-二葡萄糖苷
  参考文献：
  名称：

  景天景天具有抑制脂质蓄积活性的黄酮糖苷

  摘要：

  三个新的黄酮醇苷，sarmenosides V-VII（1 - 3）中，从全植物分离垂盆（Crassulaseae）。的结构1 - 3分别光谱分析的基础上确定的。在S. sarmentosum中的类黄酮成分中，发现1和3具有油酸-白蛋白诱导的脂质蓄积抑制活性。

  DOI：

  10.1016/j.phytol.2011.07.012

文献信息

• Kodama, Tohru; Ishida, Hidekatsu; Kokubo, Tetsuro, Agricultural and Biological Chemistry, 1990, vol. 54, # 12, p. 3283 - 3288
  作者：Kodama, Tohru、Ishida, Hidekatsu、Kokubo, Tetsuro、Yamakawa, Takashi、Noguchi, Hiroshi

  DOI：——

  日期：——
• Wolbis, Maria, Acta Poloniae Pharmaceutica, 1993, vol. 50, # 2-3, p. 149 - 152
  作者：Wolbis, Maria

  DOI：——

  日期：——
• Antioxidant Effects of Isorhamnetin 3,7-Di-<i>O</i>-β-<scp>d</scp>-glucopyranoside Isolated from Mustard Leaf (<i>Brassica juncea</i>) in Rats with Streptozotocin-Induced Diabetes
  作者：Takako Yokozawa、Hyun Young Kim、Eun Ju Cho、Jae Sue Choi、Hae Young Chung

  DOI：10.1021/jf0202133

  日期：2002.9.1

  To investigate the effects of isorhamnetin 3,7-di-O-beta-D-glucopyranoside (isorhamnetin diglucoside), a major flavonoid compound of mustard leaf, on oxidative stress due to diabetes mellitus, in vivo and in vitro studies were carried out. Oral administration of isorhamnetin diglucoside (10 or 20 mg/kg of body weight/day for 10 days) to rats with streptozotocin-induced diabetes significantly reduced serum levels of glucose and 5-(hydroxymethyl)furfural (5-HMF), which is glycosylated with hemoglobin and is an indicator of oxidative stress. After intraperitoneal administration, isorhamnetin diglucoside did not show these activities. In addition, after oral administration, the thiobarbituric acid-reactive substance levels of serum, and liver and kidney mitochondria declined significantly compared with the control group in a dose-dependent manner, whereas after intraperitoneal administration these levels fell only slightly. On the basis of the oral and intraperitoneal results, it was hypothesized that isorhamnetin diglucoside was converted to its metabolite in vivo, and its conversion to its aglycone, isorhamnetin, by beta-glucosidase was confirmed; isorhamnetin acted as an antioxidant. Moreover, it was observed that isorhamnetin diglucoside had no effect on the 1,1-diphenyl-2-picrylhydrazyl radical, whereas isorhamnetin showed a potent antioxidant effect in vitro. In addition, intraperitoneal administration of isorhamnetin reduced serum glucose and 5-HMF levels. Furthermore, lipid peroxidation in blood, liver, and kidney associated with diabetes mellitus declined after the administration of isorhamnetin. These results suggest that isorhamnetin diglucoside is metabolized in vivo by intestinal bacteria to isorhamnetin and that isorhamnetin plays an important role as an antioxidant.
• Flavonol glycosides with lipid accumulation inhibitory activity from Sedum sarmentosum
  作者：Toshio Morikawa、Kiyofumi Ninomiya、Yi Zhang、Tomomi Yamada、Seikou Nakamura、Hisashi Matsuda、Osamu Muraoka、Takao Hayakawa、Masayuki Yoshikawa

  DOI：10.1016/j.phytol.2011.07.012

  日期：2012.3

  Three new flavonol glycosides, sarmenosides V–VII (1–3), were isolated from the whole plant of Sedum sarmentosum (Crassulaseae). The structures of 1–3 were determined on the basis of spectroscopic analysis. Among the flavonoid constituents from S. sarmentosum, 1 and 3 were found to show oleic acid–albumin-induced lipid accumulation inhibitory activity.

  三个新的黄酮醇苷，sarmenosides V-VII（1 - 3）中，从全植物分离垂盆（Crassulaseae）。的结构1 - 3分别光谱分析的基础上确定的。在S. sarmentosum中的类黄酮成分中，发现1和3具有油酸-白蛋白诱导的脂质蓄积抑制活性。

表征谱图