金石蚕苷 | 94079-81-9

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 金石蚕苷
• 英文名称: poliumoside
• 英文别名: [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 94079-81-9
• 化学式: C₃₅H₄₆O₁₉
• 分子量: 770.739
• InChiKey: YMWRMAOPKNYHMZ-LLVTZOIGSA-N

物化性质

• 沸点：
  1023.2±65.0 °C(Predicted)
• 密度：
  1.62
• 溶解度：
  DMSO : 100 mg/mL (129.75 mM; 需要超声) 乙醇 : 50 mg/mL (64.87 mM; 需要超声)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  304
• 氢给体数：
  11
• 氢受体数：
  19

安全信息

• WGK Germany：
  3
• 储存条件：
  室温

制备方法与用途

生物活性

Poliumoside 对晚期糖基化终产物（AGE）的形成有显著抑制作用，IC50值为19.69 μM。在大鼠晶状体醛糖还原酶测定试验中，发现 Poliumoside 对 rat lens aldose reductase (RLAR) 表现出抑制作用，IC50值为8.47 μM。

靶点

Target	Value
RLAR	8.47 μM

体外研究

Poliumoside 抑制 AGE 形成和 RLAR，IC50 值分别为19.69 μM 和 8.47 μM。此外，Poliumoside（5-30 μM；3 h）抑制 AAPH 引起的体外大鼠红细胞溶血现象。同时，在 LPS 刺激的 RAW 264.7 细胞中，Poliumoside（12.5-100 μM；预处理2 h）也抑制 TNF-α 和 IL-6 的释放。

体内研究

Poliumoside 抑制乳酸鱼胚胎的血管扩张。

化学性质

类白色结晶粉末，溶于水，来源于广东紫珠。

用途

金石蚕苷具有抗菌、消炎和抗病毒作用。主要用于含量测定/鉴定/药理实验等。其药理药效为散瘀止血、消肿止痛；叶可用于治疗吐血、咯血、衄血、便血，外用可治疗外伤出血。

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 金石蚕苷 在 吡啶 作用下， 以9 mg的产率得到
  参考文献：
  名称：

  Brandioside, a phenylpropanoid glycoside from Brandisia hancei

  摘要：

  A new phenylpropanoid glycoside, brandioside, was isolated from Brandisia hancei. Its structure, [beta-(3',4'-dihydroxylphenyl)-ethyl]-(2-O-acetyl)-(3,6-O-di-alpha -L-rhamnopyranosyl)-(4-O-caffeoyl)-beta-D-glucopyranoside, was established by chemical and spectroscopic methods.

  DOI：

  10.1016/0031-9422(91)83759-e

文献信息

• Identification and occurrence of phenylethanoid and iridoid glycosides in six Polish broomrapes (Orobanche spp. and Phelipanche spp., Orobanchaceae)
  作者：Dariusz Jedrejek、Sylwia Pawelec、Renata Piwowarczyk、Łukasz Pecio、Anna Stochmal

  DOI：10.1016/j.phytochem.2019.112189

  日期：2020.2

  There are about 200 holoparasitic broomrapes (Orobanchaceae) known worldwide, however, only several species have been so far investigated phytochemically. Among Orobanche s.l. are both rare and endangered species, as well as onerous crop pests. This study aims to give a phytochemical description, both qualitative and quantitative, of six broomrape species (Orobanche and Phelipanche taxa) growing in Poland, including species that have not been tested in detail (O. caryophyllacea, O. linen, O. picridis, and P. arenaria). Sixteen metabolites, including 14 phenylethanoid glycosides (PhGs) and 2 iridoid glycosides (IrGs), were isolated and identified using NMR spectroscopy and hydrolysis, revealing the presence of two previously undescribed PhGs in P. ramosa, named ramoside A and 2'-acetylramoside A. In addition, in the example of O. caryophyllacea, we have reported as the first occurrence of IrGs in broomrapes. Concentrations of phenylethanoids, the main constituents of broomrapes, in the studied plant material (flowering shoots with haustoria) were determined using the UHPLC-PDA method. It was found that P. ramosa has been the richest source of PhGs. In addition, the differences between broomrapes have been visualized using principal component and cluster analysis. The results of the antiradical DPPH test of 13 PhGs confirmed previous findings on the relation of the antioxidant potential with the structure of phenolic moieties - phenolic acid and phenylethanoid unit.
• Brandioside, a phenylpropanoid glycoside from Brandisia hancei
  作者：He Zheng-Dan、Yang Chong-Ren

  DOI：10.1016/0031-9422(91)83759-e

  日期：1991.1

  A new phenylpropanoid glycoside, brandioside, was isolated from Brandisia hancei. Its structure, [beta-(3',4'-dihydroxylphenyl)-ethyl]-(2-O-acetyl)-(3,6-O-di-alpha -L-rhamnopyranosyl)-(4-O-caffeoyl)-beta-D-glucopyranoside, was established by chemical and spectroscopic methods.