ATRACTYLOSIDE POTASSIUM SALT | 17754-44-8

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ATRACTYLOSIDE POTASSIUM SALT
• 英文别名: (-)-atractyloside potassium salt；atractyloside dipotassium salt；atractyloside；(10R)-15α-hydroxy-2β-(O²-isovaleryl-O³,O⁴-disulfo-β-D-glucopyranosyloxy)-18-nor-kaur-16-en-19-oic acid ; potassium-salt；(10R)-15α-Hydroxy-2β-(O²-isovaleryl-O³,O⁴-disulfo-β-D-glucopyranosyloxy)-18-nor-kaur-16-en-19-saeure; Kalium-Salz
• CAS: 17754-44-8；102130-43-8
• 化学式: C₃₀H₄₄O₁₆S₂*2K
• 分子量: 802.998
• InChiKey: NUMVHGNHBXVKEZ-FLPKXFLTSA-L

物化性质

• 熔点：
  234-238°C
• 溶解度：
  在水中的溶解度20 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -2.01
• 重原子数：
  49.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  255.38
• 氢给体数：
  3.0
• 氢受体数：
  15.0

安全信息

• 危险等级：
  6.1(a)
• WGK Germany：
  3

制备方法与用途

生物活性

Atractyloside potassium salt (ATR potassium salt) 是一种从 Xanthium sibiricum (Cang'erzi) 果实中分离出的毒性二萜糖苷，是一种有效的、特异性的 mitochondrial ADP/ATP carriers的抑制剂。Atractyloside potassium salt 可抑制大鼠心脏线粒体膜的 chloride channels。

靶点

Target	Value
Chloride Channel ()

化学性质 

白色结晶粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于苍耳子，苍术，白术。

用途 

用于含量测定/鉴定/药理实验等。
药理药效:有肝肾毒性

反应信息

• 作为反应物：
  描述：

  ATRACTYLOSIDE POTASSIUM SALT 在 水 、 potassium hydroxide 作用下， 反应 6.0h， 以84%的产率得到atractyligenin
  参考文献：
  名称：

  Structural Characterization and Antimicrobial Evaluation of Atractyloside, Atractyligenin, and 15-Didehydroatractyligenin Methyl Ester

  摘要：

  We report the first complete structure elucidation of the ent-kaurane diterpenoid glycoside atractyloside (1) by means of NMR and X-ray diffractometry techniques. Extensive one- and two-dimensional NMR experiments were employed to assign the proton and carbon signals of 1, and crystallography experiments established the configurations of all stereogenic centers. Furthermore, we present a novel semisynthetic route for the preparation of the highly cytotoxic aglycone derivative of 1, 15-didehydroatractyligenin methyl ester (3). All compounds were tested for their antibiotic activity against Enterococcus faecalis, Escherichia coli, and several strains of Staphylococcus aureus, including fluoroquinolone-resistant (SA1199B) and two epidemic MRSA (EMRSA-15 and -16) strains. Compound 3 exhibited moderate activity against all of the Staph. aureus strains with an MIC value of 128 mg/L.

  DOI：

  10.1021/np300080w

文献信息

• The Degradation Mechanism of Toxic Atractyloside in Herbal Medicines by Decoction
  作者：Liang-Yu Chen、Anren Hu、Chih-Jui Chang

  DOI：10.3390/molecules18022018

  日期：——

  Atractyloside (ATR) is found in many Asteraceae plants that are commonly used as medicinal herbs in China and other eastern Asian countries. ATR binds specifically to the adenine nucleotide translocator in the inner mitochondrial membrane and competitively inhibits ADP and ATP transport. The toxicity of ATR in medical herbs can be reduced by hydrothermal processing, but the mechanisms of ATR degradation are not well understood. In this study, GC-MS coupled with SPE and TMS derivatisation was used to detect ATR levels in traditional Chinese medicinal herbs. Our results suggest that ATR molecules were disrupted by decomposition, hydrolysis and saponification after heating with water (decoction) for a long period of time. Hydrothermal processing could decompose the endogenous toxic compounds and also facilitate the detoxification of raw materials used in the Chinese medicine industry.

  白术苷 (ATR) 存在于许多菊科植物中，这些植物在中国和其他东亚国家常用作药材。 ATR 特异性结合线粒体内膜中的腺嘌呤核苷酸转位子，并竞争性抑制 ADP 和 ATP 转运。通过水热处理可以降低药材中ATR的毒性，但ATR降解的机制尚不清楚。本研究采用GC-MS结合SPE和TMS衍生化技术检测中药材中的ATR水平。我们的结果表明，与水（煎剂）长时间加热后，ATR 分子会因分解、水解和皂化而受到破坏。水热处理可以分解内源性有毒化合物，也有利于中药工业原料的解毒。