echinacoside | 737806-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: echinacoside
• 英文别名: Ech；[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 737806-07-4
• 化学式: C₃₅H₄₆O₂₀
• 分子量: 786.738
• InChiKey: FSBUXLDOLNLABB-ISAKITKMSA-N

物化性质

• 沸点：
  1062.7±65.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  324
• 氢给体数：
  12
• 氢受体数：
  20

ADMET

代谢

紫锥菊苷在大鼠体内的代谢已被研究，认为涉及儿茶酚O-甲基转移酶以及未特指的UDP-葡萄糖醛酸基转移酶和硫酸基转移酶。一项关于紫锥菊苷通过人体肠道菌群代谢的研究鉴定出13种代谢物，这些代谢物是独立于人体代谢产生的。

The metabolism of echinacoside has been investigated in rats and is thought to involve catechol O-methyltransferase as well as unspecified UDP-gluc- uronosyltransferases and sulfotransferases. A study of echinacoside's metabolism by human intestinal flora identified 13 metabolites which are produced independantly of human metabolism.

来源:DrugBank

吸收、分配和排泄

• 吸收

动物研究表明口服生物利用度为0.83%。

Animal studies suggest an oral bioavailability of 0.83%.

来源:DrugBank

反应信息

• 作为反应物：
  描述：

  echinacoside 在 Aspergillus oryzae tannase 作用下， 以 水 为溶剂， 反应 24.0h， 以62%的产率得到kankanoside F
  参考文献：
  名称：

  Phenylethanoid oligoglycosides and acylated oligosugars with vasorelaxant activity from Cistanche tubulosa

  摘要：

  The methanolic extract from the dried stems of Cistanche tubulosa (Schrenk) R. Wight was found to show an inhibitory effect on contractions induced by noradrenaline in isolated rat aortic strips. From the extract, new phenylethanoid oligoglycoside constituents, kankanosides F and G, and an acylated oligosugar, kankanose, were isolated together with 14 known compounds. The structures of these new compounds were determined on the basis of their chemical and physicochemical evidence. In addition, principal constituents, kankanoside F, kankanose, echinacoside, acteoside, and cistanoside F, showed vasorelaxant activity, and several structural requirements for the activity were clarified. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.018
• 作为产物：
  描述：

  在 吡啶 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 反应 3.0h， 以81.818%的产率得到
  参考文献：
  名称：

  A general synthetic strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides

  摘要：

  报告了一种合成苯乙醇糖苷（PhG，包括紫锥菊苷1、阿克特苷2、卡尔斯洛里苷-A 3和卡尔斯洛里苷-B 4）的通用策略。该策略采用低底物浓度的糖苷化和N-甲酰吗啉调节的糖苷化方法，用于构建1,2-反式β-和α-糖苷键。所述策略不涉及参与性酰基保护基团的使用，而此基团与目标PhG化合物中存在的酯功能不相容。还对PhG化合物1-4的抗增殖特性进行了初步研究；阿克特苷2对前列腺癌细胞增殖的抑制效果最佳。

  DOI：

  10.1039/c3ob42503g

文献信息

• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• [EN] MTH1 INHIBITORS FOR TREATMENT OF CANCER<br/>[FR] INHIBITEURS MTH1 POUR LE TRAITEMENT DU CANCER
  申请人：THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING

  公开号：WO2015187088A1

  公开（公告）日：2015-12-10

  A compound of formula I, (I) or a pharmaceutically-acceptable salt thereof. The compound is useful in the treatment of cancer.

  公式I的化合物(I)或其药用可接受的盐。该化合物在治疗癌症中很有用。
• [EN] MTH1 INHIBITORS FOR TREATMENT OF INFLAMMATORY AND AUTOIMMUNE CONDITIONS<br/>[FR] INHIBITEURS DE MTH1 DESTINÉS AU TRAITEMENT DES ÉTATS INFLAMMATOIRES ET AUTO-IMMUNS
  申请人：THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING

  公开号：WO2015187089A1

  公开（公告）日：2015-12-10

  A compound of formula (I), or a pharmaceutically acceptable salt thereof, for use in the treatment of autoimmune diseases and inflammatory conditions.

  化合物的化学式（I），或其药学上可接受的盐，用于治疗自身免疫性疾病和炎症性疾病。
• Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives
  申请人：Auriol Daniel

  公开号：US20090233876A1

  公开（公告）日：2009-09-17

  The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5). These O-α-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhythmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application.

  该发明涉及通过酶催化将选择自间苯二酚或其衍生物的酚类与蔗糖的葡萄糖部分进行缩合来制备酚类衍生物。所述酚类衍生物的生产是通过葡萄糖转移酶（EC 2.4.1.5）实现的。所选酚类的这些O-α-葡糖苷是新的，其在水中的溶解度高于它们的原始多酚，并且在化妆品和药用组合物中具有有用的应用，如抗氧化、抗病毒、抗菌、免疫刺激、抗过敏、降压、抗缺血、抗心律失常、抗血栓形成、降胆固醇、抗脂质过氧化、肝脏保护、抗炎症、抗癌变突变、抗肿瘤、抗血栓形成和扩血管等配方，或者在任何其他应用领域中。
• Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases
  申请人：Scaramuzzino, Giovanni

  公开号：EP1336602A1

  公开（公告）日：2003-08-20

  New pharmaceutical compounds of general formula (I): F-(X)q where q is an integer from 1 to 5, preferably 1; -F is chosen among drugs described in the text, -X is chosen among 4 groups -M, -T, -V and -Y as described in the text. The compounds of general formula (I) are nitrate prodrugs which can release nitric oxide in vivo in a controlled and selective way and without hypotensive side effects and for this reason they are useful for the preparation of medicines for prevention and treatment of inflammatory, ischemic, degenerative and proliferative diseases of musculoskeletal, tegumental, respiratory, gastrointestinal, genito-urinary and central nervous systems.

  通式（I）的新药物化合物：F-（X）q，其中q是1到5的整数，最好是1；-F是在文本中描述的药物中选择的，-X是在文本中描述的4个组-M，-T，-V和-Y中选择的。通式（I）的化合物是硝酸盐前药，可以在体内以受控和选择性的方式释放一氧化氮，而不会产生降压副作用，因此它们非常适用于制备用于预防和治疗肌肉骨骼，皮肤，呼吸，消化，泌尿和中枢神经系统的炎症，缺血，退行性和增生性疾病的药物。