毛蕊花糖苷 | 50932-20-2

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 毛蕊花糖苷
• 英文名称: 6-O-(3,4-dihydroxybenzoyl)catalpol
• 英文别名: protocatechoyl catalpol；picroside II；verproside；veproside；6-0-3,4-dihydroxybenzoyl catalpol；[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 3,4-dihydroxybenzoate
• CAS: 50932-20-2
• 化学式: C₂₂H₂₆O₁₃
• 分子量: 498.441
• InChiKey: DBUOUVZMYWYRRI-YWEKDMGLSA-N

物化性质

• 沸点：
  822.9±65.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  208
• 氢给体数：
  7
• 氢受体数：
  13

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36
• WGK Germany：
  3
• 储存条件：
  `-20°C`

制备方法与用途

Verproside 是一种从 Pseudolysimachion 属分离出的梓醇衍生物环烯醚萜苷，通过抑制 IKK/IκB 信号级联反应来抑制 NF-κB 的活化，并减少 TNF-α 引起的 MUC5AC 表达。Verproside 具有显著的抗炎、抗氧化和抗损伤作用，在体内还是一种有效的哮喘/COPD 治疗候选药物。

反应信息

• 作为反应物：
  描述：

  毛蕊花糖苷 在 氢氧化钾 、 水 、 盐酸 作用下， 以 水 为溶剂， 反应 8.0h， 生成 梓醇
  参考文献：
  名称：

  WO2006/129964

  摘要：

  公开号：
• 作为产物：
  描述：

  longifolioside A 在 sodium hydroxide 作用下， 以 water-d2 为溶剂， 反应 24.0h， 生成 毛蕊花糖苷
  参考文献：
  名称：

  Chlorinated Iridoid Glucosides from Veronica longifolia and Their Antioxidant Activity

  摘要：

  From Veronica longifolia were isolated three chlorinated iridoid glucosides, namely, asystasioside E (6) and its 6-O-esters 6a and 6b, named longifoliosides A and B, respectively. The structures of 6a and 6b were proved by analysis of their spectroscopic data and by conversion to the catalpol ester verproside (5a) or to catalpol (5), respectively. The configuration of the previously known vanilloyl analogue, urphoside B, was shown to be the 6 beta-epimer (6c) of the structure originally reported. Longifoliosides A (6a) and B (6b) were found to exhibit radical-scavenging activity against nitric oxide, superoxide, and 2,2-diphenyl-1-picrylhydrazyl radicals.

  DOI：

  10.1021/np100366k

文献信息

• Verproside, a New Iridoid Glucoside fromVeronica officinalis L. (Scrophulariaceae)
  作者：Fatma �. Afifi-Yazar、Otto Sticher

  DOI：10.1002/hlca.19800630716

  日期：1980.10.29

  A new iridoid glucoside, verproside (2), has been isolated from Veronica officinalis L. and its structure has been established to be 6-O-protocatechuoylcatalpol.

  从Veronica officinalis L.中分离了一种新的虹彩的类环孢苷葡糖苷（2），其结构已确定为6- O-原儿茶酚基梓醇。
• A PURIFIED EXTRACT (ATC2) ISOLATED FROM PSEUDOLYSIMACHION ROTUNDUM VAR. SUBINTEGRUM CONTAINING ABUNDANT AMOUNT OF ACTIVE INGREDIENT, THE PREPARATION THEREOF, AND THE COMPOSITION COMPRISING THE SAME AS AN ACTIVE INGREDIENT FOR PREVENTING OR TREATING INFLAMMATION, ALLERGY AND ASTHMA
  申请人：Yungjin Pharmaceutical Co., Ltd.

  公开号：EP3498287A1

  公开（公告）日：2019-06-19

  The present invention is related to a purified extract with the secondary fractionation from the extract of Pseudolysimachion rotundum var subintegrum, which contains 30 - 60 % (w/w) verproside, 0.5 - 10 % (w/w) veratric acid, 2 - 20 % (w/w) catalposide, 1 - 10 % (w/w) picroside II, 1 - 10 % (w/w) isovanilloyl catalpol and 2 - 20 % (w/w) 6-O-veratroyl catalpol based on the weight of total extract (100 %) of Pseudolysimachion rotundum var subintegrum.

  本发明涉及一种从 Pseudolysimachion rotundum var subintegrum 提取物中二次分馏的纯化提取物，其中含有 30 - 60 % (w/w) verproside、0.5 - 10 % (w/w) 藜芦酸、2 - 20 % (w/w) 梓苷，1 - 10 % (w/w) 苦味苷 II、1 - 10 % (w/w) 异香草酰梓醇和 2 - 20 % (w/w) 6-O-藜芦酰梓醇（以 Pseudolysimachion rotundum var subintegrum 的总提取物重量（100 %）为基准）。
• Method of treating chronic obstructive pulmonary disease (CPD) with verproside
  申请人：YUNGJIN PHARMACEUTICAL CO., LTD

  公开号：US10172816B2

  公开（公告）日：2019-01-08

  A composition comprising a purified extract isolated from Pseudolysimachion rotundum var. subintegrum containing abundant amount of active ingredient or the compounds isolated therefrom as an active ingredient for treating a chronic obstructive pulmonary disease and the use thereof. Inventive purified extract and compounds showed potent anti-COPD activity without beta-2-receptor agonistic response through various in vivo tests as well as in vitro test. Therefore, it can be used as the therapeutics or functional health food for treating and preventing chronic obstructive pulmonary disease (COPD).

  一种包含从 Pseudolysimachion rotundum var. subintegrum 分离出来的纯化提取物的组合物，该提取物含有大量活性成分或从其中分离出来的化合物，作为治疗慢性阻塞性肺病的活性成分及其用途。通过各种体内试验和体外试验，发明的纯化提取物和化合物显示出有效的抗慢性阻塞性肺病活性，且不产生β-2受体激动反应。因此，它可用作治疗和预防慢性阻塞性肺病（COPD）的药物或功能性保健食品。
• A novel compound (KS-513) isolated from Pseudolysimachion rotundum var. subintegrum, the composition comprising the same preventing or treating allergic disease, inflammatory disease, asthma or chronic obstructive pulmonary disease and the use thereof
  申请人：YUNGJIN PHARMACEUTICAL CO., LTD

  公开号：US20180105548A1

  公开（公告）日：2018-04-19

  (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-(hydroxymethyl)-4-methoxy-2-(((2S,3R,5S5,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)octahydrooxireno[2′,3′:4,5]cyclopenta[1,2-c]pyran-6-yl 4-hydroxybenzoate}, the isomer thereof, the pharmaceutically acceptable salt or solvates thereof, a composition comprising the same as an active ingredient for treating allergic disease, inflammatory disease, asthma or chronic obstructive pulmonary disease (COPD) and the use thereof.

  本发明涉及一种化合物，及其异构体、药学上可接受的盐或溶剂合物，以及包含其作为活性成分用于治疗过敏性疾病、炎性疾病、哮喘或慢性阻塞性肺疾病（COPD）的组合物，及其用途。具体而言，所述化合物为： (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-(羟甲基)-4-甲氧基-2-(((2S,3R,5S5,6R)-3,4,5-三羟基-6-(羟甲基)四氢-2H-吡喃-2-基)氧基)八氢氧杂环烯[2',3':4,5]环戊[1,2-c]吡喃-6-基 4-羟基苯甲酸酯。
• PHARMACEUTICAL COMPOSITION COMPRISING AN EXTRACT OF PSEUDOLYSIMACHION LONGIFOLIUM AND THE CATALPOL DERIVATIVES ISOLATED THEREFROM HAVING ANTIINFLAMMATORY, ANTIALLERGIC AND ANTIASTHMATIC ACTIVITY
  申请人：Korea Research Institute of Bioscience and Biotechnology

  公开号：EP1904054A1

  公开（公告）日：2008-04-02