2'-p-hydroxybenzoyl mussaenosidic acid | 82451-20-5

• 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: 2'-p-hydroxybenzoyl mussaenosidic acid
• 英文别名: 2'-p-hydroxybenzoylmussaenosidic acid；negundoside；(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• CAS: 82451-20-5
• 化学式: C₂₃H₂₈O₁₂
• 分子量: 496.468
• InChiKey: RFCSGMIUBXUYSE-KLZCBZFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2'-p-hydroxybenzoyl mussaenosidic acid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 mussaenosidic acid
  参考文献：
  名称：

  2'-p-Hydroxybenzoyl mussaenosidic acid，一种来自 Vitex negundo 的新型环烯醚萜苷。

  摘要：

  摘要 对荆条乙醇提取物进行进一步色谱分离，分离出另一种新的环烯醚萜苷，其特征为 6'-对羟基苯甲酰麝香葡萄苷酸。

  DOI：

  10.1016/s0031-9422(00)95267-1

文献信息

• Studies on indian medicinal plants-part LXXV
  作者：Pradeep K. Dutta、Uday S. Chowdhury、Ajit K. Chakravarty、Basudeb Achari、Satyesh C. Pakrashi

  DOI：10.1016/s0040-4020(01)91547-9

  日期：1983.1

  Two new glucosidic iridoids, designated as nishindaside (2a) and negundoside (3a), have been isolated from the leaves of Vitex negundo ( Verbenaceae ). The absence of a C(3)–C(4) double bond and the presence of an equatorial 3-methoxy group in 2a, the 3-methoxy-3,4-dihydro derivative of agnuaide (1a), were established from 1H and 13C NMR analyses, corroborated by mass spectral fragmentation of the

  从荆豆（Vitex negundo）（马鞭草科）的叶子中分离出了两种新的糖苷类鸢尾酮，分别命名为nishindaside（2a）和negundoside（3a）。从1 H确定2a中无C（3）–C（4）双键和赤道3-甲氧基的存在，即agnuaide（1a）的3-甲氧基-3,4-二氢衍生物和13 C NMR分析，证实了六乙酸酯（2b）的质谱裂解。尼古多糖苷（3a）可以从碱性水解的结果及其中C-1'，C-2'和C-3'信号的变化推定为mussaenosidic acid的2'-对羟基苯甲酰基衍生物13 C NMR谱。
• Hepatoprotective activity of 2'-p-hydroxybenzoylmussaenosidic
  申请人：——

  公开号：US20040014684A1

  公开（公告）日：2004-01-22

  The present invention provides a method for treating and/or preventing hepatic disease conditions in a subject mammals including human beings, said method comprising the steps of administering to the mammal an effective dosage of composition comprising 2′-p-Hydroxy benzoyl mussaenosidic acid from plant Vitex negundo optionally as individual or in combination with one or more pharmaceutically additives.

  本发明提供了一种用于治疗和/或预防哺乳动物，包括人类的肝病状况的方法，该方法包括向哺乳动物施用包含来自牛蒡树植物的2'-p-羟基苯甲酰木鳖苷酸的有效剂量组合物，可选地与一个或多个药物添加剂单独或组合使用的步骤。
• Synthesis of novel lipidated iridoid glycosides as vaccine adjuvants: 6-O-Palmitoyl Agnuside elicit strong Th1 and Th2 response to ovalbumin in mice
  作者：Parvinder Pal Singh、Debabrata Bhunia、Yogesh Kumar Verma、Tabasum Sidiq、Anamika Khajuria、Amit Guptha、M. Preethi Pallavi、S. Surya Vamshi、Gulam N Qazi、Halmuthur M. Sampath Kumar

  DOI：10.1016/j.intimp.2013.07.018

  日期：2013.11

  Novel lipidated analogs of iridoids viz., Agnuside and Negundoside with different chain length were synthesized and tested for immune adjuvant activity in the presence of weak antigen ovalbumin. Based on in vitro assay, 6-O-palmitoyl Agnuside (AG-3) was further taken up for detailed in vivo activity and found to significantly enhance the production of anti OVA IgG titer, neutralizing antibody (IgG1 and IgG2a) titer as well as soluble mediators of a Th1 (IL-2, IFN-gamma)/Th2 response (IL-4) and proliferation of T lymphocyte subsets (CD4/CD8) and co stimulatory molecules CD80/CD86. Furthermore, the SAR studies revealed that presence of acyl group at aglycon moiety of these iridoid glycosides is crucial for immune adjuvant activity. (C) 2013 Elsevier B.V. All rights reserved.
• HEPATOPROTECTIVE ACTIVITY OF 2 -P-HYDROXYBENZOYLMUSSAENOSIDIC ACID
  申请人：Council of Scientific andIndustrial Research

  公开号：EP1503773A1

  公开（公告）日：2005-02-09
• US7259148B2
  申请人：——

  公开号：US7259148B2

  公开（公告）日：2007-08-21