echinocystic acid | 510-30-5

• 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 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: echinocystic acid
• 英文别名: Echinocystin-saeure；Echinocystsaeure；Cochalsaeure；(4aR,5R,6aS,6bR,10S,12aR)-5,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 510-30-5；545-88-0
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: YKOPWPOFWMYZJZ-QIKFJBJGSA-N

物化性质

• 熔点：
  299-300°C
• 沸点：
  585.0±50.0 °C(Predicted)
• 密度：
  1.14
• 溶解度：
  DMF:30.0(最大浓度 mg/mL);63.46(最大浓度 mM)DMSO:PBS (pH 7.2) (1:2):0.33(最大浓度 mg/mL);0.7(最大浓度 mM）
• LogP：
  7.580 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性： Echinocystic acid是从皂角（豆科植物蒙自合欢Albizzia julibrissin Durazz.的花序）中提取出来的五环三萜，具有很强的抗氧化、抗炎症和抗肿瘤特性。

化学性质： Echinocystic酸为白色粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于猪牙皂。

用途： 刺囊酸具有祛痰开窍、消肿散结的作用，并可用于含量测定、鉴定及药理实验等。

药理作用： 刺囊酸具有滋肝补血、凉血止血的功能，同时具备免疫调节和抗肿瘤活性。

反应信息

• 作为反应物：
  描述：

  echinocystic acid 在 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Discovery of Pentacyclic Triterpenoids as Potential Entry Inhibitors of Influenza Viruses

  摘要：

  Entry inhibitors are of particular importance in current efforts to develop a new generation of anti-influenza virus drugs. Here we report certain pentacyclic triterpenes exhibiting conserved structure features and with in vitro anti-influenza virus activity comparable to and even higher than that of oseltamivir. Mechanistic studies indicated that these lead triterpenoids bind tightly to the viral envelope hemagglutinin (HA), disrupting the interaction of HA with the sialic acid receptor and thus the attachment of viruses to host cells. Docking studies suggest that the binding pocket within HA for sialic acid receptor potentially acts as a targeting domain, and this is supported by structure-activity data, sialic acid competition studies, and broad anti-influenza spectrum as well as less induction of drug resistance. Our study might establish the importance of triterpenoids for development of entry inhibitors of influenza viruses.

  DOI：

  10.1021/jm5014067
• 作为产物：
  描述：

  calliandra saponin B 在 硫酸 作用下， 反应 6.0h， 生成 echinocystic acid
  参考文献：
  名称：

  Studies on the Constituents of Calliandra anomala (KUNTH) MACBR. II. Structure Elucidation of Four Acylated Triterpenoidal Saponins.

  摘要：

  根据核磁共振波谱、FAB-MS 和化学证据确定了四种新的三萜类皂苷，即 Calliandra 皂苷 B (8)、C (9)、D (10) 和 F (12)。有趣的是，这些皂苷在基因素的 3 位上有一个 N-乙酰氨基葡萄糖，在糖链的位置上有一个或两个单萜苷。

  DOI：

  10.1248/cpb.42.1111

文献信息

• New TriterpenoidN-Acetylglycosides with Molluscicidal Activity fromTetrapleura tetraptera TAUB
  作者：Marc Maillard、Kurt Hostettmann、Clement O. Adewunmi

  DOI：10.1002/hlca.19890720407

  日期：1989.6.14

  extract of the fruits of Tetrapleura tetraptera TAUB. (Mimosaceae) afforded 4 saponins 1–4, which exhibited strong molluscicidal properties against the schistosomiasis-transmitting snails Biomphalaria glabrata. Chemical, enzymatic, and spectral methods (DCI-MS, 1H-NMR, 13C-NMR) showed that they were N-acetylglycosides of oleanolic acid and of echinocystic acid. Apart from saponin 1 (aridanin), previously

  四生四足动物TAUB果实的MeOH提取物的活性导向分级分离。（含羞草），得到4个皂苷1 - 4，它表现出对强杀软体动物性质血吸虫病透射蜗牛贝罗比光滑。化学，酶和光谱方法（DCI-MS，1 H-NMR，13 C-NMR）显示它们是齐墩果酸和棘胆囊酸的N-乙酰基糖苷。除了皂苷1（aridanin），预先从该植物中分离，糖苷2 - 4是新的天然存在的化合物。
• Triterpene Derivative and Its Anti-Influenza Use
  申请人：PEKING UNIVERSITY

  公开号：US20150274766A1

  公开（公告）日：2015-10-01

  The present invention relates to the use of triterpenoid derivatives for the preparation of a medicament for preventing or treating influenza diseases, in which the substituents are as defined in the specification. The triterpenoid derivatives of the present invention have obvious inhibition effect on influenza virus, and are capable of obviously preventing influenza virus from entering cells, and can be used for preventing or treating influenza

  本发明涉及使用三萜类衍生物制备预防或治疗流感疾病药物，其中取代基如说明书所定义。本发明的三萜类衍生物对流感病毒具有明显的抑制作用，并能明显地防止流感病毒进入细胞，可用于预防或治疗流感。
• Structure of codonoside B
  作者：N. G. Alad'ina、Yu. N. El'kin、E. A. Chezhina

  DOI：10.1007/bf00597710

  日期：——
• Componds, Composition and Method for Controlling Biofolms and Bacterail Infections
  申请人：Eldridge Gary R.

  公开号：US20080145322A1

  公开（公告）日：2008-06-19

  The present invention provides compounds and compositions useful for controlling bacterial biofilms as well as for controlling and/or preventing bacterial infections. The compounds of the invention are pentacyclic acid triterpenes. Methods for controlling biofilms and for controlling and/or preventing bacterial infections are also disclosed.
• US7612045B2
  申请人：——

  公开号：US7612045B2

  公开（公告）日：2009-11-03