(4R)-2alpha,3beta,19alpha-三羟基乌苏-12-烯-23,28-二酸 | 53527-49-4

• 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
• 中文名称: (4R)-2alpha,3beta,19alpha-三羟基乌苏-12-烯-23,28-二酸
• 英文名称: 2α,3β,19α-Trihydroxy-12-ursen-24,28-dicarbonsaeure
• 英文别名: trachelosperogenin A；2α,3β,19α-trihydroxy-urs-12-ene-24,28-dioic acid；vismiaefolic acid；Corosin; 2α,3β,19-Trihydroxy-urs-12-ene-24,28-dioic acid；(2R,3R,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-2,3,12-trihydroxy-4,6a,6b,11,12,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
• CAS: 53527-49-4
• 化学式: C₃₀H₄₆O₇
• 分子量: 518.691
• InChiKey: FYGSMJAMPMZYFS-NQVBXAEWSA-N

物化性质

• 沸点：
  670.1±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  28-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]-2α,3β,19α-trihydroxyurs-12-ene-24,28-dioic acid 在 盐酸 、 水 作用下， 反应 1.0h， 生成 (4R)-2alpha,3beta,19alpha-三羟基乌苏-12-烯-23,28-二酸
  参考文献：
  名称：

  Ursane Saponins from the Stems ofFirmiana simplexand their Cytotoxic Activity

  摘要：

  Three new ursane triterpene saponins, together with twelve known ursane triterpenes were isolated from the stems of Firmiana simplex. The structures of the saponines were elucidated on the basis of spectroscopic and chemical methods. The cytotoxic activity of all compounds was evaluated in vitro against lung adenocarcinoma (A549), ovarian cancer (SK-OV-3), skin melanoma (SK-MEL-2), and colon cancer (HCT-15) human cell lines, using a sulforhodamine (SRB) assay. 23-Hydroxyursolic acid showed cytotoxicity against the tested cell lines with IC50 values ranging from 11.96 to 14.11 mu M.

  DOI：

  10.5935/0103-5053.20150113

文献信息

• Inhaltsstoffe von Fagaceae (Cupuliferae), 19. Mitt.: Triterpensaponine und Acylflavonoide ausQuercus robur var. stenocarpa Beck.
  作者：Giovanni Romussi、Brunella Parodi、Cosimo Pizza、Nunziatina De Tommasi

  DOI：10.1002/ardp.19943271008

  日期：——

  Aus den Blättern von Quercus robur L. var. stenocarpa Beck. wurde neben vier bekannten Glycosiden ein neues Triterpensaponin isoliert und als 28‐β‐D‐Glucopyranosylester der 2α,3β,19α‐Trihydroxy‐12‐oleanen‐24,28‐dicarbonsäure (1) identifiziert.

  来自 Quercus robur L. var. Stenocarpa Beck 的叶子。除了四种已知的糖苷外，还分离出一种新的三萜皂苷，并鉴定为 28-β-D-吡喃葡萄糖基酯的 2α、3β、19α-三羟基-12-齐墩果烯-24,28-二羧酸 (1)。
• A New<i>in vitro</i>Tissue Factor Inhibitory Triterpene from the Fruits of<i>Chaenomeles sinensis</i>
  作者：Ming Hong Lee、Yong Nam Han

  DOI：10.1055/s-2003-38884

  日期：2003.4

  Tissue factor (TF, tissue thromboplastin) accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor. In order to isolate TF inhibitors from the fruits of Chaenomeles sinensis, an activity-guided purification was carried out to yield four triterpenoid compounds. One compound was new and its structure was elucidated as 28-O-β-D-glucopyranosyl-2α,3β-dihydroxyolean-12-ene-24,28-dioic acid (2), named chaenomeloside A by means of spectral analysis and chemical conversion. Other compounds were trachelosperoside A-1 (1), oleanolic acid (3) and ursolic acid (4). Compound 2 and its aglycone 2a, named chaenomelogenin A inhibited by 50 % the TF activity at concentrations of 0.036 and 0.028 mM/unit of TF, respectively. Compound 1 isolated for the first time from this plant as well as 3 and 4 were inactive.

  组织因子（TF，组织凝血酶原）可加速血液凝固，激活内源性和外源性途径，作为辅助因子。为了从木瓜果实中分离出TF抑制剂，我们进行了活性导向纯化，得到了四种三萜类化合物。其中一种化合物是新的，其结构被阐明为28-O-β-D-吡喃葡萄糖基-2α,3β-二羟基齐墩果-12-烯-24,28-二酸（2），通过光谱分析和化学转化命名为木瓜苷A。其他化合物分别是木瓜苷A-1（1）、齐墩果酸（3）和熊果酸（4）。化合物2及其糖苷元2a（命名为木瓜素A）在浓度分别为0.036和0.028 mM/单位TF时，可分别抑制TF活性50%。首次从该植物中分离出的化合物1以及3和4均不具有活性。
• ACCELERATOR FOR INITIAL INSULIN SECRETION
  申请人：Use-Techno Corporation

  公开号：EP1674089A1

  公开（公告）日：2006-06-28

  The present invention provides an early insulin secretion stimulator consisting of a triterpene represented by the following general formula (1) and/or a triterpene represented by the following general formula (2). [where R1 represents COOH, etc., R11 and R12 represent CH2OH, etc., X1 represents hydrogen or OH and X11, X12, X21 and X22 represent OH, etc.]

  本发明提供了一种早期胰岛素分泌刺激剂，由以下通式（1）代表的三萜和/或以下通式（2）代表的三萜组成。 [其中 R1 代表 COOH 等，R11 和 R12 代表 CH2OH 等，X1 代表氢或 OH，X11、X12、X21 和 X22 代表 OH 等。］
• Insulin secretion potentiator
  申请人：Matsuyama Futoshi

  公开号：US20050143464A1

  公开（公告）日：2005-06-30

  The present invention provides early insulin secretion stimulators consisting of triterpenes represented by the following general formula (1) and/or triterpenes represented by the following general formula (2). [where R 1 represents COOH, etc., R 11 and R 12 represent CH 2 OH, etc., X 1 represents hydrogen or OH and X 11 , X 12 , X 21 and X 22 represent OH, etc.]
• [EN] GLUCONEOGENESIS INHIBITING AGENT<br/>[FR] AGENTS D'INHIBITION DE LA GLUCONEOGENESE
  申请人：USE TECHNO CORP

  公开号：WO2006054370A1

  公开（公告）日：2006-05-26

  [EN] The present invention provides a gluconeogenesis inhibiting agent containing as an active ingredient corosolic acid, an analogous compound of corosolic acid, or a pharmaceutically acceptable salt thereof.
  [FR] La présente invention concerne un agent d'inhibition de la gluconéogenèse, contenant en tant qu'ingrédient actif de l'acide corosolique, un analogue de l'acide corosolique ou l'un de leurs sels pharmaceutiquement acceptables.