2α-hydroxy-ursolic acid | 4547-24-4

• 物质功能分类: 生物化工
• 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: 2α-hydroxy-ursolic acid
• 英文别名: corosolic acid；corosin；2-α-hydroxyursolic acid；(1S,2R,4aS,6aS,6bR,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid；(1S,2R,4aS,6aR,6aS,6bR,10R,11R,12aR,14bS)-10,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• CAS: 4547-24-4；52213-27-1；72881-13-1；87205-98-9；114580-53-9
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: HFGSQOYIOKBQOW-AMWIWRBCSA-N

物化性质

• 熔点：
  243～245℃
• 沸点：
  573.3±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)
• 溶解度：
  在甲醇中可溶1mg/mL，透明，无色
• LogP：
  7.113 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 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
• 海关编码：
  2918195000

制备方法与用途

理化性质

科罗索酸是一种白色无定型粉末，又名植物胰岛素或2α-羟基熊果酸。它是从巴拉巴和大花紫薇中提取的α-香树脂醇型或乌斯烷型五环三萜类化合物。该物质可溶于石油醚、苯、氯仿及吡啶等有机溶剂，但不溶于水，并且在热乙醇和甲醇中的溶解度较高。

科罗索酸在无水条件下与强酸（如硫酸、磷酸、高氯酸）或中强酸（三氯乙酸）、以及Lewis酸（如氯化锌、三氯化铝、三氯化锑）反应时，会显示出颜色变化或者荧光现象。

临床应用和功效

科罗索酸作为防治肥胖症及Ⅱ型糖尿病的新药与功能性天然保健食品医药原料，在市场上受到了极大的关注。目前，它已经在美国以营养补充剂的形式上市，并正在进行三期临床试验，预计不久后将通过FDA认证。与注射胰岛素相比，科罗索酸具有口服效果显著、副作用小以及使用方便等优点。

尽管大花紫薇中含有较高浓度的科罗索酸（约1%），但总体而言，该天然产物在植物中的含量普遍很低；例如，在热水提取的大花紫薇浓缩物中，其含量仅为0.01%，而在巴拿巴叶的醇浓缩提取物中也仅有1%。Microherb公司经过多年的研发，通过先进的色谱分离技术成功提炼出98%纯度的科罗索酸，并用于减肥和治疗糖尿病的研究与临床试验。

科罗索酸的主要功效

1. 能调节体内胰岛素和血糖水平，有助于减重。
2. 具有显著降血糖效果。
3. 对炎症反应具有抑制作用，其抗炎效果优于市场上常见药物如吲哚美辛。
4. 在多种肿瘤细胞生长方面表现出抑制活性。

大花紫薇提取物

科罗索酸是一种存在于大花紫薇中的三萜类化合物。其基本骨架由多氢蒎的五环母核构成，既可以以游离形式存在于植物体内，也可以与其他成分如山楂酸（2α-羟基齐墩果酸）结合形成皂苷存在。二者在结构和化学性质上十分相似，分离较为困难。

科罗索酸能通过促进葡萄糖转运及增强细胞对葡萄糖的吸收利用来实现其降血糖效果；其作用机制类似于胰岛素，因此被称为“植物胰岛素”。多项动物实验表明，该物质能够显著降低正常大鼠和遗传性糖尿病小鼠的血糖水平。此外，它还具有减肥作用，在临床研究中发现服用含有此成分的产品后可明显减轻体重（平均减重0.908-1.816公斤），且过程温和无需节食。

科罗索酸还有多种生物活性，包括抑制TPA诱导的炎症反应、DNA聚合酶抑制效果以及对多种肿瘤细胞生长的抑制作用。这些发现使得它受到了广泛关注并被开发成各种保健品。

大花紫薇

大花紫薇（Lagerstroemia speciosa (L.) Pers.）是一种千屈菜科植物，广泛用于降血糖、抗炎及抗癌等功效的研究与应用。

参考质量标准

• 干燥失重：≤5%
• 重金属含量：≤10ppm
• 农残：≤2ppm
• 溶剂残留：≤0.5%
• 菌检：总菌数≤1000CFU/G，霉菌及酵母菌≤100CFU/G

化学性质与用途

科罗索酸可溶于石油醚、苯、氯仿和吡啶等有机溶剂，而不溶于水；它在热乙醇和甲醇中的溶解度较高。

该物质主要用于含量测定/鉴定及药理实验。同时，它具有降血糖、抗炎以及抑制肿瘤细胞生长等多种药理作用。

反应信息

• 作为产物：
  描述：

  2α-hydroxy-3-oxourosolic acid 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以85%的产率得到2α-hydroxy-ursolic acid
  参考文献：
  名称：

  Process for producing corosolic acid

  摘要：

  该发明提供了一种改进的工艺，用于从相对较大的植物中存在的熊果酸开始生产草木犀糖酸，该方法包括氧化3位羟基并利用3位羰基在2α位引入立体特异性羟基，该羟基位于3位羟基相邻的3-氧基熊果酸中。

  公开号：

  US20050020681A1

文献信息

• [EN] NOVEL STRUCTURAL ANALOGS OF COROSOLIC ACID HAVING ANTI-DIABETIC AND ANTI-INFLAMMATORY PROPERTIES<br/>[FR] NOUVEAUX ANALOGUES STRUCTURAUX D'ACIDE COROSOLIQUE PRESENTANT DES PROPRIETES ANTI-DIABETIQUE ET ANTI-INFLAMMATOIRES
  申请人：GOKARAJU GANGA RAJU

  公开号：WO2006006178A1

  公开（公告）日：2006-01-19

  This invention relates to novel corosolic acid analogs of the formula I, wherein R1, R2, R3, R4 and R5 are as indicated below in each of said analogs: 1. R1 = COCH3, R2= R3=R4= H, R5= COOH or R1, =R3=R4= H, R2= COCH3,R5= COOH 2. RI= R2= COCH3, R3=R4= H, R5= COOH 3. R1 = COC5H4N, R2= R3=R4= H, R5= COOH 4. R1 = COCH2NH2.HCI, R2= R3=R4= H, R5= COOH 5. R1 = COCH2(CH3)NH2.HCI, R2= R3=R4= H, R5= COOH 6. R1 = COCH:CHC6H2(OCH3)3, R2= R3=R4= H, R5= COOCH3 7. R1 & R2 = S02, R3=R4= H, R5= COOH 8. R1=R2=R3=R4= H, R5= CONH2 9. RI=R2=R3=R4= H, R5= CONHC6H5 10. R1=R2=R3=R4= H, R5= CONHCH2CH2NH2 11. R1=R2=R3=R4= H, R5= CON(CH2CH2)2NH 12. R1=R2=R3=R4= H, R5= CONHCH2CH20H 13. R1=R2=R3=R4= H, R5= COOCH3 14. R1 =R2= COCH3, R3=R4= H, R5= COOCH3 15. R1= R2= H, R3 & R4 = 0, R5= COOCH3 16. R1= R2= COCH3, R3 & R4 = 0, R5= COOCH3 17. R1= R2= H, R3 & R4 = 0, R5= COOH 18. R1= R2= COCH3, R3 & R4 = 0, R5= COOH 19. R1 & R2 = S02, R3 & R4 = 0, R5= COOH 20. R1= R2= H, R3 & R4 = 0, R5= CONH2 21. R1= R2=R3= H, R4 = OH, R5= CONH2 22. R1= R2=R3= H, R4 = OH, R5= COOCH3 23. R1=R2=R3=R4= H, R5= CH20H 24. R1=R2=R3=R4= H, R5= CHO 25. R1=R2=R3=R4= H, R5= COOCOC6H2(OCH3)3 26. R1=R2=R3= H, R4 & R5= OCO. These compounds exhibit good hypoglycemic and 5-lipoxygenase inhibitory activities. They also inhibit tumour growth. Pharmaceutical compositions containing known adjutants and the title compound are also within the scope of this invention.

  本发明涉及公式I的新型苦瓜酸类似物，其中在每个类似物中R1、R2、R3、R4和R5如下所示：1. R1 = CO ，R2 = R3 = R4 = H，R5 = COOH或R1 = R3 = R4 = H，R2 = CO ，R5 = COOH 2. RI = R2 = CO ，R3 = R4 = H，R5 = COOH 3. R1 = COC5H4N，R2 = R3 = R4 = H，R5 = COOH 4. R1 = COCH2NH2.HCI，R2 = R3 = R4 = H，R5 = COOH 5. R1 = COCH2（CH3）NH2.HCI，R2 = R3 = R4 = H，R5 = COOH 6. R1 = COCH：CHC6H2（O ）3，R2 = R3 = R4 = H，R5 = COO 7. R1和R2 = SO2，R3 = R4 = H，R5 = COOH 8. R1 = R2 = R3 = R4 = H，R5 = CONH2 9. RI = R2 = R3 = R4 = H，R5 = CONHC6H5 10. R1 = R2 = R3 = R4 = H，R5 = CONHCH2CH2NH2 11. R1 = R2 = R3 = R4 = H，R5 = CON（CH2CH2）2NH 12. R1 = R2 = R3 = R4 = H，R5 = CONHCH2CH20H 13. R1 = R2 = R3 = R4 = H，R5 = COO 14. R1 = R2 = CO ，R3 = R4 = H，R5 = COO 15. R1 = R2 = H，R3和R4 = 0，R5 = COO 16. R1 = R2 = CO ，R3和R4 = 0，R5 = COO 17. R1 = R2 = H，R3和R4 = 0，R5 = COOH 18. R1 = R2 = CO ，R3和R4 = 0，R5 = COOH 19. R1和R2 = SO2，R3和R4 = 0，R5 = COOH 20. R1 = R2 = H，R3和R4 = 0，R5 = CONH2 21. R1 = R2 = R3 = H，R4 = OH，R5 = CONH2 22. R1 = R2 = R3 = H，R4 = OH，R5 = COO 23. R1 = R2 = R3 = R4 = H，R5 = CH20H 24. R1 = R2 = R3 = R4 = H，R5 = CHO 25. R1 = R2 = R3 = R4 = H，R5 = COOCOC6H2（O ）3 26. R1 = R2 = R3 = H，R4和R5 = OCO。这些化合物表现出良好的降血糖和5-脂氧合酶抑制活性。它们也能抑制肿瘤生长。含有已知辅料和本发明的化合物的药物组合物也在本发明的范围内。
• Ume extract having medicinal effects and compositions containing the same
  申请人：——

  公开号：US20030072824A1

  公开（公告）日：2003-04-17

  Extracts are prepared from a leaf and a stem of ume, a kernel of ume, and an ume flower, using methanol in an amount of 5 times the volume thereof. These extracts have anti-oxidation action, gastric mucosa injury inhibiting action, aldose reductase inhibiting action, blood glucose level elevation inhibiting action, platelet agglutination accelerating action, alcohol absorption inhibiting action, anti-inflammatory action, and the like.

  从梅叶、梅枝、梅核和梅花中提取物，使用甲醇量为其5倍体积。这些提取物具有抗氧化作用、抑制胃黏膜损伤作用、醛还原酶抑制作用、抑制血糖水平升高作用、促进血小板凝聚作用、抑制酒精吸收作用、抗炎作用等。
• Novel structural analogs of corosolic acid having anti-diabetic and anti-inflammatory properties
  申请人：Gokaraju Raju Ganga

  公开号：US20070167521A1

  公开（公告）日：2007-07-19

  This invention relates to novel corosolic acid analogs of the formula I, wherein R 1 , R 2 , R 3 , R 4 and R 5 are as indicated below in each of said analogs: 1. R 1 =COCH 3 , R 2 =R 3 =R 4 =H, R 5 =COOH or R 1 , =R 3 =R 4 =H, R 2 =COCH 3 , R 5 =COOH 2. R 1 =R 2 =COCH 3 , R 3 =R 4 =H, R5=COOH 3. R 1 =COC 5 H 4 N, R 2 =R 3 =R 4 =H, R 5 =COOH 4. R 1 =COCH 2 NH 2 .HC 1 , R 2 =R 3 =R 4 =H, R 5 =COOH 5. R 1 =COCH 2 (CH 3 )NH 2 .HC 1 , R 2 =R 3 =R 4 =H, R 5 =COOH 6. R 1 =COCH:CHC 6 H 2 (OCH 3 ) 3 , R 2 =R 3 =R 4 =H, R 5 =COOCH 3 7. R 1 & R 2 =S0 2 , R 3 =R 4 =H, R 5 =COOH 8. R 1 =R 2 =R 3 =R 4 =H, R 5 =CONH 2 9. R 1 =R 2 =R 3 =R 4 =H, R 5 =CONHC 6 H 5 10. R 1 =R 2 =R 3 =R 4 =H, R 5 =CONHCH 2 CH 2 NH 2 11. R 1 =R 2 =R 3 =R 4 =H, R 5 =CON(CH2CH 2 ) 2 NH 12. R 1 =R 2 =R 3 =R 4 =H, R 5 =CONHCH 2 CH 2 0H 13. R 1 =R 2 =R 3 =R 4 =H, R 5 =COOCH 3 14. R 1 =R 2 =COCH 3 , R 3 =R 4 =H, R 5 =COOCH 3 15. R 1 =R 2 =H, R 3 & R 4 =0, R 5 =COOCH 3 16. R 1 =R 2 =COCH 3 , R 3 & R 4 =0, R 5 =COOCH 3 17. R 1 =R 2 =H, R 3 & R 4 =0, R 5 =COOH 18. R 1 =R 2 =COCH 3 , R 3 & R 4 =0, R 5 =COOH 19. R 1 & R 2 =S0 2 , R 3 & R 4 =0, R 5 =COOH 20. R 1 =R 2 =H, R 3 & R 4 =0, R 5 =CONH 2 21. R 1 =R 2 =R 3 =H, R 4 =OH, R 5 =CONH 2 22. R 1 =R 2 =R 3 =H, R 4 =OH, R 5 =COOCH 3 23. R 1 =R 2 =R 3 =R 4 =H, R 5 =CH 2 0H 24. R 1 =R 2 =R 3 =R 4 =H, R 5 =CHO 25. R 1 =R 2 =R 3 =R 4 =H, R 5 =COOCOC 6 H 2 (OCH 3 ) 3 26. R 1 =R 2 =R 3 =H, R 4 & R 5 =OCO. These compounds exhibit good hypoglycemic and 5-lipoxygenase inhibitory activities. They also inhibit tumour growth. Pharmaceutical compositions containing known adjutants and the title compound are also within the scope of this invention.

  本发明涉及式I的新型苦参酸类似物，其中在每个类似物中，R1、R2、R3、R4和R5如下所示：1. R1=CO ，R2=R3=R4=H，R5=COOH或R1=R3=R4=H，R2=CO ，R5=COOH；2. R1=R2=CO ，R3=R4=H，R5=COOH；3. R1=COC5H4N，R2=R3=R4=H，R5=COOH；4. R1=COCH2NH2.HC1，R2=R3=R4=H，R5=COOH；5. R1=COCH2（CH3）NH2.HC1，R2=R3=R4=H，R5=COOH；6. R1=COCH:CHC6H2（O ）3，R2=R3=R4=H，R5=COO ；7. R1和R2=S02，R3=R4=H，R5=COOH；8. R1=R2=R3=R4=H，R5=CONH2；9. R1=R2=R3=R4=H，R5=CONHC6H5；10. R1=R2=R3=R4=H，R5=CONHCH2CH2NH2；11. R1=R2=R3=R4=H，R5=CON（CH2CH2）2NH；12. R1=R2=R3=R4=H，R5=CONHCH2CH20H；13. R1=R2=R3=R4=H，R5=COO ；14. R1=R2=CO ，R3=R4=H，R5=COO ；15. R1=R2=H，R3和R4=0，R5=COO ；16. R1=R2=CO ，R3和R4=0，R5=COO ；17. R1=R2=H，R3和R4=0，R5=COOH；18. R1=R2=CO ，R3和R4=0，R5=COOH；19. R1和R2=S02，R3和R4=0，R5=COOH；20. R1=R2=H，R3和R4=0，R5=CONH2；21. R1=R2=R3=H，R4=OH，R5=CONH2；22. R1=R2=R3=H，R4=OH，R5=COO ；23. R1=R2=R3=R4=H，R5=CH20H；24. R1=R2=R3=R4=H，R5=CHO；25. R1=R2=R3=R4=H，R5=COOCOC6H2（O ）3；26. R1=R2=R3=H，R4和R5=OCO。这些化合物表现出良好的降血糖和5-脂氧合酶抑制活性。它们还抑制肿瘤生长。含有已知辅料和本发明所述化合物的制药组合物也属于本发明的范围。
• PENTACYCLIC TRITERPENOIDS FOR INJECTION LIPOLYSIS
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP3124047A1

  公开（公告）日：2017-02-01

  The present invention relates to a composition comprising a pentacyclic triterpenoid compound or a pharmaceutically acceptable salt thereof, and at least one further component C for use in a method for local treating or preventing a condition associated with an undesired local subcutaneous fat deposit in a mammal, wherein said compound is injected into said local subcutaneous fat deposit aiming for its reduction. Further, the present invention relates to the cosmetic use of such composition.

  本发明涉及一种组合物，该组合物包含一种五环三萜类化合物或其药学上可接受的盐，以及至少一种其他成分C，用于局部治疗或预防哺乳动物与不期望的局部皮下脂肪沉积相关的病症，其中所述化合物被注射到所述局部皮下脂肪沉积中，以减少其沉积。此外，本发明还涉及此类组合物的美容用途。
• COMPOSITION FOR THE PREVENTION OR TREATMENT OF POLYCYSTIC OVARY SYNDROME AND ITS RELATED SUMPTOMS
  申请人：Pharmamol S.R.L.

  公开号：EP3165229A1

  公开（公告）日：2017-05-10

  The present invention in one aspect concerns a composition for the prevention and/or treatment of polycystic ovary syndrome and its related symptoms, comprising a combination of Banaba extract (Lagerstroemia speciosa L.), inositol in one of its chiral or salt forms, lpomoea Batatas and a physiologically acceptable carrier. The composition can further contain lignans and be a herbal product, a food supplement, a dietetic and/or a nutritional product.

  本发明的一个方面涉及一种用于预防和/或治疗多囊卵巢综合征及其相关症状的组合物，该组合物包含巴纳巴提取物（Lagerstroemia speciosa L.）、手性或盐形式之一的肌醇、红苕和生理上可接受的载体。该组合物还可以含有木酚素，是一种草药产品、食品补充剂、膳食补充剂和/或营养产品。