Lup-20(29)-en-3-ol, (3beta)-
lupeol
CAS: 545-47-1
Molecular Formula: C30H50O
Lup-20(29)-en-3-ol, (3beta)- - Names and Identifiers
| Name | lupeol |
| Synonyms | lupeol Lupenol Clerodol HSDB 7687 MONOGYNOL NSC 90487 beta-Viscol Fagarsterol Fagarasterol Triterpene lupeol Monogynol B (6CI) Lup-20(29)-en-3beta-ol lup-20(29)-en-3-beta-ol (3-beta)-lup-20(29)-en-3-o (3-beta)-lup-20(29)-en-3-ol (3-beta)-Lup-20(29)-en-3-ol Lup-20(29)-en-3beta-ol (8CI) Lup-20(29)-en-3-ol, (3beta)- Lup-20(29)-en-3-ol, (3-beta)- Lup-20(29)-en-3-beta-ol (8CI) (3beta,14xi)-lup-20(29)-en-3-ol 1H-Cyclopenta[a]chrysene, lup-20(29)-en-3-ol deriv. |
| CAS | 545-47-1 |
| EINECS | 208-889-9 |
| InChI | InChI=1/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1 |
| InChIKey | MQYXUWHLBZFQQO-QGTGJCAVSA-N |
Lup-20(29)-en-3-ol, (3beta)- - Physico-chemical Properties
| Molecular Formula | C30H50O |
| Molar Mass | 426.73 |
| Density | 0.9457 |
| Melting Point | 215° |
| Boling Point | 482.1°C (rough estimate) |
| Specific Rotation(α) | D20 +27.2° (c = 4.8 in chloroform) |
| Flash Point | 216.9°C |
| Solubility | Insoluble in water, miscible with ether, benzene, petroleum ether, and hot ethanol. |
| Vapor Presure | 1.41E-11mmHg at 25°C |
| Appearance | White crystal |
| Color | White to Off-White |
| pKa | 15.19±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.4910 (estimate) |
| MDL | MFCD00017351 |
| Physical and Chemical Properties | Insoluble in water, with ether, benzene, petroleum ether, hot ethanol miscible. From the family Lupin polyphyllus seed bark |
Lup-20(29)-en-3-ol, (3beta)- - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | OK5763000 |
| HS Code | 29061990 |
Lup-20(29)-en-3-ol, (3beta)- - Reference
| Reference Show more | 1. Ma Xi, Zhang Liying, Li Zhijin, et al. Effect of Lupin on human hepatocellular carcinoma cell line [J]. Journal of Nanchang University (Medical Sciences), 2012, 52(12):32-34. 2. Cui Qintao, Wang Junhua, Liu Xiaochen, Wang Xuehui, Su Guobao. Protective effects of Lupin on myocardial ischemia-reperfusion injury in rats by alleviating oxidative stress [J]. Chinese Journal of Immunology, 2020,36(03):282-288. 3. Xing Wei, Song Wei, Xu Zhifeng, etc. Effect of lupeol on proliferation and apoptosis of hepatocellular carcinoma cell line SMMC-7721 [J]. World Chinese Journal of Gastroenterology, 2015, 29 (9):1411-1419. 4. Han Yue, Li Zhanjun, Li Mengyuan, Yang Fengjian. Optimization of extraction of triterpenoids from Betula alnoides by response surface methodology [J]. Forest Engineering, 2021,37(02):79-85. 5. Xue Zhao Hui et al. [IF = 3.921]. "Structure Identification of triterpen from the muscle room. Plant Food HUD Nutr. 2015 Sep;70(3):291-296 6. [IF = 5.682] Sha Huang et al."Lupeol ameliorates LPS/D-GalN induced acute hepatic damage by suppressing inflammation and oxidative stress through TGFβ1-Nrf2 signal pathway."Aging-Us. 2021 Mar 15; 13(5): 6592-6605 |
Lup-20(29)-en-3-ol, (3beta)- - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| Overview | Lupeol is a five-ring three-anvil compound that can be extracted from various fruits and vegetables such as strawberries, mangoes, and Chinese herbal medicines. It has anti-inflammatory, Anti-oxidation, promotion of wound healing and other pharmacological effects, and shows anti-cancer activity in pancreatic cancer, breast cancer, prostate cancer, melanoma and other tumors, it is clinically used for the treatment of leukemia, liver cancer, colon cancer, pancreatic cancer and other diseases. |
| pharmacological action | 1. anti-tumor effect (1) inhibitory effect on melanoma lupeol can inhibit the growth and induce differentiation of mouse melanoma. Induction of melanoma cell differentiation is achieved by activating the mitogen-activated protein kinase (MAKP) pathway, and the similarities and differences in the structure of the plume fan ring C- 3 play a key role in the activation of the MAKP pathway. Lupeol inhibits the metastasis of malignant melanoma, and its mechanism is mainly related to Wnt/β catenin (catenin) signaling pathway, but not to MAKP pathway. (2) Inhibitory effect on skin cancer in mice Lupeol has inhibitory effect on the occurrence of skin cancer and the expression of tumor markers. (3) Inhibitory effect on breast cancer Lupeol has inhibitory effect on the growth of breast cancer cells. Lupeol has inhibitory effect on estrogen receptor (ER) negative and positive breast cancer cells in a dose-and time-dependent manner. It indicates that the inhibitory effect of lupeol on breast cancer cells does not depend on ER, but it has certain correlation. Effect of lupeol on human epidermal growth factor receptor 2(HER2) in breast cancer cells. (4) Inhibition of prostate cancer cells and induction of apoptosis In endocrine-related tumors, besides breast cancer cells, lupeol also has inhibitory effect on prostate cancer. Lupeol can inhibit the growth and induce apoptosis of prostate cancer cell lines LNCaP and CWR22Rr1 in a dose-dependent manner. Its mechanism is mainly that lupeol activates fas receptor-mediated apoptosis pathway. In addition, lupeol also has a significant inhibitory effect on the growth of prostate cancer xenografts. (5) Inhibition and induction of apoptosis on pancreatic cancer Lupeol can inhibit the growth of pancreatic cancer, and inhibition of Ras pathway can induce apoptosis of pancreatic cancer cells. (6) Inhibitory effect on liver cancer cells Lupeol has inhibitory effect on the self-renewal ability of liver cancer initiatingcell (TIC) cells in vivo and in vitro. In addition, Lupeol inhibits the tumorigenic ability of TIC cells in athymic nude mice and down-regulates the expression level of TIC cell marker CD133. (7) Inhibitory effect on leukemia cells Lupeol can inhibit the growth of leukemia cells and induce apoptosis. The inhibitory effect of lupeol on leukemia cells is related to the carbonylation of the plume fan ring. (8) Inhibitory effect on other tumors Lupeol has inhibitory effect on head and neck tumors. Lupeol has a certain inhibitory effect on human ovarian cancer cells. 2. Anti-inflammatory effect 3. Antioxidant effect |
| application | 1. for the treatment of leukemia, pancreatic cancer, breast cancer, prostate cancer, melanoma, liver cancer and other tumors. 2. It can be used in the prevention of acute anti-host disease after bone marrow transplantation. (2015-11-23) |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: It has significant anti-tumor and anti-inflammatory effects. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:09
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