| Description | Betulinic acid (472-15-1) is a natural Lupane triterpenoid from white birch tree (Betula pubescens). Induces apoptosis in a variety of cell lines.1 Induces mitochondrial permeability transition pore opening.2 ?Acts as a chemosensitizer for anticancer drug treatment in chemoresistant colon cancer cell lines.3 Cell permeable. |
| Chemical Properties | colorless Needles |
| Uses | antineoplastic |
| Uses | Betulinic acid (BetA) has been used:
- to test its effects as an antiviral agent against Dengue virus (DENV)
- as a sterol regulatory element-binding protein (SREBP) inhibitor to repress the lipid metabolism and proliferation of clear cell renal cell carcinoma (ccRCC) cells
- as a treatment to test its anti-tumor properties for cell viability and apoptotic cell death assays in multiple myeloma models
|
| Uses | Betulinic Acid is a natural pentacyclic triterpenoid. Betulinic Acid displays anti-inflammatory and anti-HIV activity. Betulinic Acid selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. Betulinic Acid also exhibits TGR5 agonist activity |
| Definition | ChEBI: A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claiflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. |
| General Description | Betulinic acid is a lupane-type triterpene, which can be prepared from betulin via oxidation using chromium oxide (VI). Along with anti-HIV-1 and anti-tumor activity, it also shows other bioactivities such as anti-inflammatory, antibacterial, in vitro antimalarial, anthelmintic and antioxidant activities. |
| Biological Activity | Natural triterpenoid that displays anti-HIV and antitumor activity. Induces the production of reactive oxygen species (ROS) and activates NF- κ B. Exhibits TRG5 agonist activity (EC 50 = 1.04 μ M). |
| Biochem/physiol Actions | Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. |
| Anticancer Research | This compound is a pentacyclic triterpene obtained from Betula and Zizyphus species,which shows selective cytotoxicity against human melanoma cells (Shoeb2006). It generates reactive oxygen species, activates MAPK cascade, inhibitstopoisomerase I, inhibits angiogenesis, modulates pro-growth transcriptionalactivators, modulates the activity of aminopeptidase-N, and thereby inducesapoptosis in cancer cells (Desai et al. 2008; Fulda 2008). |
| Synthesis | Firstly, it is obtained by extraction and separation from natural plants. This method consumes a large amount of solvent, has a low yield, and the impurities are not easy to separate, so it is rarely used;
Secondly, betulinic acid is obtained by organic synthesis using betulinol as a precursor. This method has been applied to industrial production, can get industrial scale betulinic acid, is now the main source of betulinic acid on the market;
Third, with betulinol as the precursor, through the transformation of microorganisms to generate betulinic acid. This approach represents a new direction for the future of the plant extraction industry, but there are still many technical difficulties that have not been solved. |
| storage | +4°C |
| References | [1] H EHRHARDT. Betulinic acid-induced apoptosis in leukemia cells[J]. Leukemia, 2004, 18 8: 1406-1412. DOI:10.1038/sj.leu.2403406
[2] FRANZISKA B. MULLAUER Jan P M Jan H Kessler. Betulinic acid induces cytochrome c release and apoptosis in a Bax/Bak-independent, permeability transition pore dependent fashion[J]. Apoptosis, 2008, 14 2: 191-202. DOI:10.1007/s10495-008-0290-x
[3] GWON-RYUL JUNG. Effect of Betulinic Acid on Anticancer Drug-Resistant Colon Cancer Cells[J]. Basic & Clinical Pharmacology & Toxicology, 2007, 101 4: 277-285. DOI:10.1111/j.1742-7843.2007.00115.x |
| Raw materials | betulonic aldehyde |
| Preparation Products | Betulin-->(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((tert-butoxycarbonyl)amino)-5 a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate |
