Betulinic acid

Modify Date: 2024-01-02 19:03:58

Betulinic acid Structure
Betulinic acid structure
 Common Name Betulinic acid
CAS Number 472-15-1 Molecular Weight 456.700
Density 1.1±0.1 g/cm3 Boiling Point 550.0±33.0 °C at 760 mmHg
Molecular Formula C30H48O3 Melting Point 295-298 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 300.5±21.9 °C

 Use of Betulinic acid


Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties.

 Names

Name betulinic acid
Synonym More Synonyms

 Betulinic acid Biological Activity

Description Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties.
Related Catalog
Target

Topoisomerase I:5 μM (IC50)

HIV-1:1.4 μM (EC50)

In Vitro Betulinic acid is a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and prevents topoisomerase I-DNA interaction[1]. Betulinic acid (10, 20, 40, 80, and 160 µM) significantly suppresses MDA-MB-231 cell viability in a time- and dose-dependent manner after treatment for 24 or 48 h. Betulinic acid (20, 40 µM) causes decrease in Bcl-2 expression of MDA-MB-231 cells. Betulinic acid also induces morphological changes of MDA-MB-231 cells at 20 µM, and leads to ultrastructure changes of MDA-MB-231 cells at 40 µM[2]. Betulinic acid shows anti-HIV activities, with an EC50 of 1.4 µM in acutely infected H9 lymphocytes[4].
In Vivo Betulinic acid (10 and 30 mg/kg, p.o.) significantly abrogates colon shortening, and reduces malondialdehyde (MDA) and lipid hydroperoxide levels in dextran sulfate sodium (DSS)-induced colitis in mice. Betulinic acid (30 mg/kg, p.o.) restores superoxide dismutase (SOD), catalase activity and glutathione (GSH) content to control levels in DSS-induced colitis in mice. Betulinic acid (30 mg/kg, p.o.) also inhibits the DSS-induced increase in inflammatory markers. Betulinic acid (3, 10, 30 mg/kg, p.o.) suppresses acetic acid-induced writhing responses and mustard oil (MO)-induced visceral nociception in mice[3].
Cell Assay CCK-8 is used in the assay. MDA-MB-231 cells are cultured in 96-well plates at a density of 2 × 103 cells/well and then treated with DMSO vehicle or various concentrations of Betulinic acid ranging from 5 µM to 160 µM in 100 µL of medium for the indicated times. After the treatment period, the medium in each well is replaced with 110 µL of medium containing 10 µL of the CCK-8 mixture, and the plates are incubated for 1 h and 30 min at 37°C. The absorbance at a wavelength of 450 nm is measured with a microplate reader[2].
Animal Admin Female Swiss albino mice are administered vehicle (5% v/v DMSO in peanut oil) or Betulinic acid (3, 10 or 30 mg/kg) in vehicle, orally. After 1 h, acetic acid (300 mg/kg) is administered by intraperitoneal route and number of writhing response of each animal is counted for 20 min by an observer who is blind to the treatments. Writhing response is when animal rubs its abdomen on surface of table/floor with elongation of the body and extension of the hind limbs[3].
References

[1]. Chowdhury AR, et al. Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives. Med Sci Monit. 2002 Jul;8(7):BR254-65.

[2]. Gao Y, et al. Betulinic acid induces apoptosis and ultrastructural changes in MDA-MB-231 breast cancer cells. Ultrastruct Pathol. 2018 Jan-Feb;42(1):49-54.

[3]. Kalra J, et al. Betulinic acid alleviates dextran sulfate sodium-induced colitis and visceral pain in mice. Naunyn Schmiedebergs Arch Pharmacol. 2017 Dec 26.

[4]. Hashimoto F, et al. Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem. 1997 Dec;5(12):2133-43.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 550.0±33.0 °C at 760 mmHg
Melting Point 295-298 °C (dec.)(lit.)
Molecular Formula C30H48O3
Molecular Weight 456.700
Flash Point 300.5±21.9 °C
Exact Mass 456.360352
PSA 57.53000
LogP 8.94
Vapour Pressure 0.0±3.4 mmHg at 25°C
Index of Refraction 1.533
Storage condition Store at +4°C

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2942000000

 Synthetic Route

 Customs

HS Code 2918199090
Summary 2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

 Articles110

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 Synonyms

(3β)-3-Hydroxylup-20(29)-en-28-oic acid
Gratiolone
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
betulic acid
Platanol
3β-Hydroxy-20(29)-lupaene-28-oic Acid
(3b)-3-hydroxylup-20(29)-en-28-oic Acid
Lup-20(29)-en-28-oic acid, 3β-hydroxy-
Betulinic acid
MFCD00009619
MAIRIN
Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3β)-
Melaleucin
ALS-357
EINECS 207-448-8
Betulinic
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