Betulinic acid (ALS357; Lupatic acid)

Alias: Lupatic acid; ALS357; ALS 357;Betulic acid; ALS-357; Mairin
Cat No.:V1401 Purity: ≥98%
Betulinic acid (also known as ALS-357; LS-357; Mairin; Lupatic acid; Betulic acid)is a naturally occuring pentacyclic triterpenoid extracted from Syzigium claviflorum that displays anti-HIV and antitumor activity.
Betulinic acid (ALS357; Lupatic acid) Chemical Structure CAS No.: 472-15-1
Product category: Topoisomerase
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Betulinic acid (also known as ALS-357; LS-357; Mairin; Lupatic acid; Betulic acid) is a naturally occuring pentacyclic triterpenoid extracted from Syzigium claviflorum that displays anti-HIV and antitumor activity. Through an EC50 of 1.4 μ M, Betulinic acid inhibits HIV-1. By directly triggering the mitochondrial pathway of apoptosis in tumor cells in a way that is independent of both CD95 and p53, Betulinic acid specifically causes apoptosis in these cells. With an EC50 of 1.04 μM, Betulinic acid also exhibits TGR5 agonist activity.

Biological Activity I Assay Protocols (From Reference)
Targets
Topoisomerase I ( IC50 = 5 μM ); HIV-1 ( IC50 = 1.4 μM ); NF-κB
ln Vitro

Betulinic acid is a eukaryotic topoisomerase I inhibitor that inhibits topoisomerase I-DNA interaction and has an IC50 of 5 μM[1]. MDA-MB-231 cell viability is significantly suppressed by betulinic acid (10, 20, 40, 80, and 160 μM) in a time- and dose-dependent manner following treatment for 24 or 48 hours. MDA-MB-231 cells express less Bcl-2 when exposed to betulinic acid (20, 40 μM). Additionally, betulinic acid alters the morphology of MDA-MB-231 cells at 20 μM and the ultrastructure of MDA-MB-231 cells at 40 μM[2]. With an EC50 of 1.4 μM in acutely infected H9 lymphocytes, betulinic acid exhibits anti-HIV activities[4].

ln Vivo
Betulinic acid (10 and 30 mg/kg, p.o.) blocks colon shortening and lowers lipid hydroperoxide and malondialdehyde (MDA) levels in mice with colitis brought on by dextran sulfate sodium (DSS). In mice with DSS-induced colitis, betulinic acid (30 mg/kg, p.o.) restores glutathione (GSH) levels, catalase activity, and superoxide dismutase (SOD) levels to normal. Additionally, betulinic acid (30 mg/kg, p.o.) prevents the rise in inflammatory markers brought on by DSS. Mice exposed to acetic acid (3, 10, 30 mg/kg, p.o.) or mustard oil (MO) do not exhibit writhing responses or visceral nociception.
Enzyme Assay
The 25-mer annealed duplex consisting of oligonucleotide-1 and oligonicleotide-2 is subjected to an 8°C incubation period with 25 or 50 units of rat liver topoisomerase I, either in the presence or absence of betulinic acid in the binding buffer. Following incubation, the reaction mixtures are electrophoresed in a 7% non-denaturing polyacrylamide gel in 0.167 × TBE buffer at 4 °C. Ethidium bromide is then used to stain the DNA bands.
Cell Assay
The assay makes use of CCK-8. After being grown at a density of 2 × 103 cells/well in 96-well plates, MDA-MB-231 cells are treated with DMSO vehicle or different concentrations of betulinic acid (5 µM to 160 µM) in 100 µL of medium for the specified durations. Following the treatment phase, 110 µL of medium containing 10 µL of the CCK-8 mixture is added to each well, and the plates are incubated at 37°C for one hour and thirty minutes. With the aid of a microplate reader, the absorbance at 450 nm wavelength is determined[2].
Animal Protocol
Oral betulinic acid (3, 10, or 30 mg/kg) or vehicle (5% v/v DMSO in peanut oil) is given to female Swiss albino mice. An observer who is blind to the treatments counts the number of writhing responses from each animal for 20 minutes after acetic acid (300 mg/kg) is given intraperitoneally after an hour. An animal exhibits a whining response when it rubs its belly on a table or floor while extending its hind limbs and body[3].
References

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

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

[4]. 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.

[5]. Betulinic acid as new activator of NF-kappaB: molecular mechanisms and implications for cancer therapy. Oncogene. 2005 Oct 20;24(46):6945-56.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H48O3
Molecular Weight
456.7
Exact Mass
456.36
Elemental Analysis
C, 78.90; H, 10.59; O, 10.51
CAS #
472-15-1
Appearance
Solid powder
SMILES
CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=O)O
InChi Key
QGJZLNKBHJESQX-FZFNOLFKSA-N
InChi Code
InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
Chemical Name
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms
Lupatic acid; ALS357; ALS 357;Betulic acid; ALS-357; Mairin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 20~35.7 mg/mL (43.8~78.2 mM)
Ethanol: 10 mg/mL (~21.9 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1896 mL 10.9481 mL 21.8962 mL
5 mM 0.4379 mL 2.1896 mL 4.3792 mL
10 mM 0.2190 mL 1.0948 mL 2.1896 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT00346502 Withdrawn Drug: 20% betulinic acid ointment
Drug: BA
Dysplastic Nevus Syndromey University of Illinois at Chicago January 2006 Phase 1
Phase 2
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