Betulinic acid

Manufactured by Extrasynthese

Sourced in France

Betulinic acid is a naturally occurring pentacyclic triterpene compound. It is commonly extracted from the bark of the white birch tree. Betulinic acid has a molecular formula of C₃₀H₄₈O₃ and a molecular weight of 456.69 g/mol.

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6 protocols using betulinic acid

Analytical Standards for Bioactive Compounds

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The standards (purity >95%) (+)-catechin, (-)epicatechin, luteolin-7-O-glucoside, kaempferol-3-O-rutinoside, betulinic acid, ursolic acid, and rutin were all purchased from Extrasynthese (Genay Cedex, France). Quercetin-3-O-galactoside, quercetin-3-O-glucoside, and myricetin were purchased from Sigma Aldrich (Oakville, ON, Canada). Morroniside was purchased from AvaChem Scientific (San Antonio, TX, USA) and taxifolin-3-O-glucoside was isolated in-house and its structure and purity was verified through its ultraviolet (UV) spectrum, mass spectrometry (MS) and nuclear magnetic resonance (NMR) (11) . All solvents were LC-MS grade and purchased from Fisher Scientific (Ottawa, ON, Canada).

Cieniak C., Walshe-Roussel B., Liu R., Muhammad A., Saleem A., Haddad P.S., Cuerrier A., Foster B.C, & Arnason J.T. (2015). Phytochemical Comparison of the Water and Ethanol Leaf Extracts of the Cree medicinal plant, Sarracenia purpurea L. (Sarraceniaceae). Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques, 18(4).

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Evaluating Novel Betulinic Acid Derivatives

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Genistein (4’,5,7-trihydroxyisoflavone), betulin (lup-20(29)-ene-3β,28-diol) and betulinic acid ((3β)-3-Hydroxy-lup-20(29)-en-28-oic acid) were obtained from Extrasynthese, Lyon, France, and fingolimod (FTY720; 2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol) was kindly donated by V. Brinkmann, from Novartis Pharma AG, Basel, Switzerland. betulinic acid derivatives B-10 and NVX-270 were kindly provided by Prof S. Fulda, Institute for Experimental Cancer Research in Pediatrics, Goethe University Frankfurt/Main. Roswell Park Memorial Institute (RPMI) 1640 medium with Glutamax, Dulbecco’s Modified Eagle’s Medium (DMEM), phosphate-buffered saline (PBS), penicillin, streptomycin, 4-(2-hydroxyethyl)-1-piperazine ethanesulfonic acid (HEPES) and trypsin were purchased from Gibco, Karlsruhe, Germany. Fetal calf serum (FCS), LPS, ethylene diaminetetraacetic acid (EDTA) and dimethyl sulfoxide (DMSO) were purchased from Sigma Aldrich, Munich, Germany. DMSO was used as a control and to prepare 10 mM stock solutions of all of the tested substances. The highest concentration of DMSO in the medium never exceeded 0.1% and did not influence any of the tested aspects in all of the experiments presented.

Pfarr K., Danciu C., Arlt O., Neske C., Dehelean C., Pfeilschifter J.M, & Radeke H.H. (2015). Simultaneous and Dose Dependent Melanoma Cytotoxic and Immune Stimulatory Activity of Betulin. PLoS ONE, 10(3), e0118802.

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Diverse Compound Network Analysis

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The reference compound set selected for standard compound network were chosen to represent diverse scaffolds from natural products or natural product derivatives. Daunomycin (7), roxithromycin (5), erythromycin (4), puromycin (8), novobiocin (10), and cycloheximide were obtained from Sigma-Aldrich. Ursolic acid, betulinic acid, and oleanolic acid were purchased from Extrasynthese SA. Chloramphenicol (1) was obtained from Calbiochem. Azithromycin (3) and rifamycin S were purchased from TCI. Thiamphenicol (2) was acquired from Spectrum Chemicals, and actinomycin D was purchased from RPI. Mupirocin (9) was purchased from AppliChem. Epirubicin (6) was purchased from MP Biomedicals LLC, and staurosporine was purchased from LC Laboratories.
Parameters used for this study are displayed in Table S2. The resulting networks were exported in graphML format and processed in Gephi for visualization using the Force Atlas 2 algorithm with default parameters except; spacing = 10, dissuade hubs = True, prevent overlap = True.

Egan J.M., van Santen J.A., Liu D.Y, & Linington R.G. (2021). Development of an NMR-Based Platform for the Direct Structural Annotation of Complex Natural Products Mixtures. Journal of natural products, 84(4), 1044-1055.

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Analytical Characterization of Phytochemicals

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HPLC-grade methanol, LC-MS-grade acetonitrile, formic acid (>98% purity), pyridine, BSTFA, ellagic acid, rutin, and apigenin were obtained from Merck (Darmstadt, Germany). De-ionized water (18.2 MΩ cm) was supplied by a Milli-Q purification system (Millipore). Luteolin, Luteolin 7-O-glucoside, Luteolin 4′-O-glucoside, apigenin 7-O-glucoside, quercetin 3-O-glucoside, betulinic acid, oleanolic acid, and ursolic acid were purchased from Extrasynthese (Genay, France). Punicalin α+β and punicalagin α+β were obtained from Phytolab (Vestenbergsgreuth, Germany).
The reagents used for expression, purification, and biochemical assays were purchased from Microbiol (Sardinia, Italy), Sigma-Aldrich (Milano, Italy), and PerkinElmer (Milano, Italy). The reference compound Raltegravir was purchased from ChemScene (Monmouth Junction, United States), while the reference compound RDS1759 was kindly provided by Prof. Roberto Di Santo (University of Rome La Sapienza). Recombinant proteins were purified using a Biological LP chromatography system (Biorad).

Sanna C., Marengo A., Acquadro S., Caredda A., Lai R., Corona A., Tramontano E., Rubiolo P, & Esposito F. (2021). In Vitro Anti-HIV-1 Reverse Transcriptase and Integrase Properties of Punica granatum L. Leaves, Bark, and Peel Extracts and Their Main Compounds. Plants, 10(10), 2124.

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Maslinic Acid Extraction and Purification

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Maslinic acid was provided by Dr. Parra from the University of Granada (Granada, Spain). The triterpene was obtained as a pure (>95%) white powder after extraction of the olive pomace with ethyl acetate and further purification by two-step flash chromatography [14 (link)]. Betulinic acid, which was used as internal standard (I.S.), was supplied by Extrasynthèse (Genay, France). Ethyl acetate and methanol were from J.T. Baker (Deventer, The Netherlands), whereas acetonitrile was from Scharlau Chemie S.A. (Barcelona, Spain), being all of them LC-MS grade. (2-Hydroxypropyl)-β-cyclodextrin and 10% buffered formalin (pH 7.4) were provided by Sigma-Aldrich S.L. (Tres Cantos, Madrid, Spain). All other chemicals used in the preparation of solutions were of analytical reagent grade. Ultrapure water was obtained by purification through a Milli-Q® Gradient system (Merck Milliore, Madrid, Spain).

Juan M.E., Lozano-Mena G., Sánchez-González M, & Planas J.M. (2019). Reduction of Preneoplastic Lesions Induced by 1,2-Dimethylhydrazine in Rat Colon by Maslinic Acid, a Pentacyclic Triterpene from Olea europaea L.. Molecules, 24(7), 1266.

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LC-MS Metabolite Profiling of Plant Extracts

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LC-MS grade acetonitrile, HPLC-grade methanol, pyridine, BSTFA, formic acid (> 98 % purity), ellagic acid, rutin, and apigenin were purchased from Merck. De-ionized water (18.2 MΩ cm) was obtained from a Milli-Q purification system (Millipore). Luteolin, apigenin 7-O-glucoside, quercetin 3-O-glucoside, Luteolin 7-O-glucoside, Luteolin 4′-O-glucoside, betulinic acid, oleanolic acid, and ursolic acid were obtained from Extrasynthese.

Acquadro S., Civra A., Cagliero C., Marengo A., Rittà M., Francese R., Sanna C., Bertea C., Sgorbini B., Lembo D., Donalisio M, & Rubiolo P. (2020). Punica granatum Leaf Ethanolic Extract and Ellagic Acid as Inhibitors of Zika Virus Infection. Planta medica, 86(18).

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