25493-95-2Relevant academic research and scientific papers
Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A
Honda, Tadashi,Liby, Karen T.,Su, Xiaobo,Sundararajan, Chitra,Honda, Yukiko,Suh, Nanjoo,Risingsong, Renee,Williams, Charlotte R.,Royce, Darlene B.,Sporn, Michael B.,Gribble, Gordon W.
, p. 6306 - 6309 (2006)
Fifteen new betulinic acid analogues were designed, synthesized, and tested for anti-inflammatory activity. Many of these analogues effectively suppress nitric oxide (NO) production in RAW cells stimulated with interferon-γ. Analogue 10 is highly and orally active in vivo for induction of the anti-inflammatory and cytoprotective enzyme, heme oxygenase-1.
Synthesis of betulinic acid gelator and preparation method of supramolecular gel
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Paragraph 0035-0038, (2020/05/05)
The invention discloses synthesis of a betulinic acid gelator and a preparation method of supramolecular gel. The betulinic acid gelator is obtained by taking a natural penta-cyclic triterpene compound betulinic acid as a raw material and introducing pyridinium groups through simple chemical modification. The invention further discloses a supramolecular gel, which is obtained by self-assembling the gelator in a mixed solvent of chloroform and benzene solvents or cyclohexane, and the microstructure of the supramolecular gel is a regular nano fiber and nano rod structure. The gelator and supramolecular gel preparation method is simple, direct, mild in conditions and easy to operate, a new thought is provided for construction of the supramolecular gel, and a new reference is provided for application of natural triterpene compounds in the field of supramolecules.
New Class of Betulinic Acid-Based Nanoassemblies of Cabazitaxel, Podophyllotoxin, and Thiocolchicine
Colombo, Eleonora,Polito, Laura,Biocotino, Michele,Marzullo, Paola,Hyeraci, Mariafrancesca,Via, Lisa Dalla,Passarella, Daniele
supporting information, p. 895 - 898 (2020/03/16)
Betulinic acid is validated as a new self-assembly inducer for the formation of nanoparticles (NPs) in combination with different drugs. The target compounds are characterized by the presence of anticancer drugs acting on tubulin dynamics and of a linker that could be a carbon chain or a triazole-based one. Nanoparticles formed are characterized and their biological activity is evaluated.
Nanolipid-trehalose conjugates and nano-assemblies as putative autophagy inducers
Colombo, Eleonora,Biocotino, Michele,Frapporti, Giulia,Randazzo, Pietro,Christodoulou, Michael S.,Piccoli, Giovanni,Polito, Laura,Seneci, Pierfausto,Passarella, Daniele
, (2019/09/10)
The disaccharide trehalose is an autophagy inducer, but its pharmacological application is severely limited by its poor pharmacokinetics properties. Thus, trehalose was coupled via suitable spacers with squalene (in 1:2 and 1:1 stoichiometry) and with betulinic acid (1:2 stoichiometry), in order to yield the corresponding nanolipid-trehalose conjugates 1-Sq-mono, 2-Sq-bis and 3-Be-mono. The conjugates were assembled to produce the corresponding nano-assemblies (NAs) Sq-NA1, Sq-NA2 and Be-NA3. The synthetic and assembly protocols are described in detail. The resulting NAs were characterized in terms of loading and structure, and tested in vitro for their capability to induce autophagy. Our results are presented and thoroughly commented upon.
Synthesis of oxadiazole derivative of pentacyclic triterpenoid and its biological activity
Rasul, Mohammed Golam
, p. 1143 - 1147 (2019/07/12)
Triterpenoid betunilic acid is extracted from outer bark of Biscofia javanica blume from Darjeeling hilly region and carried out transformative reaction to introduce oxadiazole moiety to ring A of the triterpenoid which was identified as 28-carbomethoxy lupan (2,3-c)-1′,2′,5′-oxadiazole. The derivative obtained has been selected for its antibacterial and fungicidal activity at different concentrations with respect to the parent compound. The structures of these compounds were established based on spectroscopic (UV, IR, NMR) analysis.
Targeting mitochondria: Esters of rhodamine B with triterpenoids are mitocanic triggers of apoptosis
Wolfram, Ratna Kancana,Heller, Lucie,Csuk, René
supporting information, p. 21 - 30 (2018/04/26)
Triterpenoic acids, ursolic acid (1), oleanolic acid (2), glycyrrhetinic acid (3) and betulinic acid (4) were converted into their corresponding methyl 5–8 and benzyl esters 9–12 or benzyl amides 21–24. These derivatives served as starting materials for the synthesis of pink colored rhodamine B derivatives 25–36 which were screened for cytotoxicity in colorimetric SRB assays. All of the compounds were cytotoxic for a variety of human tumor cell lines. The activity of the benzyl ester derivatives 29–32 was lower than the cytotoxicity of the methyl esters 25–28. The benzyl amides 33–36 were the most cytotoxic compounds of this series. The most potential compound was a glycyrrhetinic acid rhodamine B benzyl amide 35. This compound showed activity against the different cancer cell lines in a two-digit to low three-digit nano-molar range. Staining experiments combined with fluorescence microscopy showed that this compound triggered apoptosis in A2780 ovarian carcinoma cells and acted as a mitocan.
Triterpenoids from the stem bark of Vitellaria paradoxa (Sapotaceae) and derived esters exhibit cytotoxicity against a breast cancer cell line
Eyong, Kenneth O.,Bairy, Guerisson,Eno, Anna A.,Taube, Joseph,Hull, Kenneth G.,Folefoc, Gabriel N.,Foyet, Harquin S.,Romo, Daniel
, p. 268 - 277 (2018/04/19)
A study of the chemical constituents of the stem bark of Vitellaria paradoxa (Sapotaceae) has resulted in the isolation and characterization of a new ursane-type triterpenoid, 2β,3β,19α-trihydroxyurs-12-en-28-oic acid (1), together with seven known compounds: betulinic acid (2), 1α,2β,3β,19α-tretrahydroxyurs-12-en-28-oic acid (3), β-sitosterol (7), sigmasterol (8), (-)-epicatechin (9), (+)-catechin (10) and quercetin (11). The structure of the novel, ursane-type acid 1 was elucidated on the basis of detailed spectroscopic analysis including IR, HRMS (ESI), 1D and 2D NMR and a comparison to previously described, related natural products. Preliminary cytotoxicity assays against the MDA-MB-231 breast cancer cell line indicated that betulinic acid 2 and its corresponding methyl ester 5 were the most active compounds tested with IC50 values of 19.9 μM (17.2–23.1 μM, 95% CI) and 32.9 μM (24.9–43.4 μM, 95% CI), respectively. Esterification of acids 1–3 afforded the corresponding methyl esters 4–6 for additional structure-activity relationship (SAR) analysis. In general, the activity against the MDA-MB-231 breast cancer cell line increased upon esterification of the triterpenoids screened.
Synthesis of Conjugates of Lupane-Type Pentacyclic Triterpenoids with 2-Aminoethane- and N-Methyl-2-Aminoethanesulfonic Acids. Assessment of in vitro Toxicity
Komissarova,Dubovitskii,Shitikova,Vyrypaev,Spirikhin,Eropkina,Lobova,Eropkin, M. Yu.,Yunusov
, p. 907 - 914 (2017/10/16)
Conjugates of betulin and betulinic and betulonic acids with 2-aminoethane- and N-methyl-2-aminoethanesulfonic acids were synthesized for the first time and were interesting as potential biologically active compounds. Experiments in vitro in MDCK cell culture using the MTT assay found that betulin and betulinic-acid derivatives with aminoethanesulfonic acid bound to triterpene C-3 or C-28 through an ester linker were less toxic than the native compounds.
Synthesis and cytotoxic activity of triterpenoid thiazoles derived from allobetulin, methyl betulonate, methyl oleanonate, and oleanonic acid
Borkova, Lucie,Adamek, Richard,Kalina, Petr,Dra?ar, Pavel,Dzubak, Petr,Gurska, Sona,Rehulka, Jiri,Hajduch, Marian,Urban, Milan,Sarek, Jan
supporting information, p. 390 - 398 (2017/12/07)
A total of 41 new triterpenoids were prepared from allobetulone, methyl betulonate, methyl oleanonate, and oleanonic acid to study their influence on cancer cells. Each 3-oxotriterpene was brominated at C2 and substituted with thiocyanate; subsequent cyclization with the appropriate ammonium salts gave N-substituted thiazoles. All compounds were tested for their in vitro cytotoxic activity on eight cancer cell lines and two non-cancer fibroblasts. 2-Bromoallobetulone (2b) methyl 2-bromobetulonate (3b), 2-bromooleanonic acid (5b), and 2- thiocyanooleanonic acid (5c) were best, with IC50 values less than 10 mm against CCRF-CEM cells (e.g., 3b: IC50=2.9 μm) as well as 2'-(diethylamino)olean-12(13)-eno[2,3-d]thiazole-28-oic acid (5 f, IC50=9.7 μm) and 2'-(N-methylpiperazino)olean-12(13)-eno[2,3-d]thiazole-28-oic acid (5k, IC50=11.4 μm). Compound 5c leads to the accumulation of cells in the G2 phase of the cell cycle and inhibits RNA and DNA synthesis significantly at 1xIC50. The G2/M cell-cycle arrest probably corresponds to the inhibition of DNA/RNA synthesis, similar to the mechanism of action of actinomycin D. Compound 5c is new, active, and nontoxic; it is therefore the most promising compound in this series for future drug development. Methyl 2-bromobetulonate (3b) and methyl 2-thiocyanometulonate (3c) were found to inhibit nucleic acid synthesis only at 5xIC50. We assume that in 3b and 3c (unlike in 5c), DNA/RNA inhibition is a nonspecific event, and an unknown primary cytotoxic target is activated at 1xIC50 or lower concentration.
Saponin of which monosaccharide units are D-mannose, as well as preparation method and application of saponin in pharmacy
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Paragraph 0034; 0035; 0036, (2016/11/17)
The invention belongs to the technical field of medicines, provides saponin of which monosaccharide units are D-mannose, as well as a preparation method and application of the saponin in pharmacy, and particularly relates to oleanolic acid saponin and betulinic acid saponin, of which the monosaccharide units are the D-mannose, a preparation method of the oleanolic acid saponin and the betulinic acid saponin, and the application of the oleanolic acid saponin and the betulinic acid saponin in preparation of anti-influenza medicines. According to the saponin disclosed by the invention, natural products including oleanolic acid and betulinic acid are used as raw materials, firstly ester groups are introduced at a C-28 position through structural modification, and then D-mannose in alpha-configuration is introduced at a C-3 position so that the saponin of which the monosaccharide units are the D-mannose and which can restrain highly pathogenic influenza virus H5N1 from infecting host cells is obtained. According to the saponin disclosed by the invention, pharmacological experiments are performed, results indicate that saponin compounds have an obvious effect of restraining the process that the highly pathogenic influenza virus H5N1 invades the host cells, and can be further used for preparing medicines for preventing or treating influenza viruses, and preparing medicines in united use with other antivirus medicines and medical compositions comprising the saponin.
