2259-06-5Relevant articles and documents
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
, p. 895 - 898 (2020)
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.
The potential of Cyathus africanus for transformation of terpene substrates
McCook, Kayanne P.,Chen, Avril R.M.,Reynolds, William F.,Reese, Paul B.
, p. 61 - 66 (2012)
The insecticidal sesquiterpenes cadina-4,10(15)-dien-3-one and aromadendr-1(10)-en-9-one were administered to the fungus Cyathus africanus ATCC 35853. Biotransformation of the former produced (4R)-9α-hydroxycadin- 10(15)-en-3-one, while the latter gave 2β-hydroxyaromadendr-1(10)-en-9-one, 2α-hydroxyaromadendr-1(10)-en-9-one and 10α-hydroxy-1β, 2β-epoxyaromadendran-9-one. The bioconversion of santonin led to the production of two analogues, 11,13-dihydroxysantonin and the hitherto unreported 8α,13-dihydroxysantonin, while cedrol yielded 3β,8β- dihydroxycedrane and 3α,8β-dihydroxycedrane. Stemod-12-ene, a diterpene, was transformed to 2-oxostemar-13-ene, a hitherto unknown analogue with a rearranged carbon framework. When methyl betulonate, a triterpenoid belonging to the lupane family, was supplied to the fungus 18α-ursane and 18α-oleanane derivatives, namely 19β-hydroxy-3-oxo-18α-oleanan- 28-oic acid and 19α-hydroxy-3-oxo-18α-ursan-28-oic acids, were generated. There are no previous reports of fungal transformation of a triterpene in which a skeletal rearrangement occurred. All substrate administration experiments were done in the presence of the terpene cyclase inhibitor chlorocholine chloride (CCC), using the single phase - pulse feed method.
Synthesis of 30-amino derivatives of lupane triterpenoids
Uzenkova,Petrenko,Shakirov,Shul ts,Tolstikov
, p. 692 - 700 (2005)
New derivatives of betulin and betulinic acid containing various amines on C-30 that are of interest as potentially biologically active agents were prepared. 2005 Springer Science+Business Media, Inc.
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity
Santos, Rita C.,Salvador, Jorge A.R.,Marin, Silvia,Cascante, Marta
, p. 6241 - 6250 (2009)
A series of new imidazole carboxylic esters (carbamates) and N-acylimidazole derivatives of betulin and betulinic acid (14-29) have been synthesized. The new compounds were screened for in vitro cytotoxicity activity against human cancer cell lines HepG2, Jurkat and HeLa. A number of compounds have shown IC50 values lower than 2 μM against the cancer cell lines tested and the vast majority has shown a better cytotoxicity profile than betulinic acid, including the betulin derivatives. N-Acylimidazole derivatives 26 and 27 (IC50 0.8 and 1.7 μM in HepG2 cells) and the C-3 carbamate derivative 16 (IC50 2.0 μM in HepG2 cells) were the most promising compounds. Based on the observed cytotoxicity, structure-activity relationships have been established.
Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145
Martin, Glenroy D.A.,Reynolds, William F.,Reese, Paul B.
, p. 701 - 710 (2004)
A new stemodinoside, stemodin-α-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2α,7β,13(S)-trihydroxystemodane (17) and 2α,3β,13(S),16α-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6α,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2β,13(S)-dihydroxystemodane (10) by the fungus yielded 2β,7β,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7β,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion.
Influence of esterification and modification of A-ring in a group of lupane acids on their cytotoxicity
Urban, Milan,Sarek, Jan,Tislerova, Iva,Dzubak, Petr,Hajduch, Marian
, p. 5527 - 5535 (2005)
The aim of this work was to find an optimal ester group for preparation of lupane derivatives connecting high cytotoxicity with good chemical and pharmacological properties. Activities of methyl-, pivaloyloxymethyl- (Pom-), and acetoxymethyl- (Acm-) esters were compared with the activity of free acids. Although the methyl- and Pom-esters were generally less active than free acids, some Acm-esters had cytotoxicity similar to or even better than the starting compounds. Cytotoxic activity was measured in five cancer cell lines.
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)
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 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.
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.
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.
