Solid-Phase Library Synthesis of Bi-Functional Derivatives of Oleanolic and Maslinic Acids and Their Cytotoxicity on Three Cancer Cell Lines

Parra, Andrés; Martin-Fonseca, Samuel; Rivas, Francisco; Reyes‐Zurita, Fernando J.; Medina-O'Donnell, Marta; Rufino‐Palomares, Eva E.; Martı́nez, Antonio; Garcı́a-Granados, Andrés; Lupiáñez, José A.; Alberício, Fernando

doi:10.1021/co500051z

Cited by 30 publications

(31 citation statements)

References 52 publications

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“…Notable among these products are pentacyclic triterpene compounds (oleanolic and maslinic acids) [37]. These natural pentacyclic triterpene compounds have revealed a wide variety of biological activities such as antiproliferative, anti-inflammatory, antiarthritic, antidiabetic, antiparasitic, antimicrobial, antiviral, anticancer, and hepatoprotective agents [38][39][40][41][42][43][44][45][46][47][48][49][50][51][52].…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted extraction versus Soxhlet extraction to determine triterpene acids in olive skins

et al. 2017

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Microwave-assisted extraction is compared with a more classical technique, Soxhlet extraction, to determine the content of triterpene acids in olive skins. The samples used in their original unmilled state and milled were extracted with ethyl acetate or methanol as solvents. The optimized operating conditions (e.g., amount and type of solvent, and time and temperature of extractions) to attain the better extraction yields have been established. For the identification and quantitation of the target compounds, an ultra high performance liquid chromatography with tandem mass spectrometry method was employed. The best results were achieved using the microwave-assisted extraction technique, which was much faster than the Soxhlet extraction method, and showed higher efficiency in the extraction of the triterpenic acids (oleanolic and maslinic).

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Section: Introductionmentioning

confidence: 99%

Microwave-assisted extraction versus Soxhlet extraction to determine triterpene acids in olive skins

et al. 2017

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“…or acyl chloride (4 equiv.) to get acyl oleanolic acid compounds (9)(10)(11)(12)(13)(14) at moderate yields of 61-89%. These acyl oleanolic acid 9-14 (1 equiv.)…”

Section: Synthesismentioning

confidence: 99%

Conjugation of Uridine with Oleanolic Acid Derivatives as Potential Antitumor Agents

Cheng

Huang

et al. 2016

Chem Biol Drug Des

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According to fused two bioactive moieties together by bonds covalently and available as a new single hybrid entity known as pharmacophore hybridization, a total of 10 targeted uridine-oleanolic acid hybrids were synthesized. Most of these hybrids showed excellent proliferation inhibition against tested Hep-G2, A549, BGC-823, MCF-7, and PC-3 tumor cell lines (IC50 < 8 μm), even with some IC50 values under 0.1 μm. The detection of cytotoxicity selectivity revealed that hybrids 5 and 18 exhibited low cytotoxicity toward normal human liver cell HL-7702. Further studies revealed that selected hybrid 5 could induce apoptosis in Hep-G2 cells through the investigation of acridine orange/ethidium bromide, Hoechst 33258 fluorescence stainings, and annexin V/propidium iodide assay. It was also found that hybrid 5 could induce mitochondrial membrane potential disruption, arrest Hep-G2 cell line at G1 phase, and activate effector caspase-3/9 to trigger cell apoptosis.

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“…And introduction of an extra N-substituent led to an increase in cytotoxicity (Kommera et al, 2010). (Parra et al, 2014) have shown that oleanolic and maslinic acids derivatives differing by 6 amino acids, coupled with the carboxyl group at C-28 of the triterpenoid skeleton, and by 10 different acyl groups attached to the hydroxyl groups of the A-ring, are more cytotoxic toward cancer cell lines B16-F10, HT29 and Hep G2 than their corresponding precursors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anticancer activity of aminopropoxytriterpenoids

et al. 2015

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Triterpenoids with aminopropoxy groups in C-28 or C-3 and C-28 positions were synthesized from betulin, erythrodiol, uvaol, oleantriol and betulinic acid Nmethylpiperazinylamide by cyanoethylation and the following catalytic hydrogenolysis. Computational estimating activity spectra of the designed compounds pointed out on their probable antineoplastic and proapoptotic activities. Their in vitro cytotoxic activity was evaluated at the National Cancer Institute, USA. Aminopropoxy derivatives of betulin, erythrodiol and oleantriol demonstrated the highest cytotoxic activity toward the most of 60 used tumor cell lines. Bisaminopropoxyerythrodiol revealed in vivo significant antineoplastic activity toward five mouse solid transplantable tumors. The results of in silico investigations and the efficacy of compounds in a broad panel of cell lines in vitro and the activity of bisaminopropoxyerythrodiol on the in vivo tumor models strongly suggest aminopropoxytriterpenoids as promising compounds for further investigation as anticancer agents. Graphical Abstract

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Solid-Phase Library Synthesis of Bi-Functional Derivatives of Oleanolic and Maslinic Acids and Their Cytotoxicity on Three Cancer Cell Lines

Cited by 30 publications

References 52 publications

Microwave-assisted extraction versus Soxhlet extraction to determine triterpene acids in olive skins

Microwave-assisted extraction versus Soxhlet extraction to determine triterpene acids in olive skins

Conjugation of Uridine with Oleanolic Acid Derivatives as Potential Antitumor Agents

Synthesis and anticancer activity of aminopropoxytriterpenoids

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