The analgesic and anti-inflammatory effect of new oleanolic acid acyloxyimino derivative

Bednarczyk–Cwynar, Barbara; Zaprutko, Lucjusz; Marciniak, Joanna; Lewandowski, Grzegorz; Szulc, Michał; Kamińska, Ewa; Wachowiak, Natalia; Mikolajczak, P.

doi:10.1016/j.ejps.2012.07.017

Cited by 38 publications

(31 citation statements)

References 32 publications

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“…All the new compounds showed a better effect in the TPA assay, with best activity for compounds 12, 14 and 15. (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) or reference drugs at the equimolar dose of 3.2 µmol/mouse for the AA and 1.4 µmol/mouse for the TPA assays, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Ferruginyl ibuprofenate (6) >1000 >1000 874 ± 34 Ferruginyl naproxenate (7) 945 ± 56 874 ± 49 >1000 Imbricatol-15-yl ibuprofenate (8) 34 ± 2 23 ± 1 79 ± 8 Imbricatol-15-yl ibuprofenate methyl ester (9) 706 ± 35 623 ± 39 746 ± 38 Imbricatol-15-yl naproxenate (10) 37 ± 2 29 ± 2 69 ± 4 Imbricatol-15-yl naproxenate methyl ester (11) 907 ± 54 601 ± 25 >1000 Oleanoyl ibuprofenate (12) 616 ± 32 526 ± 19 >1000 Oleanoyl ibuprofenate methyl ester (13) 402 ± 20 454 ± 21 742 ± 48 Oleanoyl naproxenate (14) 554 ± 22 486 ± 26 >1000 Oleanoyl naproxenate methyl ester (15) 816 ± 42 593 ± 31 >1000 The diterpene 2 presents cytotoxicity with IC50 values ranging from 111 to 148 µM. The derivatives 8 and 10 (IC50 values 23-79 µM and 29-69 µM, respectively) were more cytotoxic than the starting natural product and the synthetic anti-inflammatory agents alone.…”

Section: Estersmentioning

confidence: 99%

“…The triterpene oleanolic acid has been shown to display several relevant biological activities, including the modulation of the immune-inflammatory response [8], reduction of differentiation markers in adipocytes and suppression of inflammation associated with obesity [9]. The anti-inflammatory and analgesic effect of semisynthetic oleanolic acid derivatives was recently reported [10]. Pentacyclic triterpene acids from Ugni molinae leaves presented topical anti-inflammatory effect in mice [11].…”

Section: Introductionmentioning

confidence: 99%

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Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

et al. 2015

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Abstract:The aim of the study was to assess changes in the activity of anti-inflammatory terpenes from Chilean medicinal plants after the formation of derivatives incorporating synthetic anti-inflammatory agents. Ten new hybrid molecules were synthesized combining terpenes (ferruginol (1), imbricatolic acid (2) and oleanolic acid (3)) with ibuprofen (4) or naproxen (5). The topical anti-inflammatory activity of the compounds was assessed in mice by the arachidonic acid (AA) and 12-O-tetradecanoyl phorbol 13-acetate (TPA) induced ear edema assays. Basal cytotoxicity was determined towards human lung fibroblasts, gastric epithelial cells and hepatocytes. At 1.4 µmol/mouse, a strong anti-inflammatory effect in the TPA assay was observed for oleanoyl ibuprofenate 12 (79.9%) and oleanoyl ibuprofenate methyl ester 15 (80.0%). In the AA assay, the best activity was observed for 12 at 3.2 µmol/mouse, with 56.8% reduction of inflammation, in the same range as nimesulide (48.9%). All the OPEN ACCESSMolecules 2015, 20 11220 terpenyl-synthetic anti-inflammatory hybrids showed better effects in the TPA assay, with best activity for 6, 12 and 15. The cytotoxicity of the compounds 8 and 10 with a free COOH, was higher than that of 2. The derivatives from 3 were less toxic than the triterpene. Several of the new compounds presented better anti-inflammatory effect and lower cytotoxicity than the parent terpenes.

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Section: Resultsmentioning

confidence: 99%

Section: Estersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

et al. 2015

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“…These keto compounds were transformed via their oximes 35-38 into amines 39-42. Scheme 2. a. MeI, K2CO3, DMF, 24 h, 24 °C, 90%; b. allyl bromide, K2CO3, DMF, 24 h, 24 °C, 68%; c; benzyl bromide, K2CO3, DMF, 24 h, 24 °C, 87%; d. Jones oxidation: 28 (87%), 32 (89%), 33 (85%), 34 (88%); e. NH4OH.HCl, pyridine, 3 h reflux: 35 (93%), 36 (85%), 37 (84%), 38 (84%); f. NH4OAc, NaBH3CN, TiCl3, 24 h, 25 °C: 39 (43%), 40 (74%), 41 (42%), 42 (76%).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and cytotoxicity of 3-amino-glycyrrhetinic acid derivatives

Sahn¹,

Grupe²,

Heller³

et al. 2018

Mediterr.J.Chem.,

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The aim of this study was to prepare 3-hydroximino- and 3-amino derivatives of glycyrrhetinic acid and derivatives to evaluate their in vitro cytotoxicity for a panel of human tumor cell lines. Thus, commercially available glycyrrhetinic acid (1) was acetylated or oxidized at position C-3 and transformed into a variety of different esters and amides followed by their conversion to 3-oximes and amines. While the parent compound was not cytotoxic at all, the 3-amino esters are highly cytotoxic. Interestingly, 3-amino amides were significantly less cytotoxic than 3-amino esters. The (3b, 18b, 20b) Benzyl 3-amino-11-oxoolean-12-en-30-oate was the most cytotoxic compound of this series showing an EC50 = 1.3 mM for 518A2 melanoma cells.

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“…Therefore, terpenes containing the hydroxyl or hydroxyimino reactive groups can be used to prepare derivatives with the commercial anti-inflammatory drugs with a carboxylic function, leading to new dual compounds. Recently, its semi-synthetic acyloxyimino derivatives with analgesic and anti-inflammatory effects were also reported [9,10]. In the last decade NSAID drugs have been extensively investigated for anticancer and chemopreventive activity against various types of cancers [11,12].…”

Section: Introductionmentioning

confidence: 99%

Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives

et al. 2016

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Abstract:The current study focuses on the synthesis of several hybrid individuals combining a natural oleanolic acid skeleton and synthetic nonsteroidal anti-inflammatory drug moieties (NSAIDs). It studied structural modifications of the oleanolic acid structure by use of the direct reactivity of hydroxyl or hydroxyimino groups at position C-3 of the triterpenoid skeleton with the carboxylic function of anti-inflammatory drugs leading to new perspective compounds with high potential pharmacological activities. Novel ester-and iminoester-type derivatives of oleanolic unit with the different NSAIDs, such as ibuprofen, aspirin, naproxen, and ketoprofen, were obtained and characterized. Moreover, preliminary research of compounds obtaining structure stability under acidic conditions was examined and the PASS method of prediction of activity spectra for substances was used to estimate the potential biological activity of these compounds.

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The analgesic and anti-inflammatory effect of new oleanolic acid acyloxyimino derivative

Cited by 38 publications

References 32 publications

Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

Synthesis and cytotoxicity of 3-amino-glycyrrhetinic acid derivatives

Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives

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