Bioactive Oleanane, Lupane and Ursane Triterpene Acid Derivatives

Silva, Maria de L. e; David, Juceni P.; Silva, Lidércia C. R. C.; Santos, Rauldenis Almeida Fonseca; David, Jorge; Lima, Luciano da Silva; Reis, Pedro Sanches dos; Fontana, Renato

doi:10.3390/molecules171012197

Cited by 53 publications

(33 citation statements)

References 17 publications

(17 reference statements)

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“…In addition to a significant antitumor effect, betu linic acid shows antioxidant properties [16,17] and alcoholic extracts of plants containing betulinic acid also reveal the anti inflammatory effect [18]. This compound was found in experiments on obesity in rats [19] to inhibit lipase activity and induce adipocyte lipolysis.…”

Section: Introductionmentioning

confidence: 99%

Genotoxic and mutagenic properties of synthetic betulinic acid and betulonic acid

2015

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Section: Introductionmentioning

confidence: 99%

Genotoxic and mutagenic properties of synthetic betulinic acid and betulonic acid

2015

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“…Inspired by the cited evidence, in this study, we conjugated five different acyl OA derivatives ( 3a – 3e ) [15, 19, 20, 25, 26] with uracil. The synthetic routes are outlined in Schemes 1 and 2.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of acyl oleanolic acid-uracil conjugates and their anti-tumor activity

Wei-bin

Huang

et al. 2016

Chemistry Central Journal

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BackgroundOleanolic acid, which can be isolated from many foods and medicinal plants, has been reported to possess diverse biological activities. It has been found that the acylation of the hydroxyl groups of the A-ring in the triterpene skeleton of oleanolic acid could be favorable for biological activities. The pyrimidinyl group has been constructed in many new compounds in various anti-tumor studies.ResultsFive acyl oleanolic acid-uracil conjugates were synthesized. Most of the IC50 values of these conjugates were lower than 10.0 μM, and some of them were even under 0.1 μM. Cytotoxicity selectivity detection revealed that conjugate 4c exhibited low cytotoxicity towards the normal human liver cell line HL-7702. Further studies revealed that 4c clearly possessed apoptosis inducing effects, could arrest the Hep-G2 cell line in the G1 phase, induce late-stage apoptosis, and activate effector caspase-3/9 to trigger apoptosis.ConclusionsConjugates of five different acyl OA derivatives with uracil were synthesized and identified as possessing high selectivity toward tumor cell lines. These conjugates could induce apoptosis in Hep-G2 cells by triggering caspase-3/9 activity.Graphical abstractFive acyl oleanolic aicd-uracil conjugates were synthesized. These conjugates exhibited selective cytotoxicity toward tumor cells achieved via inducing apoptosis by activation of caspase-3/9. Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-016-0217-5) contains supplementary material, which is available to authorized users.

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“…1,2 Picene derivatives were found to be present in abundance as pentacyclic triterpenes and triterpenoids which are often bioactive and present a huge therapeutic potential. Many pentacyclic triterpenes namely oleane, oleanolic acid and ursane are reported to possess promising antitumor, [3][4][5] antiviral, 6 antidiabetic, 7 anti-inflammatory 8 activities. Also a derivative of picene, namely octadecahydro-picene-2,3,14,15-tetranone isolated and purified from the root bark of Zizyphus nummularia, reported to possess anti-cancer and anti-inflammatory activities.…”

Section: Introductionmentioning

confidence: 99%