Separação semipreparativa de α e β-amirina por cromatografia líquida de alta eficiência

Dias, Marluce Oliveira; Hamerski, Lidilhone; Pinto, Ângelo C.

doi:10.1590/s0100-40422011000400026

Cited by 39 publications

(32 citation statements)

References 3 publications

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“…Retention times were similar to those observed when these triterpenes were analyzed in mixture. 34 The 1 H and 13 C NMR spectra of compound 3 confirmed the structure of betulin (3). 24,25 For triterpene 4, in addition to six singlets for methyl groups (H-23 data available in the literature 24,35 allowed the unequivocal identification of this structure as 29-hydroxy-oleanolic acid (4).…”

Section: Resultsmentioning

confidence: 64%

Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis

Magina¹,

Dalmarco²,

Dalmarco³

et al. 2012

Quím. Nova

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Recebido em 10/10/11; aceito em 17/1/12; publicado na web em 15/5/12 A chemical investigation of Eugenia brasiliensis Lam. (Myrtaceae) leaves led to the isolation of a-amyrin and b-amyrin (in a mixture), betulin, 29-hydroxy-oleanolic acid, quercetin, catechin and gallocatechin. Herein, the identification of 29-hydroxy-oleanolic acid is reported for the first time in the Myrtaceae family. Moreover, in this study, the extract, fractions and six of the seven compounds were monitored for toxicity toward Artemia salina, antibacterial and acetylcholinesterase inhibitory activity. The crude ethanol extract of the leaves and fractions were found be active on A. salina toxicity bioassay.

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Section: Resultsmentioning

confidence: 64%

Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis

Magina¹,

Dalmarco²,

Dalmarco³

et al. 2012

Quím. Nova

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“…These triterpenes are promising raw materials for the semi-synthesis of triterpene derivatives, since these compounds are easily purified and available in high amounts throughout Amazon region. 25 However, the isomers are not easy to separate, 26 and have usually been studied as a binary mixture, especially α-amyrin and β-amyrin, from oleanane and ursane skeletons, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…26 The high purity of this mixture was considered based on the only two peaks in the analyses of gas chromatography (GC) and high performance liquid chromatography (HPLC). These two analyses, performed and published previously, were used to define, together with proton nuclear magnetic resonance ( 1 H NMR), the amount of these α-and β-amyrins in this mixture was 66 and 34%, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…For a solution of Protium resin 26 (0.100 g) in acetone (10 mL), Jones reagent was slowly added until green-blue color. Then, isopropanol (2 mL) was added and, after 10 min, the product was washed with aqueous solution of oxalic acid (10%, 3 × 10 mL) and water (3 × 10 mL), dried with sodium sulfate (Na 2 SO 4 ) and the solvent evaporated, under vacuum.…”

Section: Lup-20(29)-en-3-one (10)mentioning

confidence: 99%

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Anti-Trypanosoma Activity and Synergistic Effects of Natural and Semi-Synthetic Triterpenes and Predominant Cell Death through Autophagy in Amastigote Forms

Bossolani

Ueda-Nakamura

Silva

et al. 2017

J. Braz. Chem. Soc.

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Chagas' disease is a parasitic disease with unsatisfactory treatment, mainly in chronic stage. This study aimed to evaluate the trypanocidal activity and action mechanisms of α/β-amyrin and its semisynthetic derivatives, together with four isolated natural triterpenes, tested against trypomastigote and amastigote forms. The structure-activity relationship was suggested and cytotoxicity was measured. In general, greater polar compounds may have improved the selectivity to the protozoan. Action mechanisms were only performed for the amastigotes of Trypanosoma cruzi by evaluating the ultrastructural alterations, membrane permeability, mitochondrial membrane potential and cell volume, since the majority of compounds displayed promising antiamastigote activities. Triterpenes promoted changes on mitochondrial membrane potential and ultrastructural features that suggest autophagy processes. Both combinations between α/β-amyrin and 3-O-acetyl-11-oxo-α/β-amyrin and 3-O-acetyl-α/β-amyrin with benznidazole displayed synergistic effects against amastigotes and antagonistic effects on LLCMK 2 cells. The antiamastigote activities, chemical derivatization, drug combinations and action mechanisms revealed to be crucial approaches toward this chronic disease.

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“…The mixture of α/β-amyrin (31a, 31b), previously purified from Protium sp. resin, 42 and lupeol (19), derived from Vellozia sp., 43 were subjected to classic esterification and oxidation reactions to give derivatives in good yields (Schemes 1 and 2). These reference compounds were used in co-injection assays or for comparison of retention time as an additional tool to confirm GC-MS results (Supplementary Information).…”

Section: 35mentioning

confidence: 99%

Chemical Constituents of Psychotria nemorosa Gardner and Antinociceptive Activity

Calixto

Cordeiro

Giorno

et al. 2016

J. Braz. Chem. Soc.

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Through dereplication strategies using gas chromatography-mass spectrometry (GC-MS) and ultra fast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS), the ethanol extract from Psycotria nemorosa leaves (Rubiaceae) showed to be composed of: cinnamic acid, dihydroactinidiolide, 4-hydroxy-β-ionone, phytol, isophytol, 4,8,12,16-tetramethylheptadecan-4-olide, lupeol, a mixture of α/β-amyrin, the keto and acetylated derivatives, besides stigmast-4-en-3-one, campesterol, stigmasterol and γ-sitosterol by GC-MS. Likewise, by UFLC-MS/MS, the main compounds identified were: butin, resveratrol, rutin, kaempferol 7-O-β-D-glucopyranoside, deacetylasperuloside, epiloganin, hordenine, strictosidine, N-methyl-1,2,3,4-tetrahydro-β-carboline and N-formyl-tryptamine. The antinociceptive activity of the crude extract ant its fractions was reported.

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Separação semipreparativa de α e β-amirina por cromatografia líquida de alta eficiência

Cited by 39 publications

References 3 publications

Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis

Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis

Anti-Trypanosoma Activity and Synergistic Effects of Natural and Semi-Synthetic Triterpenes and Predominant Cell Death through Autophagy in Amastigote Forms

Chemical Constituents of Psychotria nemorosa Gardner and Antinociceptive Activity

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