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1.
Chem Biodivers ; 19(6): e202101004, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35514039

RESUMO

An undescribed C22-quassinoid named sergeolide A (1) and fifteen known quassinoids (2-16) were obtained from the seeds of Brucea javanica (Simaroubaceae). All chemical structures were established based on spectroscopic data and X-ray diffraction analysis. Sergeolide A (1) is the first example of a naturally occurring C22-quassinoid bearing a butenolide group fused the A ring of the bruceolide skeleton from Brucea genus. And this is the first report of the NMR data for desmethyl-bruceines B (2) and C (3) and the crystal structure for bruceolide (11). In addition, all isolates were evaluated for their anti-pancreatic adenocarcinoma activity by measuring the growth inhibitory of the MIA PaCa-2 cell lines. Consequently, compounds 1, 7-10, and 12-16 exhibited potent anti-pancreatic cancer activity in vitro (IC50 =0.054∼0.357 µM).


Assuntos
Adenocarcinoma , Brucea , Quassinas , Adenocarcinoma/tratamento farmacológico , Brucea/química , Brucea javanica , Humanos , Estrutura Molecular , Quassinas/análise , Quassinas/química , Quassinas/farmacologia , Sementes/química
2.
Acta Chim Slov ; 68(4): 765-772, 2021 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-34918749

RESUMO

Phytochemicals in the water extract of Eurycoma longofolia roots were identified using both solid-liquid and liquid-liquid extraction based fractionation techniques. A reversed phase C18 solid phase extraction (SPE) was used as solid-liquid extraction, whereas solvent partition was applied as liquid-liquid extraction. Total saponin was increased after fractionation. A few known quassinoids; eurycomanone, 13a(21)-epoxyeurycomanone, pasakbumin D, 13ß,18-dihydroeurycomanol and 13ß,21-dihydroxyeurycomanol were identified from the 40% and 60% methanol fractions of SPE. Solvent partition extract using ethyl acetate was found to have the highest saponin content compared to butanol and chloroform fractions. Subsequent acetone precipitation of the organic fractions recovered a formylated hexose trimer and other saccharide-containing compounds. Ethyl acetate effectively recovered saponins from E. longofolia water extract using liquid-liquid extraction followed by acetone precipitation.


Assuntos
Eurycoma/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Cromatografia Líquida de Alta Pressão , Eurycoma/metabolismo , Extração Líquido-Líquido , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/análise , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Quassinas/análise , Quassinas/isolamento & purificação , Extração em Fase Sólida , Solventes/química , Espectrometria de Massas em Tandem , Água/química
3.
Pak J Biol Sci ; 24(12): 1226-1235, 2021 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34989200

RESUMO

<b>Background and Objective:</b> The use of the roots of the pasak bumi (<i>E. longifolia</i> Jack) to treat cancer has been studied widely, however, the scientific basis of these plants used as an anticancer drug is widely unknown. The purpose of this study was to examine the anticancer activity of ethyl acetate and non-ethyl acetate fractions of pasak bumi roots in Raji cells. <b>Materials and Methods:</b> The cytotoxicity test is using the direct cell count method with trypan blue staining. The growth inhibition is using doubling time analysis of Raji cells. Observation of the apoptotic events of Raji cells used ethidium bromide staining, while observing the expression of p53 protein in Raji cells was done by immunohistochemical staining. <b>Results:</b> The results of the cytotoxicity and doubling time test showed that the activity of the non-ethyl acetate fraction was greater than that of the roots of pasak bumi. The lower concentration of non-ethyl acetate fraction of pasak bumi roots was able to delay the multiplication time of Raji cells which was greater than that of ethyl acetate. The results of the cytotoxicity and doubling time test showed that the activity of the non-ethyl acetate fraction was greater than that of the roots of pasak bumi. <b>Conclusion:</b> It can be concluded that the ethyl acetate and non-ethyl acetate fractions of the roots of pasak bumi have cytotoxic and antiproliferative activity on Raji cells, however they cannot induce apoptosis in Raji cells. The death of Raji cells is through the mechanism of inhibiting Raji cell proliferation as evidenced by an increase in p53 protein expression.


Assuntos
Antineoplásicos/análise , Extratos Vegetais/farmacologia , Quassinas/metabolismo , Rajidae/metabolismo , Animais , Antineoplásicos/metabolismo , Extratos Vegetais/análise , Extratos Vegetais/metabolismo , Extratos Vegetais/uso terapêutico , Quassinas/análise
4.
Biomed Chromatogr ; 32(12): e4358, 2018 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-30089336

RESUMO

Brusatol, a quassinoid isolated from the traditional Chinese medicine Brucea javanica, has been reported to be an inhibitor of Nrf2 pathway and has great potential to be developed into a novel chemotherapeutic adjuvant. However, the in vivo process of brusatol has not been comprehensively explained yet. Therefore, this paper focused on the pharmacokinetic metabolism and excretion of brusatol in rats using a simple and reproducible LC-MS/MS method. The results indicated that the plasma concentration of brusatol decreased rapidly; the average cumulative excretion rate in urine was 5.82% during 24 h, and 0.71% in bile during 12 h. High-resolution mass spectrometry was applied for the identification of metabolites; as a result, four metabolites were detected and the structure was tentatively deduced on the base of the MS2 data, Compound Discoverer 2.0 and Mass Frontier 7.0 software. Hydroxylation, hydrolysis and glucuronidation were suggested as major metabolic pathways in vivo. The in vivo process and detection of metabolites of brusatol might improve the understanding of the mechanism of its anticancer effect and provide valuable information for its safety estimation, which will be essential to the new drug development.


Assuntos
Metabolômica/métodos , Quassinas/análise , Quassinas/farmacocinética , Animais , Fezes/química , Limite de Detecção , Modelos Lineares , Masculino , Metaboloma , Quassinas/metabolismo , Ratos , Ratos Wistar , Reprodutibilidade dos Testes
5.
Fitoterapia ; 124: 188-192, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29154863

RESUMO

Aqueous extracts of the roots of Eurycoma longifolia are traditionally used to improve sexual performance, to treat infertility and other sexual dysfunctions but also to increase muscle strength. Nowadays, many different products are commercially available which are promoted as E. longifolia extracts and claim to possess beneficial aphrodisiac effects. Since such herbal aphrodisiac preparations have been recently the target of fraudulent product counterfeiting and because eurycomanone, one of the main quassinoids of E. longifolia, is suspected to possess toxic effects at higher concentrations, a highly selective HPLC-DAD/ELSD method has been established to analyze commercially available products and extracts of plant material. The presented method was established by the use of a mixture of 27 reference compounds for qualitative issues and fully validated according to the ICH guidelines for the quantification of three quassinoides: laurycolactone A, longilactone, and eurycomanone. The calibration curves of these showed a linearity over a range of 0.05 to 1.0mg/ml, with a regression coefficient not lower than R2=0.9969. The inter-day and intra-day precision (indicated as relative standard deviation) of the developed method was <2.9%. The recovery ranged from -3.3% to +6.0%. Eight randomly purchased products have been analyzed with this method, but only five of them contained E. longifolia compounds in detectable amounts. The concentration of eurycomanone in these products varied from 0.22±0.002mg eurycomanone per capsule to 1.84±0.08mg corresponding to a maximal recommended daily intake of 0.76±0.02 to 31.90±0.21mg.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Eurycoma/química , Extratos Vegetais/análise , Raízes de Plantas/química , Quassinas/análise
6.
Pharm Biol ; 55(1): 2234-2239, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-29130786

RESUMO

CONTEXT: Eurycomanone is found in the Eurycoma longifolia Jack (Simaroubaceae) tree, exhibits significant antimalarial activity, improves spermatogenesis, suppresses expression of lung cancer cell tumour markers and regulates signalling pathways involved in proliferation, cell death and inflammation. OBJECTIVES: Establishment of cell suspension culture of E. longifolia to determine the eurycomanone accumulation during cultures. MATERIALS AND METHODS: Callus of E. longifolia was cultured in MS medium supplemented with 0.8% agar, 30/L sucrose, 1.25 mg/L NAA and 1 mg/L KIN for biomass production. Cell suspension culture was established by transferring friable calli to the same medium without agar. Eurycomanone content during cell culture was determined by HPLC with a C18 column, flow rate of 0.8 mL/min, run time of 17.5 min, detector wavelength of 254 nm. The stationary phase was silica gel and the mobile phase was acetonitric:H2O. Roots of 5 year-old trees were used as the control. RESULTS: The cells from 3 g of inoculum increased in biomass with a maximum value of 16 g fresh weight (0.7 g dry weight) at 14th day of culture. The cell growth then decreased from day 14 to day 20. Eurycomanone was produced during culture from the beginning to 20th day, its highest content (1.7 mg/g dry weight) also obtained at 14th day (the control is 2.1 mg/g dry weight). DISCUSSION AND CONCLUSIONS: Cell suspension culture of E. longifolia is a suitable procedure to produce eurycomanone. The yield of eurycomanone biosynthesis in 14 days-old cells are relatively high, approximately 0.8 times the control.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Eurycoma/química , Extratos Vegetais/isolamento & purificação , Quassinas/isolamento & purificação , Biomassa , Técnicas de Cultura de Células , Extratos Vegetais/análise , Extratos Vegetais/biossíntese , Raízes de Plantas , Quassinas/análise , Quassinas/biossíntese , Fatores de Tempo
7.
Biomed Chromatogr ; 30(11): 1873-1876, 2016 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-27012305

RESUMO

A sensitive LC-MS/MS method for the determination of bruceine D in rat plasma was developed. The analyte and IS were separated on a Luna C18 column (2.1 × 50 mm, 1.7 µm) using a mobile phase of acetonitrile and 0.1% formic acid in water (40:60, v/v) at a flow rate of 0.25 mL/min. The selected reaction monitoring mode was chosen to monitor the precursor-to-product ion transitions of m/z 409.2 → 373.2 for bruceine D and m/z 469.2 → 229.3 for IS using a negative ESI mode. The method was validated over a concentration range of 0.5-2000 ng/mL for bruceine D. Total chromatography time for each run was 3.5 min. The method was successfully applied to a pharmacokinetic study of bruceine D in rats. Copyright © 2016 John Wiley & Sons, Ltd.


Assuntos
Antimaláricos/sangue , Antineoplásicos Fitogênicos/sangue , Cromatografia Líquida de Alta Pressão/métodos , Quassinas/sangue , Espectrometria de Massas em Tandem/métodos , Animais , Antimaláricos/análise , Antineoplásicos Fitogênicos/análise , Brucea/química , Limite de Detecção , Masculino , Quassinas/análise , Ratos , Ratos Sprague-Dawley , Reprodutibilidade dos Testes , Espectrometria de Massas por Ionização por Electrospray/métodos
8.
Shokuhin Eiseigaku Zasshi ; 56(5): 185-93, 2015.
Artigo em Japonês | MEDLINE | ID: mdl-26537647

RESUMO

A novel HPLC-based method employing molar absorption coefficient ratios to 4-hydroxybenzoic acid (4HBA) was developed for the determination of quassin and neoquassin in Jamaica quassia extract, which is used as a food additive in Japan. Based on comparisons of quantitative NMR (qNMR) spectra and HPLC chromatograms of an artificial mixture of quassin, neoquassin, and 4HBA, the molar absorption coefficient ratios of quassin and neoquassin to 4HBA were determined as 0.84 and 0.85, respectively. Quassin and neoquassin were quantified in food additives by qNMR and HPLC based on molar absorption coefficient ratios using 1,4-bis(trimethylsilyl)benzene-d4 and 4HBA as internal standards, respectively. The differences in quantitation values between qNMR and HPLC analyses were below 1.2%. Our proposed novel HPLC-based quantitation method employing the molar absorption coefficient ratios is a reliable tool for determining levels of quassin and neoquassin in food additives and processed foods.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Aditivos Alimentares/química , Extratos Vegetais/química , Quassia/química , Quassinas/análise , Análise de Alimentos/métodos , Hidroxibenzoatos , Espectroscopia de Ressonância Magnética/métodos
9.
J Sep Sci ; 38(13): 2260-6, 2015 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-25914245

RESUMO

Tongkat Ali (Eurycoma longifolia) is one of the most popular traditional herbs in Southeast Asia and generally consumed as forms of dietary supplements, tea, or drink additives for coffee or energy beverages. In this study, the liquid chromatography with tandem mass spectrometry method for the simultaneous quantitation of six major quassinoids of Tongkat Ali (eurycomanone, 13,21-dihydroeurycomanone, 13α(21)-epoxyeurycomanone, 14,15ß-dihydroxyklaineanone, eurycomalactone, and longilactone) was developed and validated. Using the developed method, the content of the six quassinoids was measured in Tongkat Ali containing dietary supplement tablets or capsules, and the resulting data were used to confirm the presence of Tongkat Ali in those products. Among the six quassinoids, eurycomanone was the most abundant quassinoid in all samples tested. The developed method would be useful for the quality assessment of Tongkat Ali containing dietary supplements.


Assuntos
Cromatografia Líquida/métodos , Suplementos Nutricionais/análise , Eurycoma/química , Quassinas/análise , Espectrometria de Massas em Tandem/métodos
10.
J Chromatogr A ; 1218(14): 1861-77, 2011 Apr 08.
Artigo em Inglês | MEDLINE | ID: mdl-21367427

RESUMO

An extensive comparative study on the electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) mass spectrometry using automated flow injection analysis (FIA), was performed on eurycomanone (1), 13α(21)-epoxyeurycomanone (2), eurycomanol (3), eurycomanol-2-O-ß-d-glucopyranoside (4), and 13,21-dihydroeurycomanone (5), the bioactive markers isolated from Eurycoma longifolia. The effects of eluent mixture (methanol or acetonitrile in water) and acidic modifiers (acetic acid, formic acid and trifluoroacetic acid) on the ionization efficiency of the markers were also investigated. The ESI in the positive ion mode with methanol containing 0.1% (v/v) acetic acid was selected for the subsequent optimization of nebulizer pressure, dry gas flow, dry gas temperature and capillary voltage to improve the sensitivity of the total ion chromatogram (TIC). Fragmentation of the analytes was further investigated by varying the capillary exit offset voltage and fragmentation amplitude in positive mode of ESI. The detection limits (LODs) were determined in isolation mode (selected ion monitoring, SIM). Their limits of detection (LODs) ranged between 0.03 and 0.1µgmL(-1) while the intra-day and inter-day precisions were less than 5.72% and 4.82%, respectively. The method was next applied for the simultaneous analysis of the markers to standardize various batches of manufactured extracts of E. longifolia for potential use as antimalarial products. Multiple Reaction Monitoring (MRM) mode was used for the quantification of analytes which gave protonated molecular ion, [M+H](+). For those without pseudo-molecular ions, SIM mode was used to quantify the analytes. The batches contained 5.65-9.95% of eurycomanone (1), 5.21-19.75% of eurycomanol (3) and 7.59-19.95% of eurycomanol-2-O-ß-d-glucopyranoside (4) as major quassinoids whereas, 13α(21)-epoxyeurycomanone (2), and 13,21-dihydroeurycomanone (5) were much lower in concentrations of 0.78-3.90% and 0.47-1.76%, respectively.


Assuntos
Antimaláricos/química , Cromatografia Líquida/métodos , Eurycoma/química , Extratos Vegetais/química , Quassinas/análise , Espectrometria de Massas por Ionização por Electrospray/métodos , Antimaláricos/normas , Análise de Injeção de Fluxo/métodos , Modelos Lineares , Quassinas/isolamento & purificação , Reprodutibilidade dos Testes , Sensibilidade e Especificidade
11.
J Agric Food Chem ; 58(5): 2807-11, 2010 Mar 10.
Artigo em Inglês | MEDLINE | ID: mdl-20196620

RESUMO

Quassia amara wood chips are used by organic farmers as a valid alternative to synthetic insecticides. The powder of Q. amara contains high levels of quassin, neoquassin and picrasinoside B. In this study we developed a liquid chromatography mass spectrometry method for the rapid and accurate quantification of the insecticide quassinoids on fruits and vegetables. Quassinoids were extracted from fruits and vegetables with acetonitrile and separated on a Zorbax Column Eclipse XDB C8 by isocratic elution with a mobile phase consisting of water and methanol with 0.1% of formic acid. Using a high-performance liquid chromatograph coupled with an electrospray ionization tandem mass spectrometer (HPLC/ESI-MS/MS), quassinoids were selectively and simultaneously detected monitoring the multiple reaction (MRM) transitions of proton adduct precursor ions: m/z 389.5 --> 222.9 for quassin, 391.5 --> 372.9 for neoquassin and 576.1 --> 394.5 for picrasinoside B. For all quassinoids calibration was linear over a working range of 1 and 100 microg/kg with r > 0.991. Limit of determination (LOD) and limit of quantification (LOQ) for both quassinoids were 0.5 and 1 microg/kg respectively while for picrasinoside B they were 5 and 10 microg/kg. Quassinoid recoveries ranged from 85.3% to 105.3% with coefficients of variation between 2.5% and 12.8% for fruit and vegetables. The presence of interfering compounds in the fruit and vegetable extract was evaluated and found to be minimal. Due to the linear behavior it was concluded that the multiple reaction transitions of precursor ions can be used for analytical purposes, i.e. for identification and quantification of quassin, neoquassin, and picrasinoside B in fruit and vegetable extracts at trace levels.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Quassinas/análise , Espectrometria de Massas por Ionização por Electrospray/métodos , Espectrometria de Massas em Tandem/métodos , Limite de Detecção
12.
J Ethnopharmacol ; 111(1): 40-2, 2007 Apr 20.
Artigo em Inglês | MEDLINE | ID: mdl-17157466

RESUMO

In French Guiana, Quassia amara L. (Simaroubaceae) leaf tea is a well-known widely used traditional antimalarial remedy. Impact of the vegetal sampling condition on in vivo and in vitro antimalarial activity was assessed. Traditional infusions were prepared with juvenile or mature leaves, both either fresh or dried. Results showed that growing stage and freshness of vegetal material exert a striking effect on antimalarial activity, both in vitro and in vivo. By far, leaf tea made from fresh juvenile (FJ) Quassia amara leaves was the most active. In vitro, active component (simalikalactone D) concentration correlates biological activities, although unexplained subtle variations were observed. In vivo, tea made with dried juvenile (DJ) leaves displays a peculiar behavior, meaning that some components may help simalikalactone D delivery or may be active in vivo only, therefore enhancing the expected curative effect of the traditional preparation.


Assuntos
Antimaláricos/farmacologia , Bebidas , Dessecação , Malária/tratamento farmacológico , Plasmodium falciparum/efeitos dos fármacos , Plasmodium yoelii , Quassia/crescimento & desenvolvimento , Animais , Antimaláricos/química , Antimaláricos/normas , Antimaláricos/uso terapêutico , Cromatografia Líquida de Alta Pressão , Guiana Francesa , Malária/parasitologia , Camundongos , Testes de Sensibilidade Parasitária , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Folhas de Planta/crescimento & desenvolvimento , Controle de Qualidade , Quassia/química , Quassinas/análise
13.
Shokuhin Eiseigaku Zasshi ; 44(6): 328-31, 2003 Dec.
Artigo em Japonês | MEDLINE | ID: mdl-15038116

RESUMO

Jamaica quassia extract, a natural bittering agent, is described as "a substance extracted from bark of Jamaica quassia (Quassia excelsa Sw.)" in the List of Existing Food Additives in Japan. The constituents in Jamaica quassia extract product were investigated as a part of an ongoing study to evaluate its quality and safety as a food additive. The main constituents of the extract were identified as quassin and two isomers of neoquassin by using LC/MS. The main constituent, quassin, was isolated and the structure was determined by spectral means. The quantification of their main constituents was performed by HPLC using quassin as a standard, and the concentrations of quassin and total of neoquassin isomers were 21.4% and 55.5%. In addition, it was confirmed that Jamaica quassia extract was different from quassia extract, which is extracted from bark of Picrasma quassioides Benn. belonging to the same family as Q. excelsa, by comparing their HPLC profiles.


Assuntos
Aditivos Alimentares/análise , Quassia/química , Cromatografia Líquida de Alta Pressão , Cromatografia Líquida , Espectrometria de Massas , Extratos Vegetais/análise , Quassinas/análise
14.
Zhong Yao Cai ; 21(8): 398-400, 1998 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-12569845

RESUMO

Three active components were isolated from treated dry-fruits of Brucea javanica (L.) Merr by chromatographic methods, and they were identified as Brusatol (I), Bruceine D (II), Bruceosidae A (III) by means of UV, IR, 1H-NMR, 13C-NMR spectroscopic analysis methods.


Assuntos
Brucea/química , Plantas Medicinais/química , Quassinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Quassinas/análise , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta
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