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Simultaneous separation and identification of limonoids from citrus using liquid chromatography-collision-induced dissociation mass spectra 总被引:2,自引:0,他引:2
Limonoids are considered as potential cancer chemopreventive agents and are widely distributed in the Citrus genus as aglycones and glucosides. In the present study, reversed-phase HPLC coupled with CID mass spectra was developed for the simultaneous separation and identification of aglycones and glucosides of limonoids from citrus. Five aglycones such as limonin, deacetyl nomilin, ichangin, isolimonoic acid and nomilin were identified by positive ion CID MS/MS, whereas five glucosides, viz. limonin glucoside, isoobacunoic acid glucoside, obacunone glucoside, deacetyl nomilinic acid glucoside and nomilinic acid glucoside were analyzed by negative ion CID mass spectra. The developed method was successfully applied to complex citrus samples for the separation and identification of aglycones and glucosides. Citrus seeds were extracted with methanol and partially purified and analyzed by LC-CID mass spectra. The separation was achieved by C-18 column; eight limonoids were identified by comparing the retention times and mass spectral fragmentation. To the best of our knowledge, this is the first report on the identification of citrus limonoids using CID technique. 相似文献
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High performance liquid chromatography (HPLC) method has been developed for simultaneous quantification of limonoid aglycones and glucosides on a reversed phase C18 column using a binary solvent system, coupled with diode array detector. Seven limonoids such as limonin, nomilin, isolimonic acid, ichangin, isoobacunoic acid, limonin 17-β-d glucopyranoside and deacetyl nomilinic acid 17-β-d glucopyranoside were separated and detected at 210 nm. Furthermore, limonoids were separated, identified and quantified in four varieties of citrus fruits and seeds using developed method. Limonin and limonin glucoside were found to be the predominant limonoid aglycone and glucoside, respectively, in all tested samples. The sensitivity of the method was found to be 0.25–0.50 μg for tested limonoids. 相似文献
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Metal complexation and tandem mass spectrometry were used to differentiate C- and O-bonded flavonoid monoglucoside isomers. Electrospray ionization of solutions containing a flavonoid glycoside and a metal salt led to the generation of the key [M(II) (L) (L-H)](+) complexes, where M is the metal ion and L is the flavonoid glycoside. Thirteen flavonoid monoglucosides were examined in combination with Ca(II), Mg(II), Co(II), Ni(II), and Cu(II). Collisional activated dissociation (CAD) of the [M(II) (L) (L-H)](+) complexes resulted in diagnostic mass spectra, in contrast to the CAD mass spectra of the protonated, deprotonated, and sodium-cationized flavonoid glucosides. Five common sites of glycosylation could be predicted based on the fragmentation patterns of the flavonoid glucoside/magnesium complexes, while flavonoid glucoside/calcium complexes also were effective for location of the glycosylation site when MS(3) was employed. Cobalt, nickel and copper complexation had only limited success in this application. The metal complexation methods were also applied for characterization of a flavonoid rhamnoside, and the dissociation pathways of the metal complexes indicate that flavonoid rhamnosides have distinctive dissociation features from flavonoid glucosides. 相似文献
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Tian Q Li D Barbacci D Schwartz SJ Patil BS 《Rapid communications in mass spectrometry : RCM》2003,17(22):2517-2522
Electron ionization (EI) mass spectrometry was used to differentiate four structurally closely related citrus limonoid aglycones, including limonin, nomilin, obacunone, and deacetylnomilin. The limonoids were isolated and purified from citrus seeds. Structures of major fragment ions were elucidated by high-resolution mass spectrometry (HRMS) and fragmentation pathways were proposed. The fragmentation patterns observed in the EI spectra can be used as important references for the positive characterization of limonoid aglycones. 相似文献
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Lopes-Lutz D Dettmann J Nimalaratne C Schieber A 《Molecules (Basel, Switzerland)》2010,15(12):8543-8552
The phenolic profile of Amazon grape fruit (Pourouma cecropiifolia Martius) was investigated by high-performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS/MS). For this purpose, suitable extraction and liquid chromatographic methods were developed. Anthocyanins, flavonols and chlorogenic acids were found mainly in the peel. Besides the main anthocyanins, i.e. delphinidin 3-glucoside, cyanidin 3-glucoside and cyanidin 3-(6"-malonyl)glucoside, several minor anthocyanins were identified in the peel. Among these, cyanidin 3,5-diglucoside, delphinidin 3-galactoside, cyanidin 3-rutinoside, cyanidin 3-(3"-malonyl)glucoside, malvidin 3-glucoside, pelargonidin 3-glucoside, peonidin 3-glucoside and petunidin 3-glucoside were characterized on the basis of their fragmentation patterns in MS/MS experiments. The total anthocyanin content in the peel was 420.26±3.07 mg kg(-1) fresh weight. The pulp contained mainly 5-O-caffeoylquinic acid (210.39±3.43 mg kg(-1) fresh weight). Rutin was the predominant flavonol found in Amazon grape (peel 155.45 ± 2.06 mg kg(-1) fresh weight and pulp 2.64±1.21 mg kg(-1) fresh weight). Total polyphenols content was higher in the peel than in the pulp. 相似文献
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Iridoid and lignan glycosides from Citharexylum spinosum L 总被引:1,自引:0,他引:1
From the aerial parts of Citharexylum spinosum L., one new iridoid glucoside, the 7-ss-O-acetate (1) of lamiide, along with four known iridoid glucosides, lamiide (2), lamiidoside (3), duranterectoside C (4), 8-epiloganin (5) and one known lignan glucoside (+)-lyonirenisol-3a-O-ss-D-glucopyranoside (6) were isolated. The compound structures were established by one- and two-dimensional 1H- and 13C-NMR as well as by ESI-MS spectra. 相似文献
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Characterization of alkyl polyglycosides by both reversed-phase and normal-phase modes of high-performance liquid chromatography 总被引:4,自引:0,他引:4
Alkyl polyglycosides today represent the most important sugar surfactant. Nonionic sugar surfactants produced via different synthetic routes are mixtures of alkyl homologues, oligomers, anomers and isomers. Alkyl homologues and oligomers of alkyl mono- and diglucosides were separated by reversed-phase high-performance liquid chromatography (HPLC) with methanol-water as the mobile phase using a gradient elution. The gradient was optimized in respect to a simultaneous separation of alkyl glycosides according to their alkyl chain length and alkyl polyoxyethylene glucosides with regard to their length of the polyoxyethylene spacer. The separation of alkyl glycosides into alpha- and beta-anomers was carried out by normal-phase HPLC with isooctane-ethyl acetate (60:40, v/v)-2-propanol in the gradient mode. Light scattering detection was used. Matrix-assisted laser desorption ionization time-of-flight mass spectra of alkyl glucosides and dodecyl glucosides with oxyethylene spacer groups are presented. 相似文献
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高效液相色谱/电喷雾-离子阱-飞行时间质谱分析鉴定中药虎杖中的主要化学成分 总被引:3,自引:0,他引:3
建立了快速、准确鉴别中药虎杖中化学成分的液相色谱-质谱法。采用高效液相色谱/电喷雾-离子阱-飞行时间质谱(HPLC/ESI-IT-TOF MS)对蒽醌类以及羟基二苯乙烯类对照品,包括大黄素、大黄酚、大黄素甲醚、大黄酸、芦荟大黄素和虎杖苷进行了分析,总结其多级裂解规律。建立了虎杖甲醇提取物的液相色谱分离条件及质谱检测条件,根据负离子模式下获得的各组分多级质谱数据,对比对照品碎裂特征并参考文献,对主要色谱峰进行指认,共鉴别了10个化合物,包括白藜芦醇-4′-O-葡萄糖苷、虎杖苷、大黄素-8-O-葡萄糖苷、白藜芦醇、决明松-8-O-葡萄糖苷、大黄素-1-O-葡萄糖苷、决明松-8-O-(6′-乙酰基)葡萄糖苷、大黄素甲醚-8-O-葡萄糖苷、大黄素甲醚-8-O-(6′-乙酰基)葡萄糖苷和大黄素,其中决明松-8-O-(6′-乙酰基)葡萄糖苷和大黄素甲醚-8-O-(6′-乙酰基)葡萄糖苷为虎杖中新发现的成分。研究结果表明,在中药化学成分研究工作中,采用电喷雾-离子阱-飞行时间质谱可提高中药化学成分的分析效率并有利于新化合物的发现和鉴别。 相似文献
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E‐Hu Liu Ting Zhou Guo‐Bin Li Jing Li Xiu‐Ning Huang Feng Pan Ning Gao 《Journal of separation science》2012,35(2):263-272
The multiple bioactive constituents in Hedyotis diffusa Willd. (H. diffusa) were extracted and characterized by high‐performance liquid chromatography/electrospray ionization tandem mass spectrometry (HPLC‐ESI‐MSn). The optimized separation condition was obtained using an Agilent ZorBax SB‐C18 column (4.6×150 mm, 5 μm) and gradient elution with water (containing 0.1% formic acid) and acetonitrile (containing 0.1% formic acid), under which baseline separation for the majority of compounds was achieved. Among the compounds detected, 14 iridoid glucosides, 10 flavonoids, 7 anthraquinones, 1 coumarin and 1 triterpene were unambiguously identified or tentatively characterized based on their retention times and mass spectra in comparison with the data from standards or references. The fragmentation behavior for different types of constituents was also investigated, which could contribute to the elucidation of these constituents in H. diffusa. The present study reveals that even more iridoid glycosides were found in H. diffusa than hitherto assumed. The occurrence of two iridoid glucosides and five flavonoids in particular has not yet been described. This paper marks the first report on the structural characterization of chemical compounds in H. diffusa by a developed HPLC‐ESI‐MSn method. 相似文献
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E De Rijke A Zafra-Gómez F Ariese U A Brinkman C Gooije 《Journal of chromatography. A》2001,932(1-2):55-64
Isoflavones, their glucosides and their glucoside malonates were determined in red clover leaf extracts using reversed-phase LC coupled to atmospheric pressure chemical ionisation mass spectrometry (APCI-MS), UV and fluorescence detectors and the stability of the malonates was investigated. Extracts can be stored at least 1-2 weeks at -20 degrees C without loss of malonates. In LC-separated fractions the malonates are most stable when stored at low temperature after evaporation to dryness. The concentrations of eight major isoflavones ranged from 0.04 to 5 mg/g leaves. 相似文献
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Two major iridoid glucosides, namely plantarenaloside, a neurotrophic compound, and boschnaloside, an antibacterial iridoid glucoside, have been isolated from the shoots of Incarvillea emodi (a wild ornamental plant). The compounds are characterised by NMR spectral data and ESI mass spectrometery. This is the first ever report on the isolation of iridoid glucosides from I. emodi (Bignoniaceae). 相似文献
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The development of delayed bitterness in citrus products is a major problem to citrus producers and juice processors worldwide. A rapid and sensitive liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) method has been developed to quantify the recognized precursors of limonoid derived delayed bitterness, limonoate and nomilinoate A-ring lactones, in a wide variety of citrus juices. The limonoid A-ring lactones were isolated by solid-phase extraction from juice samples, analyzed by negative ion LC-ESI-MS and quantified utilizing the standard addition method. 相似文献
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While surfactants are commonly used in preparing protein samples, their presence in a protein sample can potentially affect the enzymatic digestion process and the subsequent analysis of the resulting peptides by mass spectrometry. The extent of the tolerance of matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) to surfactant interference in peptide analysis is very much dependent on the matrix/sample preparation method. In this work the effects of four commonly used surfactants, namely n-octyl glucoside (OG), Triton X-100 (TX-100), 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate (CHAPS) and sodium dodecyl sulfate (SDS), for biological sample preparation on trypsin digestion and MALDI-MS of the resulting digest are examined in detail within the context of using a two-layer method for MALDI matrix/sample preparation. Non-ionic and mild surfactants, such as OG, TX-100 or CHAPS, are found to have no significant effect on trypsin digestion with surfactant concentrations up to 1%. However, TX-100 and CHAPS interfere with the subsequent peptide analysis by MALDI-MS and should be removed prior to peptide analysis. OG is an MS-friendly surfactant and no effect is observed for MALDI peptide analysis. The effect of SDS on trypsin digestion in terms of the number of peptides generated and the overall protein sequence coverage by these peptides is found to be protein dependent. The use of SDS to solubilize hydrophobic membrane proteins, followed by trypsin digestion in the presence of 0.1% SDS, results in a peptide mixture that can be analyzed directly by MALDI-MS. These peptides are shown to provide better sequence coverage compared with those obtained without the use of SDS in the case of bacteriorhodopsin, a very hydrophobic transmembrane protein. This work illustrates that MALDI-MS with the two-layer sample preparation method can be used for direct analysis of protein digests with no or minimum sample cleanup after proteins are digested in a solution containing surfactants. 相似文献
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Otsuka H Shitamoto J He DH Matsunami K Shinzato T Aramoto M Takeda Y Kanchanapoom T 《Chemical & pharmaceutical bulletin》2007,55(11):1600-1605
Further extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of Tricalysia dubia afforded five new ent-kaurane glucosides (4-8) and one new labdane glucoside (9), together with a known megastigmane glucoside, sammangaoside B (1), and monoterpene glucosides (2, 3). The structures of the new compounds were elucidated by analyses of one- and two-dimensional NMR spectroscopic data. The absolute configuration of the 9-position of sammangaoside B was revised to S and its total stereochemistry was established by the modified Mosher's method. 相似文献
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Rui Min Vivian Goh Kim Huey Ee Aileen Pua Yunle Huang Shao Quan Liu Benjamin Lassabliere Bin Yu 《Journal of mass spectrometry : JMS》2022,57(2):e4810
In this study, neutral loss scan and high-resolution MS/MS were used in combination to detect and tentatively identify various flavonoid and limonoid glycosides in navel orange albedo, juice, peel and pulp. These compound classes are of research interest due to their flavour and bioactive properties, and although flavonoid glycosides have been previously studied in other food matrices, to the best of our knowledge, neutral loss scans have not been used for the elucidation of limonoid glycosides. Neutral loss masses of 120, 162 and 308 Da were selected for the detection of hexose, rutinose and neohesperidose-substituted flavonoids, whereas 197 Da was explored for limonoid glycosides due to their tendency to form ammonium adducts. Fragmentation patterns obtained from targeted MS/MS were then used to differentiate rutinose and neohesperidose substituents as well as flavonoid subclasses of flavones, flavanones and flavonols. Additionally, high-resolution MS/MS was also used for the identification of aglycones by accurate mass (to four decimal places), allowing for the differentiation of aglycones with similar unit masses but different chemical formulas. In total, 19 flavonoid glycosides and six limonoid glycosides were detected. This workflow allows for a rapid screening of flavonoid and limonoid glycosides in citrus, which can be further extended to other food products such as tea. 相似文献
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Tříska J Vrchotová N Olejníčková J Jílek R Sotolář R 《Molecules (Basel, Switzerland)》2012,17(3):2773-2783
A method for identification of highly fluorescent compounds in vine leaves infected by Plasmopara viticola was developed using reversed phase liquid chromatography with simultaneous diode array and fluorometric detection. Fluorescent compounds were extracted from leaves with a methanol-water mixture (70:30). Separation by HPLC was performed using a C(18) column and gradient elution with water-acetonitrile mixtures (20-80% of acetonitrile). The main unknown fluorescent compound was identified by line spectral comparison with a standard obtained by UV photoisomerization of trans-resveratrol glucoside, and its structure was confirmed by liquid chromatography-mass spectrometry. Identification and structural elucidation of the fluorescent compound in the leaves of Vitis vinifera allows early detection of Plasmopara viticola invasion. 相似文献