Mass Spectrometry (LC-MS-MS) As a Tool in the Maillard Reaction Optimisation and Characterisation of New 6-methoxy-tetrahydro-β-carboline Derivatives

Goh, Teik Beng; Mordi, Mohd Nizam; Mansor, Sharif Mahsufi

doi:10.17576/jsm-2015-4401-18

Cited by 4 publications

(12 citation statements)

References 11 publications

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“…The ion product 2b with an abundance of 38% was obtained by protonation of the hydroxy group on the furfuryl alcohol moiety, followed by elimination of H 2 O generating an ionic 2-methyl furan moiety at C-1 on 2b-1 ( Figure 2 B). The suggested mass fragmentation pathway of this β-carboline is well in agreement with similar compounds reported in literature [ 34 , 35 , 36 , 37 , 38 ]. The fragmentation behaviors of the predicted flazin derivative ( 2 ) with a piperidine ring having a furfuryl alcohol moiety at C-1 were proposed based on the observed MS 2 fragment values (m/z); I, compound 2 exact mass: 312.1110 (C 17 H 16 N 2 O 4 ); precursor ion ( 2a ), MS 1 : 313.1176 (C 17 H 17 N 2 O 4 + ); inducted ion ( 2a-1 ), MS 1 : 313.1176 (C 17 H 17 N 2 O 4 + ); product ion ( 2a-2 ) MS 2 : 240.1060 (C 15 H 14 N 2 O 4 + ); neutral loss: 75.0320 (C 2 H 5 NO 2 ).…”

Section: Resultssupporting

confidence: 90%

Food-Derived β-Carboline Alkaloids Ameliorate Lipid Droplet Accumulation in Human Hepatocytes

et al. 2022

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Lipid droplet accumulation (LDA) in hepatocytes is the initial stage of nonalcoholic fatty liver disease (NAFLD). In the search for natural compounds for the prevention of NAFLD, a series of β-carboline alkaloid derivatives, inspired by flazin and its derivative, newly identified in Crassostrea gigas Thunberg. extracts, were examined for LDA inhibition (LDAI) activity in oleic acid–loaded hepatocytes (HepG2). Eight compounds with a piperidine or pyridine C-ring were chemically synthesized (1–8). Among them, compounds 2 and 4 (flazin) with a carboxy group at C-3 and furfuryl alcohol moiety at C-1 showed low cytotoxicity and they exhibited significant LDAI activity. Compound 2 with piperidine C-ring was identified for the first time in C. gigas extract, and ameliorated the lipid accumulation with the LDAI value of 25.4%. Active compounds 2 and 4 significantly inhibited triacylglycerol species accumulation in cells. These compounds upregulated ATGL and downregulated SREBP1, FASN, and SCD1 genes, suggesting that they activated lipolysis and suppressed lipogenesis, respectively. These results suggest that β-carboline alkaloids, especially compounds 2 and 4, might be potentially useful for preventing NAFLD.

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Section: Resultssupporting

confidence: 90%

Food-Derived β-Carboline Alkaloids Ameliorate Lipid Droplet Accumulation in Human Hepatocytes

et al. 2022

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“…GNPS, a global interactive online platform, is one of the leading dereplication platforms for natural product chemistry. GNPS, which includes a mass spectrometry search tool (MASST) coupled with a reference database of food metabolites, is emerging as a powerful resource for understanding the molecular landscape of foods [32][33][34][35]. The metabolomic mass profiles of the eight selected BEs collected from the Hokkaido area were screened using the GNPS based on MS/MS data in the positive ionization mode.…”

Section: Resultsmentioning

confidence: 99%

“…This partially suggests the cleavage of glucoside metabolites to form aglycone metabolites and the appearance of new metabolites, including 34. The GNPS molecular network generated the data of ion parent detected from the BE initial sample (in green color), BE derivatized sample (purple), and a combination of both extract samples, leading to the identification of 16 molecules (34)(35)(36)(37)(38)(39)(40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50), including the unknown ion parent predicted to be β-carboline alkaloid 34 (Figure 3). The ion parents are represented by nodes in the molecular network (MN), with chemically related metabolites clustered together.…”

Section: Molecular Networking and Detection Of β-Carboline 34 In Modi...mentioning

confidence: 99%

“…The results demonstrated that 51 nodes were assigned to the parent ions of the beans, organized as 5 constructed clusters (Figure 3B). The detected unknown parent ion 339.1339 (34) in the GNPS database was predicted to be β-carboline with a piperidine C-ring and a vanillin moiety at C-1 corresponding to MS 1 : 339.1339 (C19H19NO4 + ). Thus, in this study, the targeted compound 34 was chemically prepared and its structure was confirmed by extensive spectroscopical analysis of the βcarboline alkaloid compound ( 1 H-NMR, 13 C-NMR, and Dept 135, Supporting Information).…”

Section: Molecular Networking and Detection Of β-Carboline 34 In Modi...mentioning

confidence: 99%

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Identification of a β-Carboline Alkaloid from Chemoselectively Derived Vanilla Bean Extract and Its Prevention of Lipid Droplet Accumulation in Human Hepatocytes (HepG2)

Dibwe,

Takeishi,

Oba

et al. 2023

Molecules

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Targeting bioactive compounds to prevent lipid droplet accumulation in the liver, we explored an antioxidative extract from vanilla bean (Vainilla planifolia) after chemo-selective derivatization through heating and acid modification. The chemical analysis of vanilla bean extract through chemoselective derivatization resulted in the identification of sixteen compounds (34–50) using LC-MS/MS analysis. A β-carboline alkaloid with a piperidine C-ring and a vanillin moiety at C-1 (34) was identified by molecular networking and diagnostic fragmentation filtering approaches. β-carboline alkaloid 34 exhibited significant inhibitory activity of lipid droplet accumulation (LDAI) in oleic acid-loaded hepatocellular carcinoma HepG2 cells. The LDAI activity was associated with both activation of lipolysis and suppression of lipogenesis in the cells. The study indicates that crude plant extracts, following chemoselective derivatization, may contain bioactive compounds that could be beneficial in preventing hepatosteatosis and could serve as a source of lead compounds for drug development. This approach may be useful to investigate other mixtures of natural products and food resources.

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“…The fragmentation behavior of indole alkaloids was found to be almost similar to that described in the literature. 39 MS/MS spectra of each compound are presented in Table S1.…”

Section: Tandem Mass Spectral Features Of the Analyzed Alkaloidsmentioning

confidence: 99%

High-Throughput Detection of an Alkaloidal Plant Metabolome in Plant Extracts Using LC-ESI-QTOF-MS

et al. 2021

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Plant alkaloids represent a diverse group of nitrogen-containing natural products. These compounds are considered valuable in drug discovery and development. High-throughput identification of such plant secondary metabolites in complex plant extracts is essential for drug discovery, lead optimization, and understanding the biological pathway. The present study aims to rapidly identify different classes of alkaloids in plant extracts through the liquid chromatography with electrospray ionization-tandem mass spectrometry (LC−ESI-MS/MS) approach using 161 isolated and purified alkaloids. These are biologically important unique alkaloids belonging to different sub-classes such as isoquinoline, quinoline, indole, tropane, pyridine, piperidine, quinolizidine, aporphine, steroidal, and terpenoid. The majority of these are not available commercially and are known to manifest valuable biological activities. Four pools of a maximum of 50 phytostandards each were prepared, based on their log P value to minimize co-elution for rapid and cost-effective analyses. MS/MS spectra were acquired in the positive ionization mode by using their [M + H] + and/or [M + Na] + with both the average collisional energy (25.5−62 eV) and individual collisional energies (10, 20, 30, and 40 eV). Accurate mass, high-resolution mass spectrometry (HR-MS) data, MS/MS data, and retention times were curated for each compound. The developed LC−MS/MS method was successfully used to interrogate and fast dereplicate alkaloids in 13 medicinal plant extracts and a herbal formulation. A total of 56 alkaloids were identified based on the reference standard retention times (RTs), HR-MS spectra, and/or MS/MS spectra. The MS data have been submitted to the MetaboLights online database (MTBLS2914). The mass spectrometric and chromatographic data will be useful for the discovery of new congeners and the study of biological pathways of alkaloids in the plant kingdom.

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Mass Spectrometry (LC-MS-MS) As a Tool in the Maillard Reaction Optimisation and Characterisation of New 6-methoxy-tetrahydro-β-carboline Derivatives

Cited by 4 publications

References 11 publications

Food-Derived β-Carboline Alkaloids Ameliorate Lipid Droplet Accumulation in Human Hepatocytes

Food-Derived β-Carboline Alkaloids Ameliorate Lipid Droplet Accumulation in Human Hepatocytes

Identification of a β-Carboline Alkaloid from Chemoselectively Derived Vanilla Bean Extract and Its Prevention of Lipid Droplet Accumulation in Human Hepatocytes (HepG2)

High-Throughput Detection of an Alkaloidal Plant Metabolome in Plant Extracts Using LC-ESI-QTOF-MS

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