Discovery of Neolignan Glycosides with Acetylcolinesterase Inhibitory Activity from Huangjinya Green Tea Guided by Ultra Performance Liquid Chromatography–Tandem Mass Spectrometry Data and Global Natural Product Social Molecular Networking

Wu, Hao-Yue; Ke, Jia-Ping; Wang, Wei; Kong, Ya-Shuai; Zhang, Peng; Ling, Tie-Jun; Bao, Guan‐Hu

doi:10.1021/acs.jafc.9b05605

Cited by 22 publications

(10 citation statements)

References 31 publications

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“…The sample was macerated in potassium bromide (99.99%, Sigma-Aldrich) and fused in a pellet under pressure. The H and 13 C NMR analyses of compounds 1-8 were conducted on a spectrometer Bruker DRX-400, operating at MHz for Fig. S18.…”

Section: Experimental Information -Ir Nmr and Gc-ms Analysismentioning

confidence: 99%

Should We Think Positive or Negative About Dihydrobenzofuran Neolignans? an ESI-MS/MS Study

Dias¹,

Crevelin²,

Palaretti³

et al. 2020

Preprint

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This study elucidates the gas-phase fragmentation pathways of a series of biologically active benzofuran neolignans (BNs) and dihydrobenzofuran neolignans (DBNs) by means of electrospray ionization accurate-mass tandem and sequential mass spectrometry (ESI-MS/MS and ESI-MSn) and thermochemical data estimated by using Computational Chemistry and the B3LYP/6-31+G(d,p) model. In their deprotonated forms, these compounds produced more diagnostic product ions as compared to the corresponding protonated molecules. Moreover, a series of odd-electron product ions (radical anions) were detected, which has not been reported for protonated DBNs. Direct C2H3O2• elimination from the precursor ion (deprotonated molecule) only occurred for the BNs and can help to distinguish these compounds from the DBNs. Although the product ion [M‒CH3OH]‒ emerged in the spectrum of all the DBNs analyzed here, the mechanism through which this ion originates strongly depends on specific structural features, so that further [M‒CH3OH]‒ fragmentation generates important diagnostic product ions. Comparison between the ESI-MS/MS data of these compounds in the negative ion mode (deprotonated molecule) and in the positive ion mode (protonated molecule) revealed that the negative ion mode provides much more information (at least one diagnostic product ion emerged for all the analyzed compounds) and does not require the use of additives to produce the precursor ions (deprotonated molecules).

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Section: Experimental Information -Ir Nmr and Gc-ms Analysismentioning

confidence: 99%

Should We Think Positive or Negative About Dihydrobenzofuran Neolignans? an ESI-MS/MS Study

Dias¹,

Crevelin²,

Palaretti³

et al. 2020

Preprint

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show abstract

“…Although nuclear magnetic resonance (NMR) spectroscopy is the technique of choice to elucidate the structure of DBNs and BNs, electrospray ionization mass spectrometry (ESI‐MS) has been extensively used to identify these compounds in complex mixtures (e.g. crude plant extracts) or at very low concentrations 11–13 . For this purpose, ESI tandem mass spectrometry (ESI‐MS/MS) is combined with liquid chromatography (LC), thus avoiding the need for purifying and re‐isolating known compounds 11–13 .…”

Section: Introductionmentioning

confidence: 99%

“…crude plant extracts) or at very low concentrations. [11][12][13] For this purpose, ESI tandem mass spectrometry (ESI-MS/MS) is combined with liquid chromatography (LC), thus avoiding the need for purifying and re-isolating known compounds. [11][12][13] However, in these cases, knowledge of the fragmentation pattern of the compounds under ESI-MS/MS conditions is often necessary.…”

Section: Introductionmentioning

confidence: 99%

“…[11][12][13] For this purpose, ESI tandem mass spectrometry (ESI-MS/MS) is combined with liquid chromatography (LC), thus avoiding the need for purifying and re-isolating known compounds. [11][12][13] However, in these cases, knowledge of the fragmentation pattern of the compounds under ESI-MS/MS conditions is often necessary. 14 Recently, Dias and co-workers systematically investigated the gasphase fragmentation of protonated DBNs 1-5 and 7 and BNs 6 and 8 ( Figure 1) by combining experimental ESI-MS/MS, accurate-mass data, multiple-stage mass spectrometry (MS n ), and thermochemical data estimated using computational chemistry.…”

Section: Introductionmentioning

confidence: 99%

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Electrospray ionization tandem mass spectrometry of deprotonated dihydrobenzofuran neolignans

Dias

Crevelin

Palaretti

et al. 2020

Rapid Comm Mass Spectrometry

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RationaleAlthough dihydrobenzofuran neolignans (DBNs) display a wide diversity of biological activities, the identification of their in vivo metabolites using liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI‐MS/MS) remains a challenge to be overcome. Recently, ESI‐MS/MS data of protonated DBNs have been reported, but they were shown to be limited due to the scarcity of diagnostic ions.MethodsThe gas‐phase fragmentation pathways of a series of biologically active synthetic benzofuran neolignans (BNs) and DBNs were elucidated by means of negative ESI accurate‐mass tandem and sequential mass spectrometry, and thermochemical data estimated using computational chemistry and the B3LYP/6‐31+G(d,p) model.ResultsDeprotonated DBNs produced more diagnostic product ions than the corresponding protonated molecules. Moreover, a series of odd‐electron product ions (radical anions) were detected, which has not been reported for protonated DBNs. Direct C2H3O2• elimination from the precursor ion (deprotonated molecule) only occurred for the BNs and can help to distinguish these compounds from the DBNs. The mechanism through which the [M − H − CH3OH]− ion is formed is strongly dependent on specific structural features.ConclusionsThe negative ion mode provides much more information than the positive ion mode (at least one diagnostic product ion was detected for all the analyzed compounds) and does not require the use of additives to produce the precursor ions (deprotonated molecules).

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“…Therefore, FBMN has recently been used in an increasing number of research reports as a method for the comprehensive investigation of natural products. 23,[28][29][30][31] In this study, we first established a solid-state fermentation system that stabilizes EGCG by β-CD inclusion complexation. The fungi isolated from FBT were incubated in the system and screened for analogues of EGCG within the LC-MS data using FBMN.…”

Section: Introductionmentioning

confidence: 99%

Feature-Based Molecular Networking Analysis of the Metabolites Produced by in vitro Solid-State Fermentation Reveals Pathways for the Bioconversion of Epigallocatechin Gallate

Xie¹,

Kong²,

Li³

et al. 2020

Preprint

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Dark teas are prepared by a microbial fermentation process. Flavan-3-ol B-ring fission analogues (FBRFAs) are some of the key bioactive constituents that characterise dark teas. The precursors and the synthetic mechanism involved in the formation of FBRFAs are not known. Using a unique solid-state fermentation system with β-cyclodextrin inclusion complexation, as well as targeted chromatographic isolation, spectroscopic identification, and Feature-based Molecular Networking (FBMN) on the Global Natural Products Social Molecular Networking (GNPS) web-platform, we reveal that dihydromyricetin and the FBRFAs, including teadenol A and fuzhuanin A, are derived from epigallocatechin gallate (EGCG) upon exposure to fungal strains isolated from Fuzhuan brick tea. In particular the strains from subphylum Pezizomycotina were key drivers for these B-/C-ring oxidation transformations. These are the same transformations seen during the fermentation process of dark teas. These discoveries set the stage to enrich dark teas and other food products for these health promoting constituents.

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Discovery of Neolignan Glycosides with Acetylcolinesterase Inhibitory Activity from Huangjinya Green Tea Guided by Ultra Performance Liquid Chromatography–Tandem Mass Spectrometry Data and Global Natural Product Social Molecular Networking

Cited by 22 publications

References 31 publications

Should We Think Positive or Negative About Dihydrobenzofuran Neolignans? an ESI-MS/MS Study

Should We Think Positive or Negative About Dihydrobenzofuran Neolignans? an ESI-MS/MS Study

Electrospray ionization tandem mass spectrometry of deprotonated dihydrobenzofuran neolignans

Feature-Based Molecular Networking Analysis of the Metabolites Produced by in vitro Solid-State Fermentation Reveals Pathways for the Bioconversion of Epigallocatechin Gallate

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