Investigation of serum amino acids involved in gallic acid detoxification of formaldehyde by liquid chromatography/tandem mass spectrometry and neutral loss scan

Jiang, Haipeng; Cai, Nian; Ju, Xin; Huang, Juan; Xian, Wang

doi:10.1002/rcm.8278

Cited by 9 publications

(4 citation statements)

References 31 publications

(34 reference statements)

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“…The settings of the mass window for neutral loss and the RT difference window were both validated by the detection of the spiked samples in replicates. Neutral loss strategy had already been applied to the screenings of derived designer drugs, post‐translational modifications of proteins, glycated proteins, reactive metabolites and so on, 56–60 through triple quadrupole MS or QTOF‐MS operated in the neutral loss scan mode. Different from them, the neutral loss strategy here was carried on QTOF‐MS operated in the AIF scan mode, which could provide a “real” non‐targeted screening.…”

Section: Resultsmentioning

confidence: 99%

Non‐targeted screening of pyranosides in Rhodiola crenulata using an all ion fragmentation‐exact neutral loss strategy combined with liquid chromatography‐quadrupole time‐of‐flight mass spectrometry

Tian

Zhou

et al. 2021

Phytochemical Analysis

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Introduction Pyranosides as one kind of natural glycosides contain a pyran ring linked to an aglycone in the structure. They occur widely in plants and possess diverse biological activities. The discovery of new pyranosides not only contributes to research on natural products but also may promote pharmaceutical development. Objectives A non‐targeted liquid chromatography‐quadrupole time‐of‐flight mass spectrometry method coupled with an all ion fragmentation‐exact neutral loss (AIF‐ENL) strategy was developed for the screening of pyranosides in plants. Methods Pyranosides in various types were collected as a model. The AIF‐ENL strategy comprised three steps: AIF spectrum acquisition and generation, ENL‐based searching and identification, and confirmation of structural type using target second‐stage mass spectrometry (MS/MS). The strategy was systematically evaluated based on the matrix effects, fragmentation stability, scan rate and screening efficiency and finally applied to Rhodiola crenulata (Hook. f. et Thoms) H. Ohba. Results The method was proved to be an efficient tool for the screening of pyranosides. When it was applied to R. crenulata, a total of 24 pyranoside candidates were detected. Among them, six were tentatively identified on the basis of the agreement of their elemental composition with the reported. The other 18 were detected in R. crenulata for the first time. Conclusion The method offers a new platform for discovering pyranosides. In addition, the developed non‐targeted strategy can also be used for other natural products, such as flavonoids and coumarins, as long as there is a common fragmentation behaviour in their MS/MS to generate characteristic neutral losses or fragments.

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Section: Resultsmentioning

confidence: 99%

Non‐targeted screening of pyranosides in Rhodiola crenulata using an all ion fragmentation‐exact neutral loss strategy combined with liquid chromatography‐quadrupole time‐of‐flight mass spectrometry

Tian

Zhou

et al. 2021

Phytochemical Analysis

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“…To gain more insight into how S. fusiger was able to grow on fruiting bodies of M. rosea , metabolic profiling of the pertrimethylsilylated methanol/ethyl acetate (1:1, v / v ) crude extract of S. fusiger was performed by means of GC‐MS; this revealed the presence of high amounts of gallic acid, which is a well‐known polyphenol with antioxidative and prooxidative properties, that might protect S. fusiger from the harmful effects of formaldehyde (Figures S39 and S40). It is known that gallic acid reacts in living organisms with formaldehyde and amino acids to produce Mannich adducts, and thus, detoxify formaldehyde (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

Formaldehyde as a Chemical Defence Agent of Fruiting Bodies of Mycena rosea and its Role in the Generation of the Alkaloid Mycenarubin C

et al. 2020

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Mycenarubin C, a previously unknown red pyrroloquinoline alkaloid, was isolated from fruiting bodies of the mushroom Mycena rosea and its structure was elucidated mainly by NMR spectroscopy and mass spectrometry. Unlike mycenarubin A, the major pyrroloquinoline alkaloid in fruiting bodies of M. rosea, mycenarubin C, contains an eight‐membered ring with an additional C1 unit that is hitherto unprecedented for pyrroloquinoline alkaloids known in nature. Incubation of mycenarubin A with an excess of formaldehyde revealed that mycenarubin C was generated nearly quantitatively from mycenarubin A. An investigation into the formaldehyde content of fresh fruiting bodies of M. rosea showed the presence of considerable amounts of formaldehyde, with values of 5 μg per gram of fresh weight in fresh fruiting bodies. Although mycenarubin C did not show bioactivity against selected bacteria and fungi, formaldehyde inhibits the growth of the mycoparasite Spinellus fusiger at concentrations present in fruiting bodies of M. rosea. Therefore, formaldehyde might play an ecological role in the chemical defence of M. rosea against S. fusiger. In turn, S. fusiger produces gallic acid—presumably to detoxify formaldehyde by reaction of this aldehyde with amino acids and gallic acid to Mannich adducts.

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“…However, Jiang et al (2018) creatively investigated the detoxification effect of gallic acid as an FA trapping agent and reported, for the first time, the involvement of AAs in the detoxification of FA by polyphenols. Most prior studies have concentrated on the antioxidant properties of gallic acid and measured the FA concentration in serum with and without the addition of gallic acid using the 2,4‐dinitrophenylhydrazine derivatisation method.…”

Section: Drugs To Eliminate Endogenous Fa Accumulationmentioning

confidence: 99%

“…In a study byHuang et al (2019), male Kunming breed mice exhibited severe cognitive impairment after exposure to 3 mg/m 3 FA for 14 days. Their findings revealed that the FA-exposed group exhibited significantly increased iNOS, IL-1, TNF-and caspase-3 levels and significantly decreased levels of reduced GSH, suggesting that EGCG activated the Nrf2 signalling pathway and reduced the FA-induced oxidative damage.However,Jiang et al (2018) creatively investigated the detoxification effect of gallic acid as an FA trapping agent and reported, for the first time, the involvement of AAs in the detoxification of FA by polyphenols. Most prior studies have concentrated on the antioxidant properties of gallic acid and measured the FA concentration in serum with and without the addition of gallic acid using the 2,4-dinitrophenylhydrazine derivatisation method.…”

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confidence: 99%

Dual effects of endogenous formaldehyde on the organism and drugs for its removal

Chen,

Zhang

et al. 2023

J of Applied Toxicology

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Endogenous formaldehyde (FA) is produced in the human body via various mechanisms to preserve healthy energy metabolism and safeguard the organism. However, endogenous FA can have several negative effects on the body through epigenetic alterations, including cancer growth promotion; neuronal, hippocampal and endothelial damages; atherosclerosis acceleration; haemopoietic stem cell destruction and haemopoietic cell production reduction. Certain medications with antioxidant effects, such as glutathione, vitamin E, resveratrol, alpha lipoic acid and polyphenols, lessen the detrimental effects of endogenous FA by reducing oxidative stress, directly scavenging endogenous FA or promoting its degradation. This study offers fresh perspectives for managing illnesses associated with endogenous FA exposure.

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Investigation of serum amino acids involved in gallic acid detoxification of formaldehyde by liquid chromatography/tandem mass spectrometry and neutral loss scan

Cited by 9 publications

References 31 publications

Non‐targeted screening of pyranosides in Rhodiola crenulata using an all ion fragmentation‐exact neutral loss strategy combined with liquid chromatography‐quadrupole time‐of‐flight mass spectrometry

Non‐targeted screening of pyranosides in Rhodiola crenulata using an all ion fragmentation‐exact neutral loss strategy combined with liquid chromatography‐quadrupole time‐of‐flight mass spectrometry

Formaldehyde as a Chemical Defence Agent of Fruiting Bodies of Mycena rosea and its Role in the Generation of the Alkaloid Mycenarubin C

Dual effects of endogenous formaldehyde on the organism and drugs for its removal

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