The Effect of 4-hydroxybenzaldehyde on the γ-aminobutyric Acid Type A Receptor

Zhang, Jingli; Mohamad, Habsah; Wong, Jia Hui; Bilal, Muhammad; Ismail, Abdul Halim; Lloyd, Amelia; Yusoff, Abdul Aziz Mohamed; Osman, Hasnah; Wong, Kok Tong; Idris, Zamzuri; Abdullah, Jafri Malin

doi:10.21315/mjms2017.24.2.12

Cited by 6 publications

(4 citation statements)

References 12 publications

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“…4-OHBA has previously been shown to be formed naturally. For instance, it is an active component of Gastrodia elata , a Chinese herbal medicine used to treat headaches and migraines, and of Dendrocalamus asper bamboo shoots. , In addition, 4-OHBA could be formed in natural processes from tyrosine, including in the Maillard reaction that occurs during cooking of food . It is also a precursor to vanillin that is produced in vanilla beans and is an important volatile component of vanilla aroma and flavor. , To be able to make a quantitative conclusion about the precursor of this adduct in humans, further studies must be done.…”

Section: Discussionmentioning

confidence: 99%

Discovery of Novel N-(4-Hydroxybenzyl)valine Hemoglobin Adducts in Human Blood

Degner

Carlsson

Karlsson

et al. 2018

Chem. Res. Toxicol.

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Humans are exposed to a wide range of electrophilic compounds present in our diet and environment or formed endogenously as part of normal physiological processes. These electrophiles can modify nucleophilic sites of proteins and DNA to form covalent adducts. Recently, powerful untargeted adductomic approaches have been developed for systematic screening of these adducts in human blood. Our earlier untargeted adductomics study detected 19 unknown adducts to N-terminal valine in hemoglobin (Hb) in human blood. We now describe a full characterization of one of these adducts, which corresponds to the addition of a 4-hydroxybenzyl (4-OHBn) group to N-terminal valine in Hb to form N-(4-hydroxybenzyl)valine (4-OHBn-Val). The adduct structure was determined by comparison of its accurate mass, HPLC retention time, and MS/MS fragmentation to that of authentic standards prepared by chemical synthesis. Average 4-OHBn-Val adduct concentrations in 12 human blood samples were estimated to 380 ± 160 pmol/g Hb. Two possible routes of 4-OHBnVal adduct formation are proposed using two different precursor electrophiles: 4-quinone methide (4-QM) and 4-hydroxybenzaldehyde (4-OHBA). We found that 4-QM reacts rapidly with valine to form the 4-OHBn-Val adduct; however, the quinone methide is unstable under physiological conditions due to hydrolysis. It was shown that 4-OHBA forms reversible Schiff base adducts with valine, which can be stabilized via reduction in blood generating the 4-OHBn-Val adduct. In addition, trace amounts of isomeric 2-hydroxybenzyl-valine (2-OHBn-Val) adducts were detected in 12 human blood samples (estimated mean adduct level, 5.0 ± 1.4 pmol/g Hb). Further studies are needed to quantify the contributions from identified possible precursor electrophiles to the observed hydroxybenzyl adducts in humans.

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Section: Discussionmentioning

confidence: 99%

Discovery of Novel N-(4-Hydroxybenzyl)valine Hemoglobin Adducts in Human Blood

Degner

Carlsson

Karlsson

et al. 2018

Chem. Res. Toxicol.

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“…According to relevant literature reports, 21,22 2,6‐dimethoxyphenol has antibacterial and antioxidant effects. 4‐Hydroxybenzaldehyde is one of the main components of bamboo shoots, which has anti‐cerebral thrombosis, anti‐platelet aggregation and anti‐inflammatory effects 23–25 . Vanillin, as a popular flavor and fragrance compound, has attracted less attention due to its biological activity.…”

Section: Resultsmentioning

confidence: 99%

Quality assessment of Succus Bambusae oral liquids based on gas chromatography/mass spectrometry fingerprints and chemometrics

Feng

et al. 2021

Rapid Comm Mass Spectrometry

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Rationale Succus Bambusae is consumed as a kind of herbal medicine and natural beverage in China. However, the current quality standards for Succus Bambusae are low and lack safety indicators, which makes it difficult to effectively guarantee its quality. Therefore, it is of great significance to study the identification and quality control technology for the product. Methods We have developed a set of qualitative and quantitative methods based on gas chromatography/mass spectrometry (GC/MS) for the analysis of volatile components in Succus Bambusae oral liquid (SBOL). Combining GC/MS fingerprint analysis and related chemometrics algorithms, with similarity evaluation, Hotelling T2 and distance to Model X (DModX) as criteria, the quality consistency of different batches was evaluated, and SBOL samples from different manufacturers were differentiated. Results Twenty‐nine volatile components were preliminarily identified from 40 batches of SBOL samples from six manufacturers, and six Q‐markers (Quality Markers) for the SBOLs were discussed and determined using GC/MS. The products from different manufacturers were distinguished using chemometrics. Conclusions The results showed that the quality of the SBOL samples from different batches and different manufacturers fluctuated greatly, which suggested that research into the raw materials and manufacturing techniques should be strengthened to improve the quality of SBOL and ensure its quality consistency.

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“…These new antibiotics can serve as essential tools to treat infections that were once manageable but have now become perilous [36,37]. Hel- 7) [24], arbutin cinnamate (8) [25], tremulacinol (9) [28], catechol (10) [32], 4-hydroxybenzaldehyde (11) [33], kaempferol 3-rutinoside (12) [34], and narcissin (13) [35] based on the comparison of their NMR spectra with the reported data and LC/MS analysis.…”

Section: Evaluation Of Antibacterial Activity Of the Isolated Compoun...mentioning

confidence: 99%

“…We identified the known compounds as 5-O-trans-p-coumaroyl quinic acid methyl ester (2) [27], tremulacin (3) [28], citrusin C (4) [29], benzyl 3-O-β-D-glucopyranosyl-7hydroxybenzoate (5) [30], tremuloidin (6) [31], 1-[O-β-D-glucopyranosyl(1→2)β-D-glucopyranosyl]oxy-2-phenol (7) [24], arbutin cinnamate (8) [25], tremulacinol (9) [28], catechol (10) [32], 4-hydroxybenzaldehyde (11) [33], kaempferol 3-rutinoside (12) [34], and narcissin (13) [35] based on the comparison of their NMR spectra with the reported data and LC/MS analysis.…”

Section: Evaluation Of Antibacterial Activity Of the Isolated Compoun...mentioning

confidence: 99%

Chaenomelin, a New Phenolic Glycoside, and Anti-Helicobacter pylori Phenolic Compounds from the Leaves of Salix chaenomeloides

Kim,

Kang,

et al. 2024

Plants

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Salix chaenomeloides Kimura, commonly known as pussy willow, is a deciduous shrub and tree belonging to the Salicaceae family. The genus Salix spp. has been known as a healing herb for the treatment of fever, inflammation, and pain relief. The current study aimed to investigate the potential bioactive natural products from S. chaenomeloides leaves and evaluate their antibacterial activity against Helicobacter pylori. A phytochemical investigation of the ethanol (EtOH) extract of S. chaenomeloides leaves led to the isolation of 13 phenolic compounds (1–13) from the ethyl acetate (EtOAc) fraction, which showed antibacterial activity against H. pylori strain 51. The chemical structure of a new phenolic glycoside, chaenomelin (1), was established by a detailed analysis of 1D and 2D (1H-1H correlation spectroscopy (COSY), heteronuclear single-quantum coherence (HSQC), and heteronuclear multiple-bond correlation (HMBC)) nuclear magnetic resonance (NMR), high-resolution electrospray ionization mass spectroscopy (HR-ESIMS), and chemical reactions. The other known compounds were identified as 5-O-trans-p-coumaroyl quinic acid methyl ester (2), tremulacin (3), citrusin C (4), benzyl 3-O-β-d-glucopyranosyl-7-hydroxybenzoate (5), tremuloidin (6), 1-[O-β-d-glucopyranosyl(1→2)-β-d-glucopyranosyl]oxy-2-phenol (7), arbutin cinnamate (8), tremulacinol (9), catechol (10), 4-hydroxybenzaldehyde (11), kaempferol 3-rutinoside (12), and narcissin (13), based on the comparison of their NMR spectra with the reported data and liquid chromatography/mass spectrometry (LC/MS) analysis. The isolated compounds were evaluated for antibacterial activity against H. pylori strain 51. Among the isolates, 1-[O-β-d-glucopyranosyl(1→2)-β-d-glucopyranosyl]oxy-2-phenol (7) and arbutin cinnamate (8) exhibited antibacterial activity against H. pylori strain 51, with inhibitions of 31.4% and 33.9%, respectively, at a final concentration of 100 μM. These results were comparable to that of quercetin (38.4% inhibition), which served as a positive control. Generally, these findings highlight the potential of the active compounds 7 and 8 as antibacterial agents against H. pylori.

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The Effect of 4-hydroxybenzaldehyde on the γ-aminobutyric Acid Type A Receptor

Cited by 6 publications

References 12 publications

Discovery of Novel N-(4-Hydroxybenzyl)valine Hemoglobin Adducts in Human Blood

Discovery of Novel N-(4-Hydroxybenzyl)valine Hemoglobin Adducts in Human Blood

Quality assessment of Succus Bambusae oral liquids based on gas chromatography/mass spectrometry fingerprints and chemometrics

Chaenomelin, a New Phenolic Glycoside, and Anti-Helicobacter pylori Phenolic Compounds from the Leaves of Salix chaenomeloides

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