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International Journal of Molecular... Jan 2023Nowadays, bioactive natural products play key roles in drug development due to their safety profile and strong antioxidant power. Vanillin is a natural phenolic compound... (Review)
Review
Nowadays, bioactive natural products play key roles in drug development due to their safety profile and strong antioxidant power. Vanillin is a natural phenolic compound found in several vanilla beans and widely used for food, cosmetic, and pharmaceutical products. Besides its industrial applications, vanillin possesses several beneficial effects for human health, such as antioxidant activity in addition to anti-inflammatory, anti-mutagenic, anti-metastatic, and anti-depressant properties. Moreover, vanillin exhibits neuroprotective effects on multiple neurological disorders and neuropathophysiological conditions. This study reviews the mechanisms of action by which vanillin prevents neuroinflammation and neurodegeneration in vitro and in vivo systems, in order to provide the latest views on the beneficial properties of this molecule in chronic neurodegenerative diseases and neuropathophysiological conditions.
Topics: Humans; Neurodegenerative Diseases; Antioxidants; Benzaldehydes; Anti-Inflammatory Agents
PubMed: 36768141
DOI: 10.3390/ijms24031817 -
Oxidative Medicine and Cellular... 2016Bioactive natural products play critical roles in modern drug development, especially anticancer agents. It has been widely reported that various pharmacological... (Review)
Review
Bioactive natural products play critical roles in modern drug development, especially anticancer agents. It has been widely reported that various pharmacological activities of such compounds are related to their antioxidant properties. Vanillin is a natural substance widely found in many plant species and often used in beverages, foods, cosmetics, and pharmaceutical products. Antioxidant and anticancer potential have been described for this compound. Considering the importance of vanillin in the area of human health and food and pharmaceuticals sectors, in this review, we discuss the role of vanillin on redox status and its potential contribution to the prevention and the treatment of cancer.
Topics: Antineoplastic Agents; Antioxidants; Apoptosis; Benzaldehydes; Biological Products; Humans; Neoplasms; Oxidation-Reduction
PubMed: 28077989
DOI: 10.1155/2016/9734816 -
International Immunopharmacology Oct 2014To evaluate the antiallergic effects of oral benzaldehyde in a murine model of allergic asthma and rhinitis, we divided 20 female BALB/c mice aged 8-10 weeks into...
To evaluate the antiallergic effects of oral benzaldehyde in a murine model of allergic asthma and rhinitis, we divided 20 female BALB/c mice aged 8-10 weeks into nonallergic (intraperitoneally sensitized and intranasally challenged to normal saline), allergic (intraperitoneally sensitized and intranasally challenged to ovalbumin), and 200- and 400-mg/kg benzaldehyde (allergic but treated) groups. The number of nose-scratching events in 10 min, levels of total and ovalbumin-specific IgE in serum, differential counts of inflammatory cells in bronchoalveolar lavage (BAL) fluid, titers of Th2 cytokines (IL-4, IL-5, IL-13) in BAL fluid, histopathologic findings of lung and nasal tissues, and expressions of proteins involved in apoptosis (Bcl-2, Bax, caspase-3), inflammation (COX-2), antioxidation (extracellular SOD, HO-1), and hypoxia (HIF-1α, VEGF) in lung tissue were evaluated. The treated mice had significantly fewer nose-scratching events, less inflammatory cell infiltration in lung and nasal tissues, and lower HIF-1α and VEGF expressions in lung tissue than the allergic group. The number of eosinophils and neutrophils and Th2 cytokine titers in BAL fluid significantly decreased after the treatment (P<0.05). These results imply that oral benzaldehyde exerts antiallergic effects in murine allergic asthma and rhinitis, possibly through inhibition of HIF-1α and VEGF.
Topics: Animals; Anti-Allergic Agents; Asthma; Benzaldehydes; Bronchoalveolar Lavage Fluid; Cell Count; Cytokines; Disease Models, Animal; Female; Hypoxia-Inducible Factor 1, alpha Subunit; Immunoglobulin E; Lung; Mice, Inbred BALB C; Nasal Mucosa; Ovalbumin; Rhinitis, Allergic; Vascular Endothelial Growth Factor A
PubMed: 25107441
DOI: 10.1016/j.intimp.2014.07.029 -
International Journal of Molecular... May 2009Tyrosinase is a multifunctional, glycosylated, and copper-containing oxidase, which catalyzes the first two steps in mammalian melanogenesis and is responsible for... (Review)
Review
Tyrosinase is a multifunctional, glycosylated, and copper-containing oxidase, which catalyzes the first two steps in mammalian melanogenesis and is responsible for enzymatic browning reactions in damaged fruits during post-harvest handling and processing. Neither hyperpigmentation in human skin nor enzymatic browning in fruits are desirable. These phenomena have encouraged researchers to seek new potent tyrosinase inhibitors for use in foods and cosmetics. This article surveys tyrosinase inhibitors newly discovered from natural and synthetic sources. The inhibitory strength is compared with that of a standard inhibitor, kojic acid, and their inhibitory mechanisms are discussed.
Topics: Benzaldehydes; Benzoates; Biological Products; Enzyme Inhibitors; Melanins; Monophenol Monooxygenase; Polyphenols; Protein Binding; Steroids
PubMed: 19582213
DOI: 10.3390/ijms10062440 -
Nicotine & Tobacco Research : Official... Mar 2022Tobacco product flavors may change the sensory properties of nicotine, such as taste and olfactory cues, which may alter nicotine reward and aversion and nicotine taking...
INTRODUCTION
Tobacco product flavors may change the sensory properties of nicotine, such as taste and olfactory cues, which may alter nicotine reward and aversion and nicotine taking behavior. The hedonic or aversive value of a taste stimulus can be evaluated by examining affective orofacial movements in rodents.
AIMS AND METHODS
We characterized taste responses to various oral nicotine concentrations using the taste reactivity test in rats. We also evaluated the impact of menthol and benzaldehyde (cherry, almond) flavorants on both ingestive and aversive responses to oral nicotine. Adult Sprague-Dawley rats (n = 5-10 per sex per group) were implanted with intraoral catheters and received 20 infusions (200 µl/ea). Nicotine (1-100 µg/mL) was evaluated in taste reactivity test to determine taste responses to nicotine. Later, the effects of menthol (50 µg/mL) and benzaldehyde (100 µg/mL) on the taste responses to nicotine were determined.
RESULTS
Nicotine at low concentrations (3 µg/mL in males, 1 µg/mL in females) elicited significantly greater ingestive responses compared with water, whereas higher nicotine concentrations (≥30 µg/mL in males, ≥10 µg/mL in females) elicited significant aversive reactions. Thus, intraoral nicotine induced both hedonic and aversive responses in a concentration- and sex-dependent manner. Females were more sensitive to nicotine's concentration. The addition of menthol or benzaldehyde significantly increased the hedonic responses to nicotine, and significantly decreased the aversive nicotine responses.
CONCLUSIONS
Oral nicotine induces both hedonic and aversive taste responses, which may represent liking and disliking. Menthol and benzaldehyde can alter the orosensory experience of nicotine, which may influence nicotine's abuse liability.
IMPLICATIONS
Our work represents a model to study impact of flavors on oral nicotine liking and disliking responses in rats. Moreover, our findings show that menthol and benzaldehyde alter the orosensory experience of nicotine, suggesting that both could influence nicotine's abuse liability.
Topics: Animals; Benzaldehydes; Female; Humans; Male; Menthol; Nicotine; Rats; Rats, Sprague-Dawley; Taste
PubMed: 34918123
DOI: 10.1093/ntr/ntab241 -
Microbial Cell Factories May 2023Aromatic α-hydroxy ketones, such as S-2-hydroxypropiophenone (2-HPP), are highly valuable chiral building blocks useful for the synthesis of various pharmaceuticals and...
BACKGROUND
Aromatic α-hydroxy ketones, such as S-2-hydroxypropiophenone (2-HPP), are highly valuable chiral building blocks useful for the synthesis of various pharmaceuticals and natural products. In the present study, enantioselective synthesis of 2-HPP was investigated by free and immobilized whole cells of Pseudomonas putida ATCC 12633 starting from readily-available aldehyde substrates. Whole resting cells of P. putida, previously grown in a culture medium containing ammonium mandelate, are a source of native benzoylformate decarboxylase (BFD) activity. BFD produced by induced P. putida resting cells is a highly active biocatalyst without any further treatment in comparison with partially purified enzyme preparations. These cells can convert benzaldehyde and acetaldehyde into the acyloin compound 2-HPP by BFD-catalyzed enantioselective cross-coupling reaction.
RESULTS
The reaction was carried out in the presence of exogenous benzaldehyde (20 mM) and acetaldehyde (600 mM) as substrates in 6 mL of 200 mM phosphate buffer (pH 7) for 3 h. The optimal biomass concentration was assessed to be 0.006 g dry cell weight (DCW) mL. 2-HPP titer, yield and productivity using the free cells were 1.2 g L, 0.56 g 2-HPP/g benzaldehyde (0.4 mol 2-HPP/mol benzaldehyde), 0.067 g 2-HPP g DCW h, respectively, under optimized biotransformation conditions (30 °C, 200 rpm). Calcium alginate (CA)-polyvinyl alcohol (PVA)-boric acid (BA)-beads were used for cell entrapment. Encapsulated whole-cells were successfully employed in four consecutive cycles for 2-HPP production under aerobic conditions without any noticeable beads degradation. Moreover, there was no production of benzyl alcohol as an unwanted by-product.
CONCLUSIONS
Bioconversion by whole P. putida resting cells is an efficient strategy for the production of 2-HPP and other α-hydroxyketones.
Topics: Pseudomonas putida; Carboxy-Lyases; Benzaldehydes; Hydroxypropiophenone; Stereoisomerism; Ketones; Acetaldehyde
PubMed: 37131175
DOI: 10.1186/s12934-023-02073-7 -
Blood Advances Nov 2022
Topics: Benzaldehydes; Pyrazines; Pyrazoles
PubMed: 35984638
DOI: 10.1182/bloodadvances.2022007702 -
Chemical & Pharmaceutical Bulletin Feb 2021The concise syntheses of two alkylated hydroquinone natural products, violaceoids A and C, were accomplished by a protecting-group-free method employing the commercially...
The concise syntheses of two alkylated hydroquinone natural products, violaceoids A and C, were accomplished by a protecting-group-free method employing the commercially available 2,5-dihydroxybenzaldehyde as the starting material. The key strategy of the syntheses is the utilization of alkenylboronic acid as both the coupling and temporary protective reagents to efficiently introduce the requisite alkenyl side chain of violaceoid A. Moreover, the synthesis of violaceoid C is reported here for the first time.
Topics: Alkylation; Benzaldehydes; Biological Products; Hydroquinones; Temperature
PubMed: 33239487
DOI: 10.1248/cpb.c20-00816 -
International Journal of Molecular... Oct 2022Nanometer-size Co-ZIF (zeolitic imidazolate frameworks) catalyst was prepared for selective oxidation of toluene to benzaldehyde under mild conditions. The typical...
Nanometer-size Co-ZIF (zeolitic imidazolate frameworks) catalyst was prepared for selective oxidation of toluene to benzaldehyde under mild conditions. The typical characteristics of the metal-organic frameworks (MOFs) material were affirmed by the XRD, SEM, and TEM, the BET surface area of this catalyst was as high as 924.25 m/g, and the diameter of particles was near 200 nm from TEM results. The Co metal was coated with 2-methyl glyoxaline, and the crystalline planes were relatively stable. The reaction temperatures, oxygen pressure, mass amount of N-hydroxyphthalimide (NHPI), and reaction time were discussed. The Co-ZIF catalyst gave the best result of 92.30% toluene conversion and 91.31% selectivity to benzaldehyde under 0.12 MPa and 313 K. The addition of a certain amount of NHPI and the smooth oxidate capacity of the catalyst were important factors in the high yield of benzaldehyde. This nanometer-size catalyst showed superior performance for recycling use in the oxidation of toluene. Finally, a possible reaction mechanism was proposed. This new nanometer-size Co-ZIF catalyst will be applied well in the selective oxidation of toluene to benzaldehyde.
Topics: Toluene; Benzaldehydes; Catalysis; Oxidation-Reduction
PubMed: 36361670
DOI: 10.3390/ijms232112881 -
Biomolecules Jan 2022Excretory-secretory products (ESPs) are the main research targets for investigating the hosts and helminths interaction. Parasitic worms can migrate to parasitic sites...
Benzaldehyde Attenuates the Fifth Stage Larval Excretory-Secretory Product of -Induced Injury in Mouse Astrocytes via Regulation of Endoplasmic Reticulum Stress and Oxidative Stress.
Excretory-secretory products (ESPs) are the main research targets for investigating the hosts and helminths interaction. Parasitic worms can migrate to parasitic sites and avoid the host immune response by secreting this product. is an important food-borne zoonotic parasite that causes severe neuropathological damage and symptoms, including eosinophilic meningitis or meningoencephalitis in humans. Benzaldehydes are organic compounds composed of a benzene ring and formyl substituents. This compound has anti-inflammatory and antioxidation properties. Previous studies showed that 3-hydroxybenzaldehyde (3-HBA) and 4-hydroxybenzaldehyde (4-HBA) can reduce apoptosis in ESP-treated astrocytes. These results on the protective effect underlying benzaldehyde have primarily focused on cell survival. The study was designed to investigate the molecular mechanisms of endoplasmic reticulum stress (ER stress) and oxidative stress in astrocytes in ESP-treated astrocytes and to evaluate the therapeutic consequent of 3-HBA and 4-HBA. First, we initially established the RNA-seq dataset in each group, including normal, ESPs, ESPs + 3-HBA, and ESPs + 4-HBA. We also found that benzaldehyde (3-HBA and 4-HBA) can stimulate astrocytes to express ER stress-related molecules after ESP treatment. The level of oxidative stress could also be decreased in astrocytes by elevating antioxidant activity and reducing ROS generation. These results suggested that benzaldehyde may be a potential therapeutic compound for human angiostrongyliasis to support brain cell survival by inducing the expression levels of ER stress- and oxidative stress-related pathways.
Topics: Angiostrongylus cantonensis; Animals; Astrocytes; Benzaldehydes; Endoplasmic Reticulum Stress; Larva; Mice; Oxidative Stress
PubMed: 35204678
DOI: 10.3390/biom12020177