Bioactive β-Carbolines in Food: A Review

Piechowska, Paulina; Zawirska‐Wojtasiak, Renata; Mildner–Szkudlarz, Sylwia

doi:10.3390/nu11040814

Cited by 70 publications

(60 citation statements)

References 48 publications

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“…In this study, we screened the effects of compounds 1-6 obtained from garlic on adipocyte differentiation and identified that (1R,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (compound 6) can disrupt lipid accumulation in adipocytes by promoting lipolysis and disturbing lipogenesis (Figure 7). While there is abundant evidence demonstrating the neuroprotective and anticancer effects of bioactive β-carbolines from diverse natural products [38][39][40][41], the metabolic effects of β-carbolines are not well defined. To the best of our knowledge, we report, for the first time, the effects of garlic-derived β-carboline alkaloids on adipogenesis and lipid metabolism.…”

Section: Effects Of Compound 6 On Lipid Metabolismmentioning

confidence: 99%

Anti-adipogenic Effect of β-Carboline Alkaloids from Garlic (Allium sativum)

Baek

Nam

et al. 2019

Foods

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Garlic (Allium sativum L.) is utilized worldwide for culinary and medicinal use and has diverse health benefits. As part of our ongoing research to identify bioactive components from natural resources, phytochemical analysis of the methanolic extract of garlic led to the isolation and characterization of six compounds: Three eugenol diglycosides (1-3) and three β-carboline alkaloids (4-6). In particular, the absolute configurations of β-carboline alkaloids (5 and 6) were established by gauge-including atomic orbital nuclear magnetic resonance chemical shift calculations, followed by DP4+ analysis. Here, we evaluated the effects of compounds 1-6 on 3T3-L1 preadipocyte adipogenesis and lipid metabolism. 3T3-L1 adipocyte differentiation was evaluated using Oil Red O staining; the expression of adipogenic genes was detected using RT-qPCR. Among compounds 1-6, (1R,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (6) inhibited 3T3-L1 preadipocyte adipogenesis and reduced the expression of adipogenic genes (Fabp4, PPARγ, C/EBPβ, Adipsin, and Adipoq). Moreover, it markedly decreased the actylation of α-tubulin, which is crucial for cytoskeletal remodeling during adipogenesis. Anti-adipogenic effects were observed upon treatment with compound 6, not only during the entire process, but also on the first two days of adipogenesis. Additionally, treatment with compound 6 regulated the expression of genes involved in adipocyte lipid metabolism, decreasing the lipogenic gene (SREBP1) and increasing lipolytic genes (ATGL and HSL). We provide experimental evidence of the health benefits of using (1R,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid obtained from garlic to prevent excessive adipogenesis in obesity.

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Section: Effects Of Compound 6 On Lipid Metabolismmentioning

confidence: 99%

Anti-adipogenic Effect of β-Carboline Alkaloids from Garlic (Allium sativum)

Baek

Nam

et al. 2019

Foods

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“…It can be seen that the level of carbolines in plasma increased with increasing amounts of H or NH in the experimental diet. Taking into account the level of both carbolines in the control diet without carboline additions, H increased by a factor of about four at the greatest addition, while NH increased two-fold at the greatest addition; however, the final concentration of NH was greater than H, as is typical of natural products [ 13 ].…”

Section: Resultsmentioning

confidence: 99%

“…Our literature review strongly suggests that some foods, especially coffee, can act as a rich source of β-carbolines, which may be associated with a reduced risk of serious neurodegenerative diseases, such as Parkinson’s and Alzheimer’s [ 13 ]. Human cancer cell lines have also been used in studies on the antitumor effects of some carboline derivatives [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

β-Carbolines in Experiments on Laboratory Animals

Zawirska‐Wojtasiak

Fedoruk-Wyszomirska

Piechowska

et al. 2020

IJMS

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Some studies have ascribed a protective effect against neurodegenerative diseases to the β-carbolines harman (H) and norharman (NH), which occur mostly in coffee and coffee substitutes. We determined the concentrations of β-carbolines and undesirable compounds (such as acrylamide) in roasted coffee substitute ingredients and found that chicory coffee was optimal. Two in vivo experiments were conducted with seventeen-month-old male Sprague Dawley rats fed a diet with the addition of pure carboline standards in the first stage, and chicory in the second. We observed an increase in the level of H and NH in blood plasma, as well as higher activity of animals in the battery behavioral test, particularly in the second stage. The results of in vitro studies—particularly the level of the expression in brain tissue of genes associated with aging processes and neurodegenerative diseases—clearly show the benefits of a diet rich in β-carbolines.

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“…Since its initial discovery in the year 1841, β-carboline alkaloids have been isolated from various sources, principally plants (mainly in Rutaceae, Simaroubaceae, Amaranthaceae, Caryophyllaceae, Rubiaceae and Zygophyllaceae ), marine creatures (hydroids, bryozoans, soft corals) and marine sponges ( França et al., 2014 ). They are also present in microorganisms, insects, food products ( Piechowska et al., 2019 ), alcoholic beverages, tobacco smoke, as well as human tissues and body fluids. Also, β-carbolines display a wide range of unusual biological activities like anti-cancer ( Samundeeswari et al., 2017 ), ( Carvalho et al., 2017 ), antiviral ( Brahmbhatt et al., 2010 ), antibacterial, antifungal ( Nenaah, 2010 ), antileishmanial ( Kam et al., 1999 ), antithrombotic, anti-inflammatory ( Yao et al., 2011 ) properties, among others.…”

Section: Introduction To β-Carboline and Allied Structuresmentioning

confidence: 99%

Recent evolution on synthesis strategies and anti-leishmanial activity of β-carboline derivatives – An update

Kumar

Faheem

Chandrasekhar

et al. 2020

Heliyon

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Leishmaniasis is the most widespread pathogenic disease in several countries. Currently, no effective vaccines are available, and the control of Leishmaniasis primarily relies on decade-old chemotherapy. The treatment for the Leishmaniasis is not up to the mark. Current therapy for Leishmaniasis is ancient and requires hospitalization for the administration. These medications are also highly toxic and resistant. β-carboline, a natural indole containing alkaloid, holds a vital position in the field of medicinal chemistry with a diversified pharmacological action. The current review focuses mainly on the anti-leishmanial effects of β-carboline analogs and their synthetic strategies, structural activity relationship studies (SAR). The past ten years alterations unveiled by β-carboline analogs present in phytoconstituents and various derivatives of synthesized analogs with the mechanism of action were briefly shortlisted and illustrated.

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Bioactive β-Carbolines in Food: A Review

Cited by 70 publications

References 48 publications

Anti-adipogenic Effect of β-Carboline Alkaloids from Garlic (Allium sativum)

Anti-adipogenic Effect of β-Carboline Alkaloids from Garlic (Allium sativum)

β-Carbolines in Experiments on Laboratory Animals

Recent evolution on synthesis strategies and anti-leishmanial activity of β-carboline derivatives – An update

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