Aryl hydrocarbon Receptor activation during in vitro and in vivo digestion of raw and cooked broccoli (brassica oleracea var. Italica)

Koper, Jonna; Kortekaas, Maaike; Loonen, L.M.P.; Huang, Zhan; Wells, Jerry M.; Gill, Chris; Pourshahidi, L.K.; McDougall, Gordon J.; Rowland, Ian; Pereira‐Caro, Gema; Fogliano, Vincenzo; Capuano, Edoardo

doi:10.1039/d0fo00472c

Cited by 13 publications

(7 citation statements)

References 57 publications

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“…Thus, compound 8 was elucidated as 9-hydroxy-1-methoxy-5,11-dihydroindolo[3,2- b ]carbazole-6-carbonitrile and trivially named maeruabisindole C. Indolo[3,2- b ]carbazole compounds are metabolites of indole-3-carbinol, which can occur from the breakdown of a glucobrassinin under acid condition [ 20 ]. In the stomach, they can be formed during the digestion of Brassica vegetables and are beneficial to gut immune function [ 21 ]. The biosynthesis of maeruabisindole C has been proposed and shown in Figure 4 .…”

Section: Resultsmentioning

confidence: 99%

Eight Indole Alkaloids from the Roots of Maerua siamensis and Their Nitric Oxide Inhibitory Effects

et al. 2022

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Maerua siamensis (Capparaceae) roots are used for treating pain and inflammation in traditional Thai medicine. Eight new indole alkaloids, named maeruanitriles A and B, maeroximes A–C, and maeruabisindoles A–C, were isolated from them. Spectroscopic methods and computational analysis were applied to determine the structure of the isolated compounds. Maeroximes A–C possesses an unusual O-methyloxime moiety. The bisindole alkaloid maeruabisindoles A and B possess a rare azete ring, whereas maeruabisindole C is the first indolo[3,2-b]carbazole derivative found in this plant family. Five compounds [maeruanitriles A and B, maeroxime C, maeruabisindoles B, and C] displayed anti-inflammatory activity by inhibiting nitric oxide (NO) production in the lipopolysaccharide-induced RAW 264.7 cells. Maeruabisindole B was the most active inhibitor of NO production, with an IC50 of 31.1 ± 1.8 μM compared to indomethacin (IC50 = 150.0 ± 16.0 μM) as the positive control.

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Section: Resultsmentioning

confidence: 99%

Eight Indole Alkaloids from the Roots of Maerua siamensis and Their Nitric Oxide Inhibitory Effects

et al. 2022

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“…AhR Activity: The AhR activity was measured using a luciferase reporter assay method as described previously. [35] In brief, HepG2-Lucia AhR reporter cells (InvivoGen, San Diego, CA) were grown and maintained according to the manufactures instructions. To induce AhR, 20 µL samples separately from three independent replicates and 180 µL cell suspension containing about 20 000 cells were added per well in triplicate to a flat-bottom 96-well plate (Corning, USA), which diluted samples by ten times.…”

Section: Methodsmentioning

confidence: 99%

Substrate‐Driven Differences in Tryptophan Catabolism by Gut Microbiota and Aryl Hydrocarbon Receptor Activation

Huang

Schoones

Wells

et al. 2021

Molecular Nutrition Food Res

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Scope: This study aims to investigate the effect of tryptophan sources on tryptophan catabolism by gut microbiota and the aryl hydrocarbon receptor (AhR) activation. Methods and Results: Four substrates (free tryptophan, soybean protein, single and clustered soybean cells) containing an equimolar amount of tryptophan, but with a different bioaccessibility are studied using in vitro batch fermentation. Tryptophan catabolites are identified by LC-MS/MS. AhR activity is measured by HepG2-Lucia AhR reporter cells. The total amount of tryptophan-derived catabolites increases with decreasing level of substrate complexity. Indole is the major catabolite produced from tryptophan and it is the most abundant in the free tryptophan fermentation. Indole-3-acetic acid and indole-3-aldehyde are abundantly generated in the soybean protein fermentation. The soybean cell fermentation produced high concentrations of tryptamine. Interestingly, large amounts of short-chain fatty acids (SCFAs) are also found in the soybean cell and protein fermentation. Both tryptophan-derived catabolites and SCFAs are able to increase AhR reporter activity over time in all four groups. Conclusion: This study illustrates that bacterial catabolism of tryptophan and resulting AhR activation in the gut is modulated by the food matrix, suggesting a role for food design to improve gut health.

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“…Cruciferous plants, (cabbage, kale, broccoli, rape seed etc.) are especially rich in glucosinolates, precursor compounds for AHR ligands [94]. "Eat your veggies", was thus a popular piece of advice resulting from these mouse experiments on protective AHR-activity in the gut [91,95].…”

Section: Ligand Diversity-a Challenging Question Then and Nowmentioning

confidence: 99%

Trajectory Shifts in Interdisciplinary Research of the Aryl Hydrocarbon Receptor—A Personal Perspective on Thymus and Skin

Esser

2021

IJMS

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Identifying historical trajectories is a useful exercise in research, as it helps clarify important, perhaps even “paradigmatic”, shifts in thinking and moving forward in science. In this review, the development of research regarding the role of the transcription factor “aryl hydrocarbon receptor” (AHR) as a mediator of the toxicity of environmental pollution towards a link between the environment and a healthy adaptive response of the immune system and the skin is discussed. From this fascinating development, the opportunities for targeting the AHR in the therapy of many diseases become clear.

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Aryl hydrocarbon Receptor activation during in vitro and in vivo digestion of raw and cooked broccoli (brassica oleracea var. Italica)

Abstract: Glucosinolates in broccoli can be converted upon chewing and processing into Aryl hydrocarbon Receptor (Ahr) ligands.

Cited by 13 publications

References 57 publications

Eight Indole Alkaloids from the Roots of Maerua siamensis and Their Nitric Oxide Inhibitory Effects

Eight Indole Alkaloids from the Roots of Maerua siamensis and Their Nitric Oxide Inhibitory Effects

Substrate‐Driven Differences in Tryptophan Catabolism by Gut Microbiota and Aryl Hydrocarbon Receptor Activation

Trajectory Shifts in Interdisciplinary Research of the Aryl Hydrocarbon Receptor—A Personal Perspective on Thymus and Skin

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