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Advances in Bioactive Glucosinolates and Derivatives

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A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Bioactives and Nutraceuticals".

Deadline for manuscript submissions: closed (15 April 2024) | Viewed by 6829

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Dr. Gina Rosalinda De Nicola

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CREA Research Centre for Vegetable and Ornamental Crops, Via dei Fiori 8, 51017 Pescia, Italy
Interests: phytochemistry; isolation and characterization of glucosinolates and derivatives; evaluation of biological potential of glucosinolates and derivatives; identification of molecular mechanisms of biological actions; biostimulants; biopesticides; nutraceuticals; bioaccessibility; bioavailability
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Dear Colleagues,

Glucosinolates are bio-relevant thiosaccaridic secondary metabolites present in a large number of plants, mainly of the order Brassicales, including common leaf and root vegetables, oilseed and ornamental crops cultivated worldwide. The occurrence of glucosinolates coincides with the presence of specific thioglucosidases, the myrosinases, which can hydrolyze these compounds into a variety of reactive transient and stable products, some of which have noteworthy bioactive properties. The knowledge about the glucosinolate–myrosinase system is continuously evolving and attracting a community of scientists of several disciplines involved in multidisciplinary research projects.

This Special Issue welcomes papers covering all aspects of glucosinolates and their derivatives, including: their screening in different wild and cultivated plant species; their isolation, enrichment and enzymatic transformation; their chemical synthesis, modification and characterization; the evaluation of their in vitro and in vivo bioactivity; the elucidation of their mechanisms of action; and the investigation of their stability and functionality for their potential practical application in different fields.

Dr. Gina Rosalinda De Nicola
Guest Editor

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Keywords

glucosinolate
isothiocyanate
myrosinase
Brassicales
chemical characterization
biological characterization
mechanism of action
stability
functionality
biopesticides
biostimulants
nutraceuticals

Published Papers (5 papers)

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Research

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19 pages, 1358 KiB

Open AccessArticle

Formation of DNA Adducts by 1-Methoxy-3-indolylmethylalcohol, a Breakdown Product of a Glucosinolate, in the Mouse: Impact of the SULT1A1 Status—Wild-Type, Knockout or Humanised

by Hansruedi Glatt, Sarah Yasmin Weißenberg, Anke Ehlers, Alfonso Lampen, Albrecht Seidel, Fabian Schumacher, Wolfram Engst and Walter Meinl

Int. J. Mol. Sci. 2024, 25(7), 3824; https://doi.org/10.3390/ijms25073824 - 29 Mar 2024

Viewed by 858

Abstract

We previously found that feeding rats with broccoli or cauliflower leads to the formation of characteristic DNA adducts in the liver, intestine and various other tissues. We identified the critical substances in the plants as 1-methoxy-3-indolylmethyl (1-MIM) glucosinolate and its degradation product 1-MIM-OH. DNA adduct formation and the mutagenicity of 1-MIM-OH in cell models were drastically enhanced when human sulfotransferase (SULT) 1A1 was expressed. The aim of this study was to clarify the role of SULT1A1 in DNA adduct formation by 1-MIM-OH in mouse tissues in vivo. Furthermore, we compared the endogenous mouse Sult1a1 and transgenic human SULT1A1 in the activation of 1-MIM-OH using genetically modified mouse strains. We orally treated male wild-type (wt) and Sult1a1-knockout (ko) mice, as well as corresponding lines carrying the human SULT1A1-SULT1A2 gene cluster (tg and ko-tg), with 1-MIM-OH. N²-(1-MIM)-dG and N⁶-(1-MIM)-dA adducts in DNA were analysed using isotope-dilution UPLC-MS/MS. In the liver, caecum and colon adducts were abundant in mice expressing mouse and/or human SULT1A1, but were drastically reduced in ko mice (1.2–10.6% of wt). In the kidney and small intestine, adduct levels were high in mice carrying human SULT1A1-SULT1A2 genes, but low in wt and ko mice (1.8–6.3% of tg-ko). In bone marrow, adduct levels were very low, independently of the SULT1A1 status. In the stomach, they were high in all four lines. Thus, adduct formation was primarily controlled by SULT1A1 in five out of seven tissues studied, with a strong impact of differences in the tissue distribution of mouse and human SULT1A1. The behaviour of 1-MIM-OH in these models (levels and tissue distribution of DNA adducts; impact of SULTs) was similar to that of methyleugenol, classified as “probably carcinogenic to humans”. Thus, there is a need to test 1-MIM-OH for carcinogenicity in animal models and to study its adduct formation in humans consuming brassicaceous foodstuff. Full article

(This article belongs to the Special Issue Advances in Bioactive Glucosinolates and Derivatives)

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14 pages, 6122 KiB

Open AccessArticle

The Antioxidant Properties of Glucosinolates in Cardiac Cells Are Independent of H₂S Signaling

by Félix Harvey, Boluwaji Aromokunola, Sabine Montaut and Guangdong Yang

Int. J. Mol. Sci. 2024, 25(2), 696; https://doi.org/10.3390/ijms25020696 - 05 Jan 2024

Cited by 1 | Viewed by 1113

Abstract

The organic sulfur-containing compounds glucosinolates (GSLs) and the novel gasotransmitter H₂S are known to have cardioprotective effects. This study investigated the antioxidant effects and H₂S-releasing potential of three GSLs ((3E)-4-(methylsulfanyl)but-3-enyl GSL or glucoraphasatin, 4-hydroxybenzyl GSL or glucosinalbin, and (R_S)-6-(methylsulfinyl)hexyl GSL or glucohesperin) in rat cardiac cells. It was found that all three GSLs had no effect on cardiac cell viability but were able to protect against H₂O₂-induced oxidative stress and cell death. NaHS, a H₂S donor, also protected the cells from H₂O₂-stimulated oxidative stress and cell death. The GSLs alone or mixed with cysteine, N-acetylcysteine, glutathione, H₂O₂, iron and pyridoxal-5′-phosphate, or mouse liver lysates did not induce H₂S release. The addition of GSLs also did not alter endogenous H₂S levels in cardiac cells. H₂O₂ significantly induced cysteine oxidation in the cystathionine gamma-lyase (CSE) protein and inhibited the H₂S production rate. In conclusion, this study found that the three tested GSLs protect cardiomyocytes from oxidative stress and cell death but independently of H₂S signaling. Full article

(This article belongs to the Special Issue Advances in Bioactive Glucosinolates and Derivatives)

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17 pages, 3181 KiB

Open AccessArticle

Isothiocyanates as Tubulin Polymerization Inhibitors—Synthesis and Structure–Activity Relationship Studies

by Renata Grzywa, Mateusz Psurski, Anna Gajda, Tadeusz Gajda and Łukasz Janczewski

Int. J. Mol. Sci. 2023, 24(18), 13674; https://doi.org/10.3390/ijms241813674 - 05 Sep 2023

Cited by 1 | Viewed by 947

Abstract

Among the various substances that interfere with the microtubule formation process, isothiocyanates (ITCs) are the group of compounds for which the binding mode and mechanism of action have not yet been explained. To better understand the structure–activity relationship of tubulin-isothiocyanate interactions, we designed and synthesized a series of sixteen known and novel, structurally diverse ITCs, including amino acid ester-derived isothiocyanates, bis-isothiocyanates, analogs of benzyl isothiocyanate, and phosphorus analogs of sulforaphane. All synthesized compounds and selected natural isothiocyanates (BITC, PEITC, AITC, and SFN) were tested in vitro to evaluate their antiproliferative activity, tubulin polymerization inhibition potential, and influence on cell cycle progression. The antiproliferative activity of most of the newly tested compounds exceeded the action of natural isothiocyanates, with four structures being more potent as tubulin polymerization inhibitors than BITC. As a confirmation of anti-tubulin activity, the correlation between polymerization inhibition and cell cycle arrest in the G₂/M phase was observed for the most active compounds. In light of the biological results indicating significant differences in the impact of structurally diverse isothiocyanate on tubulin polymerization, in silico analysis was conducted to analyze the possible mode of isothiocyanate-tubulin binding and to show how it can influence the polymerization reaction. Full article

(This article belongs to the Special Issue Advances in Bioactive Glucosinolates and Derivatives)

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Review

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13 pages, 1200 KiB

Open AccessReview

The Immunomodulatory Effects of Sulforaphane in Exercise-Induced Inflammation and Oxidative Stress: A Prospective Nutraceutical

by Ruheea Taskin Ruhee and Katsuhiko Suzuki

Int. J. Mol. Sci. 2024, 25(3), 1790; https://doi.org/10.3390/ijms25031790 - 01 Feb 2024

Viewed by 1079

Abstract

Sulforaphane (SFN) is a promising molecule for developing phytopharmaceuticals due to its potential antioxidative and anti-inflammatory effects. A plethora of research conducted in vivo and in vitro reported the beneficial effects of SFN intervention and the underlying cellular mechanisms. Since SFN is a newly identified nutraceutical in sports nutrition, only some human studies have been conducted to reflect the effects of SFN intervention in exercise-induced inflammation and oxidative stress. In this review, we briefly discussed the effects of SFN on exercise-induced inflammation and oxidative stress. We discussed human and animal studies that are related to exercise intervention and mentioned the underlying cellular signaling mechanisms. Since SFN could be used as a potential therapeutic agent, we mentioned briefly its synergistic attributes with other potential nutraceuticals that are associated with acute and chronic inflammatory conditions. Given its health-promoting effects, SFN could be a prospective nutraceutical at the forefront of sports nutrition. Full article

(This article belongs to the Special Issue Advances in Bioactive Glucosinolates and Derivatives)

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Other

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24 pages, 3367 KiB

Open AccessHypothesis

The Rationale for Sulforaphane Favourably Influencing Gut Homeostasis and Gut–Organ Dysfunction: A Clinician’s Hypothesis

by Christine A. Houghton

Int. J. Mol. Sci. 2023, 24(17), 13448; https://doi.org/10.3390/ijms241713448 - 30 Aug 2023

Viewed by 2279

Abstract

Given the increasing scientific, clinical and consumer interest in highly prevalent functional gastrointestinal disorders, appropriate therapeutic strategies are needed to address the many aspects of digestive dysfunction. Accumulating evidence for the crucifer-derived bioactive molecule sulforaphane in upstream cellular defence mechanisms highlights its potential as a therapeutic candidate in targeting functional gastrointestinal conditions, as well as systemic disorders. This article catalogues the evolution of and rationale for a hypothesis that multifunctional sulforaphane can be utilised as the initial step in restoring the ecology of the gut ecosystem; it can do this primarily by targeting the functions of intestinal epithelial cells. A growing body of work has identified the colonocyte as the driver of dysbiosis, such that targeting gut epithelial function could provide an alternative to targeting the microbes themselves for the remediation of microbial dysbiosis. The hypothesis discussed herein has evolved over several years and is supported by case studies showing the application of sulforaphane in gastrointestinal disorders, related food intolerance, and several systemic conditions. To the best of our knowledge, this is the first time the effects of sulforaphane have been reported in a clinical environment, with several of its key properties within the gut ecosystem appearing to be related to its nutrigenomic effects on gene expression. Full article

(This article belongs to the Special Issue Advances in Bioactive Glucosinolates and Derivatives)

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