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Advances in Bioactive Glucosinolates and Derivatives
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Advances in Bioactive Glucosinolates and Derivatives

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 (20 July 2024) | Viewed by 14162

Special Issue Editor

Dr. Gina Rosalinda De Nicola

E-Mail Website
Guest Editor
Research Centre for Vegetables and Ornamental Crops, Council for Agricultural Research and Economics (CREA), Via dei Fiori 8, 51017 Pescia, Italy
Interests: glucosinolate; isothiocyanate; myrosinase; Brassicales; nutraceuticals; biopesticides; biostimulants
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

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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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

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Keywords

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

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Published Papers (7 papers)

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Research

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21 pages, 6667 KiB  
Article
Comparative Metabolomic Analysis of Moringa oleifera Leaves of Different Geographical Origins and Their Antioxidant Effects on C2C12 Myotubes
by Roberta Ceci, Mariateresa Maldini, Piergiorgio La Rosa, Paolo Sgrò, Garima Sharma, Ivan Dimauro, Mark E. Olson and Guglielmo Duranti
Int. J. Mol. Sci. 2024, 25(15), 8109; https://doi.org/10.3390/ijms25158109 - 25 Jul 2024
Viewed by 933
Abstract
Moringa oleifera is widely grown throughout the tropics and increasingly used for its therapeutic and nutraceutical properties. These properties are attributed to potent antioxidant and metabolism regulators, including glucosinolates/isothiocyanates as well as flavonoids, polyphenols, and phenolic acids. Research to date largely consists of [...] Read more.
Moringa oleifera is widely grown throughout the tropics and increasingly used for its therapeutic and nutraceutical properties. These properties are attributed to potent antioxidant and metabolism regulators, including glucosinolates/isothiocyanates as well as flavonoids, polyphenols, and phenolic acids. Research to date largely consists of geographically limited studies that only examine material available locally. These practices make it unclear as to whether moringa samples from one area are superior to another, which would require identifying superior variants and distributing them globally. Alternatively, the finding that globally cultivated moringa material is essentially functionally equivalent means that users can easily sample material available locally. We brought together accessions of Moringa oleifera from four continents and nine countries and grew them together in a common garden. We performed a metabolomic analysis of leaf extracts (MOLE) using an LC-MSMS ZenoTOF 7600 mass spectrometry system. The antioxidant capacity of leaf samples evaluated using the Total Antioxidant Capacity assay did not show any significant difference between extracts. MOLE samples were then tested for their antioxidant activity on C2C12 myotubes challenged with an oxidative insult. Hydrogen peroxide (H2O2) was added to the myotubes after pretreatment with different extracts. H2O2 exposure caused an increase in cell death that was diminished in all samples pretreated with moringa extracts. Our results show that Moringa oleifera leaf extract is effective in reducing the damaging effect of H2O2 in C2C12 myotubes irrespective of geographical origin. These results are encouraging because they suggest that the use of moringa for its therapeutic benefits can proceed without the need for the lengthy and complex global exchange of materials between regions. Full article
(This article belongs to the Special Issue Advances in Bioactive Glucosinolates and Derivatives)
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13 pages, 2470 KiB  
Article
Variations of Major Glucosinolates in Diverse Chinese Cabbage (Brassica rapa ssp. pekinensis) Germplasm as Analyzed by UPLC-ESI-MS/MS
by Seong-Hoon Kim, Kingsley Ochar, Kanivalan Iwar, Yoon-Jung Lee, Hae Ju Kang and Young-Wang Na
Int. J. Mol. Sci. 2024, 25(9), 4829; https://doi.org/10.3390/ijms25094829 - 29 Apr 2024
Cited by 3 | Viewed by 1069
Abstract
In this study, the variability of major glucosinolates in the leaf lamina of 134 Chinese cabbage accessions was investigated using Acquity ultra-performance liquid chromatography (UPLC-ESI-MS/MS). A total of twenty glucosinolates were profiled, of which glucobrassicanapin and gluconapin were identified as the predominant glucosinolates [...] Read more.
In this study, the variability of major glucosinolates in the leaf lamina of 134 Chinese cabbage accessions was investigated using Acquity ultra-performance liquid chromatography (UPLC-ESI-MS/MS). A total of twenty glucosinolates were profiled, of which glucobrassicanapin and gluconapin were identified as the predominant glucosinolates within the germplasm. These two glucosinolates had mean concentration levels above 1000.00 μmol/kg DW. Based on the principal component analysis, accessions IT186728, IT120044, IT221789, IT100417, IT278620, IT221754, and IT344740 were separated from the rest in the score plot. These accessions exhibited a higher content of total glucosinolates. Based on the VIP values, 13 compounds were identified as the most influential and responsible for variation in the germplasm. Sinigrin (r = 0.73), gluconapin (r = 0.78), glucobrassicanapin (r = 0.70), epiprogoitrin (r = 0.73), progoitrin (r = 0.74), and gluconasturtiin (r = 0.67) all exhibited a strong positive correlation with total glucosinolate at p < 0.001. This indicates that each of these compounds had a significant influence on the overall glucosinolate content of the various accessions. This study contributes valuable insights into the metabolic diversity of glucosinolates in Chinese cabbage, providing potential for breeding varieties tailored to consumer preferences and nutritional demands. Full article
(This article belongs to the Special Issue Advances in Bioactive Glucosinolates and Derivatives)
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19 pages, 1358 KiB  
Article
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 1627
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. [...] Read more.
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  
Article
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 - 5 Jan 2024
Cited by 1 | Viewed by 1874
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, [...] Read more.
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 (RS)-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  
Article
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 - 5 Sep 2023
Cited by 1 | Viewed by 1573
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 [...] Read more.
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  
Review
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 - 1 Feb 2024
Cited by 4 | Viewed by 2647
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 [...] Read more.
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  
Hypothesis
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
Cited by 2 | Viewed by 3527
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 [...] Read more.
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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