Synthesis of aromatic and indole alpha-glucosinolates

Vo, Quan V.; Rochfort, Simone; Nam, Pham Cam; Nguyen, T.; Nguyen, Trung T.; Mechler, Ádám

doi:10.1016/j.carres.2017.11.004

Cited by 16 publications

(12 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Owing to their interesting biological activities, natural GSLs have been the target of several total syntheses . Additionally, the syntheses of several artificial GSLs bearing unnatural or isotopically labeled aglycones and glucose units as well as α‐anomeric GSLs have been reported. Very recently, Tatibouët and co‐workers reported a mannoside–GSL glycoconjugate as labeling probe for lectins .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

et al. 2019

View full text Add to dashboard Cite

The synthesis of the first example of a fluorescent glucosinolate (GSL)–BODIPY conjugate based on an azide‐containing artificial GSL precursor (GSL‐N3) is reported. Biochemical evaluation of the artificial GSLs revealed that the compounds are converted to the corresponding isothiocyanates in the presence of myrosinase. Furthermore, myrosinase‐catalyzed hydrolysis in the presence of plant specifier proteins yielded the expected alternative products, namely nitriles. The easy assembly of the fluorescent GSL–BODIPY conjugate by click chemistry from GSL‐N3 holds potential for application as a fluorescence labeling tool to investigate GSL‐associated processes.

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Natural GRP was isolated from broccoli seeds and purified following the literature. 16 To approximately 9 g of broccoli seeds 90 mL of boiling water was added, and the mixture boiled for 5 min. The bulk of the water was decanted and the seeds transferred to a mortar with 15 mL of water.…”

Section: Isolation and Purification Of Grp From Broccoli Seedsmentioning

confidence: 99%

“…GRP was obtained from the crude residue by HPLC (mobile phase 1 vol. % CH 3 CN, 99 % aqueous 0.1 % formic acid) 16 as a colorless liquid (35.7 mg). The NMR and MS data of the isolated GRP matched with the literature values.…”

Section: Isolation and Purification Of Grp From Broccoli Seedsmentioning

confidence: 99%

Anti-inflammatory activity of synthetic and natural glucoraphanin

Nam

Dinh

et al. 2019

JSCS

Self Cite

View full text Add to dashboard Cite

Glucoraphanin is one of the best known glucosinolates because of its health benefits. The compound is known to eliminate carcinogens in tissue and hence is frequently studied for its cancer preventative properties. In this work, the total synthesis of α-and β-glucoraphanin epimers was attempted. β-Glucoraphanin potassium salt was successfully synthesized in high overall yield, whereas the α-epimer was found to be unstable as it decomposed in the final step of the total synthesis. The anti-inflammatory activity of the synthetic glucoraphanin was determined by inhibition of the release of tumor necrosis factor alpha (TNF-α) secretion in lipopolysaccharide-stimulated THP-1 cells. It was shown that in the presence of either the synthetic or natural glucoraphanin, TNF-α secretion was significantly reduced (≈52 % inhibition) at a concentration of 15 μM.

show abstract

“…Besides the naturally available sources of GSs, recently, the prediction of new, efficient bioactive GSs/GSHPs and their derivatives have been evaluated. Among them include ITC derivatives with higher antimicrobial activity [ 22 ], chemopreventive properties [ 23 ], herbicidal activity [ 24 ], antimicrobial activity [ 25 ], anti-tumor activity [ 26 ], ITCs with moderate anti-inflammatory [ 27 , 28 , 29 ] and ITCs with similar anti-proliferative activity as natural ITCs [ 30 ].…”

Section: Introductionmentioning

confidence: 99%

Human, Animal and Plant Health Benefits of Glucosinolates and Strategies for Enhanced Bioactivity: A Systematic Review

et al. 2020

View full text Add to dashboard Cite

Glucosinolates (GSs) are common anionic plant secondary metabolites in the order Brassicales. Together with glucosinolate hydrolysis products (GSHPs), they have recently gained much attention due to their biological activities and mechanisms of action. We review herein the health benefits of GSs/GSHPs, approaches to improve the plant contents, their bioavailability and bioactivity. In this review, only literature published between 2010 and March 2020 was retrieved from various scientific databases. Findings indicate that these compounds (natural, pure, synthetic, and derivatives) play an important role in human/animal health (disease therapy and prevention), plant health (defense chemicals, biofumigants/biocides), and food industries (preservatives). Overall, much interest is focused on in vitro studies as anti-cancer and antimicrobial agents. GS/GSHP levels improvement in plants utilizes mostly biotic/abiotic stresses and short periods of phytohormone application. Their availability and bioactivity are directly proportional to their contents at the source, which is affected by methods of food preparation, processing, and extraction. This review concludes that, to a greater extent, there is a need to explore and improve GS-rich sources, which should be emphasized to obtain natural bioactive compounds/active ingredients that can be included among synthetic and commercial products for use in maintaining and promoting health. Furthermore, the development of advanced research on compounds pharmacokinetics, their molecular mode of action, genetics based on biosynthesis, their uses in promoting the health of living organisms is highlighted.

show abstract

Synthesis of aromatic and indole alpha-glucosinolates

Cited by 16 publications

References 28 publications

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

Anti-inflammatory activity of synthetic and natural glucoraphanin

Human, Animal and Plant Health Benefits of Glucosinolates and Strategies for Enhanced Bioactivity: A Systematic Review

Contact Info

Product

Resources

About