First Total Synthesis of 4-Methylthio-3-butenyl Glucosinolate

Yamazoe, Sayumi; Hasegawa, Koji; Shigemori, Hideyuki

doi:10.1271/bbb.80862

Cited by 6 publications

(4 citation statements)

References 9 publications

(8 reference statements)

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“…On the basis of the above, the top four GSL components that are responsible for different N application rates included glucocheirolin, 4-methylthio-3-butenyl GSL, 4-methylthiobutyl GSL, and 2( R )-hydroxybutenyl GSL. Previous studies have indicated that the glucocheirolin content positively responds to N application rates and plays an important role in pest control and defense against human disease. , Yamazoe et al . further suggested that 4-methylthio-3-butenyl GSL showed strong antioxidant and cytotoxic capacities.…”

Section: Discussionmentioning

confidence: 99%

“…Previous studies have indicated that the glucocheirolin content positively responds to N application rates and plays an important role in pest control and defense against human disease. 35,36 Yamazoe et al 37 further suggested that 4-methylthio-3-butenyl GSL showed strong antioxidant and cytotoxic capacities. These results suggest that the variety Shaanyou28 is N-sensitive in terms of the GSL content, unlike Ganza1.…”

Section: ■ Discussionmentioning

confidence: 99%

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Identifying Key Metabolites Associated with Glucosinolate Biosynthesis in Response to Nitrogen Management Strategies in Two Rapeseed (Brassica napus) Varieties

Wang

Zhang

et al. 2022

J. Agric. Food Chem.

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A high glucosinolate (GSL) concentration, an undesirable substance, has severely restricted rapeseed (Brassica species) development. We performed widely targeted metabolomics analysis based on the ultra-high-performance liquid chromatography−electrospray ionization−tandem mass spectrometry (UPLC−ESI−MS/MS) technology to analyze the metabolic profiles and identify the differential metabolites and GSL components in response to different nitrogen (N) levels in two rapeseed varieties. A total of 341 metabolites and 38 GSL components were detected in the seeds. A total of 188 differential metabolites, including 34 GSL components, were identified in response to different treatments, which were mapped into 2-oxocarboxylic acid metabolism, tryptophan metabolism, and GSL biosynthesis. Key indicators of GSL components highly responsible for different N levels under two contrasting varieties were recognized, i.e., 1-methylpropyl GSL and 4-methylthiobutyl GSL. This study suggests that the efficient N management and variety selection are important strategies for developing rapeseed with low GSLs.

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Section: Discussionmentioning

confidence: 99%

Section: ■ Discussionmentioning

confidence: 99%

Identifying Key Metabolites Associated with Glucosinolate Biosynthesis in Response to Nitrogen Management Strategies in Two Rapeseed (Brassica napus) Varieties

Wang

Zhang

et al. 2022

J. Agric. Food Chem.

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“…To generate the key-hydroximoyl chlorides, the nitrovinyl pathway thus appears as a real improvement compared to the nitronate pathway, by facilitating the benchwork and shortening the synthetic sequence. Nevertheless, as recently illustrated by a total synthesis of glucoraphasatin (4-methylsulfanyl-3-butenyl GL) [40], the aldoxime pathway still remains a method of choice whenever the functionality of the chain can endure halonium species.…”

Section: The Nitrovinyl Pathwaymentioning

confidence: 99%

Glucosinolates: The synthetic approach

Rollin

Tatibouët

2010

Comptes Rendus. Chimie

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Acting generally as bio-precursors of isothiocyanates, glucosinolates (GLs) are important thiosaccharidic metabolites which occur in all plant families of the order Brassicalesnamely in our daily vegetables. All known GLs (ca 120 characterized molecules) display a remarkable structural homogeneity invariably based on a b-D-glucopyrano unit and an Osulfated anomeric (Z)-thiohydroximate function connected to a side chain which constitution, depending on plant species, is the sole structural variant. Dedicated extractive methods allow one to isolate a number of GLs from adequate plant material, but in many cases, organic synthesis brings crucial help for the production of natural GLs. In other respects, synthesis is the only way to elaborate a diversified range of artificial GL analogues. This account summarizes the varied synthetic approaches developed by us and by others since the early 1960s.

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“…Starting from a sulfoxide-oxime precursor, isotopically labelled 4-methylsulfinylbutyl GL (glucoraphanin) was synthesized by Botting et al for analysis and metabolic studies [ 17 , 18 ]. 4-Methylsulfanylbut-3-enyl GL (glucoraphasatin) and 13 C-labelled 4-methylsulfanylbutyl GL (glucoerucin) were also synthesized [ 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway

et al. 2018

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A general pathway was devised to synthesize ω-methylsulfanylalkyl glucosinolates, which represent an important class of structurally homogeneous plant secondary metabolites. The required thiofunctionalized hydroximoyl chlorides were obtained from the corresponding α,ω-nitroalkyl methylsulfide precursors, involving as the key-step, a nitronate chlorination strategy. A coupling reaction with 1-thio-beta-d-glucopyranose, followed by O-sulfation of the intermediate thiohydroximate and final deprotection of the sugar moiety afforded the target compounds.

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First Total Synthesis of 4-Methylthio-3-butenyl Glucosinolate

Cited by 6 publications

References 9 publications

Identifying Key Metabolites Associated with Glucosinolate Biosynthesis in Response to Nitrogen Management Strategies in Two Rapeseed (Brassica napus) Varieties

Identifying Key Metabolites Associated with Glucosinolate Biosynthesis in Response to Nitrogen Management Strategies in Two Rapeseed (Brassica napus) Varieties

Glucosinolates: The synthetic approach

ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway

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