Glucosinolate Chemistry: Synthesis of <i>O</i>‐Glycosylated Derivatives of Glucosinalbin

Gueyrard, David; Iori, Renato; Tatibouët, Arnaud; Rollin, Patrick

doi:10.1002/ejoc.201000246

Cited by 16 publications

(10 citation statements)

References 34 publications

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“…The resulting MIC-1 was analyzed by 1 H- 13 C nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The data obtained by the analysis were consistent with those previously reported ( Gueyrard et al, 2010 ) and the structure of MIC-1 was confirmed to be correct ( Figure 1A ).…”

Section: Methodssupporting

confidence: 90%

Isothiocyanate From Moringa oleifera Seeds Inhibits the Growth and Migration of Renal Cancer Cells by Regulating the PTP1B-dependent Src/Ras/Raf/ERK Signaling Pathway

Xie

Qian

Yang

et al. 2022

Front. Cell Dev. Biol.

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Moringa oleifera Lam. is a tropical and subtropical plant that has been used for centuries as both food and traditional medicine. 4-[(α-L-Rhamnosyloxy) benzyl] isothiocyanate (MIC-1) is an active substance in M. oleifera, with anti-cancer activity. However, whether MIC-1 exerts anti-renal cancer effects is unknown. Therefore, the aim of the present study was to evaluate the effects of MIC-1 on the growth and migration of renal cell carcinoma (RCC) cells and to identify the putative underlying mechanism. We found that, among 30 types of cancer cells, MIC-1 exerted the strongest growth inhibitory effects against 786-O RCC cells. In addition, MIC-1 (10 μM) significantly inhibited the growth of five RCC cell lines, including 786-O, OSRC-2, 769-P, SK-NEP-1, and ACHN cells, but was not toxic to normal renal (HK2) cells. Also, MIC-1 suppressed 786-O and 769-P cell migration and invasion abilities, and reduced the expression of matrix metalloproteinase (MMP)-2 and MMP-9. Furthermore, MIC-1 induced apoptosis and cell cycle arrest, increased Bax/Bcl-2 ratio, and decreased cell cycle-related protein expression in 786-O cells and 769-P cells. Molecular docking and small-molecule interaction analyses with PTP1B both showed that MIC-1 inhibited PTP1B activity by binding to its active site through hydrogen bonding and hydrophobic interactions. Additionally, MIC-1 could suppress the growth and migration of 786-O cells by inhibiting PTP1B-mediated activation of the Src/Ras/Raf/ERK signaling pathway. In vivo experiments further showed that MIC-1 markedly inhibited the growth of xenograft tumors in mice, and greatly increased Bax/Bcl-2 ratio in tumor tissues. In addition, MIC-1 had no effect on the PTP1B-dependent Src/Ras/Raf/ERK signaling pathway in HCT-116 cells, Hep-G2 cells, and A431 cells. Overall, our data showed that MIC-1 could be a promising, non-toxic, natural dietary supplement for the prevention and treatment of renal cancer.

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Section: Methodssupporting

confidence: 90%

Isothiocyanate From Moringa oleifera Seeds Inhibits the Growth and Migration of Renal Cancer Cells by Regulating the PTP1B-dependent Src/Ras/Raf/ERK Signaling Pathway

Xie

Qian

Yang

et al. 2022

Front. Cell Dev. Biol.

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“…As a consequence, the isothiocyanate may be better taken up by herbivores or be transported over longer distances in the soil, thereby potentiating the effect of glucomoringin conversion products on pathogens and herbivores in the plant's environment. Current attempts to synthesize different glycosylated forms of sinalbin, including glucomoringin, may help to assess the role of side-chain glycosylation on the biological effect (Gueyrard et al, 2010).…”

Section: Resultsmentioning

confidence: 99%

“…Similarly, in many tropical countries extracts of the leaves, seeds and roots of Moringa tree species, belonging to the family Moringaceae, are used for a large range of medical uses (Eilert et al, 1981;Kumar et al, 2010). The main glucosinolate found in this tree is 4-(α-L-rhamnosyloxy) benzyl glucosinolate or glucomoringin, a rhamnose derivative of sinalbin (Amaglo et al, 2010;Bennett et al, 2003;Gueyrard et al, 2010;Mekonnen and Drager, 2003).…”

Section: Introductionmentioning

confidence: 99%

Isolation and identification of 4-α-rhamnosyloxy benzyl glucosinolate in Noccaea caerulescens showing intraspecific variation

et al. 2015

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Glucosinolates are secondary plant compounds typically found in members of the Brassicaceae and a few other plant families. Usually each plant species contains a specific subset of the ∼ 130 different glucosinolates identified to date. However, intraspecific variation in glucosinolate profiles is commonly found. Sinalbin (4-hydroxybenzyl glucosinolate) so far has been identified as the main glucosinolate of the heavy metal accumulating plant species Noccaea caerulescens (Brassicaceae). However, a screening of 13 N. caerulescens populations revealed that in 10 populations a structurally related glucosinolate was found as the major component. Based on nuclear magnetic resonance (NMR) and mass spectrometry analyses of the intact glucosinolate as well as of the products formed after enzymatic conversion by sulfatase or myrosinase, this compound was identified as 4-α-rhamnosyloxy benzyl glucosinolate (glucomoringin). So far, glucomoringin had only been reported as the main glucosinolate of Moringa spp. (Moringaceae) which are tropical tree species. There was no apparent relation between the level of soil pollution at the location of origin, and the presence of glucomoringin. The isothiocyanate that is formed after conversion of glucomoringin is a potent antimicrobial and antitumor agent. It has yet to be established whether glucomoringin or its breakdown product have an added benefit to the plant in its natural habitat.

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“…“Specialist” plants, which can be considered for convenient isolation of one specific GL in reasonable amount, are in very limited number [ 11 , 12 , 13 ]. This is particularly the case for thiofunctionalized GLs, for which the synthetic approach should be privileged to make available attractive substrates for biological studies [ 14 , 15 ]. Nevertheless, since our pioneering work [ 16 ], only a small number of syntheses have focused on GLs bearing an external thio-function in the aglycon part.…”

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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Glucosinolate Chemistry: Synthesis of O‐Glycosylated Derivatives of Glucosinalbin

Cited by 16 publications

References 34 publications

Isothiocyanate From Moringa oleifera Seeds Inhibits the Growth and Migration of Renal Cancer Cells by Regulating the PTP1B-dependent Src/Ras/Raf/ERK Signaling Pathway

Isothiocyanate From Moringa oleifera Seeds Inhibits the Growth and Migration of Renal Cancer Cells by Regulating the PTP1B-dependent Src/Ras/Raf/ERK Signaling Pathway

Isolation and identification of 4-α-rhamnosyloxy benzyl glucosinolate in Noccaea caerulescens showing intraspecific variation

ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway

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