Ascorbigen and other indole-derived compounds from Brassica vegetables and their analogs as anticarcinogenic and immunomodulating agents

Preobrazhenskaya, M. N.; Бухман, В. М.; Королев, А. М.; Efimov, S. A.

doi:10.1016/0163-7258(93)90012-3

Cited by 82 publications

(36 citation statements)

References 24 publications

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“…During sauerkraut preparation, indole GLS glucobrassicin (GB) yields first an unstable isothiocyanate that further degrades with loss of S to form the intermediate indole-3-carbinol (I3C) that spontaneously reacts with L-ascorbic acid forming ABG at acid pH (Zeligs 1998). It has been reported that ABG is not present in intact plant tissues (Preobrazhenskaya et al 1993) or it is present in low quantities in just shredded cabbage because a certain amount of GB might have been hydrolysed by the endogenous myrosinase as a consequence of cell damage (Ciska and Pathak 2004;Martinez-Villaluenga et al 2009;Peñas et al 2010). ABG formation is strongly dependent on the pH and the already formed ABG remains relatively stable at pH 4-5 characteristics of fermented cabbage products (Aleksandrova et al 1992).…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Determination of Ascorbigen in Sauerkrauts

et al. 2011

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Ascorbigen (ABG), 2-C-(indol-3-yl)methyl-α-Lxylo-hex-3-ulofuranosono-1,4-lactone, was synthesised and its structure and purity was confirmed by means of 1 H NMR and 13 C NMR spectra and HPLC-PDA, respectively. The electrochemical behaviour of ABG was studied by cyclic voltammetry (CV) method for pH within the range of 3.0-7.0 and further characterisation was performed by differential pulse voltammetry (DPV) at pH 5.0. Voltammetric studies of ABG at glassy carbon electrode showed one irreversible oxidation peak (centred at E p =0.950 V for pH 5.0). The anodic peak current potential related to the irreversible oxidation of ABG was shifted towards more positive potentials with decreasing pH values. The linear response between concentration of ABG within the range of 0.08-0.75 mM and recorded current was observed. The DPV method was shown to be more sensitive when compared to the CV method. ABG showed a significant reducing activity provided by CV, whilst the antioxidant activity of ABG against O 2 −• was negligible. Electrochemical behaviour of ABG standard was applied successfully for the quantification of natural ABG in sauerkrauts by DPV and HPLC-CoulArray methods. Based on the developed analytical methods, ABG content increased during natural fermentation of cabbage at 0.5% and 1.5% NaCl levels, and results were comparable with those found in the literature.

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Section: Introductionmentioning

confidence: 99%

Electrochemical Determination of Ascorbigen in Sauerkrauts

et al. 2011

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“…Indole-3-carbinol (I3C) conjugates are highly expressed in cruciferous vegetables, such as broccoli, Brussels sprouts, and cauliflower (1,2), and this compound and its metabolites have been linked to the cancer chemopreventive and chemoprotective effects of vegetables (3)(4)(5)(6)(7). I3C is highly unstable in the acid environment of the gut and undergoes heterodimerization and rearrangement to give several products (8), including 3,3 ¶-diindolylmethane (DIM), which also exhibits anticancer activities through modulation of multiple pathways, including activation of the aryl hydrocarbon receptor (AhR; ref.…”

Section: Introductionmentioning

confidence: 99%

Nur77 Agonists Induce Proapoptotic Genes and Responses in Colon Cancer Cells through Nuclear Receptor–Dependent and Nuclear Receptor–Independent Pathways

et al. 2007

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Nerve growth factor-induced BA (NGFI-BA, Nur77) is an orphan nuclear receptor with no known endogenous ligands; however, recent studies on a series of methylene-substituted diindolylmethanes (C-DIM) have identified 1,1-bis(3 ¶-indolyl)-1-(phenyl)methane (DIM-C-Ph) and 1,1-bis(3 ¶-indolyl)-1-(p-anisyl)methane (DIM-C-pPhOCH 3 ) as Nur77 agonists. Nur77 is expressed in several colon cancer cell lines (RKO, SW480, HCT-116, HT-29, and HCT-15), and we also observed by immunostaining that Nur77 was overexpressed in colon tumors compared with normal colon tissue. DIM-C-Ph and DIM-C-pPhOCH 3 decreased survival and induced apoptosis in RKO colon cancer cells, and this was accompanied by induction of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) protein. The induction of apoptosis and TRAIL by DIM-C-pPhOCH 3 was significantly inhibited by a small inhibitory RNA for Nur77 (iNur77); however, it was evident from RNA interference studies that DIM-C-pPhOCH 3 also induced Nur77-independent apoptosis. Analysis of DIM-C-pPhOCH 3 -induced gene expression using microarrays identified several proapoptotic genes, and analysis by reverse transcription-PCR in the presence or absence of iNur77 showed that induction of programmed cell death gene 1 was Nur77 dependent, whereas induction of cystathionase and activating transcription factor 3 was Nur77 independent. DIM-C-pPhOCH 3 (25 mg/kg/d) also inhibited tumor growth in athymic nude mice bearing RKO cell xenografts. These results show that Nur77-active C-DIM compounds represent a new class of anti-colon cancer drugs that act through receptordependent and receptor-independent pathways. [Cancer Res 2007;67(2):674-83]

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“…The indole moiety is a heterocycle found in a large array of natural products and pharmaceuticals possessing anti-allergic [2], central-nervous-system depressant [3], muscle relaxant [4], and anti-cancer [5,6] properties. Consequently, synthetic approaches toward indoles have long been a topic of fundamental interest to organic and medicinal chemists [7,8].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of ethyl 5-chloro-2-indolecarboxylate, C11H10ClNO2

Wu¹,

Liu²,

Wu³

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound was prepared following the reported procedure [1]. In a typical experiment 0.2 g (yield 89%) of the title compound was obtained. The single crystals were obtained by slow evaporation from an ethanol solution at room temperature. Experimental detailsHydrogen atoms bonded to carbon were positioned geometrically, with C-H = 0.95 to 0.99 Å, and constrained to ride on their parent atoms, with U iso (H) =1.2U eq (C). Positional parameters and the U iso value of the hydrogen atom H1N were refined freely. DiscussionThe indole moiety is a heterocycle found in a large array of natural products and pharmaceuticals possessing anti-allergic [2], central-nervous-system depressant [3], muscle relaxant [4], and anti-cancer [5,6] properties. Consequently, synthetic approaches toward indoles have long been a topic of fundamental interest to organic and medicinal chemists [7,8]. The Fischer indole synthesis is the most widely used method for the preparation of indole derivatives [9,10]. The crystal structure of methyl indole-3-carboxylate [11], as well as the structures of some esters of indole-2-carboxylic acid are known [12][13][14]. The title crystal structure is built by the C 11 H 10 ClNO 2 molecules, in which all bond lengths and angles are in normal ranges. The finding of a nearly planar molecule is in good agreement with the structure of methyl 5-chloro-1H-indole-2-carboxylate [15]. An examination of the deviations from the least-squares planes through individual rings shows that rings A (N1/C1/C2/C3/C8) and B (C3-C8) are each planar. The indole ring system is planar, with a puckering amplitude Q = 0.0069 Å [16]. The mean plane of the methoxy carbonyl group is s slightly twisted with a dihedral angle of 2.06(15)°with respect to the indole ring system. Intermolecular N-H···O hydrogen bonds between C=O and N1-H1N link the molecules, forming centrosymmetric dimers.

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Ascorbigen and other indole-derived compounds from Brassica vegetables and their analogs as anticarcinogenic and immunomodulating agents

Cited by 82 publications

References 24 publications

Electrochemical Determination of Ascorbigen in Sauerkrauts

Electrochemical Determination of Ascorbigen in Sauerkrauts

Nur77 Agonists Induce Proapoptotic Genes and Responses in Colon Cancer Cells through Nuclear Receptor–Dependent and Nuclear Receptor–Independent Pathways

Crystal structure of ethyl 5-chloro-2-indolecarboxylate, C11H10ClNO2

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