Glucosinalbin

The Antioxidant Properties of Glucosinolates in Cardiac Cells Are Independent of H(2)S Signaling.[Pubmed:38255773]

Int J Mol Sci. 2024 Jan 5;25(2):696.

The organic sulfur-containing compounds glucosinolates (GSLs) and the novel gasotransmitter H(2)S are known to have cardioprotective effects. This study investigated the antioxidant effects and H(2)S-releasing potential of three GSLs ((3E)-4-(methylsulfanyl)but-3-enyl GSL or glucoraphasatin, 4-hydroxybenzyl GSL or Glucosinalbin, and (R(S))-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 H(2)O(2)-induced oxidative stress and cell death. NaHS, a H(2)S donor, also protected the cells from H(2)O(2)-stimulated oxidative stress and cell death. The GSLs alone or mixed with cysteine, N-acetylcysteine, glutathione, H(2)O(2), iron and pyridoxal-5'-phosphate, or mouse liver lysates did not induce H(2)S release. The addition of GSLs also did not alter endogenous H(2)S levels in cardiac cells. H(2)O(2) significantly induced cysteine oxidation in the cystathionine gamma-lyase (CSE) protein and inhibited the H(2)S production rate. In conclusion, this study found that the three tested GSLs protect cardiomyocytes from oxidative stress and cell death but independently of H(2)S signaling.

Glucosinolates of Sisymbrium officinale and S. orientale.[Pubmed:36500524]

Molecules. 2022 Dec 2;27(23):8431.

Glucosinolates (GSLs) from Sysimbrium officinale and S. orientale were analyzed qualitatively and quantitatively by their desulfo-counterparts using UHPLC-DAD-MS/MS. Eight GSLs were identified in S. officinale, including Val-derived (glucoputranjivin) and Trp-derived (4-hydroxyglucobrassicin, glucobrassicin, 4-methoxyglucobrassicin, and neoglucobrassicin) as the major ones followed by Leu-derived (Isobutyl GSL), Ile-derived (glucocochlearin) and Phe/Tyr-derived (Glucosinalbin). Different S. orientale plant parts contained six GSLs, with Met-derived (progoitrin, epiprogoitrin, and gluconapin) and homoPhe-derived (gluconasturtiin) as the major ones, followed by Glucosinalbin and neoglucobrassicin. GSL breakdown products obtained by hydrodistillation (HD) and microwave-assisted distillation from S. officinale, as well as isopropyl isothiocyanate, as the major volatile in both isolates, were tested for their cytotoxic activity using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Generally, all volatile isolates showed similar activity toward the three cancer cell lines. The best activity was shown by isopropyl isothiocyanate at a concentration of 100 microg/mL after 72 h of incubation, with 53.18% for MDA-MB-231, 56.61% for A549, and 60.02% for the T24 cell line.

In vitro and in vivo biotransformation of glucosinolates from mashua (Tropaeolum tuberosum) by lactic acid bacteria.[Pubmed:36444024]

Food Chem. 2023 Mar 15;404(Pt A):134631.

Mashua (Tropaeolum tuberosum) is an Andean tuber with a high content of glucosinolates (GLSs). GLSs subjected to biotransformation by plant enzymes or enzymes of the gastrointestinal microbiota give rise to biologically active compounds, to which chemo preventive properties are attributed. In this work, the biotransformation of mashua GLSs was evaluated in vitro by six strains of lactic acid bacteria (LAB) and in vivo using rats with and without previous LAB dosing. The results showed that L. rhamnosus GG utilized the totality of Glucosinalbin and glucotropaeolin, and 46.7 % of glucoaubrietin. Four GLSs derivatives were detected. The GLSs were absorbed and metabolized by the rats with low contents in feces (0.02 %) and urine (0.59 %) and were detected up to 3 h after consumption in plasma. The results showed that probiotic bacteria play an important role in transforming GLSs into beneficial compounds for the health of consumers.

Building comprehensive glucosinolate profiles for brassica varieties.[Pubmed:35961082]

Talanta. 2023 Jan 1;251:123814.

Brassica plants play an important role in common agricultural practices, such as livestock feed or biofumigation, due to the bioactivity of the natural degradation products of glucosinolate metabolites. Therefore, the ability to survey comprehensive glucosinolate profiles for individual brassicas is essential for informing proper species selection for the intended application. Current methods for glucosinolate identification and quantification involve complex or unconventional procedures, and proper reference materials are not readily available. Therefore, researchers with limited resources that require glucosinolate profiles are at an extreme disadvantage. In this work, a simple and accurate HPLC-MS method was developed and validated to build preliminary glucosinolate profiles for three agriculturally relevant forage brassica varieties [turnip (B. rapa L.), canola (B. napus L.), and rapeseed (B. napus L.)]. The average glucosinolate content across three herbage collection dates for canola, rapeseed and turnip were 2.9 +/- 0.9 mg g(-1), 6.4 +/- 1.3 mg g(-1), and 14 +/- 3.4 mg g(-1), respectively. GLS concentrations are reported in milligrams of glucosinolate, calculated as sinigrin equivalents, per gram of dry plant material. This semi-quantitative approach for reporting total GLS content in brassicas is accurate within 15%. Several minor individual glucosinolates were identified that have not been previously reported in canola, rapeseed and turnip species, including glucotropaeolin and 4-hydroxyglucobrassicin (canola), glucoraphanin and glucoberteroin (rapeseed), and Glucosinalbin and glucobarbarin (turnip). This non-targeted screen of several forage brassica varieties demonstrates the inherent variation in both the individual glucosinolate content and the total glucosinolate profile among brassicas, and highlights the importance of such glucosinolate characterization in agricultural practices. Additionally, the method developed in this study can be used as a tool for researchers with limited resources to build accurate glucosinolate profiles of brassica plants.

Lepidium graminifolium L.: Glucosinolate Profile and Antiproliferative Potential of Volatile Isolates.[Pubmed:34500622]

Molecules. 2021 Aug 27;26(17):5183.

Glucosinolates (GSLs) from Lepidium graminifolium L. were analyzed qualitatively and quantitatively by their desulfo-counterparts using UHPLC-DAD-MS/MS technique and by their volatile breakdown products-isothiocyanates (ITCs) using GC-MS analysis. Thirteen GSLs were identified with arylaliphatic as the major ones in the following order: 3-hydroxybenzyl GSL (glucolepigramin, 7), benzyl GSL (glucotropaeolin, 9), 3,4,5-trimethoxybenzyl GSL (11), 3-methoxybenzyl GSL (glucolimnanthin, 12), 4-hydroxy-3,5-dimethoxybenzyl GSL (3,5-dimethoxysinalbin, 8), 4-hydroxybenzyl GSL (Glucosinalbin, 6), 3,4-dimethoxybenzyl GSL (10) and 2-phenylethyl GSL (gluconasturtiin, 13). GSL breakdown products obtained by hydrodistillation (HD) and CH(2)Cl(2) extraction after hydrolysis by myrosinase for 24 h (EXT) as well as benzyl ITC were tested for their cytotoxic activity using MTT assay. Generally, EXT showed noticeable antiproliferative activity against human bladder cancer cell line UM-UC-3 and human glioblastoma cell line LN229, and can be considered as moderately active, while IC(50) of benzyl ITC was 12.3 mug/mL, which can be considered as highly active.

Chemical profiling and separation of bioactive secondary metabolites in Maca (Lepidium peruvianum) by normal and reverse phase thin layer chromatography coupled to desorption electrospray ionization-mass spectrometry.[Pubmed:33410238]

J Mass Spectrom. 2021 Feb;56(2):e4690.

Maca is a Peruvian tuberous root of the Brassicaceae family grown in the central Andes between altitudes of 4000 and 4500 m. The medicinal plant is a nutraceutical with important biological activities and health effects. In this study, we report a rapid high-performance thin layer chromatography (HPTLC)-(-)desorption electrospray ionization (DESI)-mass spectrometry (MS) method to profile and separate intact glucosinolates without prior biochemical modifications from the hydromethanolic extracts of two phenotypes, red and black Maca (Lepidium peruvianum) seeds. In the first stage of the plant's life cycle, aromatic glucosinolates were the main chemical constituents whereby six aromatic, three indole, and one aliphatic glucosinolate were tentatively identified. At the seedling stage, glucolepigramin/Glucosinalbin was the most predominant precursor, rather than Glucotropaeolin, which is mainly found in hypocotyls and roots. These findings lead us to suggest that glucolepigramin/Glucosinalbin play a major role as active precursors in the biosynthetic pathways of other secondary metabolites in the early stages of plant development. Between red and black Maca seeds, only minor differences in the relative abundances of glucosinolates were observed rather than different plant metabolites. For the first time, we report six potential plant antibiotics, phytoanticipins: glycosylated ascorbigens and dihydroascorbigens from Maca seeds. We also investigated a targeted reverse phase C(18) functionalized TLC-DESI-MS method with high sensitivity and specificity for Brassicaceae fatty acids in Maca seeds and health supplements such as black Maca root lyophilized powder and tinctures. The investigation of secondary metabolites by normal and reverse phase TLC-DESI-MS methods, described in this study, can aid in their identification as they begin to emerge in later stages of development in plant tissues such as leaves, hypocotyls, and roots.

Investigation of the glucosinolates in Hesperis matronalis L. and Hesperis laciniata All.: Unveiling 4'-O-beta-d-apiofuranosylglucomatronalin.[Pubmed:31918339]

Carbohydr Res. 2020 Feb;488:107898.

The glucosinolate (GSL) profiles of wild-growing plants from the genus Hesperis, i.e. Hesperis laciniata All. (leaf, stem, flower, and root) from Croatia and Hesperis matronalis L. (leaf, stem, flower, seed, and root) from Canada, were established by LC-MS. During this investigation, 5-(methylsulfanyl)pentyl- (3), 6-(methylsulfanyl)hexyl- (4), 6-(methylsulfinyl)hexyl- (6), and 4'-alpha-l-rhamnopyranosyloxybenzyl- (17) GSLs were identified. In addition, the presence of 7-(methylsulfinyl)heptyl GSL (18), hydroxy-(alpha-l-rhamnopyranosyloxy)benzyl GSL, and of one d-apiosylated analogue of 17 were suggested. Moreover, one new GSL, 4'-O-beta-d-apiofuranosylglucomatronalin (19) was isolated from H. laciniata (flower, steam and leaf) and characterized by spectroscopic data interpretation. Finally, we report the presence of 3, 4, 6, 19, Glucosinalbin (12), and 4-hydroxyglucobrassicin (20) in H. matronalis and hypothesize the presence of glucomatronalin (13) and 3-hydroxy-6-(methylsulfanyl)hexyl GSL (21).

Bunias erucago L.: Glucosinolate Profile and In Vitro Biological Potential.[Pubmed:30791395]

Molecules. 2019 Feb 19;24(4):741.

Bunias erucago belongs to the Brassicaceae family, which represents a forgotten crop of the Euro-Mediterranean area. The aim of the present study was to determine the glucosinolate profile in different plant parts and biological properties (antioxidant, anticholinesterase, and cytotoxic activities) of the isolates containing glucosinolate breakdown products. The chemical profiles were determined by using HPLC-PDA-MS/MS of desulfoglucosinolates and GC-MS of glucosinolate degradation products. The analysis of B. erucago showed the presence of seven glucosinolates: gluconapin (1), glucoraphasatin (2), glucoraphenin (3), glucoerucin (4), glucoraphanin (5), glucotropaeolin (6), and Glucosinalbin (7). The total glucosinolate content ranged from 7.0 to 14.6 micromol/g of dry weight, with the major glucosinolate Glucosinalbin in all parts. The antioxidant activity of all volatile isolates was not notable. At a tested concentration of 227 mug/mL, flower hydro-distillate (FH) showed good AChE inhibition, i.e., 40.9%, while root hydro-distillate (RH) had good activity against BChE, i.e., 54.3%. FH showed the best activity against both tested human bladder cancer cell lines, i.e., against T24 after 72 h, which have IC(50) of 16.0 mug/mL, and against TCCSUP after 48 h with IC(50) of 7.8 mug/mL, and can be considered as highly active. On the other hand, RH showed weak activity against tested cancer cells.

Identification of Glucosinolates in Seeds of Three Brassicaceae Species Known to Hyperaccumulate Heavy Metals.[Pubmed:27981800]

Chem Biodivers. 2017 Mar;14(3).

Plants from the Brassicaceae family are known to contain secondary metabolites called glucosinolates. Our goal was to establish by LC/MS the glucosinolate profile of seeds of three Brassicaceae species known to hyperaccumulate heavy metals. We investigated Alyssum fallacinum auct. non Hausskn., Iberis intermedia Guers., and Noccaea caerulescens (J. Presl & C. Presl) F. K. Mey. Our results indicate that A. fallacinum seeds contain glucoiberin and glucoibervirin, which had not been previously identified in this plant. Furthermore, we report for the first time the presence of glucoiberin, glucoibervirin, glucotropaeolin, and sinigrin in I. intermedia. We have detected for the first time glucoconringiin in N. caerulescens. In addition, Glucosinalbin, 4-hydroxyglucobrassicin, and glucomoringin were also detected.

Natural occurrence of bisphenol F in mustard.[Pubmed:26555822]

Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2016;33(1):137-46.

Bisphenol F (BPF) was found in mustard up to a concentration of around 8 mg kg(-1). Contamination of the raw products or caused by the packaging could be ruled out. Also, the fact that only the 4,4'-isomer of BPF was detected spoke against contamination from epoxy resin or other sources where technical BPF is used. Only mild mustard made of the seeds of Sinapis alba contained BPF. In all probability BPF is a reaction product from the breakdown of the glucosinolate Glucosinalbin with 4-hydroxybenzyl alcohol as an important intermediate. Hot mustard made only from brown mustard seeds (Brassica juncea) or black mustard seeds (Brassica nigra) contained no BPF. BPF is structurally very similar to bisphenol A and has a similar weak estrogenic activity. The consumption of a portion of 20 g of mustard can lead to an intake of 100-200 microg of BPF. According to a preliminary risk assessment, the risk of BPF in mustard for the health of consumers is considered to be low, but available toxicological data are insufficient for a conclusive evaluation. It is a new and surprising finding that BPF is a natural food ingredient and that this is the main uptake route. This insight sheds new light on the risk linked to the family of bisphenols.

Phytochemical analysis and antimicrobial activity of Cardaria draba (L.) Desv. volatiles.[Pubmed:21674789]

Chem Biodivers. 2011 Jun;8(6):1170-81.

Two different volatile isolates from the aerial parts of Cardaria draba (L.) Desv., obtained either by hydrodistillation (Extract I) or by CH(2) Cl(2) extraction subsequent to hydrolysis by exogenous myrosinase (Extract II), were characterized by GC-FID and GC/MS analyses. The main volatiles obtained by hydrodistillation, i.e., 4-(methylsulfanyl)butyl isothiocyanate (1; 28.0%) and 5-(methylsulfanyl)pentanenitrile (2; 13.8%), originated from the degradation of glucoerucin. In Extract I, also volatiles without sulfur and/or nitrogen were identified. These were mostly hexadecanoic acid (10.8%), phytol (10.2%), dibutyl phthalate (4.5%), and some other compounds in smaller percentages. Extract II contained mostly glucosinolate degradation products. They originated from glucoraphanin, viz., 4-(methylsulfinyl)butyl isothiocyanate (3; 69.2%) and 5-(methylsulfinyl)pentanenitrile (4; 4.5%), Glucosinalbin, viz., 2-(4-hydroxyphenyl)acetonitrile (5; 7.2%), and glucoerysolin, viz., 4-(methylsulfonyl)butyl isothiocyanate (6; 5.0%). Moreover, the volatile samples were evaluated for their antimicrobial activity using the disc-diffusion method and determining minimum inhibitory concentrations (MIC). All volatile isolates expressed a wide range of growth inhibition activity against both Gram-positive and Gram-negative bacteria and fungi. The MIC values varied between 4 and 128 mug/ml.

Soluble and total myrosinase activity in defatted Crambe abyssinica meal.[Pubmed:11262038]

J Agric Food Chem. 2001 Feb;49(2):840-5.

Crambe defatted meal contains 4-6% w/w of glucosinolates, with epiprogoitrin accounting for >90% of the total. This feature limits the use of the meal as feed due to the antinutritional properties of myrosinase-glucosinolate breakdown products. In this context, myrosinase activity assumes particular importance. In this study the total and soluble myrosinase activities have been evaluated directly on defatted meals of eight Crambe abyssinica varieties. The pH-stat method, which is the most suitable for assays in heterogeneous solid-water systems, was used. The total myrosinase activity in C. abyssinica varieties, determined using epiprogoitrin as substrate, ranged from 288 to 653 units g(-1). These activity values were up to 26 times higher than those obtained using other substrates, namely, sinigrin, Glucosinalbin, glucotropaeolin, progoitrin, and glucoraphenin. Crambe myrosinase is unusual in that, unlike other Brassicaceae containing a typical main glucosinolate, it does not show the same specificity toward its natural substrates.

Inhibition of carcinogenesis by some minor dietary constituents.[Pubmed:3916195]

Princess Takamatsu Symp. 1985;16:193-203.

Previous work has shown that food contains a large number of minor dietary constituents that can inhibit the occurrence of cancer. Additional inhibitors from four different natural sources will be the subject of this presentation. 1. Citrus fruit oils. Orange, tangerine, lemon, and grapefruit oils given p.o. induce increased glutathione (GSH) S-transferase activity in tissues of the mouse. When fed in the diet prior to and during the course of administration of benzo(a)pyrene (BP), the four citrus fruit oils inhibit formation of tumors of both the forestomach and lungs of mice. When fed either before or after the administration of 7,12-dimethylbenz(a)anthracene (DMBA) orange oil inhibits mammary tumor formation. 2. Garlic oil. Allyl methyl trisulfide (AMT), a constituent of garlic oil, has been synthesized recently. When given p.o. 96 and 48 hr prior to BP, AMT inhibits the occurrence of forestomach tumors in mice. 3. Green coffee beans. Two diterpene esters, kahweol palmitate and cafestol palmitate, which are potent inducers of GSH S-transferase activity have been isolated from coffee beans. When administered p.o. prior to DMBA the two diterpene esters inhibit mammary tumor formation. 4. Cruciferous vegetables. Several glucosinolates occur in cruciferous vegetables. Efficient procedures for the isolation of these compounds have been developed recently. The inhibitory effects of three of these i.e. glucobrassicin, glucotropaeolin, and Glucosinalbin were studied in several animal models. Glucobrassicin caused substantial inhibition of BP-induced neoplasia of the lung and forestomach of the mouse and DMBA-induced neoplasia of the breast in rats. Glucosinalbin and glucotropaeolin are less active in these systems. In addition to protective effects, indoles derived from the hydrolysis of glucobrassicin have potential harmful properties. The implications of multiple properties and factors which may determine their consequence will be discussed.