Benzyl Glucosinolate Research Articles

Dose–response effect of Red Maca (Lepidium meyenii) on benign prostatic hyperplasia induced by testosterone enanthate

The main goal of this study was to determine the effect of a freeze-dried aqueous extract of the red variety of Lepidium meyenii (Red Maca) on testosterone-induced benign prostatic hyperplasia (BPH) in adult rats of the Holtzman strain. Rats were treated with freeze-dried aqueous extract of Red Maca at doses of 0, 0.01, 0.05, 0.1, and 0.5 g/kg body wt. A positive control group received Finasteride (0.6 mg/kg body wt.). After treatment, the animals were sacrificed, and the ventral prostate was extracted, and weighed. HPLC was used to determine the presence of glucosinolates in Red Maca. The prostate weight diminished in a dose-dependent fashion in rats treated with Red Maca. The effect of Red Maca was better than that observed with Finasteride. Finasteride, but not Red Maca, reduced seminal vesicles weight. Analysis of the HPLC indicated the presence of benzyl glucosinolate (Glucotropaeolin) with a content of 0.639%. Serum testosterone levels were not affected by Red Maca. Moreover, serum testosterone levels were not related to prostate or seminal vesicles weight in rats treated with vehicle and Red Maca. In conclusion, Red Maca administered orally in rats seems to exert an inhibitory effect at a level post DHT conversion, on the BPH-induced experimentally, although a direct measure of reductase action would still be required.

Glucosinolate Survey of Cultivated and Feral Mashua (Tropaeolum tuberosum Ruíz & Pavón) in the Cuzco Region of Peru

ABSTRACT Glucosinolates (GSL) present in cultivated and feral accessions of mashua (Tropaeolum tuberosum Ruiz & Pavon) were identified and quantified by High Performance Liquid Chromatography (HPLC) analysis. The main glucosinolates detected were aromatic: 4–Hydroxybenzyl GSL (OHB, Glucosinalbin), Benzyl GSL (B, Glucotropaeolin), and m–Methoxybenzyl GSL (MOB, Glucolimnathin). The total amount of GSL observed ranged from 0.27 to 50.74 micromols per gram (μMol/g) of dried tuber tissue. Most of the low-content GSL accessions are distributed within the cultivated population with a total GSL concentration lower than 5.00 μMol/g of dried tuber tissue. The highest total and specific GSL (OHB, B, and MOB) contents (more than 25.00 μMol/g of dried tuber tissue) were observed in the feral population with few exceptions. In addition, only six different GSL profiles were found: Only MOB; only B; OHB and B; OHB and MOB; B and MOB; and OHB, B and MOB.

Altering glucosinolate profiles modulates disease resistance in plants

Plant diseases are major contributing factors for crop loss in agriculture. Here, we show that Arabidopsis plants with high levels of novel glucosinolates (GSs) as a result of the introduction of single CYP79 genes exhibit altered disease resistance. Arabidopsis expressing CYP79D2 from cassava accumulated aliphatic isopropyl and methylpropyl GS, and showed enhanced resistance against the bacterial soft-rot pathogen Erwinia carotovora, whereas Arabidopsis expressing the sorghum CYP79A1 or over-expressing the endogenous CYP79A2 accumulated p-hydroxybenzyl or benzyl GS, respectively, and showed increased resistance towards the bacterial pathogen Pseudomonas syringae. In addition to the direct toxic effects of GS breakdown products, increased accumulation of aromatic GSs was shown to stimulate salicylic acid-mediated defenses while suppressing jasmonate-dependent defenses, as manifested in enhanced susceptibility to the fungus Alternaria brassicicola. Arabidopsis with modified GS profiles provide important tools for evaluating the biological effects of individual GSs and thereby show potential as biotechnological tools for the generation of plants with tailor-made disease resistance.

Antiamoebic activity of benzyl glucosinolate from Lepidium virginicum.

In a continuation of our search for potential antiprotozoal agents from plants, we found that a crude extract from the roots of Lepidium virginicum exhibited antiprotozoal activity against Entamoeba histolytica trophozoites (IC(50) of 100.1 micro g/mL). Bioassay-guided fractionation resulted in the isolation of one known glucosinolate responsible for such activity. This compound was identified as benzyl glucosinolate. It showed in vitro activity against Entamoeba histolytica strain HM1-IMSS (IC(50) of 20.4 micro g/mL). The results support the anecdotal reports for the traditional use of L. virginicum roots in the control of diarrhoea and dysentery in the highlands of Chiapas, Mexico.

Profiling glucosinolates and phenolics in vegetative and reproductive tissues of the multi-purpose trees Moringa oleifera L. (horseradish tree) and Moringa stenopetala L.

Moringa species are important multi-purpose tropical crops, as human foods and for medicine and oil production. There has been no previous comprehensive analysis of the secondary metabolites in Moringa species. Tissues of M. oleifera from a wide variety of sources and M. stenopetala from a single source were analyzed for glucosinolates and phenolics (flavonoids, anthocyanins, proanthocyanidins, and cinnamates). M. oleifera and M. stenopetala seeds only contained 4-(alpha-l-rhamnopyranosyloxy)-benzylglucosinolate at high concentrations. Roots of M. oleifera and M. stenopetala had high concentrations of both 4-(alpha-l-rhamnopyranosyloxy)-benzylglucosinolate and benzyl glucosinolate. Leaves from both species contained 4-(alpha-l-rhamnopyranosyloxy)-benzylglucosinolate and three monoacetyl isomers of this glucosinolate. Only 4-(alpha-l-rhamnopyranosyloxy)-benzylglucosinolate was detected in M. oleifera bark tissue. M. oleifera leaves contained quercetin-3-O-glucoside and quercetin-3-O-(6' '-malonyl-glucoside), and lower amounts of kaempferol-3-O-glucoside and kaempferol-3-O-(6' '-malonyl-glucoside). M. oleifera leaves also contained 3-caffeoylquinic acid and 5-caffeoylquinic acid. Leaves of M. stenopetala contained quercetin 3-O-rhamnoglucoside (rutin) and 5-caffeoylquinic acid. Neither proanthocyanidins nor anthocyanins were detected in any of the tissues of either species.

Separation and purification of glucosinolates from crude plant homogenates by high-speed counter-current chromatography

Glucosinolates are anionic, hydrophilic plant secondary metabolites which are of particular interest due to their role in the prevention of cancer and other chronic and degenerative diseases. The separation and purification of glucosinolates from a variety of plant sources (e.g. seeds of broccoli, arugula and the horseradish tree), was achieved using high-speed counter-current chromatography (HSCCC). A high-salt, highly polar system containing 1-propanol–acetonitrile–saturated aqueous ammonium sulfate–water (1:0.5:1.2:1), was run on a semi-preparative scale and then transferred directly to preparative scale. Up to 7 g of a concentrated methanolic syrup containing about 10% glucosinolates was loaded on an 850-ml HSCCC column, and good separation and recovery were demonstrated for 4-methylsulfinylbutyl, 3-methylsulfinylpropyl, 4-methylthiobutyl, 2-propenyl and 4-(rhamnopyranosyloxy)benzyl glucosinolates. Multiple injections (5 to 6 times) were performed with well-preserved liquid stationary phase under centrifugal force. Pooled sequential runs with broccoli seed extract yielded about 20 g of its predominant glucosinolate, glucoraphanin, which was produced at >95% purity and reduced to powdered form.

Glucosinolates of seven medicinal plants from Thailand

Nasturtium montanum was shown to contain glucobrassicin, 9-methylthionyl glucosinolate, oct-7-enyl glucosinolate, non-7-enyl glucosinolate, dec-7-enyl glucosinolate, methylsulfonyloctyl glucosinolate, methylsulfonylnonyl glucosinolate, methylsulfonyldecyl glucosinolate, benzyl glucosinolate, and Cleome chelidonii contained glucocapparin and glucocleomin. Raphanus sativus contained sulforaphene, plus sulforaphane, glucodehydroerucin, and gluconapin; Lepidum sativum contained benzyl glucosinolate and glucotropaeolin; Eruca versicaria contained glucoerucin; Cleome viscosa contained glucocapparin and glucocleomin, while Gynandropsis gynandra contained glucocapparin.

Analysis of EPG Recorded Probing by Cabbage Aphid on Host Plant Parts with Different Glucosinolate Contents

Probing behavior of adult apterous Brevicoryne brassicae (L.) was monitored with the electical penetration graph (EPG) technique on Sinapis alba L. Old, young, and mature leaves, as well as the generally preferred stems were compared with respect to probing activity and glucosinolate content. Compared to leaves, EPGs on stems showed much prolonged initial probes, which more often led to phloem-phase waveforms and successively to sustained phloem ingestion. However, reaching the first phloem phase within a probe was delayed on stems so that the time to the first phloem phase within the experiment was rather similar on the different plant parts. This suggests that superficial (epidermal and mesophyll) factors are more favorable in stems than in leaves but for deeper tissues, i.e., mesophyll and vascular bundle cells, the situation seems reversed, except for the phloem sieve elements, which seemed more or at least equally suitable. 3-Butenyl, p-hydroxybenzyl, and benzyl glucosinolates were found in all parts. It is concluded that further research on distribution and compartmentation of glucosinolates within plant tissues is needed for a better understanding of the correlations found with some B. brassicae probing parameters.

In VitroandIn VivoAntitumor Activity of Benzyl Isothiocyanate: A Natural Product fromTropaeolum majus

Cultured cells of Tropaeolum majus produce significant amounts of benzyl glucosinolate which, through enzymatic hydrolysis, results in the production of benzyl isothiocyanate (BITC). This study reports on the in vitro anticancer properties of BITC against a variety of human and murine tumor cell lines by four independent methods; SRB, MTT, cell counting, and clonogenic assays. Regardless of the assay used, BITC showed promising cytotoxicity in the low micromolar range (0.86 to 9.4 microM) against four human ovarian carcinoma cell lines (SKOV-3, 41-M, CHl, CHlcisR), a human lung tumor (H-69), a murine leukemia (L-1210), and a murine plasmacytoma (PC6/sens). The L1210 cells were most sensitive. BITC administered to mice bearing the ADJ/PC6 plasmacytoma subcutaneous tumor showed toxic effects at a dose of 200 mg/kg (within 24 h of drug administration) but no reduction in tumor mass. However, the growth inhibitory properties of BITC against a range of tumor cell types warrant further in vivo anti-tumor evaluation as well as its biotechnological production.

Glucosinolate Metabolism in Rapeseed Embryos: Effect of Feeding Glucosinolate Precursors and Uptake of Glucosinolate by Different Plant Cultivars

Embryos excised from the developing seed of Brassica napus cultivar Golden were cultured in vitro in the presence of 3-butenyl glucosinolate and desulfo-2-propenyl glucosinolate, potential precursors to the seed glucosinolates 2-hydroxy-3-butenyl and 2-propenyl glucosinolate, respectively. No increase in 2-hydroxy-3-butenyl or in 2-propenyl glucosinolate content was observed in the embryos during the culture period, suggesting that embryos lack the biosynthetic capacity to hydroxylate or to sulfate the 3-butenylordesulfo-2-propenyl glucosinolate precursors. Short term uptake experiments demonstrated that benzyl glucosinolate uptake by embryos is competitively inhibited by 3-indolylmethyl glucosinolate, indicating that these two glucosinolate substrates may be served by a common carrier protein. Additionally, glucosinolate uptake by embryos of the high glucosinolate cultivars B. napus Golden and Brassica campestris RSOO was compared to uptake by the low glucosinolate cultivars B. napus Westar and B. campestris Tobin. Results indicate that reduced seed glucosinolate content of the low cultivars cannot be attributed to reduced rates of glucosinolate uptake by the embryo. We suggest that reduced amount of glucosinolate in tissues of the maternal plant is responsible for the reduced seed glucosinolate content.

Kinetic Properties of Myrosinase in Hydrated Reverse Micelles

AbstractThe enzymatic activity of myrosinase (thioglucoside glucohydrolase, EC 3.2.3.1) solubilized in reverse micelles, which were formed in isooctane by bis(2‐ethylhexyl) sodium sulfosuccinate (AOT), was studied using sinigrin (allyl glucosinolate) and glucotropeolin (benzyl glucosinolate) as substrates. The enzyme in reverse micelles follows Michaelis‐Menten kinetics for both substrates, showing similar kinetic values, whereas in water solution sinigrin seems to be the better substrate. The effect of the water concentration, W0 (W0=[H20]/[AOT]), on the steady‐state velocity of the myrosinase does not induce the bell‐shaped activity profile observed for many other enzymes. The optimal W0 for both substrates appears to be widespread between 10 and 40. The pH profile of myrosinase activity in reverse micelles shows an increase of activity from pH 4 to pH 6. Above this value and up to pH 9, the activity remains constant, establishing a broad plateau at its maximum. It was demonstrated that myrosinase activity in reverse micelles, as well as in water solution, strongly depends on the temperature, showing an extraordinary maximum of activity with both substrates around 60 °C. As in water, the enzyme appears to be strongly activated by ascorbate in reverse micelles with both sinigrin and glucotropeolin. All the above properties of the enzyme in reverse micelles, and in particular (i) the possibility of varying the water concentration and the pH within relatively wide ranges, (ii) the high thermal stability of the enzyme together with the exceptionally high optimum reaction temperature, and (iii) the activation of the enzyme by ascorbate more than in water solutions, strongly suggest the use of this enzyme solubilized in reverse micelles to good advantage for producing biologically interesting nitrogen‐and sulfur‐containing compounds from glucosinolate hydrolysis.

Benzyl isothiocyanate in onion ( Allium cepa L.) and mushroom ( Agaricus bisporus)—A re-examination

Modern chemical and physico-chemical techniques have been applied to the analysis of benzyl isothiocyanate and glucosinolate in onion ( Allium cepa L.) and mushroom ( Agaricus bisporus). No such compounds could be detected above the limits of the analytical methods used and earlier claims for the presence of these compounds in these foods must be regarded as tentative.

On the determination of papaya seed adulteration of black pepper

Determination of the amount of benzyl glucosinolate (glucotropaeolin) in black pepper seed and products affords a sensitive method of determining the degree of adulteration with papaya seed. The glucotropaeolin may be estimated directly using gas chromatography, or indirectly by measuring the glucose which is quantitatively released following enzymic treatment. No attempt has been made to optimise the conditions of the extraction since, as described, the method allows detection of 0·1% papaya seed contamination/adulteration.

Studies on glucosinolate degradation in Lepidium sativum seed extracts

Analysis of Lepidium sativum seeds showed the presence of allyl, 2-phenethyl and benzyl glucosinolates, the first two being reported for the first time from this source. The effects of temperature, pH of the extraction medium and the length of time allowed for autolysis were assessed on the benzyl glucosinolate degradation products in seed extracts. In particular benzyl thiocyanate was not produced at higher temperatures but at ambient and lower temperatures it exceeded isothiocyanate. Nitrile was always the major product under the conditions studied, ever at pH levels as high as 7.4. Five new possible benzyl glucosinolate degradation products were detected and evidence is presented that benzaldehyde and benzyl alcohol could be secondary products formed thermally from isothocyanate and thiocyanate, respectively. Benzyl mercaptan and benzyl methyl sulphide also appear to be thermally produced.

Localization of benzyl glucosinolate and thioglucosidase in Carica papaya fruit

Macerated papaya seeds and pulp contained benzyl isothiocyanate, produced by the enzymatic hydrolysis of benzyl glucosinolate by thioglucosidase. The substrate and enzyme were localized in different areas. In mature papaya seeds, thioglucosidase was found in sarcotestae but not in endosperms, while the reverse was true for benzyl glucosinolate, which constituted more than 6% (w/w) of the endosperms. Both the enzyme and substrate were present in embryos and the amount of the latter was 3·9% (w/w). In immature papaya pulp, benzyl glucosinolate was localized principally, if not exclusively, in the latex, ranging from 7·3 to 11·6% of the dry wt of latex fluid. No thioglucosidase activity was found in papaya latex. The possible significance of the localization of this enzyme-substrate system and aspects concerning functions of papaya latex are discussed.

The biosynthesis of the thioglucoside moiety of benzyl glucosinolate

Phenylacetothiohydroxamat und Thioglukose wurden als mogliche biosynthetische Quellen des thioglukosidischen Schwefelatoms in Benzylglukosinolat (Glucotropaeolin), dem Senfolglukosid der Kapuzinerkresse (Tropaeolum majus L.) untersucht. Die experimentellen Ergebnisse deuten darauf hin, dass Thioglukose eine direkte Vorstufe ist, die mit einer von Phenylalanin abgeleiteten Stickstoffverbindung reagiert.