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PubMed2005

A phytochrome-dependent embryonic factor modulates gibberellin responses in the embryo and micropylar endosperm of Datura ferox seeds.

The promotion of germination by phytochrome is associated with extensive changes both in the embryo and in the micropylar region of the endosperm (ME) of Datura ferox seeds. These changes require de novo gibberellins (GAs) biosynthesis in the embryo, the site where the light stimulus is perceived. GAs stimulate embryo growth potential and move to ME, promoting the expression of genes related with weakening. We report here that, in addition, phytochrome stimulates the sensitivity of the seeds to gibberellic acid (GA). The phytochrome-induced signal is produced in the embryo and enhances the stimulus by GA of embryo growth potential (EGP) and the promotion of the expression of proteins thought to participate in ME weakening: endo-beta-mannanase (EC 3.2.1.78), endo-beta-mannosidase (EC 3.2.1.25) and expansin. Our results suggest that the cytokinins may be a component of the embryonic signal. Phytochrome also modulates DfPHOR and DfMYB transcript levels in ME. These genes show a high identity with components of GAs signaling identified in other species. Expression of DfPHOR in the ME is apparently regulated by phytochrome through the supply of GAs from the embryo to ME, whereas DfMYB expression is regulated by an embryonic factor with some of the characteristics of the one that modulates seed sensitivity to GAs.

Datura↗

PubMed2005

Indirect cost of a defensive trait: variation in trichome type affects the natural enemies of herbivorous insects on Datura wrightii.

The costs and benefits of defensive traits in plants can have an ecological component that arises from the effect of defenses on the natural enemies of herbivores. We tested if glandular trichomes in Datura wrightii, a trait that confers resistance to several species of herbivorous insects, impose an ecological cost by decreasing rates of predation by the natural enemies of herbivores. For two common herbivores of D. wrightii, Lema daturaphila and Tupiocoris notatus, several generalized species of natural enemies exhibited lower rates of predation on glandular compared to non-glandular plants. Lower rates of predation were associated with reductions in the residence time and foraging efficiency of natural enemies on plants with glandular trichomes, but not with direct toxic effects of glandular exudate. Our results suggest that the benefit of resistance to herbivores conferred by glandular trichomes might be offset by the detrimental effect of this trait on the natural enemies of herbivores, and that the fitness consequences of this trichome defense might depend on the composition and abundance of the natural-enemy community.

Analysis of Variance↗

PubMed2005

Biological activity of acyl glucose esters from Datura wrightii glandular trichomes against three native insect herbivores.

Datura wrightii is dimorphic for leaf trichome type in southern California. "Sticky" plants produce glandular trichomes that secrete acylsugars, whereas velvety plants produce nonglandular trichomes. Glandular trichomes confer resistance to some potential insect herbivores and are associated with reduced feeding in the field by two native coleopteran herbivores: the tobacco flea beetle, Epitrix hirtipennis, and a weevil, Trichobaris compacta. In contrast, another native beetle, Lema daturaphila, damages sticky and velvety plants similarly in the field. A series of choice and no-choice "ester removal" and "ester addition" feeding experiments were performed in the laboratory to evaluate the role of acylsugars in feeding by all three insect species. Consumption of sticky leaves after their esters were removed by washing was compared to consumption of unwashed sticky leaves and velvety leaves in ester removal experiments. Consumption of velvety leaves was measured after acylsugars were applied to those leaves in controlled amounts in the ester addition experiments. Consumption by E. hirtipennis was reduced by acylsugars in all experiments. Consumption by T. compacta was reduced by acylsugars in the ester removal experiments, but not in the ester addition experiments. The location of the acylsugars at the tip of a long trichome, rather than simply on the leaf surface, may be an important component of the biological activity of acylsugars against T. compacta in nature. Consumption by L. daturaphila was not significantly reduced by acylsugars in any experiment. The acylsugars caused no significant mortality of any of the three insect species.

Animals↗

PubMed1977

Mydriasis from Datura wrightii.

A 4-year-old girl had painless, uniocular mydriasis after picking flowers. Pharmacologic testing with 1% pilocarpine confirmed the probability that an atropine-like agent had been instilled in the affected eye. The flowers were identified as Datura wrightii and contained scopolamine, hyoscyamine, and atropine on thin-layer chromatography.

Child, Preschool↗

PubMed1987

Lectin affinity high-performance liquid chromatography: interactions of N-glycanase-released oligosaccharides with leukoagglutinating phytohemagglutinin, concanavalin A, Datura stramonium agglutinin, and Vicia villosa agglutinin.

We have developed a lectin affinity high-performance liquid chromatography technique for analysis of oligosaccharides using columns of silica-bound lectins. Purified leukoagglutinating phytohemagglutinin (L-PHA), concanavalin A (Con A), Datura stramonium agglutinin (DSA), and Vicia villosa agglutinin (VVA) were covalently coupled to periodate-oxidized diol-silica by reductive amination. Homogeneous oligosaccharides of known structure, purified following release from Asn with N-glycanase and reduction with NaBH4, were tested for their ability to interact with the silica-bound lectins. The characteristic elution position obtained for each oligosaccharide was reproducible and correlated with specific structural features. The oligosaccharide specificities displayed by silica-bound L-PHA, Con A, and DSA were virtually identical to those established utilizing lectin-agarose conjugates. Analysis of oligosaccharides by lectin affinity HPLC allowed further definition of the specificity of VVA for N-glycanase-released, reduced oligosaccharides. Lectin affinity HPLC is rapid and convenient, providing an important structure-specific dimension to oligosaccharide analysis. This technique is particularly useful when utilized in conjunction with anion-exchange and ion-suppression amine adsorption HPLC methods, which fractionate on the basis of charge and size, respectively. In addition to their utility for oligosaccharide characterization, these affinity columns demonstrate the high degree of oligosaccharide specificity displayed by plant and animal lectins.

Agglutinins↗

PubMed1991

The formation of 3 alpha- and 3 beta-acetoxytropanes by Datura stramonium transformed root cultures involves two acetyl-CoA-dependent acyltransferases.

Tropine (tropan-3 alpha-ol) is an intermediate in the formation of hyoscyamine. An acyltransferase activity that can acetylate tropine using acetylcoenzyme A as cosubstrate has been found in transformed root cultures of Datura stramonium. A further acyltransferase activity that acetylates pseudotropine (tropan-3 beta-ol) with acetyl-coenzyme A is also present. These two activities can be partially resolved by anion-exchange chromatography, some fractions containing only the pseudotropine-utilizing activity. The basic properties of these two enzymes are reported and their roles in forming the observed alkaloid spectrum of D. stramonium roots discussed.

Acetyltransferases↗

PubMed1994

The reduction of tropinone in Datura stramonium root cultures by two specific reductases.

In tropane-alkaloid producing plants and root cultures, the reduction of tropinone is a branch-point in secondary metabolism. Two different reductases stereospecifically form the isomeric alcohols tropine (tropan-3 alpha-ol) and pseudotropine (tropan-3 beta-ol). We describe here the purification and characterization of both reductases from transformed root cultures of Datura stramonium. The tropine-forming reductase (TR I, EC 1.1.1.206) was purified 108-fold, the pseudotropine-forming enzyme (TR II, EC 1.1.1.236) was purified 3410-fold to homogeneity. The native molecular weights, both determined by gel chromatography, were 50,700 (TR I) and 77,700 (TR II). In SDS gel electrophoresis a subunit with an M(r) of 27,700 could be identified for TR II. Isoelectric points are at 5.2 (TR I) and 5.7 (TR II). Km values for the physiological substrate tropinone are 1.30 mM (TR I) and 0.11 mM (TR II). NADPH as a cosubstrate shows Km values of 58 microM (TR I) and 16 microM (TR II). NADH is not accepted by either enzyme. The reverse reaction (i.e. oxidation of the alcohol to tropinone) was found only for TR I with a Km of 180 microM. From a detailed analysis of the catalytic activities of TR I and TR II with a range of substrate analogues some key features of the mechanism of reaction can be proposed. The catalytic properties of TR I and TR II are compared with each other and with TR I and TR II activities from other solanaceous species from which these enzymes have been described.

Alcohol Oxidoreductases↗

PubMed1984

Datura intoxication in Riyadh.

Cases of stramonium poisoning due to deliberate abuse by young adults have been widely reported. There are also a few reports of accidental poisoning in children from contaminated food. The taste and shape of Datura stramonium makes it unattractive to both man and animals and, therefore, ingestion by children in ignorance of its toxicity is rare. Three such cases are described in this paper. In Saudi Arabia stramonium abuse is unheard of and poisoning of children as a result of food contamination is very unlikely. Cases of ingestion in ignorance are, however, likely to occur frequently since D. stramonium grows in many parts of the country. The doses taken under the circumstances, though toxic, were small. The patients, therefore, suffered mainly the peripheral signs of the anti-cholinergic action of atropine, the principal D. stramonium alkaloid. Central nervous system manifestations and toxic psychosis were minimal in contrast to intentional misuse or accidental poisoning. Due to the special susceptibility of children to atropine toxicity and the relatively small lethal dose (less than or equal to 10 mg), treatment with the specific antidote, physostigmine salicylate, is emphasized for all but the mildest cases, in addition to any symptomatic treatment that might be needed.

Child↗

PubMed1993

Biological activities of fumonisins, mycotoxins from Fusarium moniliforme, in jimsonweed (Datura stramonium L.) and mammalian cell cultures.

Fumonisins A1, A2, B1, B2 and B3 are a series of mycotoxins produced by strains of Fusarium moniliforme. Fumonisins are hydroxylated long-chain alkylamines esterified with propanetricarboxylic acid moieties that represent approximately half the mol. wt of the toxins. The A-series fumonisins are N-acetylated, whereas the B series contains free amino groups. Hydrolytic removal of the propanetricarboxylic acid moieties from fumonisins B1 and B2 yields the corresponding aminopentols, AP1 and AP2, respectively. These compounds were tested for toxicity on widely differing bioassay systems, representing plant and animal systems. The plant bioassay system employed jimsonweed (Datura stramonium L.) leaves and leaf discs in which toxicity was detected as electrolyte leakage, photobleaching and quantitation of chlorophyll reduction. The animal bioassay system employed cultured mammalian cell lines in which toxicity was detected as inhibition of cell proliferation. Fumonisins B1, B2 and B3 at 50 micrograms/ml or less were effective toxins after exposure periods greater than 24 hr in all plant and animal bioassay systems examined, except 3T3 mouse fibroblasts, whereas fumonisins A1 and A2 exhibited little or no activity. However, the hydrolytic degradation products AP1 and AP2 exhibited toxicity similar to or greater than B-series fumonisins in all test systems, including substantial toxicity to 3T3 mouse fibroblasts.

Animals↗

PubMed1995

[Datura stramonium poisoning: the diagnosis is clinical, treatment is symptomatic].

Datura stramonium is a hallucinogenic plant found in urban or rural areas. It contains three main toxic alkaloids: atropine, scopolamine, and hyosciamine. Consumption of any part of the plant can result in severe anticholinergic toxicity. Clinical symptoms are those seen in atropine poisoning, particularly hallucinations and mydriasis. Prognostic is good in this study. Patients always require hospitalisation because of agitated behavior. Symptomatic treatment is efficient. Clinicians should be aware of the potential abuse of botanicals such as jimson weed to avoid excessive investigations.

Adolescent↗

PubMed1993

Toxicity study of the main alkaloids of Datura ferox in broilers.

Seeds of the weed Datura ferox are frequent contaminants of raw materials used for animal feed. These seeds produce various toxic effects and contain mainly the alkaloids scopolamine and hyoscyamine. In this 3-month toxicity study, a mixture of scopolamine and hyoscyamine (98:2) was incorporated at four total alkaloid levels (1.5, 15, 75 or 150 mg/kg feed) into a control diet fed to 100 broilers. Alkaloid feeding caused significant reductions in the body weight gain of birds, especially of those fed a dose of 150 mg alkaloid/kg feed. Growth-retarding effects, however, were transient, as no changes in body weight gain were noted after 52 days of alkaloid feeding. Alkaloid-treated broilers showed no significant differences from controls with respect to the cardiac rate and breathing frequency nor in relation to plasma aspartate aminotransferase, alanine aminotransferase and alkaline phosphatase activities. In contrast, plasma leucine aminopeptidase activity was significantly reduced after 3 months in all alkaloid-fed birds. Autopsy and histological examination of tissues by light and electron microscopy revealed no pathological changes associated with alkaloid feeding. Broilers appeared generally healthy and behaved normally throughout. These data should be considered in the formulation of new, improved regulations defining the maximum allowable alkaloid content of D. ferox seeds contaminating raw materials destined for use as broiler feed.

Animal Feed↗

PubMed1988

Isolation and structure of a pseudopeptide gamma-L-glutamyl-L-aspartic acid from Datura stramonium that impairs learning retention in mice.

Datura stramonium contains a compound that impairs learning retention in mice. It has been purified to homogeneity and its structure has been established as that of a gamma-L-glutamyl-L-aspartate. The biological activity of this pseudodipeptide has been found to be identical with that of the corresponding synthetic one. It has also been compared to those of various synthetic di- and tripeptides containing L- and/or D-enantiomers of the constitutive amino acids. The results show that the activity is associated with a peptidic structure containing only one type of enantiomer.

Amino Acid Sequence↗

PubMed2004

Analysis of biologically active compounds in potatoes (Solanum tuberosum), tomatoes (Lycopersicon esculentum), and jimson weed (Datura stramonium) seeds.

Potatoes and tomatoes, members of the Solanaceae plant family, serve as major, inexpensive low-fat food sources providing for energy, high-quality protein, fiber, vitamins, pigments, as well as other nutrients. These crops also produce biologically active secondary metabolites, which may have both adverse and beneficial effects in the diet. This limited overview, based largely on our studies with the aid of HPLC, TLC, ELISA, GC-MS, and UV spectroscopy, covers analytical aspects of two major potato trisaccharide glycoalkaloids, alpha-chaconine and alpha-solanine, and their hydrolysis products (metabolites) with two, one, and zero carbohydrate groups; the potato water-soluble nortropane alkaloids calystegine A3 and B2; the principal potato polyphenolic compound chlorogenic acid; potato inhibitors of digestive enzymes; the tomato tetrasaccharide glycoalkaloids dehydrotomatine and alpha-tomatine and hydrolysis products; the tomato pigments beta-carotene, lycopene, and chlorophyll; and the anticholinergic alkaloids atropine and scopolamine present in Datura stramonium (jimson weed) seeds that contaminate grain and animal feed. Related studies by other investigators are also mentioned. Accurate analytical methods for these food ingredients help assure the consumer of eating a good-quality and safe diet.

Chromatography, High Pressure Liquid↗

PubMed2006

Solid-liquid extraction and cation-exchange solid-phase extraction using a mixed-mode polymeric sorbent of Datura and related alkaloids.

Tropane alkaloids solid-liquid extraction methods were developed and comprised ambient pressure ones: extraction with hot solvent, extraction at room temperature, on ultrasonic bath as well as pressurised liquid extraction (PLE) techniques. The highest yields of l-hyoscyamine in methanol PLE method (3 x 5 min, 110 degrees C) and scopolamine extracted with 1% tartaric acid in methanol (15 min, 90 degrees C) were determined. A mixed-mode reversed-phase cation-exchange solid-phase extraction (SPE) procedure was optimised for simultaneous recoveries of L-hyoscyamine, scopolamine, scopolamine-N-oxide from plant extracts as well as quaternary alkaloid representative: scopolamine-N-methyl bromide. First three alkaloids were efficiently eluted (recoveries 80-100%) from an Oasis MCX cartridge with methanol-10% ammonia (3:1, v/v) solution, whereas for the quaternary salt tetrahydrofuran-methanol-25% ammonia (6:1:3, v/v) was used with recoveries 52-6%. HPTLC-densitometric assay on silica gel plates was elaborated at 205 nm without derivatization and included: single development (over a distance 9.5 cm) with acetone-methanol-water-25% ammonia (85:5:5:8, v/v) mobile phase for L-hyoscyamine and scopolamine separation, whereas for scopolamine-N-oxide and scopolamine-N-methyl bromide a second development (to a distance 5.5 cm) with acetonitrile-methanol-85% formic acid (120:5:5, v/v) was applied. Newly elaborated RP-HPLC-diode array detection method was performed on Waters XTerra RP-18 column with gradient of acetonitrile in 15 mM ammonia solution and alkaloids were baseline separated within 20 min. Both chromatographic methods were validated and their quantitative results were compared. Good correlation between HPLC and HPTLC quantitative results was measured (correlation coefficients of mean values were 0.92086 and 0.99995 for L-hyoscyamine and scopolamine, respectively). In the RP-HPLC method, which was from 1.5- up to 7-fold more sensitive than HPTLC, limits of detection (LOD) and limits of quantitation (LOQ, in bracket) were (in ng/microl) as follows: 0.25 (0.82) for L-hyoscyamine, 0.29 (0.97) for scopolamine, 0.13 (0.45) for scopolamine-N-oxide and 0.58 (1.91) for scopolamine-N-methyl bromide. By the use of the optimised chromatographic methods, 14 various samples from the leaves and fruits of Datura sp. were screened for L-hyoscyamine and scopolamine contents and the most promising samples were established.

Alkaloids↗

PubMed2006

Alkaloid patterns in some varieties of Datura stramonium.

A comparative GC-MS investigation of the alkaloid patterns of three varieties of Datura stramonium vars. stramonium, tatula and godronii, was carried out. Twenty-five tropane alkaloids were identified in the plant organs. Alkaloid patterns of the roots, leaves and seeds of the varieties grown at equal conditions in Bulgaria were very similar. In contrast, alkaloid pattern of D. stramonium var. stramonium, grown in Egypt, showed significant differences indicating that it is influenced more strongly by the environmental factors than genetic ones.

Datura stramonium↗

PubMed2004

Evaluation of hypoglycemic and antihyperglycemic effects of Datura metel (Linn.) seeds in normal and alloxan-induced diabetic rats.

The seed powder of Datura metel was tested for its hypoglycemic activity in normal and alloxan-induced diabetic rats. Graded doses (25, 50 and 75 mg/kg, p.o.) of the seed powder when given to both normal and diabetic rats produced significant reduction in blood glucose at the 8 h. The effect was found to be dose dependent with all treatments at the doses administered.

Animals↗

PubMed2005

Expression of an antisense Datura stramonium S-adenosylmethionine decarboxylase cDNA in tobacco: changes in enzyme activity, putrescine-spermidine ratio, rhizogenic potential, and response to methyl jasmonate.

S-adenosylmethionine decarboxylase activity (SAMDC; EC 4.1.1.21) leads to spermidine and spermine synthesis through specific synthases which use putrescine, spermidine and decarboxylated S-adenosylmethionine as substrates. In order to better understand the regulation of polyamine (PA), namely spermidine and spermine, biosynthesis, a SAMDC cDNA of Datura stramonium was introduced in tobacco (Nicotiana tabacum L. cv. Xanthi) in antisense orientation under the CaMV 35S promoter, by means of Agrobacterium tumefaciens and leaf disc transformation. The effect of the genetic manipulation on PA metabolism, ethylene production and plant morphology was analysed in primary transformants (R0), and in the transgenic progeny (second generation, R1) of self-fertilised primary transformants, relative to empty vector-transformed (pBin19) and wild-type (WT) controls. All were maintained in vitro by micropropagation. Primary transformants, which were confirmed by Southern and northern analyses, efficiently transcribed the antisense SAMDC gene, but SAMDC activity and PA titres did not change. By contrast, in most transgenic R1 shoots, SAMDC activity was remarkably lower than in controls, and the putrescine-to-spermidine ratio was altered, mainly due to increased putrescine, even though putrescine oxidising activity (diamine oxidase, EC 1.4.3.6) did not change relative to controls. Despite the reduction in SAMDC activity, the production of ethylene, which shares with PAs the common precursor SAM, was not influenced by the foreign gene. Some plants were transferred to pots and acclimatised in a growth chamber. In these in vivo-grown second generation transgenic plants, at the vegetative stage, SAMDC activity was scarcely reduced, and PA titres did not change. Finally, the rhizogenic potential of in vitro-cultured leaf explants excised from antisense plants was significantly diminished as compared with WT ones, and the response to methyl jasmonate, a stress-mimicking compound, in terms of PA conjugation, was higher and differentially affected in transgenic leaf discs relative to WT ones. The effects of SAMDC manipulation are discussed in relation to plant generation, culture conditions and response to stress.

Acetates↗

PubMed2000

Biosynthetic studies on the tropane ring system of the tropane alkaloids from Datura stramonium.

Isotopic labelling experiments have been carried out in Datura stramonium root cultures with the following isotopically labelled precursors; [2H3]- [2-13C, 2H3]-, [1-13C, 18O2]-acetates, 2H2O, [2H3-methyl]-methionine, [2-13C]-phenyllactate, [3-2H]-tropine and [2'-13C, 3-2H]-littorine. The study explored the incorporation of isotope into the tropane ring system of littorine 1 and hyoscyamine 2 and revealed that deuterium from acetate is incorporated only into C-6 and C-7, and not into C-2 and C-4 as previously reported. Oxygen-18 was not retained at a detectable level into the C(3)-O bond from [1-13C, 18O2]-acetate. The intramolecular nature of the rearrangement of littorine 1 to hyoscyamine 2 is revealed again by a labelling study using [2'-13C, 3-2H]-littorine, [2-13C]-phenyllactate and [3-2H]-tropine.

Alkaloids↗