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Phytochemie - Neueste Forschungsartikel der Fachverlage


 
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Phytochemistry Reviews - published by Springer -
... is an international review journal that publishes peer-reviewed papers in three issues annually. The journal examines topical issues, some of which result from meetings organized by the Phytochemical Society of Europe. The journal also presents original review papers advancing knowledge of plants in respect to their chemistry, function, biosynthesis, effects on other plants, animal physiology and pathology.

Phytochemical Analysis - published by Wiley-Interscience -
... is devoted to the publication of original articles on the utilization of analytical methodology in the plant sciences.



Aktuelle wissenschaftliche Fachartikel der genannten Journale:


Simultaneous determination of 76As, 122Sb and 153Sm in Chinese medicinal herbs by epithermal neutron activation analysis

Optimal conditions for the simultaneous determination of As, Sb and Sm in Chinese medicinal herbs using epithermal neutron activation analysis were investigated. The minimum detectable concentrations of 76As, 122Sb and 153Sm in lichen and medicinal herbs depended on the weight of the irradiated sample, and irradiation and decay durations. Optimal conditions were obtained by wrapping the irradiated target with 3.2 mm borated polyethylene neutron filters, which were adopted to screen the original reactor fission neutrons and to reduce the background activities of 38Cl, 24Na and 42K. Twelve medicinal herbs, commonly consumed by Taiwanese children as a diuretic treatment, were analysed since trace elements, such as As and Sb, in these herbs may be toxic when consumed in sufficiently large quantities over a long period. Various amounts of medicinal herbs, standardised powder, lichen and tomato leaves were weighed, packed into polyethylene bags, irradiated and counted under different conditions. The results indicated that about 350 mg of lichen irradiated for 24 h and counted for 20 min following a 30-60 h decay period was optimal for irradiation in a 1011 n/cm s epithermal neutron flux. The implications of the content of the studied elements in Chinese medicinal herbs are discussed. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 27 Aug 2008 | 12:56 pm CEST

A validated reverse-phase HPLC analytical method for the quantification of phenolic compounds in Baccharis dracunculifolia

Baccharis dracunculifolia, which has great potential for the development of new phytotherapeutic medicines, is the most important botanical source of the southeastern Brazilian propolis, known as green propolis on account of its color.To develop a reliable reverse-phase HPLC chromatographic method for the analysis of phenolic compounds in both B. dracunculifolia raw material and its hydroalcoholic extracts.The method utilised a C18 CLC-ODS (M) (4.6 × 250 mm) column with nonlinear gradient elution and UV detection at 280 nm. A procedure for the extraction of phenolic compounds using aqueous ethanol 90%, with the addition of veratraldehyde as the internal standard, was developed allowing the quantification of 10 compounds: caffeic acid, coumaric acid, ferulic acid, cinnamic acid, aromadendrin-4[prime]-methyl ether, isosakuranetin, drupanin, artepillin C, baccharin and 2,2-dimethyl-6-carboxyethenyl-2H-1-benzopyran acid.The developed method gave a good detection response with linearity in the range 20.83-800 µg/mL and recovery in the range 81.25-93.20%, allowing the quantification of the analysed standards.The method presented good results for the following parameters: selectivity, linearity, accuracy, precision, robustness, as well as limit of detection and limit of quantitation. Therefore, this method could be considered as an analytical tool for the quality control of B. dracunculifolia raw material and its products in both cosmetic and pharmaceutical companies. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 27 Aug 2008 | 12:56 pm CEST

Mathematical modelling of aliphatic glucosinolate chain length distribution in Arabidopsis thaliana leaves

Abstract  Aliphatic glucosinolates are a major class of defensive secondary metabolites in plants that are mostly derived from methionine. Occurring in different chain lengths, they show a structural diversity arising from the variable number of chain elongation cycles taking place during their biosynthesis. The key enzymes in determining glucosinolate chain length are the methylthioalkylmalate (MAM) synthases, MAM1 and MAM3, with MAM3 showing a broader substrate specificity than MAM1. A comparison of the measurements of wild type and MAM1 knockout mutant plants shows the following distinct changes in glucosinolate chain length profiles:
(1)  a reversal of the relative proportions of the two shortest glucosinolates,
(2)  a significant increase in the concentration of the longest glucosinolate,
(3)  an increase in total glucosinolate content in the mutant.
MAM3 knockout mutants on the contrary differ from wild type plants by a pronounced abundance of the second shortest glucosinolate and the depletion of the two longest glucosinolates. To clarify the contribution of the multifunctional enzymes MAM1 and MAM3 to the glucosinolate profile of Arabidopsis thaliana leaves, we simulated glucosinolate biosynthesis in a kinetic model, taking into account the structure of the pathway and measured enzymatic properties. The predicted glucosinolate profiles show all characteristics of the actual differences between wild-type and MAM1 mutants or MAM3 mutants, respectively. The model strongly supports experimental indications that the two MAM activities are not independent of each other. In particular, it showed that an elevated expression of MAM3 in the MAM1 mutant is critical in determining the glucosinolate profile of this plant line. The simulation was critical for this finding since it allowed us to assess the individual effects of two processes—the knocking out of MAM1 and the overexpression of MAM3—that are difficult to separate experimentally.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9107-3
  • Authors
    • Beate Knoke, Friedrich Schiller University Department of Bioinformatics Ernst-Abbe-Platz 2 07743 Jena Germany
    • Susanne Textor, Max Planck Institute for Chemical Ecology Department of Biochemistry Hans-Knöll-Strasse 8 07745 Jena Germany
    • Jonathan Gershenzon, Max Planck Institute for Chemical Ecology Department of Biochemistry Hans-Knöll-Strasse 8 07745 Jena Germany
    • Stefan Schuster, Friedrich Schiller University Department of Bioinformatics Ernst-Abbe-Platz 2 07743 Jena Germany

Quelle: Phytochemistry Reviews | 16 Aug 2008 | 11:01 am CEST

Application of Scion image software to the simultaneous determination of curcuminoids in turmeric (Curcuma longa)

Curcumin, desmethoxycurcumin and bisdesmethoxycurcumin are bioactive constituents of turmeric (Curcuma longa). Owing to their different potency, quality control of turmeric based on the content of each curcuminoid is more reliable than that based on total curcuminoids. However, to perform such an assay, high-cost instrument is needed.To develop a simple and low-cost method for the simultaneous quantification of three curcuminoids in turmeric using TLC and the public-domain software Scion Image.The image of a TLC chromatogram of turmeric extract was recorded using a digital scanner. The density of the TLC spot of each curcuminoid was analysed by the Scion Image software. The density value was transformed to concentration by comparison with the calibration curve of standard curcuminoids developed on the same TLC plate.The polynomial regression data for all curcuminoids showed good linear relationship with R2 > 0.99 in the concentration range of 0.375-6 µg/spot. The limits of detection and quantitation were 43-73 and 143-242 ng/spot, respectively. The method gave adequate precision, accuracy and recovery. The contents of each curcuminoid determined using this method were not significantly different from those determined using the TLC densitometric method.TLC image analysis using Scion Image is shown to be a reliable method for the simultaneous analysis of the content of each curcuminoid in turmeric. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 5 Aug 2008 | 9:19 am CEST

Physiological effects of broccoli consumption

Abstract  Epidemiological studies suggest that broccoli can decrease risk for cancer. Broccoli contains many bioactives, including vitamins C and E, quercetin and kaempferol glycosides and, like other members of the Brassicaceae, several glucosinolates, including glucobrassicin (3-indolylmethyl glucosinolate) and glucoraphanin (4-methylsulphinylbutyl glucosinolate). A key bioactive component responsible for much of this activity may be sulforaphane (1-isothiocyanato-4-methylsulfinylbutane), a hydrolysis product of glucoraphanin. Sulforaphane not only upregulates a number of phase II detoxification enzymes involved in clearance of chemical carcinogens and reactive oxygen species, but has anti-tumorigenic properties, causing cell cycle arrest and apoptosis of cancer cells. The bioequivalency of sulforaphane and whole broccoli have not been fully evaluated, leaving it unclear whether whole broccoli provides a similar effect to purified sulforaphane, or whether the presence of other components in broccoli, such as indole-3-carbinol from glucobrassicin, is an added health benefit. Dietary indole-3-carbinol is known to alter estrogen metabolism, to cause cell cycle arrest and apoptosis of cancer cells and, in animals, to decrease risk for breast cancer. Recent research suggests that both dietary broccoli and the individual components sulforaphane and indole-3-carbinol may offer protection from a far broader array of diseases than cancer, including cardiovascular and neurodegenerative diseases. A common link between these oxidative degenerative diseases and cancer may be aggravation by inflammation. A small body of literature is forming suggesting that both indole-3-carbinol and sulforaphane may protect against inflammation, inhibiting cytokine production. It remains to be seen whether cancer, cardiovascular disease, dementia and other diseases of aging can all benefit from a diet rich in broccoli and other crucifers.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9106-4
  • Authors
    • Elizabeth H. Jeffery, University of Illinois 260 Bevier Hall, 905 S Goodwin Ave Urbana IL 61801 USA
    • Marcela Araya, University of Illinois 260 Bevier Hall, 905 S Goodwin Ave Urbana IL 61801 USA

Quelle: Phytochemistry Reviews | 16 Jul 2008 | 8:10 am CEST

New evidence for the molecular-chemical diversity of potato plant rhizodeposits obtained by pyrolysis-field Ionisation mass spectrometry

Introduction - Detailed descriptions of the molecular-chemical diversity in plant rhizodeposits are scarce. The vast majority of our knowledge is derived from a priori methods of analysis, such as GC-MS and HPLC.Objective - To analyse the composition of rhizodeposits from the potato cultivar Solanum tuberosum L. cv. Albatros by pyrolysis -field ionisation mass spectrometry (Py-FIMS) and to explain differences in relation to plant growth stage and photoperiod.Methodology - Potato (Solanum tuberosum L.) plants were grown in non-sterile, native soil under controlled environmental conditions (plant chamber). Rhizodeposit samples were collected by leaching during two different growth stages and after the physiological day- and night-cycle. All leachate samples were investigated by Py-FIMS. Mass spectrometric data were evaluated by multivariate statistics.Results - Screening of the rhizodeposits by Py-FIMS revealed a broad range of m/z signals. Low-molecular-weight substances of m/z 15-56 (8.1-18.6%), alkylaromatics (12.0-15.9%), phenols and lignin monomers (8.8-13.1%) and carbohydrates (6.0-11.2%) comprised the largest proportions of total ion intensity (TII). Mass signals with significantly different abundance at the various sampling dates were assigned to compound classes of carbohydrates, phenols and lignin monomers, lignin dimers, lipids, N-containing compounds, sterols, peptides and free fatty acids; these were supplemented by marker signals for N-acetylmuramic acid from bacterial cell walls and signal molecules for the regulation of secondary pathways such as 4-hydroxycinnamic acid and linolenic acid.Conclusion - Py-FIMS was well suited to detect the molecular-chemical diversity of potato plant rhizodeposits and, compared with traditional a priori analytical methods, provided detailed evidence for significant differences in the composition of rhizodeposits depending on growth stage and diurnal period. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 11 Jul 2008 | 6:56 am CEST

Assessment of different sample processing procedures applied to the determination of melatonin in plants

Introduction - Melatonin, an indoleamine well known in vertebrates and structurally related to other important substances such as tryptophan or indole-3-acetic acid, is also present in the plant kingdom although its specific function(s) remain to be established. The emerging field of melatonin studies in plants has progressed very slowly, mainly due to the problems associated with melatonin quantification in plants.Objective - Two commonly used procedures for plant samples are compared. The analytical characteristics of both procedures are quantitatively presented using different solvents and small amounts of fresh biological material, and the respective recovery rates and quantitative limits are presented. Some improvements are suggested.Methodology - Two different sample extraction procedures were compared: a direct-sample extraction (DSE) and a homogenised- sample extraction (HSE). Melatonin was then determined in the respective plant samples by HPLC with fluorescence detection.Results - Using the DSE procedure, more than 94% melatonin was recovered from standard solutions, whereas levels higher than 93% were recovered from the spiked plant samples, with little difference between ethyl acetate and chloroform extractions. In the case of HSE, the recoveries of melatonin were approximately half and never higher than 55%. The ultrasonic treatment proposed in the DSE procedure showed different levels of efficiency (2-20%), depending on the sample.Conclusion - This study has established that, with the direct sample extraction procedure, higher recovery rates are obtained both in standard solutions and in plant samples. The straightforwardness and reproducibility of the extraction procedure is accompanied by the high sensitivity obtained with fluorescence detection. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 11 Jul 2008 | 6:56 am CEST

A Rapid and effective method for RNA extraction from different tissues of grapevine and other woody plants

Introduction - RNA quality and integrity are critical for many studies in plant molecular biology. High-quality RNA extraction from grapevine and other woody plants is problematic due to the presence of polysaccharides, polyphenolics and other compounds that bind or co-precipitate with the RNA.Objective - To develop an optimised cetyltrimethylammonium bromide (CTAB)-based protocol, to reduce the time and cost of extraction without reducing quality and yield of RNA extracted from polysaccharide-rich tissues of several plants.Methodology - Several changes were introduced to the original CTAB protocol. All centrifugation steps were carried out at 4°C, the sample weight was decreased and the concentrations of PVP-40 and LiCl were increased reducing incubation time prior to RNA precipitation. This rapid CTAB protocol was compared with six different RNA extraction methods from three grapevine tissues, namely, in vitro plantlets, and leaves and mature canes from actively growing field vines.Results - The rapid CTAB method gave high-quality RNA in only 3 h at low cost with efficiency equal to or higher than that obtained with other time-consuming and expensive protocols. The procedure was applied to RNA extraction from other grapevine tissues and other woody species including olive, lemon, poplar, chestnut, apple, pear, peach, cherry, apricot, plum and kiwi fruit. RNA of high quality could be isolated from all tissues and from all species.Conclusion - The study has shown that the improvement of a CTAB-based protocol allows the rapid isolation of high-quality RNA from grapevine and many woody species. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 10 Jul 2008 | 9:11 am CEST

Chemical fingerprinting of Lawsonia inermis L. using HPLC, HPTLC and densitometry

Introduction - Lawsonia inermis L. is a natural red colouring agent, commonly named "Henna", which is used to dye skin and hair. The aim of this study was to evaluate the quality of L. inermis that is commercially available as a raw plant material or preparation in order to guarantee good quality products.Objective - To develop a simple protocol for the qualification of different samples labelled as L. inermis by using the HPTLC densitometry method and to identify possible adulterations with other plants.Methodology - Samples of leaves of L. inermis were extracted with methanol. Two chromatographic methods were developed to determine the chemical fingerprinting of L. inermis. The first was based on HPTLC identification followed by densitometric measurements at 337 nm. The second was based on RP-HPLC separation with gradient elution and photodiode array detection at 337 nm. Samples of Cassia obovata Collad., and Indigofera tinctoria L., were treated in the same way.Results - The simplicity of the sample preparation, and the possibility of analysing several samples of herbal products simultaneously in a short time, make HPTLC the method of choice. The HPTLC method was feasible for the comprehensive quality evaluation of herbal products. From the comparison of their "fingerprint", it was possible to detect substitution of plants that are different from those declared on the label.Conclusion - The HPTLC may be used as a rapid method by which to control the quality of raw plant materials and formulations based on the title plant. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 10 Jul 2008 | 9:11 am CEST

Study on the extraction, purification and quantification of jasmonic acid, abscisic acid and indole-3-acetic acid in plants

Introduction - Jasmonic acid (JA), abscisic acid (ABA) and indole-3-acetic acid (IAA) are important plant hormones. Plant hormones are difficult to analyse because they occur in small concentrations and other substances in the plant interfere with their detection.Objective - To develop a new, inexpensive procedure for the rapid extraction and purification of IAA, ABA and JA from various plant species.Methodology - Samples were prepared by extraction of plant tissues with methanol and ethyl acetate. Then the extracts were further purified and enriched with C18 cartridges. The final extracts were derivatised with diazomethane and then measured by GC-MS. The results of the new methodology were compared with those of the Creelman and Mullet procedure.Results - Sequential elution of the assimilates from the C18 cartridges revealed that IAA and ABA eluted in 40% methanol, while JA subsequently eluted in 60% methanol. The new plant hormone extraction and purification procedure produced results that were comparable to those obtained with the Creelman and Mullet's procedure. This new procedure requires only 0.5 g leaf samples to quantify these compounds with high reliability and can simultaneously determine the concentrations of the three plant hormones.Conclusion - A simple, inexpensive method was developed for determining endogenous IAA, ABA and JA concentrations in plant tissue. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 10 Jul 2008 | 9:11 am CEST

An acylated flavonol glycoside and hydrolysable tannins from Callistemon lanceolatus flowers and leaves

Introduction - Callistemon lanceolatus DC. (Myrtaceae) is a plant rich in polyphenols, and is used as anticough, antibronchitis and insecticide in folk medicine. Because of the biological importance of plant polyphenols, particularly tannins, a phytochemical study was of interest to investigate the constitutive poyphenols in the extracts of flowers and leaves.Objective - To avoid time-consuming methodology for isolation of a complex mixture of known metabolites, HPLC-ESI/MS was employed for fast picking up of the new compounds followed by identification of the structures with UV and one- and two-dimensional NMR.Methodology - Flowers and leaves were separately extracted with hot aqueous methanol under reflux (70°C). Pre-isolation of the total extracts was achieved through column chromatographic fractionation on polyamide with water-methanol for gradient elution. The main fractions were purified using repeated column chromatography on cellulose and/or Sephadex LH-20 with suitable eluents. HPLC-ESI/MS analyses were carried out in the single ion monitoring (SIM) and negative ion modes. The pure compounds in methanol-water (1:1) were analysed by direct infusion ESI/MS. Final structure elucidation was obtained by one- and two-dimensional NMR.Results - Two new metabolites namely quercetin 3-O-[beta]-D-glucuronopyranoside n-butyl ester (1) and n-butylgallate 4-O-(2[prime],6[prime]-di-O-galloyl)-[beta]-d-glucopyranoside (4) along with nine known ones were identified from the aqueous methanol extracts of flowers and leaves.Conclusion - The study has shown that Callistemon lanceolatus is rich in polyphenols. HPLC-ESI/MS may be used, in negative ion mode, as an efficient and rapid analytical tool for investigating complex plant extracts. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 10 Jul 2008 | 9:11 am CEST

Influence of the extraction mode on the yield of hyperoside, vitexin and vitexin-2[prime][prime]-O-rhamnoside from Crataegus monogyna Jacq. (hawthorn)

Introduction - The extract of Crataegus monogyna shows sedative, hypotensive, vasodilator and cardio-tonic actions. Although several papers dealing with the extraction of metabolites from Crataegus have been published, the plant productivity in terms of bioactive compounds is not easily understandable as yet.Objective - To investigate the influence of the extraction mode on the yield of bioactive compounds from Crataegus monogyna Jacq. in order to evaluate plant productivity.Methodology - Samples were prepared by extraction of powdered material obtained from top branches, flowers and leaves. Soxhlet extraction, maceration and ultrasound- and microwave-assisted extraction at different experimental conditions were investigated for the exhaustive extraction of hyperoside, vitexin and vitexin-2[prime][prime]-O-rhamnoside. The phytocomponents were identified and quantified by HPLC-UV/PAD, comparing HPLC retention times and UV spectra of individual peaks with those of the standards analysed under the same conditions.Results - An easy-to-use HPLC isocratic method suitable for the quantification of hyperoside, vitexin and vitexin-2[prime][prime]-O-rhamnoside in raw plant extracts was developed. The optimised HPLC methodology was applied to evaluate different extraction procedures. The ultrasound and microwave-assisted extraction protocols showed higher extraction efficiency than the others. In particular, the optimised microwave protocol gave rise to the highest extraction efficiency with high reproducibility.Conclusions - A microwave protocol combined with isocratic HPLC analysis is proposed for the rapid screening of plant materials collected in different environmental conditions in order to evaluate the productivity of Crataegus monogyna Jacq. and to find out the best ecological conditions to cultivate hawthorn in Northern Italy. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 10 Jul 2008 | 9:11 am CEST

Safety assessment of food and herbal products containing hepatotoxic pyrrolizidine alkaloids: interlaboratory consistency and the importance of N-oxide determination

Introduction - Two recent mass spectrometry-based reports concerning Senecio scandens yielded remarkably dissimilar pyrrolizidine alkaloid constituents. In both studies, and in a related analysis of Senecio scandens and Tussilago farfara using micellar electrokinetic chromatography, the presence of hazardous N-oxides of the alkaloids was either not considered or was inadequately considered. This raises concerns about the effectiveness of the methodologies used in these, and similar, studies in assessing the pyrrolizidine alkaloid content and the safety of food, food supplements and medicines for human use.Objective - To highlight essential analytical requirements for confident assessment of pyrrolizidine alkaloid-related safety of food and herbal products for human use.Methodology - Direct infusion-ESI MS and HPLC-ESI MS were used to analyse samples derived from liquid-liquid partitioning experiments and from strong cation exchange, solid-phase extraction of pyrrolizidine alkaloids and their N-oxides.Results - A simple solvent partitioning experiment using pure senecionine and senecionine-N-oxide, two constituents reported in one of the mass spectrometry-based studies of S. scandens, clearly demonstrated the inadequacy of the reported method to detect and quantitate hazardous pyrrolizidine alkaloid N-oxide components. A preliminary LCMS analysis of commercially-prepared extracts of comfrey roots (Symphytum officinale and S. uplandicum s. l.) was used as a model to highlight the analytical importance of N-oxides in the safety assessment of pyrrolizidine alkaloid-containing medicinal herbs.Conclusions - This study highlighted significant differences in the reported identification of pyrrolizidine alkaloids from the same plant species, and clearly demonstrated the inadequacy of some procedures to include N-oxides in the assessment of pyrrolizidine alkaloid-related safety of food and herbal products. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 10 Jul 2008 | 9:11 am CEST

Plant-mediated effects in the Brassicaceae on the performance and behaviour of parasitoids

Abstract  Direct and indirect plant defences are well studied, particularly in the Brassicaceae. Glucosinolates (GS) are secondary plant compounds characteristic in this plant family. They play an important role in defence against herbivores and pathogens. Insect herbivores that are specialists on brassicaceous plant species have evolved adaptations to excrete or detoxify GS. Other insect herbivores may even sequester GS and employ them as defence against their own antagonists, such as predators. Moreover, high levels of GS in the food plants of non-sequestering herbivores can negatively affect the growth and survival of their parasitoids. In addition to allelochemicals, plants produce volatile chemicals when damaged by herbivores. These herbivore induced plant volatiles (HIPV) have been demonstrated to play an important role in foraging behaviour of insect parasitoids. In addition, biosynthetic pathways involved in the production of HIPV are being unraveled using the model plant Arabidopsis thialiana. However, the majority of studies investigating the attractiveness of HIPV to parasitoids are based on experiments mainly using crop plant species in which defence traits may have changed through artificial selection. Field studies with both cultivated and wild crucifers, the latter in which defence traits are intact, are necessary to reveal the relative importance of direct and indirect plant defence strategies on parasitoid and plant fitness. Future research should also consider the potential conflict between direct and indirect plant defences when studying the evolution of plant defences against insect herbivory.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9104-6
  • Authors
    • Rieta Gols, Wageningen University Laboratory of Entomology P.O. Box 8031 6700 EH Wageningen The Netherlands
    • Jeffrey A. Harvey, Netherlands Institute of Ecology Department of Multitrophic Interactions P.O. Box 40 6666 ZG Heteren The Netherlands

Quelle: Phytochemistry Reviews | 9 Jul 2008 | 8:28 am CEST

Glucosinolates and biofumigation: fate of glucosinolates and their hydrolysis products in soil

Abstract  The bioactive hydrolysis products of glucosinolates, particularly the isothiocyanates, can be used to control soil pests and weeds by incorporating glucosinolate-containing plant material in soil—a practice known as biofumigation. The fate of glucosinolates and their hydrolysis products in soil determines both the efficacy and environmental impact of biofumigation. Knowledge of the processes by which these compounds are sorbed, degraded or otherwise lost from the soil is fundamental to developing effective, but environmentally benign biofumigation strategies. Effective biofumigation relies on maximum hydrolysis of the glucosinolate in the plant tissue to generate high isothiocyanate concentrations in the soil after incorporation. This is favoured by maximum cell disruption, by addition of water, and a high soil temperature. Residual glucosinolates are very weakly sorbed, readily leached and are microbially degraded and mineralised in soil. In contrast, isothiocyanates are strongly sorbed by the organic matter in soil, react strongly with nucleophilic groups present in soil, and are prone to volatilization losses in addition to microbial degradation and mineralisation. These loss processes are influenced by soil type, water content and temperature. Using appropriate incorporation strategies, sufficiently high isothiocyanate concentrations (>100 nmol g−1) can be achieved in soil using biofumigation for effective suppression of susceptible pests. The relatively rapid sorption and degradation of the isothiocyanates in the period of days after incorporation minimizes the risks of persistence in the environment or leaching. Biofumigation is therefore a promising technique which can be further developed to form part of IPM (Integrated Pest Management) strategies to reduce reliance on synthetic pesticides with minimal unintended impacts on the environment.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9105-5
  • Authors
    • Anne Louise Gimsing, University of Copenhagen Department of Natural Sciences, Faculty of Life Sciences Thorvaldsensvej 40 1871 Frederiksberg C Denmark
    • John A. Kirkegaard, CSIRO Plant Industry GPO Box 1600 Canberra ACT 2601 Australia

Quelle: Phytochemistry Reviews | 9 Jul 2008 | 8:28 am CEST

Flavonoid glucuronides with anti-leukaemic activity from Polygonum amphibium L.

Introduction - The chemical and pharmaceutical studies carried out on species from Polygonum L. genus showed biological activity both of the extracts and the components isolated from them. These results were the impulse to examine Polygonum amphibium L.Objective - The aim of this study was the isolation of active components from methanol extract and the determination of their cytotoxic effect on human leukaemic cell lines.Methodology - Three flavonoid components from butanol soluble fractions of methanol extract by CC and PC preparative chromatography were isolated. Their structures were established on the basis of 1H, 13C and correlation (DEPT, H-H, COSY, HMQC, HMBC) NMR, UV and FAB-MS spectroscopic techniques. The evaluation of the anti-leukaemic activities of 1 and 2 against Jurkat and HL60 cell lines was carried out in vitro using annexin V fluorescence assay.Results - Two new flavonoid glucuronides, quercetin-3-O-[beta]-glucuronide (1) and quercetin-3-O-[alpha]-rhamnosyl-(1 [rarr] 2)-[beta]-glucuronide (2), and kaempferol-3-O-[alpha]-rhamnosyl-(1 [rarr] 2)-[beta]-glucuronide (3), were isolated from Polygonum amphibium L. It was demonstrated that the glucuronides of quercetin are able to induce apoptosis in the tested human leukaemic cells. These compounds penetrate through cytoplasm to the cellular nucleus of the cultured cells, and give intensive apoptotic responses in the stimulated leukaemic cells. The number of apoptotic cells increased with the concentration (1 nm to 10 µm) of 1 or 2 and periods of exposure (1-3 days).Conclusion - Compounds 1 and 2 may be considered good candidates for leukaemia chemotherapeutic agents. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 25 Jun 2008 | 1:44 pm CEST

Analysis of pharmaceutical samples of Resina Draconis by HPLC-PAD

Introduction: The quality evaluation of traditional Chinese medicine (TCM) represents a particular challenge owing to the complexity of the matrix, which renders separation and identification of the individual components extremely difficult. In recent years, fingerprinting of TCMs has played a dominant role in quality control. Resina Draconis was authorised as a new TCM in 1991, but a satisfactory HPLC fingerprint method for this preparation has not yet been published.Objective: To develop a simple and reliable protocol for the quality control of Resina Draconis using an HPLC-PAD method.Methodology: The TCM was extracted with methanol at room temperature. Chromatography was carried out using a Lichrospher C18 column eluted with a linear gradient of acetonitrile (A) and water containing 0.1% phosphoric acid (B), initially at 30:70 (A:B) and changing to 60:40 in 90 min. UV (PAD) spectra were acquired in the range 210-400 nm.Results: Four chromatograms of samples of Resina Draconis obtained from different pharmaceutical factories showed 20 peaks in common. The average chromatogram was taken as a template from which the correlation coefficients and cosine ratios of the samples were determined. Whereas the contents of individual components in each sample were different, overall the samples were extremely similar one to another, and the products from different pharmaceutical factories were consistent.Conclusion: A reliable and validated HPLC method has been developed for the fingerprint analysis of Resina Draconis that can be applied for the quality control of this TCM. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 10 Jun 2008 | 11:13 am CEST

Preparative isolation of closely-related xanthones from Gentianella amarella ssp. acuta by High-speed countercurrent chromatography

Introduction - A methanolic extract from Gentianella amarella ssp. acuta was shown to contain several xanthones exhibiting acetylcholinesterase inhibitory activity. These xanthones were difficult to separate by conventional LC techniques, which prevented the isolation of pure compounds in sufficient amounts to perform in-depth biological testing.Objective - To develop a suitable preparative method for the separation of closely related xanthones.Methodology - The methanolic extract was first partitioned with solvents of increasing polarity, in order to separate glycosides from xanthone aglycones. High-speed countercurrent chromatography (HSCCC) methods were then optimised for the fractionation of both polar and non-polar extracts.Results - The use of HSCCC enabled the separation of xanthones which co-eluted by HPLC. Ten closely related xanthones - three of which were isomeric - were successfully isolated by developing suitable solvent systems. All compounds were obtained in sufficient amounts to allow further biological assays (e.g. up to 250 mg), including even minor compounds that were not detectable by analytical HPLC.Conclusion - The orthogonality of HSCCC with HPLC and the absence of solid-phase supports enabled the detection, separation and preparative isolation of closely related compounds which were difficult to resolve by other techniques. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 10 Jun 2008 | 11:13 am CEST

Root and shoot glucosinolates: a comparison of their diversity, function and interactions in natural and managed ecosystems

Abstract  The role of glucosinolates in aboveground plant–insect and plant–pathogen interactions has been studied widely in both natural and managed ecosystems. Fewer studies have considered interactions between root glucosinolates and soil organisms. Similarly, data comparing local and systemic changes in glucosinolate levels after root- and shoot-induction are scarce. An analysis of 74 studies on constitutive root and shoot glucosinolates of 29 plant species showed that overall, roots have higher concentrations and a greater diversity of glucosinolates than shoots. Roots have significantly higher levels of the aromatic 2-phenylethyl glucosinolate, possibly related to the greater effectiveness and toxicity of its hydrolysis products in soil. In shoots, the most dominant indole glucosinolate is indol-3-ylglucosinolate, whereas roots are dominated by its methoxyderivatives. Indole glucosinolates were the most responsive after jasmonate or salicylate induction, but increases after jasmonate induction were most pronounced in the shoot. In general, root glucosinolate levels did not change as strongly as shoot levels. We postulate that roots may rely more on high constitutive levels of glucosinolates, due to the higher and constant pathogen pressure in soil communities. The differences in root and shoot glucosinolate patterns are further discussed in relation to the molecular regulation of glucosinolate biosynthesis, the within-tissue distribution of glucosinolates in the roots, and the use of glucosinolate-containing crops for biofumigation. Comparative studies of tissue-specific biosynthesis and regulation in relation to the biological interactions in aboveground and belowground environments are needed to advance investigations of the evolution and further utilization of glucosinolates in natural and managed ecosystems.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9101-9
  • Authors
    • Nicole M. van Dam, Netherlands Institute of Ecology (NIOO-KNAW) PO Box 40 6666 ZG Heteren The Netherlands
    • Tom O. G. Tytgat, Netherlands Institute of Ecology (NIOO-KNAW) PO Box 40 6666 ZG Heteren The Netherlands
    • John A. Kirkegaard, CSIRO, Plant Industry GPO Box 1600 2610 Canberra ACT Australia

Quelle: Phytochemistry Reviews | 6 Jun 2008 | 7:49 am CEST

A quantitative genetics and ecological model system: understanding the aliphatic glucosinolate biosynthetic network via QTLs

Abstract  Plants’ sessile nature has led them to develop chemical defenses, secondary metabolites, to directly cope with environmental changes rather than escape to more favorable sites. The diversity and fluctuation in biological stresses faced by a plant have generated extraordinary genetic diversity controlling the synthesis and regulation of secondary metabolites that is only now being explored. The glucosinolate secondary metabolites, amino acid derived thioglucosides specific to the order Capparales, is a model system for understanding the molecular basis of complex quantitative traits and their potential ecological role. This review focuses on the extensive progress being made towards understanding the complete molecular basis underlying the glucosinolate genetic diversity at both biosynthetic and regulatory loci. This has identified a highly interactive genetic network whereby biosynthetic loci have additional functions as regulatory loci and laid the foundation for glucosinolates to be a model system for understanding quantitative traits in a broader context.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9102-8
  • Authors
    • Daniel J. Kliebenstein, University of California, Davis Department of Plant Sciences One Shields Avenue Davis CA 95616 USA

Quelle: Phytochemistry Reviews | 5 Jun 2008 | 12:05 pm CEST

Glucosinolates and the clubroot disease: defense compounds or auxin precursors?

Abstract  The clubroot disease is caused by the obligate biotrophic protist Plasmodiophora brassicae and is one of the most damaging for the family of Brassicaceae. Since many economically important crops belong to this plant family, the understanding of mechanisms how the disease is developing, are of high importance. Glucosinolates, a group of secondary plant products in the family of Brassicaceae, have long been associated with clubroot disease symptoms. Measurements showed that several glucosinolates are induced in root galls. While aliphatic glucosinolates are regarded as defense compounds, analysis of Brassica cultivars as well as Arabidopsis thaliana mutants provided correlative evidence between disease severity and indole glucosinolate content. The latter have been discussed as precursors for auxin biosynthesis. Since high auxin levels are associated with large root galls, indole glucosinolates could contribute directly or indirectly to the extent of disease development. Transcriptome and proteome experiments have revealed evidence for the involvement of genes from the glucosinolate and auxin pathway in gall formation. These data have been complemented by expression and mutant analysis. It can be concluded that regulation of glucosinolate and IAA biosynthesis might differ in Brassica and Arabidopsis.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9096-2
  • Authors
    • Jutta Ludwig-Müller, Technische Universität Dresden Institut für Botanik 01062 Dresden Germany

Quelle: Phytochemistry Reviews | 31 May 2008 | 8:50 am CEST

Methylthioalkylmalate synthases: genetics, ecology and evolution

Abstract  Glucosinolates display an enormous amount of structural variation, both within and between species. This diversity is thought to have evolved in response to challenges imposed on plants by their biotic environment. During the past decade, glucosinolates and myrosinase-catalyzed glucosinolate hydrolysis have become excellent examples for understanding functional diversification in plant secondary metabolism and plant defence. Methylthioalkylmalate (MAM) synthase genes and enzymes are central to the diversification of aliphatic glucosinolate structures in Arabidopsis thaliana and related plants. This review summarizes efforts to elucidate how MAM-mediated diversity in aliphatic glucosinolate structures is generated and maintained. It also attempts to put variability in methionine carbon chain elongation during glucosinolate biosynthesis into an ecological and evolutionary context.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9097-1
  • Authors
    • Markus Benderoth, Max Planck Institute for Chemical Ecology AG Genetics and Evolution Hans-Knöll-Str. 8 07745 Jena Germany
    • Marina Pfalz, Max Planck Institute for Chemical Ecology AG Genetics and Evolution Hans-Knöll-Str. 8 07745 Jena Germany
    • Juergen Kroymann, Max Planck Institute for Chemical Ecology AG Genetics and Evolution Hans-Knöll-Str. 8 07745 Jena Germany

Quelle: Phytochemistry Reviews | 31 May 2008 | 8:50 am CEST

Indole glucosinolate breakdown and its biological effects

Abstract  Most species in the Brassicaceae produce one or more indole glucosinolates. In addition to the parent indol-3-ylmethylglucosinolate (IMG), other commonly encountered indole glucosinolates are 1-methoxyIMG, 4-hydroxyIMG, and 4-methoxyIMG. Upon tissue disruption, enzymatic hydrolysis of IMG produces an unstable aglucone, which reacts rapidly to form indole-3-acetonitrile and indol-3-ylmethyl isothiocyanate. The isothiocyanate, in turn, can react with water, ascorbate, glutathione, amino acids, and other plant metabolites to produce a variety of physiologically active indole compounds. Myrosinase-initiated breakdown of the substituted indole glucosinolates proceeds in a similar manner to that of IMG. Induction of indole glucosinolate production in response to biotic stress, experiments with mutant plants, and artificial diet assays suggest a significant role for indole glucosinolates in plant defense. However, some crucifer-feeding specialist herbivores recognize indole glucosinolates and their breakdown products as oviposition and/or feeding stimulants. In mammalian diets, IMG can have both beneficial and deleterious effects. Most IMG breakdown products induce the synthesis of phase 1 detoxifying enzymes, which may in some cases prevent carcinogenesis, but in other cases promote carcinogenesis. Recent advances in indole glucosinolate research have been fueled by their occurrence in the well-studied model plant Arabidopsis thaliana. Knowledge gained from genetic and biochemical experiments with A. thaliana can be applied to gain new insight into the ecological and nutritional properties of indole glucosinolates in other plant species.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9098-0
  • Authors
    • Niels Agerbirk, University of Copenhagen Faculty of Life Science 1871 Frederiksberg C Denmark
    • Martin De Vos, Boyce Thompson Institute for Plant Research 1 Tower Road Ithaca NY 14853 USA
    • Jae Hak Kim, Boyce Thompson Institute for Plant Research 1 Tower Road Ithaca NY 14853 USA
    • Georg Jander, Boyce Thompson Institute for Plant Research 1 Tower Road Ithaca NY 14853 USA

Quelle: Phytochemistry Reviews | 31 May 2008 | 8:50 am CEST

Preface

Preface

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9100-x
  • Authors
    • Kirsi-Marja Oksman-Caldentey, VTT Technical Research Centre of Finland P.O. Box 1000 02044 Espoo Finland

Quelle: Phytochemistry Reviews | 14 May 2008 | 8:15 am CEST

Glucosinolates, isothiocyanates and human health

Abstract  Concurrent with the increase in our knowledge of the genetic and environmental factors that lead to glucosinolate accumulation in plants, and the role of these compounds and their derivatives in mediating plant–herbivore interactions, there has been significant advances in our understanding of how glucosinolates and their products may contribute to a reduction in risk of carcinogenesis and heart disease when consumed as part of the diet. In this paper, we review the epidemiological evidence for the health promoting effects of cruciferous vegetables, the processes by which glucosinolates and isothiocyanates are absorbed and metabolised by humans, with particular regard to the role of glutathione S-transferases, and the biological activity of isothiocyanates towards mammalian cells and tissues.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9103-7
  • Authors
    • Maria Traka, Institute of Food Research Phytochemicals and Health Programme Colney Lane Norwich NR4 7UA UK
    • Richard Mithen, Institute of Food Research Phytochemicals and Health Programme Colney Lane Norwich NR4 7UA UK

Quelle: Phytochemistry Reviews | 14 May 2008 | 8:15 am CEST

Production of recombinant allergens in plants

Abstract  A large percentage of allergenic proteins are of plant origin. Hence, plant-based expression systems are considered ideal for the recombinant production of certain allergens. First attempts to establish production of plant-derived allergens in plants focused on transient expression in Nicotiana benthamiana infected with recombinant viral vectors. Accordingly, allergens from birch and mugwort pollen, as well as from apple have been expressed in plants. Production of house dust mite allergens has been achieved by Agrobacterium-mediated transformation of tobacco plants. Beside the use of plants as production systems, other approaches have focused on the development of edible vaccines expressing allergens or epitopes thereof, which bypasses the need of allergen purification. The potential of this approach has been convincingly demonstrated for transgenic rice seeds expressing seven dominant human T cell epitopes derived from Japanese cedar pollen allergens. Parallel to efforts in developing recombinant-based diagnostic and therapeutic reagents, different gene-silencing approaches have been used to decrease the expression of allergenic proteins in allergen sources. In this way hypoallergenic ryegrass, soybean, rice, apple, and tomato were developed.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9099-z
  • Authors
    • Georg Schmidt, University of Salzburg Christian Doppler Laboratory for Allergy Diagnosis and Therapy, Department of Molecular Biology Hellbrunnerstr. 34 5020 Salzburg Austria
    • Gabriele Gadermaier, University of Salzburg Christian Doppler Laboratory for Allergy Diagnosis and Therapy, Department of Molecular Biology Hellbrunnerstr. 34 5020 Salzburg Austria
    • Heidi Pertl, University of Salzburg Molecular Plant Biophysics and Biotechnology, Department of Molecular Biology Salzburg Austria
    • Marc Siegert, University of Salzburg Molecular Plant Biophysics and Biotechnology, Department of Molecular Biology Salzburg Austria
    • Kirsi-Marja Oksman-Caldentey, VTT Technical Research Centre of Finland Espoo Finland
    • Anneli Ritala, VTT Technical Research Centre of Finland Espoo Finland
    • Martin Himly, University of Salzburg Christian Doppler Laboratory for Allergy Diagnosis and Therapy, Department of Molecular Biology Hellbrunnerstr. 34 5020 Salzburg Austria
    • Gerhard Obermeyer, University of Salzburg Molecular Plant Biophysics and Biotechnology, Department of Molecular Biology Salzburg Austria
    • Fatima Ferreira, University of Salzburg Christian Doppler Laboratory for Allergy Diagnosis and Therapy, Department of Molecular Biology Hellbrunnerstr. 34 5020 Salzburg Austria

Quelle: Phytochemistry Reviews | 14 May 2008 | 8:15 am CEST

Quantification of seed oil from species with varying oil content using supercritical fluid extraction

Introduction: The quantity and composition of seed oil affects seed viability and storability and hence the value of a species as a resource for nutrition and plant conservation. Supercritical fluid extraction with carbon dioxide (SFE-CO2) offers a rapid, environmentally friendly alternative to traditional solvent extraction.Objective: To develop a method using SFE-CO2 to quantify the seed oil content in a broad range of species with high to low oil contents.Methodology: Seed oil was extracted using SFE-CO2 from four crop species representing high, medium and low oil content: Helianthus annuus, Asteraceae, with ca. 55% oil; Brassica napus, Brassicaceae, with ca. 50% oil; Glycine max, Fabaceae, with ca. 20% oil; and Pisum sativum, Fabaceae, with ca. 2% oil. Extraction pressures of 5000, 6000 and 7500 psi and temperatures of 40, 60 and 80°C were examined and a second step using 15% ethanol as a modifier included. Oil yields were compared with that achieved from Smalley Butt extraction. The optimised SFE-CO2 method was validated on six species from taxonomically distant families and with varying oil contents: Swietenia humilis (Meliaceae), Stenocereus thurberi (Cactaceae), Sinapis alba (Brassicaceae), Robinia pseudoacacia (Fabaceae), Poa pratensis (Poaceae) and Trachycarpus fortunei (Arecaceae).Results: The two-step extraction at 6000 psi and 80°C produced oil yields equivalent to or higher than Smalley Butt extraction for all species, including challenging species from the Brassicaceae family.Conclusion: SFE-CO2 enables the rapid analysis of seed oils across a broad range of seed oil contents. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 12 May 2008 | 9:12 am CEST

Fingerprint of Hedyotis diffusa Willd. by HPLC-MS

A HPLC-MS fingerprint method has been developed based on the consistent chromatographic features of the major chemical constituents among 10 batches of Hedyotis diffusa Willd. Chromatographic separation was conducted on a Hypersil-Keystone Hypurity C18 column using methanol:water:acetic acid as the mobile phase. Major compounds, including oleanolic acid, ursolic acid and ferulic acid, were analysed by HPLC-MS. Their analysis was ascertained by comparison with data derived from the standard compounds. The HPLC-MS fingerprint was successfully applied to analyse and differentiate samples from different geographical origins, or processing methods. H. diffusa was well distinguished from Hedyotis chrysotricha by HPLC-MS. Therefore the establishment of fingerprint of H. diffusa is critical in assessing and controlling its overall quality. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 29 Apr 2008 | 10:34 am CEST

Evaluation of viability assays for anthocyanins in cultured cells

The MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay is a widely accepted cytotoxicity assay which can produce inaccurate results due to possible interference with the antioxidant property of anthocyanins. Alternative methods to the MTT assay, such as BrdU (DNA-based) and CellTiter-Glo (ATP-based) assays were evaluated to assess anthocyanin cytotoxicity, derived from blackberry in LNCaP, MCF-7 and MDA-MB-453 cell lines. The standard cell counting method was the reference assay. Greater correlation of cell viability values following anthocyanin exposure was obtained from multiple cell lines with the alternative assays when compared with cell counting. MTT and cell counting results were not always correlated, albeit this was a function of cell type. In particular, poor correlations between cell counting and MTT procedures used to assess cytotoxicity of anthocyanins were observed in the MDA-MB-453 cell lines. Comparison of cytotoxicity derived from alternative assays and the MTT assays with the cell counting method was dependent on the assay procedure and the cell type. The LC50 of blackberry crude extract ranged from 0.4 to 9.4 mg/mL between assays and across all cell lines, whereas a semi-purified anthocyanin extract was not cytotoxic. Cytotoxicity evaluation of polyphenolic-rich extracts using BrdU and CellTiter-Glo assays as alternatives to the MTT method is recommended. Copyright © 2008 John Wiley & Sons, Ltd.

Quelle: Phytochemical Analysis | 25 Apr 2008 | 8:14 am CEST

Microbial metabolism of dietary phenolic compounds in the colon

Abstract  Plant foods contain substantial amounts of phenolic compounds. Dietary interventions with phenolic supplementation show that phenolic compounds are transformed into phenolic acids or lactone structures by intestinal microbiota. The colon is the main site of microbial fermentation. The metabolites circulate in plasma and are excreted via urine. The entero-hepatic circulation ensures that their residence time in plasma is extended compared to that of their parent compounds. Thus these metabolites may exert systemic effects, which however have not been studied adequately. In particular the health implications of microbial metabolites of flavonoids, mostly phenolic acids, are unknown. This review aims to elucidate the microbial metabolism of most of the phenolic classes: flavonoids, isoflavonoids, lignans, phenolic acids and tannins. Some examples of biological activity studies of flavonoid and lignan metabolites are given. Biological significance of enterolactone, a mammalian plant lignan metabolite, has been studied quite extensively, but convincing evidence of the health benefits of the diverse pool of microbial metabolites is still scarce. Hopefully, novel tools in systems biology and the constant search for biomarkers will elucidate the role of the phenolic metabolome in health and in the prevention of chronic diseases. In conclusion, the colon is not only an excretion route, but also an active site of metabolism and deserves further attention from the scientific community.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9095-3
  • Authors
    • Anna-Marja Aura, VTT Technical Research Centre of Finland P.O. Box 1000 Tietotie 2 02044 VTT, Espoo Finland

Quelle: Phytochemistry Reviews | 10 Apr 2008 | 8:53 am CEST

Secondary metabolism in cannabis

Abstract   Cannabis sativa L. is an annual dioecious plant from Central Asia. Cannabinoids, flavonoids, stilbenoids, terpenoids, alkaloids and lignans are some of the secondary metabolites present in C. sativa. Earlier reviews were focused on isolation and identification of more than 480 chemical compounds; this review deals with the biosynthesis of the secondary metabolites present in this plant. Cannabinoid biosynthesis and some closely related pathways that involve the same precursors are disscused.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9094-4
  • Authors
    • Isvett Josefina Flores-Sanchez, Leiden University Pharmacognosy Department, Institute of Biology P.O. Box 9502 2300 RA Leiden The Netherlands
    • Robert Verpoorte, Leiden University Pharmacognosy Department, Institute of Biology P.O. Box 9502 2300 RA Leiden The Netherlands

Quelle: Phytochemistry Reviews | 8 Apr 2008 | 9:15 am CEST

Phytoestrogens as natural prodrugs in cancer prevention: a novel concept

Abstract  It has been generally accepted that regular consumption of fresh fruits and vegetables is linked with a relatively low incidence of cancers (e.g. breast, cervix, and colon). A number of plant-derived compounds have been identified that are considered to play a role in cancer prevention. However, at present there is no satisfactory explanation for the cancer preventative properties of the above-mentioned compound groups. The current review is an effort to develop a consistent and unambiguous model that explains how some plant-derived compounds can prevent tumour development. The model is based on recent discoveries in the fields of genomics and drug-metabolism; notably, the discovery that CYP1 genes are highly expressed in developing tumour cells but not in the surrounding tissue, and that a variety of plant-derived compounds are substrates for the CYP1 enzymes. Our hypothesis is that some dietary compounds act as prodrugs, i.e. compounds with little or no biological effect as such, but become pharmaceutically effective when activated. More specifically, we state that the abovementioned prodrugs are only activated in CYP1-expressing cells—i.e. cells in the early stages of tumour development—to be converted into compounds which inhibit cell growth. Thus, the prodrugs selectively kill precancerous cells early in tumour development. The review focuses on the identification of naturally-occurring prodrugs that are activated by the tumour-specific CYP1 enzymes and aims to assess their role in cancer prevention.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9093-5
  • Authors
    • Randolph R. J. Arroo, De Montfort University Leicester School of Pharmacy The Gateway Leicester LE1 9BH UK
    • Vasilis Androutsopoulos, De Montfort University Leicester School of Pharmacy The Gateway Leicester LE1 9BH UK
    • Asma Patel, De Montfort University Leicester School of Pharmacy The Gateway Leicester LE1 9BH UK
    • Somchaiya Surichan, De Montfort University Leicester School of Pharmacy The Gateway Leicester LE1 9BH UK
    • Nicola Wilsher, De Montfort University Leicester School of Pharmacy The Gateway Leicester LE1 9BH UK
    • Gerry A. Potter, De Montfort University Leicester School of Pharmacy The Gateway Leicester LE1 9BH UK

Quelle: Phytochemistry Reviews | 26 Mar 2008 | 3:56 pm CET

Needs for new plant-derived pharmaceuticals in the post-genome era: an industrial view in drug research and development

Abstract  Plant metabolites have been the successful source of drugs and provided considerable value not only to the pharmaceutical industry but also to human health problems. Although pharmaceutical companies significantly decreased their activities in natural product discovery during the past few decades, various multidisciplinary approaches have been made to create new opportunities for finding innovative plant derived pharmaceuticals in post-genome era. Strategies to integrate the knowledge on medicinal plants into rational drug screening, the unique biodiversity of plant metabolites into random drug screening, and the chemical diversity of plant metabolites into combinatorial chemistry have been reviewed with concrete examples. Innovative biotechnologies in plant cell and tissue cultures, and the latest achievements in metabolic engineering and genetic modification should significantly improve the production sustainability and efficiency of plant-derived pharmaceuticals.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9092-6
  • Authors
    • Ying Wang, Novartis Pharma AG Novartis Institute for Biomedical Research WSJ-507.6.04 4002 Basel Switzerland

Quelle: Phytochemistry Reviews | 11 Mar 2008 | 9:29 am CET

Metabolomics: back to basics

Abstract  Metabolomics has developed into a major tool in functional genomics and plant systems biology. The various methods used for metabolomic analysis will be discussed from the analytical methods back to the preanalytical phase and the biological experiment. Particularly aspects of the preanalytical phase of the analysis is dealt with, including the risks of artefact formation with the various commonly used solvents. Metabolomics is like a snap shot, and conclusions from dynamic systems must be drawn with great care as demonstrated with a biosynthetic study of salicylate in Catharanthus roseus cell cultures.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9091-7
  • Authors
    • R. Verpoorte, Institute of Biology, Leiden University Division of Pharmacognosy, Section Metabolomics Leiden The Netherlands
    • Y. H. Choi, Institute of Biology, Leiden University Division of Pharmacognosy, Section Metabolomics Leiden The Netherlands
    • N. R. Mustafa, Institute of Biology, Leiden University Division of Pharmacognosy, Section Metabolomics Leiden The Netherlands
    • H. K. Kim, Institute of Biology, Leiden University Division of Pharmacognosy, Section Metabolomics Leiden The Netherlands

Quelle: Phytochemistry Reviews | 11 Mar 2008 | 9:29 am CET

Transgenic plants for animal health: plant-made vaccine antigens for animal infectious disease control

Abstract  A variety of plant species have been genetically modified to accumulate vaccine antigens for human and animal health and the first vaccine candidates are approaching the market. The regulatory burden for animal vaccines is less than that for human use and this has attracted the attention of researchers and companies, and investment in plant-made vaccines for animal infectious disease control is increasing. The dosage cost of vaccines for animal infectious diseases must be kept to a minimum, especially for non-lethal diseases that diminish animal welfare and growth, so efficient and economic production, storage and delivery are critical for commercialization. It has become clear that transgenic plants are an economic and efficient alternative to fermentation for large-scale production of vaccine antigens. The oral delivery of plant-made vaccines is particularly attractive since the expensive purification step can be avoided further reducing the cost per dose. This review covers the current status of plant-produced vaccines for the prevention of disease in animals and focuses on barriers to the development of such products and methods to overcome them.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9088-2
  • Authors
    • J. J. Joensuu, University of Helsinki Department of Applied Biology P.O. Box 27 00014 Helsinki Finland
    • V. Niklander-Teeri, University of Helsinki Department of Applied Biology P.O. Box 27 00014 Helsinki Finland
    • J. E. Brandle, Agriculture and Agri-Food Canada Southern Crop Protection and Food Research Centre 1391 Sandford Street London ON Canada N5V 4T3

Quelle: Phytochemistry Reviews | 8 Mar 2008 | 11:11 am CET

Molecular pharming in cereal crops

Abstract  There are many different agricultural expression systems that can be used for the large-scale production of recombinant proteins, but field-grown cereal crops are among the most attractive because recombinant proteins can be targeted to accumulate in the seed, and specifically in the endosperm, which has evolved naturally as a protein storage tissue. Within the developing endosperm, proteins are supplied with molecular chaperones and disulfide isomerases to facilitate folding and assembly, while the mature tissue is desiccated to prevent proteolytic degradation. Proteins expressed in cereal seeds can therefore remain stable for years in ambient conditions. Recent basic research has revealed a surprising diversity of protein targeting mechanisms in the endosperm, which can help to control post-translational modification and accumulation. Applied research and commercial development has seen several pharmaceutical proteins produced in cereals reach late stage preclinical development and the first clinical trials, with a number of companies now dedicated to developing cereal-based production platforms. In this review we discuss the basic science of molecular pharming in cereals, some of the lead product candidates, and challenges that remain to be addressed including the emerging regulatory framework for plant-made pharmaceuticals.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9087-3
  • Authors
    • Koreen Ramessar, Universitat de Lleida Department de Produccio Vegetal I Ciencia Forestal Av. Alcalde Rovira Roure, 191 25198 Lleida Spain
    • Teresa Capell, Universitat de Lleida Department de Produccio Vegetal I Ciencia Forestal Av. Alcalde Rovira Roure, 191 25198 Lleida Spain
    • Paul Christou, Universitat de Lleida Department de Produccio Vegetal I Ciencia Forestal Av. Alcalde Rovira Roure, 191 25198 Lleida Spain

Quelle: Phytochemistry Reviews | 23 Feb 2008 | 6:59 pm CET

Acetogenic anthraquinones: biosynthetic convergence and chemical evidence of enzymatic cooperation in nature

Abstract  Phenylanthraquinones belong to the quite rare class of fully unsymmetric biaryls, consisting of two different molecular portions, an anthraquinone part, chrysophanol, and a phenyl part, 2,4-dihydroxy-6-methoxyacetophenone, linked together by phenol-oxidative coupling. The biosynthesis of these two moieties, from eight and four acetate units, respectively, bears some unique features: Chrysophanol is the first example of an acetogenic natural product that is, in an organism-specific manner, formed via more than one folding mode: In eukaryotes, like, e.g., in fungi, in higher plants, and in insects, it is formed via folding mode F, while in prokaryotes it originates through mode S. It has, more recently, even been found to be synthesized by a third pathway, which we have named mode S′. It is thus the first example of biosynthetic convergence in polyketide biosynthesis. The monocyclic “southern” portion of the molecule, which is much simpler (arising from only four acetate units and without decarboxylation), unexpectedly does not show the anticipated randomization of the C2-labeling in the aromatic ring, but has clearly localized C2 units, excluding any symmetric intermediate like, e.g., 2,4,6-trihydroxyacetophenone. This is confirmed by competitive feeding experiments with specifically 13C2-labeled acetophenones, showing the O-methylation to be the decisive symmetry-preventing step, which hints at a close collaboration of the participating enzymes. The results make knipholone an instructive example of structure, function, and evolution of polyketide synthases and O-methyltransferases, and their cooperation.

  • Content Type Journal Article
  • DOI 10.1007/s11101-008-9090-8
  • Authors
    • Gerhard Bringmann, University of Würzburg, Am Hubland Institute of Organic Chemistry 97074 Würzburg Germany
    • Andreas Irmer, University of Würzburg, Am Hubland Institute of Organic Chemistry 97074 Würzburg Germany

Quelle: Phytochemistry Reviews | 22 Feb 2008 | 4:48 pm CET


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Internetchemie ? 2007 - 2008 A. J. - aktualisiert am 13.04.2008