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Phytochemistry - Current Research Articles



Current research articles: Phytochemistry

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Phytochemistry - published by Elsevier

Phytochemistry is the international journal of pure and applied plant chemistry, plant biochemistry and molecular biology.




Current articles of the journal:



The plant cell wall integrity maintenance mechanism – A case study of a cell wall plasma membrane signaling network

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Thorsten Hamann

Some of the most important functions of plant cell walls are protection against biotic/abiotic stress and structural support during growth and development. A prerequisite for plant cell walls to perform these functions is the ability to perceive different types of stimuli in both qualitative and quantitative manners and initiate appropriate responses. The responses in turn involve adaptive changes in cellular and cell wall metabolism leading to modifications in the structures originally required for perception. While our knowledge about the underlying plant mechanisms is limited, results from Saccharomyces cerevisiae suggest the cell wall integrity maintenance mechanism represents an excellent example to illustrate how the molecular mechanisms responsible for stimulus perception, signal transduction and integration can function. Here I will review the available knowledge about the yeast cell wall integrity maintenance system for illustration purposes, summarize the limited knowledge available about the corresponding plant mechanism and discuss the relevance of the plant cell wall integrity maintenance mechanism in biotic stress responses.

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Posted on 12 April 2015 | 3:46 pm


Ectopic phytocystatin expression increases nodule numbers and influences the responses of soybean (Glycine max) to nitrogen deficiency

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Marian D. Quain , Matome E. Makgopa , James W. Cooper , Karl J. Kunert , Christine H. Foyer

Cysteine proteases and cystatins have many functions that remain poorly characterised, particularly in crop plants. We therefore investigated the responses of these proteins to nitrogen deficiency in wild-type soybeans and in two independent transgenic soybean lines (OCI-1 and OCI-2) that express the rice cystatin, oryzacystatin-I (OCI). Plants were grown for four weeks under either a high (5mM) nitrate (HN) regime or in the absence of added nitrate (LN) in the absence or presence of symbiotic rhizobial bacteria. Under the LN regime all lines showed similar classic symptoms of nitrogen deficiency including lower shoot biomass and leaf chlorophyll. However, the LN-induced decreases in leaf protein and increases in root protein tended to be smaller in the OCI-1 and OCI-2 lines than in the wild type. When LN-plants were grown with rhizobia, OCI-1 and OCI-2 roots had significantly more crown nodules than wild-type plants. The growth nitrogen regime had a significant effect on the abundance of transcripts encoding vacuolar processing enzymes (VPEs), LN-dependent increases in VPE2 and VPE3 transcripts in all lines. However, the LN-dependent increases of VPE2 and VPE3 transcripts were significantly lower in the leaves of OCI-1 and OCI-2 plants than in the wild type. These results show that nitrogen availability regulates the leaf and root cysteine protease, VPE and cystatin transcript profiles in a manner that is in some cases influenced by ectopic OCI expression. Moreover, the OCI-dependent inhibition of papain-like cysteine proteases favours increased nodulation and enhanced tolerance to nitrogen limitation, as shown by the smaller LN-dependent decreases in leaf protein observed in the OCI-1 and OCI-2 plants relative to the wild type.

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Posted on 12 April 2015 | 3:46 pm


Sphingolipid metabolism is strikingly different between pollen and leaf in Arabidopsis as revealed by compositional and gene expression profiling

Publication date: Available online 17 March 2015
Source:Phytochemistry

Author(s): Kyle D. Luttgeharm , Athen N. Kimberlin , Rebecca E. Cahoon , Ronald L. Cerny , Johnathan A. Napier , Jonathan E. Markham , Edgar B. Cahoon

Although sphingolipids are essential for male gametophytic development in Arabidopsis thaliana, sphingolipid composition and biosynthetic gene expression have not been previously examined in pollen. In this report, electrospray ionization (ESI)–MS/MS was applied to characterization of sphingolipid compositional profiles in pollen isolated from wild type Arabidopsis Col-0 and a long-chain base (LCB) ?4 desaturase mutant. Pollen fractions were highly enriched in glucosylceramides (GlcCer) relative to levels previously reported in leaves. Accompanying the loss of the ?4 unsaturated LCB sphingadiene (d18:2) in the ?4 desaturase mutant was a 50% reduction in GlcCer concentrations. In addition, pollen glycosylinositolphosphoceramides (GIPCs) were found to have a complex array of N-acetyl-glycosylated GIPCs, including species with up to three pentose units that were absent from leaf GIPCs. Underlying the distinct sphingolipid composition of pollen, genes for key biosynthetic enzymes for GlcCer and d18:2 synthesis and metabolism were more highly expressed in pollen than in leaves or seedlings, including genes for GlcCer synthase (GCS), sphingoid base C-4 hydroxylase 2 (SBH2), LCB ?8 desaturases (SLD1 and SLD2), and LOH2 ceramide synthase (LOH2). Overall, these findings indicate strikingly divergent sphingolipid metabolism between pollen and leaves in Arabidopsis, the significance of which remains to be determined.

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Posted on 12 April 2015 | 3:46 pm


The role of cell wall-based defences in the early restriction of non-pathogenic hrp mutant bacteria in Arabidopsis

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Kathy Mitchell , Ian Brown , Paul Knox , John Mansfield

We have investigated the cause of the restricted multiplication of hrp mutant bacteria in leaves of Arabidopsis. Our focus was on early interactions leading to differentiation between virulent wild-type and non-pathogenic hrpA mutant strains of Pseudomonas syringae pv. tomato. An initial drop in recoverable bacteria detected 0–4h after inoculation with either strain was dependent on a functional FLS2 receptor and H2O2 accumulation in challenged leaves. Wild-type bacteria subsequently multiplied rapidly whereas the hrpA mutant was restricted within 6h. Despite the early restriction, the hrpA mutant was still viable several days after inoculation. Analysis of intercellular washing fluids (IWFs), showed that high levels of nutrients were readily available to bacteria in the apoplast and that no diffusible inhibitors were produced in response to bacterial challenge. Histochemical and immunocytochemical methods were used to detect changes in polysaccharides (callose, two forms of cellulose, and pectin), arabinogalactan proteins (AGPs), H2O2 and peroxidase. Quantitative analysis showed very similar changes in localisation of AGPs, cellulose epitopes and callose 2 and 4h after inoculation with either strain. However from 6 to 12h after inoculation papillae expanded only next to the hrp mutant. In contrast to the similar patterns of secretory activity recorded from mesophyll cells, accumulation of H2O2 and peroxidase was significantly greater around the hrpA mutant within the first 4h after inoculation. A striking differential accumulation of H2O2 was also found in chloroplasts in cells next to the mutant. Ascorbate levels were lower in the IWFs recovered from sites inoculated with the hrp mutant than with wild-type bacteria. The critical response, observed at the right time and place to explain the observed differential behaviour of wild-type and hrpA mutant bacteria was the accumulation of H2O2, probably generated through Type III peroxidase activity and in chloroplasts. It is proposed that H2O2 and apoplastic peroxidase cross-link secreted glycoproteins and polysaccharides to agglutinate the hrp mutant. Generation of H2O2 has been identified as a likely target for effector proteins injected into plant cells by the wild-type bacteria.

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Posted on 12 April 2015 | 3:46 pm


Biosynthesis of nectrisine in Thelonectria discophora SANK 18292

Publication date: Available online 9 April 2015
Source:Phytochemistry

Author(s): Ryuki Miyauchi , Toshio Takatsu , Tetsuya Suzuki , Yasunori Ono , Yoichiro Shiba

Nectrisine, an iminosugar with a heterocyclic nitrogen-containing 5-membered ring, acts as a glycosidase inhibitor. Thelonectria discophora SANK 18292, a fungus, was identified as a nectrisine producer from its microbial library in our screening for nectrisine producing microorganisms. Biosynthesis of nectrisine produced by the fungus was studied using stable isotope tracer techniques. Incorporation of 13C-labeled d-ribose and d-xylose into nectrisine was confirmed by mass spectrometry and 13C NMR spectroscopy, which suggested that these were its precursors. Chromatographic separation of the hot water extract from the culture broth afforded not only nectrisine, but also substantial amounts of 4-amino-4-deoxyarabinitol. Incubation of the latter with the crude enzyme of the fungus at room temp. caused an increase in levels of nectrisine together with a decrease in amounts of the administered potential precursor suggesting that it is a biosynthetic intermediate. From these results, a biosynthetic pathway to nectrisine is proposed via d-xylulose 5-phosphate and 4-amino-4-deoxyarabinitol by the pentose phosphate pathway.

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Posted on 12 April 2015 | 3:46 pm


Role of the plant cell wall in gravity resistance

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Takayuki Hoson , Kazuyuki Wakabayashi

Gravity resistance, mechanical resistance to the gravitational force, is a principal graviresponse in plants, comparable to gravitropism. The cell wall is responsible for the final step of gravity resistance. The gravity signal increases the rigidity of the cell wall via the accumulation of its constituents, polymerization of certain matrix polysaccharides due to the suppression of breakdown, stimulation of cross-link formation, and modifications to the wall environment, in a wide range of situations from microgravity in space to hypergravity. Plants thus develop a tough body to resist the gravitational force via an increase in cell wall rigidity and the modification of growth anisotropy. The development of gravity resistance mechanisms has played an important role in the acquisition of responses to various mechanical stresses and the evolution of land plants.

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Posted on 12 April 2015 | 3:46 pm


Monomethyl ethers of 4,5-dihydroxypipecolic acid from Petaladenium urceoliferum: Enigmatic chemistry of an enigmatic legume

Publication date: Available online 24 March 2015
Source:Phytochemistry

Author(s): Geoffrey C. Kite , Domingos Cardoso , Gwilym P. Lewis , Charles E. Zartman , Luciano Paganucci de Queiroz , Nigel C. Veitch

Leaves of Petaladenium (Leguminosae), an Amazonian monospecific genus recently revealed as a member of the Amburaneae clade among the earliest-diverging papilionoid legumes, were found to accumulate three monomethyl ethers of 4,5-dihydroxypipecolic acids. These were characterised by spectroscopic means as the (2S,4S,5R) and (2S,4R,5S) epimers of 5-hydroxy-4-methoxypipecolic acid and (2S,4R,5R)-4-hydroxy-5-methoxypipecolic acid. These compounds were not detected in any other genera in the Amburaneae clade or the wider Angylocalyceae-Dipterygeae-Amburaneae (ADA) clade of papilionoid legumes. Hydroxypipecolic acids, however, were detected in leaves of Myrocarpus and Myroxylon (sister genera in the Amburaneae clade), Angylocalyx and Xanthocercis (sister genera in the Angylocalyceae clade) and Monopteryx (Dipterygeae clade), and were also present in Petaladenium. Iminosugars, known to be accumulated by all four genera in the Angylocalyceae clade (Alexa, Angylocalyx, Castanospermum and Xanthocercis), were found to be characteristic of this group within the ADA clade.

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Posted on 12 April 2015 | 3:46 pm


Roles of apoplastic peroxidases in plant response to wounding

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Farida Minibayeva , Richard Peter Beckett , Ilse Kranner

Apoplastic class III peroxidases (EC 1.11.1.7) play key roles in the response of plants to pathogen infection and abiotic stresses, including wounding. Wounding is a common stress for plants that can be caused by insect or animal grazing or trampling, or result from agricultural practices. Typically, mechanical damage to a plant immediately induces a rapid release and activation of apoplastic peroxidases, and an oxidative burst of reactive oxygen species (ROS), followed by the upregulation of peroxidase genes. We discuss how plants control the expression of peroxidases genes upon wounding, and also the sparse information on peroxidase-mediated signal transduction pathways. Evidence reviewed here suggests that in many plants production of the ROS that comprise the initial oxidative burst results from a complex interplay of peroxidases with other apoplastic enzymes. Later responses following wounding include various forms of tissue healing, for example through peroxidase-dependent suberinization, or cell death. Limited data suggest that ROS-mediated death signalling during the wound response may involve the peroxidase network, together with other redox molecules. In conclusion, the ability of peroxidases to both generate and scavenge ROS plays a key role in the involvement of these enigmatic enzymes in plant stress tolerance.

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Highlights

The ability of apoplastic peroxidases to generate or scavenge ROS is a key element of wound response, wound healing and cell death in plants.





Posted on 12 April 2015 | 3:46 pm


Editorial Board/Publication Information

Publication date: April 2015
Source:Phytochemistry, Volume 112









Posted on 12 April 2015 | 3:46 pm


Distinct catalytic capacities of two aluminium-repressed Arabidopsis thaliana xyloglucan endotransglucosylase/hydrolases, XTH15 and XTH31, heterologously produced in Pichia

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Yuan Zhi Shi , Xiao Fang Zhu , Janice G. Miller , Timothy Gregson , Shao Jian Zheng , Stephen C. Fry

Xyloglucan plays an important structural role in primary cell walls, possibly tethering adjacent microfibrils and restraining cell expansion. There is therefore considerable interest in understanding the role of xyloglucan endotransglucosylase/hydrolases (XTHs), which are encoded in Arabidopsis by a 33-member gene family. We compared the key catalytic properties of two very different Arabidopsis XTHs (heterologously produced in Pichia), both of which are aluminium-repressed. Reductively tritiated oligosaccharides of xyloglucan were used as model acceptor substrates. Untransformed Pichia produced no xyloglucan-acting enzymes; therefore purification of the XTHs was unnecessary. XTH15, a classical group-I/II XTH, had high XET and undetectable XEH activity in vitro; its XET K m values were 31?M XXXGol (acceptor substrate) and 2.9mg/ml xyloglucan (donor substrate). In contrast, XTH31, a group-III-A XTH, showed predominant XEH activity and only slight XET activity in vitro; its XET K m was 86?M XXXGol (acceptor), indicating a low affinity of this predominantly hydrolytic protein for a transglycosylation acceptor substrate. The K m of XTH31’s XEH activity was 1.6mg/ml xyloglucan. For both proteins, the preferred XET acceptor substrate, among five cellotetraitol-based oligosaccharides tested, was XXXGol. XTH31’s XET activity was strongly compromised when the second Xyl residue was galactosylated. XTH15’s XET activity, in contrast, tolerated substitution at the second Xyl residue. The two enzymes also showed different pH preferences, XTH31 exhibiting an unusually low pH optimum and XTH15 an unusually broad optimum. XTH31’s hydrolase activity increased almost linearly with decreasing pH in the apoplastic range, 6.2–4.5, consistent with a possible role in ‘acid growth’. In conclusion, these two Al3+-repressed XTHs differ, in several important enzymic features, from other members of the Arabidopsis XTH family.

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Posted on 12 April 2015 | 3:46 pm


Expression of a fungal glucuronoyl esterase in Populus: Effects on wood properties and saccharification efficiency

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Madhavi Latha Gandla , Marta Derba-Maceluch , Xiaokun Liu , Lorenz Gerber , Emma R. Master , Ewa J. Mellerowicz , Leif J. Jönsson

The secondary walls of angiosperms contain large amounts of glucuronoxylan that is thought to be covalently linked to lignin via ester bonds between 4-O-methyl-?-d-glucuronic acid (4-O-Me-GlcA) moieties in glucuronoxylan and alcohol groups in lignin. This linkage is proposed to be hydrolysed by glucuronoyl esterases (GCEs) secreted by wood-degrading fungi. We report effects of overexpression of a GCE from the white-rot basidiomycete Phanerochaete carnosa, PcGCE, in hybrid aspen (Populus tremula L. x tremuloides Michx.) on the wood composition and the saccharification efficiency. The recombinant enzyme, which was targeted to the plant cell wall using the signal peptide from hybrid aspen cellulase PttCel9B3, was constitutively expressed resulting in the appearance of GCE activity in protein extracts from developing wood. Diffuse reflectance FT-IR spectroscopy and pyrolysis–GC/MS analyses showed significant alternation in wood chemistry of transgenic plants including an increase in lignin content and S/G ratio, and a decrease in carbohydrate content. Sequential wood extractions confirmed a massive (+43%) increase of Klason lignin, which was accompanied by a ca. 5% decrease in cellulose, and ca. 20% decrease in wood extractives. Analysis of the monosaccharide composition using methanolysis showed a reduction of 4-O-Me-GlcA content without a change in Xyl contents in transgenic lines, suggesting that the covalent links between 4-O-Me-GlcA moieties and lignin protect these moieties from degradation. Enzymatic saccharification without pretreatment resulted in significant decreases of the yields of Gal, Glc, Xyl and Man in transgenic lines, consistent with their increased recalcitrance caused by the increased lignin content. In contrast, the enzymatic saccharification after acid pretreatment resulted in Glc yields similar to wild-type despite of their lower cellulose content. These data indicate that whereas PcGCE expression in hybrid aspen increases lignin deposition, the inhibitory effects of lignin are efficiently removed during acid pretreatment, and the extent of wood cellulose conversion during hydrolysis after acid pretreatment is improved in the transgenic lines possible due to reduced cell wall cross-links between cell wall biopolymers by PcGCE.

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Posted on 12 April 2015 | 3:46 pm


Unravelling the architecture and dynamics of tropane alkaloid biosynthesis pathways using metabolite correlation networks

Publication date: Available online 27 March 2015
Source:Phytochemistry

Author(s): Thi-Kieu-Oanh Nguyen , Arash Jamali , Arnaud Lanoue , Eric Gontier , Rebecca Dauwe

The tropane alkaloid spectrum in Solanaceae is highly variable within and between species. Little is known about the topology and the coordination of the biosynthetic pathways leading to the variety of tropine and pseudotropine derived esters in the alkaloid spectrum, or about the metabolic dynamics induced by tropane alkaloid biosynthesis stimulating conditions. A good understanding of the metabolism, including all ramifications, is however necessary for the development of strategies to increase the abundance of pharmacologically interesting compounds such as hyoscyamine and scopolamine. The present study explores the tropane alkaloid metabolic pathways in an untargeted approach involving a correlation-based network analysis. Using GC–MS metabolite profiling, the variation and co-variation among tropane alkaloids and primary metabolites was monitored in 60 Datura innoxia Mill. individuals, of which half were exposed to tropane alkaloid biosynthesis stimulating conditions by co-culture with Agrobacterium rhizogenes. Considerable variation was evident in the relative proportions of the tropane alkaloids. Remodeling of the tropane alkaloid spectrum under co-culture with A. rhizogenes involved a specific and strong increase of hyoscyamine production and revealed that the accumulation of hyoscyamine, 3-tigloyloxy-6,7-epoxytropane, and 3-methylbutyryloxytropane was controlled independently of the majority of tropane alkaloids. Based on correlations between metabolites, we propose a biosynthetic origin of hygrine, the order of esterification of certain di-oxygenated tropanes, and that the rate of acetoxylation contributes to control of hyoscyamine production. Overall, this study shows that the biosynthesis of tropane alkaloids may be far more complex and finely controlled than previously expected.

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Posted on 12 April 2015 | 3:46 pm


Graphical Contents List

Publication date: April 2015
Source:Phytochemistry, Volume 112









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Plant cellulose synthesis: CESA proteins crossing kingdoms

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Manoj Kumar , Simon Turner

Cellulose is a biopolymer of considerable economic importance. It is synthesised by the cellulose synthase complex (CSC) in species ranging from bacteria to higher plants. Enormous progress in our understanding of bacterial cellulose synthesis has come with the recent publication of both the crystal structure and biochemical characterisation of a purified complex able to synthesis cellulose in vitro. A model structure of a plant CESA protein suggests considerable similarity between the bacterial and plant cellulose synthesis. In this review article we will cover current knowledge of how plant CESA proteins synthesise cellulose. In particular the focus will be on the lessons learned from the recent work on the catalytic mechanism and the implications that new data on cellulose structure has for the assembly of CESA proteins into the large complex that synthesis plant cellulose microfibrils.

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Tobacco plants over-expressing the sweet orange tau glutathione transferases (CsGSTUs) acquire tolerance to the diphenyl ether herbicide fluorodifen and to salt and drought stresses

Publication date: Available online 25 March 2015
Source:Phytochemistry

Author(s): Luca Lo Cicero , Panagiotis Madesis , Athanasios Tsaftaris , Angela Roberta Lo Piero

The glutathione transferases (GSTs) are members of a superfamily of enzymes with pivotal role in the detoxification of both xenobiotic and endogenous compounds. In this work, the generation and characterization of transgenic tobacco plants over-expressing tau glutathione transferases from Citrus sinensis (CsGSTU1 and CsGSTU2) and several cross-mutate forms of these genes are reported. Putative transformed plants were verified for the presence of the transgenes and the relative quantification of transgene copy number was evaluated by Taqman real time PCR. The analysis of gene expression revealed that transformed plants exhibit high levels of CsGSTU transcription suggesting that the insertion of the transgenes occurred in transcriptional active regions of the tobacco genome. In planta studies demonstrate that transformed tobacco plants gain tolerance against fluorodifen. Simultaneously, the wild type CsGSTU genes were in vitro expressed and their kinetic properties were determined using fluorodifen as substrate. The results show that CsGSTU2 follows a Michaelis–Menten hyperbolic kinetic, whereas CsGSTU1 generates a sigmoid plot typical of the regulatory enzymes, thus suggesting that when working at sub-lethal fluorodifen concentrations CsGSTU2 can counteract the herbicide injury more efficiently than the CsGSTU1. Moreover, the transgenic tobacco plant over-expressing CsGSTs exhibited both drought and salinity stress tolerance. However, as we show that CsGSTUs do not function as glutathione peroxidase in vitro, the protective effect against salt and drought stress is not due to a direct scavenging activity of the oxidative stress byproducts. The transgenic tobacco plants, which are described in the present study, can be helpful for phytoremediation of residual xenobiotics in the environment and overall the over-expression of CsGSTUs can be helpful to develop genetically modified crops with high resistance to abiotic stresses.

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Posted on 12 April 2015 | 3:46 pm


Apoplastic peroxidases are required for salicylic acid-mediated defense against Pseudomonas syringae

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Nicole D. Mammarella , Zhenyu Cheng , Zheng Qing Fu , Arsalan Daudi , G. Paul Bolwell , Xinnian Dong , Frederick M. Ausubel

Reactive oxygen species (ROS) generated by NADPH oxidases or apoplastic peroxidases play an important role in the plant defense response. Diminished expression of at least two Arabidopsis thaliana peroxidase encoding genes, PRX33 (At3g49110) and PRX34 (At3g49120), as a consequence of anti-sense expression of a heterologous French bean peroxidase gene (asFBP1.1), were previously shown to result in reduced levels of ROS following pathogen attack, enhanced susceptibility to a variety of bacterial and fungal pathogens, and reduced levels of callose production and defense-related gene expression in response to the microbe associated molecular pattern (MAMP) molecules flg22 and elf26. These data demonstrated that the peroxidase-dependent oxidative burst plays an important role in the elicitation of pattern-triggered immunity (PTI). Further work reported in this paper, however, shows that asFBP1.1 antisense plants are not impaired in all PTI-associated responses. For example, some but not all flg22-elicited genes are induced to lower levels by flg22 in asFPB1.1, and callose deposition in asFPB1.1 is similar to wild-type following infiltration with a Pseudomonas syringae hrcC mutant or with non-host P. syringae pathovars. Moreover, asFPB1.1 plants did not exhibit any apparent defect in their ability to mount a hypersensitive response (HR). On the other hand, salicylic acid (SA)-mediated activation of PR1 was dramatically impaired in asFPB1.1 plants. In addition, P. syringae-elicited expression of many genes known to be SA-dependent was significantly reduced in asFBP1.1 plants. Consistent with this latter result, in asFBP1.1 plants the key regulator of SA-mediated responses, NPR1, showed both dramatically decreased total protein abundance and a failure to monomerize, which is required for its translocation into the nucleus.

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Posted on 12 April 2015 | 3:46 pm


Appreciation – Professor Godfrey Paul Bolwell MA DSc 13 December 1946–13 April 2012

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Norman G. Lewis , Richard J. Robins







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A proposed interplay between peroxidase, amine oxidase and lipoxygenase in the wounding-induced oxidative burst in Pisum sativum seedlings

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Thomas Roach , Louise Colville , Richard P. Beckett , Farida V. Minibayeva , Michel Havaux , Ilse Kranner

Plant surfaces form the barrier between a plant and its environment. Upon damage, the wound healing process begins immediately and is accompanied by a rapid production of extracellular reactive oxygen species (ROS), essential in deterring pathogens, signalling responses and cell wall restructuring. Although many enzymes produce extracellular ROS, it is unclear if ROS-producing enzymes act synergistically. We characterised the oxidative burst of superoxide (O2 ?) and hydrogen peroxide (H2O2) that follows wounding in pea (Pisum sativum L.) seedlings. Rates of ROS production were manipulated by exogenous application of enzyme substrates and inhibitors. The results indicate significant roles for di-amine oxidases (DAO) and peroxidases (Prx) rather than NADPH oxidase. The burst of O2 ? was strongly dependent on the presence of H2O2 produced by DAO. Potential substrates released from wounded seedlings included linoleic acid that, upon exogenous application, strongly stimulated catalase-sensitive O2 ? production. Moreover, a 65kD plasma membrane (PM) guaiacol Prx was found in the secretome of wounded seedlings and showed dependence on linoleic acid for O2 ? production. Lipoxygenases are suggested to modulate O2 ? production by consuming polyunsaturated fatty acids in the apoplast. Overall, a O2 ?-producing mechanism involving H2O2-derived from DAO, linoleic acid and a PM-associated Prx is proposed.

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Ambient ionization mass spectrometry imaging of rohitukine, a chromone anti-cancer alkaloid, during seed development in Dysoxylum binectariferum Hook.f (Meliaceae)

Publication date: Available online 20 March 2015
Source:Phytochemistry

Author(s): P. Mohana Kumara , Amitava Srimany , G. Ravikanth , R. Uma Shaanker , T. Pradeep

Rohitukine, a chromone alkaloid, possesses anti-inflammatory, anti-cancer and immuno-modulatory properties. It has been reported from four species, belonging to the families, Meliaceae and Rubiaceae. Stem bark of Dysoxylum binectariferum (Meliaceae) accumulates the highest amount of rohitukine (3–7% by dry weight). In this study, we examine the spatial and temporal distribution of rohitukine and related compounds during various stages of seed development in D. binectariferum using desorption electrospray ionization mass spectrometry imaging (DESI MSI). Rohitukine (m/z 306.2) accumulation increased from early seed development to seed maturity stage. The spatial distribution of rohitukine was largely restricted to the cotyledonary tissue followed by the embryo and least in the seed coat. Besides rohitukine, rohitukine acetate (m/z 348.2) and glycosylated rohitukine (m/z 468.2) were also detected, both through mass fragmentation and exact mass analysis through Orbitrap mass spectrometry. These results indicate a dynamic pattern of chromane alkaloid accumulation through seed development in D. binectariferum.

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Identification of the pI 4.6 extensin peroxidase from Lycopersicon esculentum using proteomics and reverse-genomics

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Wen Dong , Marcia Kieliszewski , Michael A. Held

The regulation of plant cell growth and early defense response involves the insolubilization of hydroxyproline-rich glycoproteins (HRGPs), such as extensin, in the primary cell wall. In tomato (Lycopersicon esculentum), insolubilization occurs by the formation of tyrosyl-crosslinks catalyzed specifically by the pI 4.6 extensin peroxidase (EP). To date, neither the gene encoding EP nor the protein itself has been identified. Here, we have identified tomato EP candidates using both proteomic and bioinformatic approaches. Bioinformatic screening of the tomato genome yielded eight EP candidates, which contained a putative signal sequence and a predicted pI near 4.6. Biochemical fractionation of tomato culture media followed by proteomic detection further refined our list of EP candidates to three, with the lead candidate designated (CG5). To test for EP crosslinking activity, we cloned into a bacterial expression vector the CG5 open-reading frame from tomato cDNA. The CG5 was expressed in Escherichia coli, fractionated from inclusion bodies, and folded in vitro. The peroxidase activity of CG5 was assayed and quantified by ABTS (2,2?-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid)) assay. Subsequent extensin crosslinking assays showed that CG5 can covalently crosslink authentic tomato P1 extensin and P3-type extensin analogs in vitro supporting our hypothesis that CG5 encodes a tomato EP.

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Posted on 12 April 2015 | 3:46 pm


Editorial for Phytochemistry issue ‘In Memory of G. Paul Bolwell: Plant Cell Wall Dynamics’

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Alessandra Devoto , Simone Ferrari , Przemys?aw Wojtaszek







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Pinoresinol reductase 1 impacts lignin distribution during secondary cell wall biosynthesis in Arabidopsis

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Qiao Zhao , Yining Zeng , Yanbin Yin , Yunqiao Pu , Lisa A. Jackson , Nancy L. Engle , Madhavi Z. Martin , Timothy J. Tschaplinski , Shi-You Ding , Arthur J. Ragauskas , Richard A. Dixon

Pinoresinol reductase (PrR) catalyzes the conversion of the lignan (?)-pinoresinol to (?)-lariciresinol in Arabidopsis thaliana, where it is encoded by two genes, PrR1 and PrR2, that appear to act redundantly. PrR1 is highly expressed in lignified inflorescence stem tissue, whereas PrR2 expression is barely detectable in stems. Co-expression analysis has indicated that PrR1 is co-expressed with many characterized genes involved in secondary cell wall biosynthesis, whereas PrR2 expression clusters with a different set of genes. The promoter of the PrR1 gene is regulated by the secondary cell wall related transcription factors SND1 and MYB46. The loss-of-function mutant of PrR1 shows, in addition to elevated levels of pinoresinol, significantly decreased lignin content and a slightly altered lignin structure with lower abundance of cinnamyl alcohol end groups. Stimulated Raman scattering (SRS) microscopy analysis indicated that the lignin content of the prr1-1 loss-of-function mutant is similar to that of wild-type plants in xylem cells, which exhibit a normal phenotype, but is reduced in the fiber cells. Together, these data suggest an association of the lignan biosynthetic enzyme encoded by PrR1 with secondary cell wall biosynthesis in fiber cells.

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Sequence heterogeneity of cannabidiolic- and tetrahydrocannabinolic acid-synthase in Cannabis sativa L. and its relationship with chemical phenotype

Publication date: Available online 9 April 2015
Source:Phytochemistry

Author(s): Chiara Onofri , Etienne P.M. de Meijer , Giuseppe Mandolino

Sequence variants of THCA- and CBDA-synthases were isolated from different Cannabis sativa L. strains expressing various wild-type and mutant chemical phenotypes (chemotypes). Expressed and complete sequences were obtained from mature inflorescences. Each strain was shown to have a different specificity and/or ability to convert the precursor CBGA into CBDA and/or THCA type products. The comparison of the expressed sequences led to the identification of different mutations, all of them due to SNPs. These SNPs were found to relate to the cannabinoid composition of the inflorescence at maturity and are therefore proposed to have a functional significance. The amount of variation was found to be higher within the CBDAS sequence family than in the THCAS family, suggesting a more recent evolution of THCA-forming enzymes from the CBDAS group. We therefore consider CBDAS as the ancestral type of these synthases.

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Posted on 12 April 2015 | 3:46 pm


A lower content of de-methylesterified homogalacturonan improves enzymatic cell separation and isolation of mesophyll protoplasts in Arabidopsis

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Vincenzo Lionetti , Felice Cervone , Giulia De Lorenzo

Cell adhesion occurs primarily at the level of middle lamella which is mainly composed by pectin polysaccharides. These can be degraded by cell wall degrading enzymes (CWDEs) during developmental processes to allow a controlled separation of plant cells. Extensive cell wall degradation by CWDEs with consequent cell separation is performed when protoplasts are isolated from plant tissues by using mixtures of CWDEs. We have evaluated whether modification of pectin affects cell separation and protoplast isolation. Arabidopsis plants overexpressing the pectin methylesterase inhibitors AtPMEI-1 or AtPMEI-2, and Arabidopsis pme3 plants, mutated in the gene encoding pectin methylesterase 3, showed an increased efficiency of isolation of viable mesophyll protoplasts as compared with Wild Type Columbia-0 plants. The release of protoplasts was correlated with the reduced level of long stretches of de-methylesterified homogalacturonan (HGA) present in these plants. Response to elicitation, cell wall regeneration and efficiency of transfection in protoplasts from transgenic plants was comparable to those of wild type protoplasts.

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Posted on 12 April 2015 | 3:46 pm


Roles of cell wall peroxidases in plant development

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Edith Francoz , Philippe Ranocha , Huan Nguyen-Kim , Elisabeth Jamet , Vincent Burlat , Christophe Dunand

Class III peroxidases (CIII Prxs) are plant specific proteins. Based on in silico prediction and experimental evidence, they are mainly considered as cell wall localized proteins. Thanks to their dual hydroxylic and peroxidative cycles, they can produce ROS as well as oxidize cell wall aromatic compounds within proteins and phenolics that are either free or linked to polysaccharides. Thus, they are tightly associated to cell wall loosening and stiffening. They are members of large multigenic families, mostly due to an elevated rate of gene duplication in higher plants, resulting in a high risk of functional redundancy between them. However, proteomic and (micro)transcriptomic analyses have shown that CIII Prx expression profiles are highly specific. Based on these omic analyses, several reverse genetic studies have demonstrated the importance of the spatio-temporal regulation of their expression and ability to interact with cell wall microdomains in order to achieve specific activity in vivo. Each CIII Prx isoform could have specific functions in muro and this could explain the conservation of a high number of genes in plant genomes.

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Posted on 12 April 2015 | 3:46 pm


Collagenase as a useful tool for the analysis of plant cellular peripheries

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Magdalena Luczak , Weronika Krzeszowiec-Jele? , Dorota Konopka-Postupolska , Przemys?aw Wojtaszek

A technique for the selective loosening of the cell wall structure and the isolation of proteins permanently knotted in the cell walls was elaborated. Following treatment with collagenase, some proteins, such as calreticulin (CRT) and auxin binding protein 1 (ABP1) were released from purified cell walls, most probably through destruction of respective interacting proteins. The results were confirmed by the immunolocalization of the ABP1 and CRT with confocal and electron microscopy. On the other hand, potential substrates of collagenase, among them annexin 1 have been recognized. Mass spectra of annexin 1 obtained after collagenase digestion and results from analysis of potential cleavage sites suggested that the mechanism of enzyme cleavage might not depend on the amino acid sequence. Summarizing, collagenase was found to be a very useful tool for exploring molecules involved in the functioning of cellular peripheries.

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Posted on 12 April 2015 | 3:46 pm


Comparative proteomic analysis of gamma-aminobutyric acid responses in hypoxia-treated and untreated melon roots

Publication date: Available online 31 March 2015
Source:Phytochemistry

Author(s): Longquan Fan , Xiaolei Wu , Zhen Tian , Kaizhi Jia , Yinghong Pan , Jingrui Li , Hongbo Gao

Hypoxia is one of the main environmental stresses that accounts for decreasing crop yield. To further investigate the mechanisms whereby exogenous GABA alleviates hypoxia injury to melon seedlings, a comparative proteomic analysis was performed using roots subjected to normal aeration and hypoxia conditions with or without GABA (5mM). The results indicated that protein spots on gels after hypoxia and hypoxia+GABA treatment were significantly changed. Three “matched sets” were analyzed from four treatments, and 13 protein spots with large significant differences in expression were identified by MALDI-TOF/TOF mass spectrometry. Exogenous GABA treatment enhanced the expression of protein in cytosolic phosphoglycerate kinase 1, exaA2 gene product, dnaJ and myb-like DNA-binding domain-containing proteins, as well as elongation factor-1 alpha and hypothetical proteins in hypoxia-induced roots. However, the hypoxia+GABA treated roots had a significantly lower expression of proteins including malate dehydrogenase, nucleoside diphosphate kinase, disease resistance-like protein, disulfide isomerase, actin, ferrodoxin NADP oxidoreductase, glutathione transferase, netting associated peroxidase. This paper describes the effect of GABA on melon plants under hypoxia-induced stress using proteomics, and supports the alleviating function of GABA in melon plants grown under hypoxic conditions.

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Posted on 12 April 2015 | 3:46 pm


Controlled expression of pectic enzymes in Arabidopsis thaliana enhances biomass conversion without adverse effects on growth

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Susanna Tomassetti , Daniela Pontiggia , Ilaria Verrascina , Ida Barbara Reca , Fedra Francocci , Gianni Salvi , Felice Cervone , Simone Ferrari

Lignocellulosic biomass from agriculture wastes is a potential source of biofuel, but its use is currently limited by the recalcitrance of the plant cell wall to enzymatic digestion. Modification of the wall structural components can be a viable strategy to overcome this bottleneck. We have previously shown that the expression of a fungal polygalacturonase (pga2 from Aspergillus niger) in Arabidopsis and tobacco plants reduces the levels of de-esterified homogalacturonan in the cell wall and significantly increases saccharification efficiency. However, plants expressing pga2 show stunted growth and reduced biomass production, likely as a consequence of an extensive loss of pectin integrity during the whole plant life cycle. We report here that the expression in Arabidopsis of another pectic enzyme, the pectate lyase 1 (PL1) of Pectobacterium carotovorum, under the control of a chemically inducible promoter, results, after induction of the transgene, in a saccharification efficiency similar to that of plants expressing pga2. However, lines with high levels of transgene induction show reduced growth even in the absence of the inducer. To overcome the problem of plant fitness, we have generated Arabidopsis plants that express pga2 under the control of the promoter of SAG12, a gene expressed only during senescence. These plants expressed pga2 only at late stages of development, and their growth was comparable to that of WT plants. Notably, leaves and stems of transgenic plants were more easily digested by cellulase, compared to WT plants, only during senescence. Expression of cell wall-degrading enzymes at the end of the plant life cycle may be therefore a useful strategy to engineer crops unimpaired in biomass yield but improved for bioconversion.

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Posted on 12 April 2015 | 3:46 pm


Reactive oxygen species in cell wall metabolism and development in plants

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Anna Kärkönen , Kazuyuki Kuchitsu

Although reactive oxygen species (ROS) are highly toxic substances that are produced during aerobic respiration and photosynthesis, many studies have demonstrated that ROS, such as superoxide anion radical ( O 2 - ) and hydrogen peroxide (H2O2), are produced in the plant cell wall in a highly regulated manner. These molecules are important signalling messengers playing key roles in controlling a broad range of physiological processes, such as cellular growth and development, as well as adaptation to environmental changes. Given the toxicity of ROS, especially of hydroxyl radical ( OH), the enzymatic ROS production needs to be tightly regulated both spatially and temporally. Respiratory burst oxidase homologues (Rboh) have been identified as ROS-producing NADPH oxidases, which act as key signalling nodes integrating multiple signal transduction pathways in plants. Also other enzyme systems, such as class III peroxidases, amine oxidases, quinone reductases and oxalate oxidases contribute to apoplastic ROS production, some especially in certain plant taxa. Here we discuss the interrelationship among different enzymes producing ROS in the plant cell wall, as well as the physiological roles of the ROS produced.

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Posted on 12 April 2015 | 3:46 pm


Structural and quantitative analysis of Equisetum alkaloids

Publication date: Available online 27 March 2015
Source:Phytochemistry

Author(s): Luise Cramer , Ludger Ernst , Marcus Lubienski , Uli Papke , Hans-Martin Schiebel , Gerold Jerz , Till Beuerle

Equisetum palustre L. is known for its toxicity for livestock. Several studies in the past addressed the isolation and identification of the responsible alkaloids. So far, palustrine (1) and N 5-formylpalustrine (2) are known alkaloids of E. palustre. A HPLC–ESI-MS/MS method in combination with simple sample work-up was developed to identify and quantitate Equisetum alkaloids. Besides the two known alkaloids six related alkaloids were detected in different Equisetum samples. The structure of the alkaloid palustridiene (3) was derived by comprehensive 1D and 2D NMR experiments. N 5-Acetylpalustrine (4) was also thoroughly characterized by NMR for the first time. The structure of N 5-formylpalustridiene (5) is proposed based on mass spectrometry results. Twenty-two E. palustre samples were screened by a HPLC–ESI-MS/MS method after development of a simple sample work-up and in most cases the set of all eight alkaloids were detected in all parts of the plant. A high variability of the alkaloid content and distribution was found depending on plant organ, plant origin and season ranging from 88 to 597mg/kg dried weight. However, palustrine (1) and the alkaloid palustridiene (3) always represented the main alkaloids. For the first time, a comprehensive identification, quantitation and distribution of Equisetum alkaloids was achieved.

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Posted on 12 April 2015 | 3:46 pm


Allium sativum produces terpenes with fungistatic properties in response to infection with Sclerotium cepivorum

Publication date: Available online 26 March 2015
Source:Phytochemistry

Author(s): Mariela Pontin , Rubén Bottini , José Luis Burba , Patricia Piccoli

This study investigated terpene biosynthesis in different tissues (root, protobulb, leaf sheath and blade) of in vitro-grown garlic plants either infected or not (control) with Sclerotium cepivorum, the causative agent of Allium White Rot disease. The terpenes identified by gas chromatography–electron impact mass spectrometry (GC-EIMS) in infected plants were nerolidol, phytol, squalene, ?-pinene, terpinolene, limonene, 1,8-cineole and ?-terpinene, whose levels significantly increased when exposed to the fungus. Consistent with this, an increase in terpene synthase (TPS) activity was measured in infected plants. Among the terpenes identified, nerolidol, ?-pinene and terpinolene were the most abundant with antifungal activity against S. cepivorum being assessed in vitro by mycelium growth inhibition. Nerolidol and terpinolene significantly reduced sclerotia production, while ?-pinene stimulated it in a concentration-dependent manner. Parallel to fungal growth inhibition, electron microscopy observations established morphological alterations in the hyphae exposed to terpinolene and nerolidol. Differences in hyphal EtBr uptake suggested that one of the antifungal mechanisms of nerolidol and terpinolene might be disruption of fungal membrane integrity.

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Posted on 12 April 2015 | 3:46 pm


Distribution and content of ellagitannins in Finnish plant species

Publication date: Available online 26 March 2015
Source:Phytochemistry

Author(s): Johanna Moilanen , Piia Koskinen , Juha-Pekka Salminen

The results of a screening study, in which a total of 82 Finnish plant species were studied for their ellagitannin composition and content, are presented. The total ellagitannin content was determined by HPLC-DAD, the detected ellagitannins were further characterized by HPLC-ESI-QTOF-MS and divided into four structurally different sub-groups. Thirty plant species were found to contain ellagitannins and the ellagitannin content in the crude extracts varied from few mgg?1 to over a hundred mgg?1. Plant families that were rich in ellagitannins (>90mgg?1 of the crude extract) were Onagraceae, Lyhtraceae, Geraniaceae, Elaeagnaceae, Fagaceae and some species from Rosaceae. Plant species that contained moderate amounts of ellagitannins (31–89mgg?1 of the crude extract) were representatives of the family Rosaceae. Plant species that contained low amounts of ellagitannins (1–30mgg?1 of the crude extract) were representatives of the families Betulaceae and Myricaceae. The specific ellagitannin composition of the species allowed their chemotaxonomic classification and the comparison between the older Cronquist’s classification and the nowadays preferred Angiosperm Phylogeny Group classification.

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Highlights

Taxonomic distribution, composition and content of ellagitannins in 82 Finnish plant species were studied. Altogether 30 species contained ellagitannins from which the most ellagitannin-rich species were Epilobium species, Lythrum salicaria, Geranium species, Hippophae rhamnoides, Quercus robur, Filipendula ulmaria, Geum urbanum and Rubus chamaemorus.





Posted on 12 April 2015 | 3:46 pm


The metabolomics of oxidative stress

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Graham Noctor , Caroline Lelarge-Trouverie , Amna Mhamdi

Oxidative stress resulting from increased availability of reactive oxygen species (ROS) is a key component of many responses of plants to challenging environmental conditions. The consequences for plant metabolism are complex and manifold. We review data on small compounds involved in oxidative stress, including ROS themselves and antioxidants and redox buffers in the membrane and soluble phases, and we discuss the wider consequences for plant primary and secondary metabolism. While metabolomics has been exploited in many studies on stress, there have been relatively few non-targeted studies focused on how metabolite signatures respond specifically to oxidative stress. As part of the discussion, we present results and reanalyze published datasets on metabolite profiles in catalase-deficient plants, which can be considered to be model oxidative stress systems. We emphasize the roles of ROS-triggered changes in metabolites as potential oxidative signals, and discuss responses that might be useful as markers for oxidative stress. Particular attention is paid to lipid-derived compounds, the status of antioxidants and antioxidant breakdown products, altered metabolism of amino acids, and the roles of phytohormone pathways.

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Posted on 12 April 2015 | 3:46 pm


Bioactive maca (Lepidium meyenii) alkamides are a result of traditional Andean postharvest drying practices

Publication date: Available online 25 March 2015
Source:Phytochemistry

Author(s): Eliana Esparza , Antonella Hadzich , Waltraud Kofer , Axel Mithöfer , Eric G. Cosio

Maca, Lepidium meyenii Walpers (Brassicaceae), is an annual herbaceous plant native to the high plateaus of the Peruvian central Andes. Its underground storage hypocotyls have been a traditional medicinal agent and dietary staple since pre-Columbian times. Reported properties include energizing and fertility-enhancing effects. Published reports have focused on the benzylalkamides (macamides) present in dry hypocotyls as one of the main bioactive components. Macamides are secondary amides formed by benzylamine and a fatty acid moiety, with varying hydrocarbon chain lengths and degree of unsaturation. Although it has been assumed that they are usually present in fresh undamaged tissues, analyses show them to be essentially absent from them. However, hypocotyls dried by traditional Andean postharvest practices or industrial oven drying contain up to 800?gg?1 dry wt (2.3?molg?1 dry wt) of macamides. In this study, the generation of macamides and their putative precursors were studied during nine-week traditional drying trials at 4200m altitude and in ovens under laboratory conditions. Freeze–thaw cycles in the open field during drying result in tissue maceration and release of free fatty acids from storage and membrane lipids up to levels of 1200?gg?1 dry wt (4.3?molg?1 dry wt). Endogenous metabolism of the isothiocyanates generated from glucosinolate hydrolysis during drying results in maximal benzylamine values of 4300?gg?1 dry wt (40.2?molg?1 dry wt). Pearson correlation coefficients of the accumulation profiles of benzylamine and free fatty acid to that of macamides showed good values of 0.898 and 0.934, respectively, suggesting that both provide sufficient substrate for amide synthesis during the drying process.

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Posted on 12 April 2015 | 3:46 pm


Absolute configurations of phytotoxins seiricardine A and inuloxin A obtained by chiroptical studies

Publication date: Available online 25 March 2015
Source:Phytochemistry

Author(s): Ernesto Santoro , Giuseppe Mazzeo , Ana G. Petrovic , Alessio Cimmino , Jun Koshoubu , Antonio Evidente , Nina Berova , Stefano Superchi

The absolute configuration (AC) of the plant phytotoxin inuloxin A, produced by Inula viscosa, and of the fungal phytotoxin seiricardine A, obtained from Seiridium fungi, pathogen for cypress, has been determined by experimental measurements and theoretical simulations of chiroptical properties of three related methods, namely, Optical Rotatory Dispersion (ORD), Electronic Circular Dichroism (ECD), and Vibrational Circular Dichroism (VCD). Computational prediction by Density Functional Theory (DFT) of VCD spectra and by Time-dependent DFT (TDDFT) of ORD and ECD spectra allowed to assign (7R,8R,10S) AC to naturally occurring (+)-inuloxin A. In the case of compound (?)-seiricardine A, which lacks useful for the analysis UV–Vis absorption, and thus provides a hardly detectable ECD spectrum and quite low ORD values, an introduction of a suitable chromophore by chemical derivatization was performed. The corresponding derivative, 2-O-p-bromobenzoate ester, gave rise to an intense ECD spectrum and higher ORD and VCD values. The comparison of computed spectra with the experimental ones allowed to assign (1S,2R,3aS,4S,5R,7aS) AC to (?)-2-O-p-bromobenzoate ester of seiricardine A and then to (?)-seiricardine A. This study further supports a recent trend of concerted application of more than a single chiroptical technique toward an unambiguous assignment of AC of flexible and complex natural products. Moreover, the use of chemical derivatization, with insertion of suitable chromophoric moieties has allowed to treat also UV–Vis transparent molecules by ECD and ORD spectroscopies.

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Posted on 12 April 2015 | 3:46 pm


Ganoderma pfeifferi – A European relative of Ganoderma lucidum

Publication date: Available online 25 March 2015
Source:Phytochemistry

Author(s): Ulrike Lindequist , Wolf-Dieter Jülich , Sabine Witt

In contrast to well-studied and broadly used Ganoderma species, such as Ganoderma lucidum and Ganoderma applanatum, knowledge regarding Ganoderma pfeifferi is very limited. Herein is an overview of the phytochemistry, biological activities and possible applications of this mushroom species. In addition to triterpenoids and polysaccharides, G. pfeifferi contains unique sesquiterpenoids and other small molecular weight compounds. Some of these compounds exhibit remarkable antimicrobial activities in vitro and in vivo against multi-resistant bacteria, such as MRSA. Antiviral properties, UV-protection abilities and other activities are also known. Potential issues arising from the conversion of research results into practical applications are discussed.

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Highlights

Ganoderma pfeifferi contains farnesylhydroquinones named ganomycins and several triterpenoid compounds. Extracts and some of the isolated compounds possess antibacterial, antiviral and other biological activities.





Posted on 12 April 2015 | 3:46 pm


Reactive oxygen species and plant resistance to fungal pathogens

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Silke Lehmann , Mario Serrano , Floriane L’Haridon , Sotirios E. Tjamos , Jean-Pierre Metraux

Reactive oxygen species (ROS) have been studied for their role in plant development as well as in plant immunity. ROS were consistently observed to accumulate in the plant after the perception of pathogens and microbes and over the years, ROS were postulated to be an integral part of the defence response of the plant. In this article we will focus on recent findings about ROS involved in the interaction of plants with pathogenic fungi. We will describe the ways to detect ROS, their modes of action and their importance in relation to resistance to fungal pathogens. In addition we include some results from works focussing on the fungal interactor and from studies investigating roots during pathogen attack.

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Posted on 12 April 2015 | 3:46 pm


Cytotoxic indole alkaloids from the fruits of Melodinus cochinchinensis

Publication date: Available online 25 March 2015
Source:Phytochemistry

Author(s): Shun Shao , Hao Zhang , Chun-Mao Yuan , Yu Zhang , Ming-Ming Cao , Hai-Yuan Zhang , Yan Feng , Xiao Ding , Qiang Zhou , Qing Zhao , Hong-Ping He , Xiao-Jiang Hao

Eight indole alkaloids, melosines A–H, together with 13 known alkaloids, were isolated from the fruits of Melodinus cochinchinensis. The structure elucidation of isolated secondary metabolites was based on comprehensive spectroscopic data analysis. Melosine B showed moderate cytotoxic activity against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW480 with IC50 values ranging from 1.6 to 8.1?M.

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Posted on 12 April 2015 | 3:46 pm


Parallel reductions in phenolic constituents resulting from the domestication of eggplant

Publication date: Available online 23 March 2015
Source:Phytochemistry

Author(s): Rachel S. Meyer , Bruce D. Whitaker , Damon P. Little , Shi-Biao Wu , Edward J. Kennelly , Chun-Lin Long , Amy Litt

Crop domestication is often accompanied by changes in metabolite compositions that alter traits such as flavor, color, or other beneficial properties. Fruits of eggplants (Solanum melongena L.) and related species are abundant and diverse in pharmacologically interesting phenolic compounds, particularly hydroxycinnamic acid (HCA) conjugates such as the antioxidant caffeoylquinic acids (CQA) and HCA-polyamine amides (HCAA). To understand metabolite variability through the lens of natural and artificial selection, HPLC-DAD was used to generate phenolic profiles for 32 compounds in fruits from 93 accessions representing 9 Solanum species. Profiles were used for identification of species-level and infraspecific chemical patterns across both genetic distance and landscape. Sampling of plant lines included the undomesticated progenitor of eggplant and Asian landraces with a genetic background associated with three Asian regions near proposed separate centers of domestication to test whether chemical changes were convergent despite different origins. Results showed ten compounds were unique to species, and ten other compounds varied significantly in abundance among species. Five CQAs and three HCA-polyamine conjugates were more abundant in wild (undomesticated) versus domesticated eggplant, indicating that artificial selection may have led to reduced phenolic levels. No chemical abundance patterns were associated with site-origin. However, one genetically distinct lineage of geographically-restricted SE Asian eggplants (S. melongena subsp. ovigerum) had a higher HCAA content and diversity than other lineages, which is suggested to be related to artificial selection for small, firm fruit. Overall, patterns show that fruit size, palatability and texture were preferentially selected over health-beneficial phytochemical content during domestication of several nightshade crops.

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Posted on 12 April 2015 | 3:46 pm


Interconverting flavonostilbenes with antibacterial activity from Sophora alopecuroides

Publication date: Available online 23 March 2015
Source:Phytochemistry

Author(s): Chuan-Xing Wan , Jian-Guang Luo , Xiao-Pu Ren , Ling-Yi Kong

Five flavonostilbenes (alopecurones H, I, J, K and L) and five known ones were isolated from roots of Sophora alopecuroides, in addition to ten other phenolic compounds. A non-enzymatic interconversion of the lavandulyl-substituted flavonostilbenes was observed among alopecurones A, H, I, and K through a Wessely–Moser rearrangement reaction; this was proven by 1D and 2D NMR, HPLC-CD–PDA and HRMS analyses. Bioassay results suggested that flavonostilbenes exhibit significant antibacterial and anti-biofilm formation activities against Staphylococcus epidermidis with MIC values ranging from 3.1 to 12.5?g/mL.

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Posted on 12 April 2015 | 3:46 pm


Interplays between the cell wall and phytohormones in interaction between plants and necrotrophic pathogens

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Majse Nafisi , Lorenzo Fimognari , Yumiko Sakuragi

The plant cell wall surrounds every cell in plants. During microbial infection, the cell wall provides a dynamic interface for interaction with necrotrophic phytopathogens as a rich source of carbohydrates for the growth of pathogens, as a physical barrier restricting the progression of the pathogens, and as an integrity sensory system that can activate intracellular signaling cascades and ultimately lead to a multitude of inducible host defense responses. Studies over the last decade have provided evidence of interplays between the cell wall and phytohormone signaling. This review summarizes the current state of knowledge about the cell wall-phytohormone interplays, with the focus on auxin, cytokinin, brassinosteroids, and abscisic acid, and discuss how they impact the outcome of plant–necrotrophic pathogen interaction.

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Highlights

This review summarizes the recent progress in understanding the interplay between cell wall and phytohormone signaling and how it impacts the ability of plants to defense themselves against necrotrophic phytopathogens.





Posted on 12 April 2015 | 3:46 pm


Amphipaniculosides A–D, triterpenoid glycosides, and amphipaniculoside E, an aliphatic alcohol glycoside from the leaves of Amphilophium paniculatum

Publication date: Available online 21 March 2015
Source:Phytochemistry

Author(s): Mamdouh Nabil Samy , Hany Ezzat Khalil , Sachiko Sugimoto , Katsuyoshi Matsunami , Hideaki Otsuka , Mohamed Salah Kamel

Four new triterpenoids; One oleanane-, one ursane- and two cycloartane-type triterpenoids, named amphipaniculosides A?D, in addition to one new aliphatic alcohol glycoside, named amphipaniculoside E, were isolated from the 1-BuOH fraction of the leaves of Amphilophium paniculatum (L.) Kunth., together with five known compounds, (+)-lyoniresinol 3?-O-?-d-glucopyranoside, (?)-lyoniresinol 3?-O-?-d-glucopyranoside, acteoside (verbascoside), isoacteoside (isoverbascoside), and luteolin 7-O-?-d-glucopyranoside. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, ROESY, HSQC, HMBC) in combination with HR-ESI-MS and by comparisons of their physical and spectroscopic data with literature values.

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Posted on 12 April 2015 | 3:46 pm


Hypoglycemic activity of withanolides and elicitated Withania somnifera

Publication date: Available online 18 March 2015
Source:Phytochemistry

Author(s): Jonathan Gorelick , Rivka Rosenberg , Avinoam Smotrich , Lumír Hanuš , Nirit Bernstein

Withania somnifera, known in India as Asghawhanda, is used traditionally to treat many medical problems including diabetes and has demonstrated therapeutic activity in various animal models as well as in diabetic patients. While much of W. somnifera’s therapeutic activity is attributed to withanolides, their role in the anti-diabetic activity of W. somnifera has not been adequately studied. In the present study, we evaluated the anti-diabetic activity of W. somnifera extract and purified withanolides, as well as the effect of various elicitors on this activity. W. somnifera leaf and root extracts increased glucose uptake in myotubes and adipocytes in a dose dependent manner, with the leaf extract more active than the root extract. Leaf but not root extract increased insulin secretion in basal pancreatic beta cells but not in stimulated cells. Six withanolides isolated from W. somnifera were tested for anti-diabetic activity based on glucose uptake in skeletal myotubes. Withaferin A was found to increase glucose uptake, with 10?M producing a 54% increase compared with control, suggesting that withaferin A is at least partially responsible for W. somnifera’s anti-diabetic activity. Elicitors applied to the root growing solutions affected the physiological state of the plants, altering membrane leakage or osmotic potential. Methyl salicylate and chitosan increased withaferin A content by 75% and 69% respectively, and extracts from elicited plants increased glucose uptake to a higher extent than non-elicited plants, demonstrating a correlation between increased content of withaferin A and anti-diabetic activity.

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Posted on 12 April 2015 | 3:46 pm


Hyperascyrones A–H, polyprenylated spirocyclic acylphloroglucinol derivatives from Hypericum ascyron Linn.

Publication date: Available online 20 March 2015
Source:Phytochemistry

Author(s): Hucheng Zhu , Chunmei Chen , Junjun Liu , Bin Sun , Guangzheng Wei , Yan Li , Jinwen Zhang , Guangmin Yao , Zengwei Luo , Yongbo Xue , Yonghui Zhang

Eight polyprenylated spirocyclic acylphloroglucinol derivatives (PSAPs), hyperascyrones A–H, were isolated from the aerial parts of Hypericum ascyron Linn., together with six known analogs. Their structures were established by spectroscopic analyses including HRESIMS, 1D and 2D NMR, and their absolute configurations were determined by electronic circular dichroism calculations (ECD, Gaussian 09). Structures of previously reported tomoeones C, D, G, and H were revised. Hyperascyrones A–H were evaluated for their cytotoxic and anti-HIV-1 activities, with hyperascyrones C and G exhibiting significant cytotoxicities against HL-60 cell lines with IC50 values of 4.22 and 8.36?M, respectively. In addition, the chemotaxonomic significance of these compounds was also discussed.

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Posted on 12 April 2015 | 3:46 pm


NO signaling in plant immunity: A tale of messengers

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Pauline Trapet , Anna Kulik , Olivier Lamotte , Sylvain Jeandroz , Stéphane Bourque , Valérie Nicolas-Francès , Claire Rosnoblet , Angélique Besson-Bard , David Wendehenne

Nitric oxide (NO) is a free radical gas involved in a myriad of plant physiological processes including immune responses. How NO mediates its biological effects in plant facing microbial pathogen attack is an unresolved question. Insights into the molecular mechanisms by which it propagates signals reveal the contribution of this simple gas in complex signaling pathways shared with reactive oxygen species (ROS) and the second messenger Ca2+. Understanding of the subtle cross-talks operating between these signals was greatly improved by the recent identification and the functional analysis of proteins regulated through S-nitrosylation, a major NO-dependent post-translational protein modification. Overall, these findings suggest that NO is probably an important component of the mechanism coordinating and regulating Ca2+ and ROS signaling in plant immunity.

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Posted on 12 April 2015 | 3:46 pm


Sterols from Hericium erinaceum and their inhibition of TNF-? and NO production in lipopolysaccharide-induced RAW 264.7 cells

Publication date: Available online 18 March 2015
Source:Phytochemistry

Author(s): Wei Li , Wei Zhou , Ji Yun Cha , Se Uk Kwon , Kwang-Hyun Baek , Sang Hee Shim , Young Mi Lee , Young Ho Kim

Erinarols G–J and 10 known ergostane-type sterols were isolated from a methanol extract of the dried fruiting bodies of Hericium erinaceum. Their chemical structures were elucidated using extensive spectroscopic analyses including 1D and 2D NMR experiments and HR-ESI-MS analysis, as well as through comparison with previously reported data. Anti-inflammatory effects of the isolated compounds were evaluated in terms of inhibition of tumor necrosis factor ? (TNF-?) and nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cells. The results showed that erinarols H and J, as well as 2 of the ergostane-type sterols exhibited inhibitory activity against TNF-? secretion, with inhibition values ranging from 33.7% to 43.3% at 10?M. Erinarols J and three ergostane-type sterols exhibited significant inhibitory effects against NO production, with inhibition values ranging from 38.4% to 71.5% at 10?M.

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Posted on 12 April 2015 | 3:46 pm


RNAi construct of a cytochrome P450 gene CYP82D109 blocks an early step in the biosynthesis of hemigossypolone and gossypol in transgenic cotton plants

Publication date: Available online 17 March 2015
Source:Phytochemistry

Author(s): Tanya A. Wagner , Jinggao Liu , Lorraine S. Puckhaber , Alois A. Bell , Howard Williams , Robert D. Stipanovic

Naturally occurring terpenoid aldehydes from cotton, such as hemigossypol, gossypol, hemigossypolone, and the heliocides, are important components of disease and herbivory resistance in cotton. These terpenoids are predominantly found in the glands. Differential screening identified a cytochrome P450 cDNA clone (CYP82D109) from a Gossypium hirsutum cultivar that hybridized to mRNA from glanded cotton but not glandless cotton. Both the D genome cotton Gossypium raimondii and A genome cotton Gossypium arboreum possessed three additional paralogs of the gene. G. hirsutum was transformed with a RNAi construct specific to this gene family and eight transgenic plants were generated stemming from at least five independent transformation events. HPLC analysis showed that RNAi plants, when compared to wild-type Coker 312 (WT) plants, had a 90% reduction in hemigossypolone and heliocides levels, and a 70% reduction in gossypol levels in the terminal leaves, respectively. Analysis of volatile terpenes by GC–MS established presence of an additional terpene (MW: 218) from the RNAi leaf extracts. The 1H and 13C NMR spectroscopic analyses showed this compound was ?-cadinen-2-one. Double bond rearrangement of this compound gives 7-hydroxycalamenene, a lacinilene C pathway intermediate. ?-Cadinen-2-one could be derived from ?-cadinene via a yet to be identified intermediate, ?-cadinen-2-ol. The RNAi construct of CYP82D109 blocks the synthesis of desoxyhemigossypol and increases the induction of lacinilene C pathway, showing that these pathways are interconnected. Lacinilene C precursors are not constitutively expressed in cotton leaves, and blocking the gossypol pathway by the RNAi construct resulted in a greater induction of the lacinilene C pathway compounds when challenged by pathogens.

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Posted on 12 April 2015 | 3:46 pm


From 2000years of Ganoderma lucidum to recent developments in nutraceuticals

Publication date: Available online 17 March 2015
Source:Phytochemistry

Author(s): Karen S. Bishop , Chi H.J. Kao , Yuanye Xu , Marcus P. Glucina , R. Russell M. Paterson , Lynnette R. Ferguson

Medicinal mushrooms have been used for centuries as nutraceuticals to improve health and to treat numerous chronic and infectious diseases. One such mushroom is Ganoderma lucidum, commonly known as Lingzhi, a species revered as a medicinal mushroom for treating assorted diseases and prolonging life. The fungus is found in diverse locations, and this may have contributed to confusion regarding the correct taxonomic classification of the genus Ganoderma. G. lucidum was first used to name a specimen found in England and thereafter was naively applied to a different Ganoderma species found in Asia, commonly known as Chinese Lingzhi. Despite the taxonomic confusion, which has largely been uncorrected, the popularity of Lingzhi has escalated across the globe. The current taxonomic situation is now discussed accurately in this Special Issue on Ganoderma. Today it is a multi-billion dollar industry wherein Lingzhi is cultivated or collected from the wild and consumed as a tea, in alcoholic beverages, and as a nutraceutical to confer numerous health benefits. Consumption of nutraceuticals has grown in popularity, and it is becoming increasingly important that active ingredients be identified and that suppliers make substantiated health claims about their products. The objective of this article is to present a review of G. lucidum over the past 2000years from prized ancient “herbal” remedy to its use in nutraceuticals and to the establishment of a 2.5 billion $ (US) industry.

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Posted on 12 April 2015 | 3:46 pm


Pectins, ROS homeostasis and UV-B responses in plant roots

Publication date: April 2015
Source:Phytochemistry, Volume 112

Author(s): Ken Yokawa , František Baluška

Light from the sun contains far-red, visible and ultra violet (UV) wavelength regions. Almost all plant species have been evolved under the light environment. Interestingly, several photoreceptors, expressing both in shoots and roots, process the light information during the plant life cycle. Surprisingly, Arabidopsis root apices express besides the UVR8 UV-B receptor, also root-specific UV-B sensing proteins RUS1 and RUS2 linked to the polar cell–cell transport of auxin. In this mini-review, we focus on reactive oxygen species (ROS) signaling and possible roles of pectins internalized via endocytic vesicle recycling system in the root-specific UV-B perception and ROS homeostasis.

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Posted on 12 April 2015 | 3:46 pm


Anti-diabetic effects of Ganoderma lucidum

Publication date: Available online 16 March 2015
Source:Phytochemistry

Author(s): Haou-Tzong Ma , Jung-Feng Hsieh , Shui-Tein Chen

Ganoderma lucidum is a white rot fungus widely used as a tonic for the promotion of longevity and health. Extracts of G. lucidum have been recognized as an alternative adjuvant treatment for diabetes. Among the many biologically active constituents of G. lucidum, polysaccharides, proteoglycans, proteins and triterpenoids have been shown to have hypoglycemic effects. G. lucidum polysaccharides have been reported to have hypoglycemic activity by increasing plasma insulin levels and decreasing plasma sugar levels in mice. Protein tyrosine phosphatase 1B is a promising therapeutic target in diabetes, and G. lucidum proteoglycan can inhibit this enzyme in vitro. Moreover, G. lucidum triterpenoids were shown to have inhibitory activity on aldose reductase and ?-glucosidase that can suppress postprandial hyperglycemia. In addition, a protein Ling Zhi-8 extracted from G. lucidum significantly decreased lymphocyte infiltration and increased the antibody detection of insulin in diabetic mice. This review summarizes most of the research about the hypoglycemic action effects of polysaccharides, proteoglycans, proteins and tritrerpenoids from G. lucidum as a guide for future research.

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Posted on 12 April 2015 | 3:46 pm





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