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Phytoalexins: Current Progress and Future Prospects
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Phytoalexins: Current Progress and Future Prospects

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 April 2014) | Viewed by 184974

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. Philippe Jeandet

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Guest Editor
Research Unit “Induced Resistance and Plant Bioprotection”, RIBP-USC INRAe 1488, University of Reims Champagne-Ardenne, 51100 Reims, France
Interests: phytoalexins; chemistry of natural products; secondary metabolites; plant defences
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Phytoalexins are antimicrobial substances of low molecular weight produced by plants in response to infection or stress, which form part of their active defense mechanisms. It is now clear that phytoalexins exhibit toxicity across much of the biological spectrum, prokaryotic and eukaryotic. Starting in the 1950s, research on phytoalexins has begun with biochemistry and bio-organic chemistry, resulting in the determination of their structure, their biological activity as well as mechanisms of their synthesis and their catabolism by microorganisms. Elucidation of the biosynthesis of numerous phytoalexins has also permitted the use of molecular biology tools for the exploration of the genes encoding enzymes of their synthesis pathways and their regulators. This has led to potential applications for increasing plant resistance to diseases. Phytoalexins display an enormous diversity belonging to various chemical families such as isoflavones, isoflavanones, pterocarpans, isoflavans, flavanones, coumestans, furanoacetylenes, phenylpropanoids, steroid glycoalkaloids, norsesquiterpenoids/sesquiterpenoids, coumarins, diterpenes, ent-kaurane-related diterpenoids, acidic sesquiterpenoids, 3-deoxyanthocyanidins, naphthaldehydes, indoles and stilbenes.

Research papers dealing with all aspects of phytoalexins, including structure elucidation; chemical synthesis; methods for phytoalexin analysis in plant extracts or biological fluids; biosynthesis studies including modulation of phytoalexin synthesis; engineering of phytoalexin biochemical pathways in plants and microbes; biological activities; structure/activity relationships; phytoalexin metabolism in planta and by micro-organisms; roles and ATP Binding Cassette (ABC) transporters or Multi-Drugs Efflux (MDE) transporters are welcome for inclusion in this Special Issue of Molecules. Review articles, particularly those dealing with the themes mentioned above are also particularly welcome for inclusion.

Prof. Dr. Philippe Jeandet
Guest Editor

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Keywords

  • phytoalexin structure elucidation
  • chemical synthesis
  • methods for phytoalexin analysis
  • biosynthetic studies and modulation of phytoalexin biosynthesis
  • molecular engineering in plants and microbes / applications
  • biological activities
  • structure/activity relationships
  • plant metabolism
  • fungal metabolism
  • transport mechanisms
  • applications


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Editorial

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623 KiB  
Editorial
Phytoalexins: Current Progress and Future Prospects
by Philippe Jeandet
Molecules 2015, 20(2), 2770-2774; https://doi.org/10.3390/molecules20022770 - 05 Feb 2015
Cited by 67 | Viewed by 10143
Abstract
Phytoalexins are low molecular weight antimicrobial compounds that are produced by plants as a response to biotic and abiotic stresses. As such they take part in an intricate defense system which enables plants to control invading microorganisms. In the 1950s, research on phytoalexins [...] Read more.
Phytoalexins are low molecular weight antimicrobial compounds that are produced by plants as a response to biotic and abiotic stresses. As such they take part in an intricate defense system which enables plants to control invading microorganisms. In the 1950s, research on phytoalexins started with progress in their biochemistry and bio-organic chemistry, resulting in the determination of their structure, their biological activity, as well as mechanisms of their synthesis and catabolism by microorganisms. Elucidation of the biosynthesis of numerous phytoalexins also permitted the use of molecular biology tools for the exploration of the genes encoding enzymes of their synthesis pathways and their regulators. This has led to potential applications for increasing plant resistance to diseases. Phytoalexins display an enormous diversity belonging to various chemical families such as for instance, phenolics, terpenoids, furanoacetylenes, steroid glycoalkaloids, sulfur-containing compounds and indoles.[...] Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)

Research

Jump to: Editorial, Review

871 KiB  
Article
A Sorghum MYB Transcription Factor Induces 3-Deoxyanthocyanidins and Enhances Resistance against Leaf Blights in Maize
by Farag Ibraheem, Iffa Gaffoor, Qixian Tan, Chi-Ren Shyu and Surinder Chopra
Molecules 2015, 20(2), 2388-2404; https://doi.org/10.3390/molecules20022388 - 30 Jan 2015
Cited by 55 | Viewed by 9205
Abstract
Sorghum responds to the ingress of the fungal pathogen Colletotrichum sublineolum through the biosynthesis of 3-deoxyanthocyanidin phytoalexins at the site of primary infection. Biosynthesis of 3-deoxyanthocyanidins in sorghum requires a MYB transcription factor encoded by yellow seed1 (y1), an orthologue of [...] Read more.
Sorghum responds to the ingress of the fungal pathogen Colletotrichum sublineolum through the biosynthesis of 3-deoxyanthocyanidin phytoalexins at the site of primary infection. Biosynthesis of 3-deoxyanthocyanidins in sorghum requires a MYB transcription factor encoded by yellow seed1 (y1), an orthologue of the maize gene pericarp color1 (p1). Maize lines with a functional p1 and flavonoid structural genes do not produce foliar 3-deoxyanthocyanidins in response to fungal ingress. To perform a comparative metabolic analysis of sorghum and maize 3-deoxyanthocyanidin biosynthetic pathways, we developed transgenic maize lines expressing the sorghum y1 gene. In maize, the y1 transgene phenocopied p1-regulated pigment accumulation in the pericarp and cob glumes. LC-MS profiling of fungus-challenged Y1-maize leaves showed induction of 3-deoxyanthocyanidins, specifically luteolinidin. Y1-maize plants also induced constitutive and higher levels of flavonoids in leaves. In response to Colletotrichum graminicola, Y1-maize showed a resistance response. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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1847 KiB  
Article
EDTA a Novel Inducer of Pisatin, a Phytoalexin Indicator of the Non-Host Resistance in Peas
by Lee A. Hadwiger and Kiwamu Tanaka
Molecules 2015, 20(1), 24-34; https://doi.org/10.3390/molecules20010024 - 23 Dec 2014
Cited by 11 | Viewed by 8960
Abstract
Pea pod endocarp suppresses the growth of an inappropriate fungus or non-pathogen by generating a “non-host resistance response” that completely suppresses growth of the challenging fungus within 6 h. Most of the components of this resistance response including pisatin production can be elicited [...] Read more.
Pea pod endocarp suppresses the growth of an inappropriate fungus or non-pathogen by generating a “non-host resistance response” that completely suppresses growth of the challenging fungus within 6 h. Most of the components of this resistance response including pisatin production can be elicited by an extensive number of both biotic and abiotic inducers. Thus this phytoalexin serves as an indicator to be used in evaluating the chemical properties of inducers that can initiate the resistance response. Many of the pisatin inducers are reported to interact with DNA and potentially cause DNA damage. Here we propose that EDTA (ethylenediaminetetraacetic acid) is an elicitor to evoke non-host resistance in plants. EDTA is manufactured as a chelating agent, however at low concentration it is a strong elicitor, inducing the phytoalexin pisatin, cellular DNA damage and defense-responsive genes. It is capable of activating complete resistance in peas against a pea pathogen. Since there is also an accompanying fragmentation of pea DNA and alteration in the size of pea nuclei, the potential biochemical insult as a metal chelator may not be its primary action. The potential effects of EDTA on the structure of DNA within pea chromatin may assist the transcription of plant defense genes. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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1304 KiB  
Article
Study of Leaf Metabolome Modifications Induced by UV-C Radiations in Representative Vitis, Cissus and Cannabis Species by LC-MS Based Metabolomics and Antioxidant Assays
by Guillaume Marti, Sylvain Schnee, Yannis Andrey, Claudia Simoes-Pires, Pierre-Alain Carrupt, Jean-Luc Wolfender and Katia Gindro
Molecules 2014, 19(9), 14004-14021; https://doi.org/10.3390/molecules190914004 - 05 Sep 2014
Cited by 42 | Viewed by 11316
Abstract
UV-C radiation is known to induce metabolic modifications in plants, particularly to secondary metabolite biosynthesis. To assess these modifications from a global and untargeted perspective, the effects of the UV-C radiation of the leaves of three different model plant species, Cissus antarctica Vent [...] Read more.
UV-C radiation is known to induce metabolic modifications in plants, particularly to secondary metabolite biosynthesis. To assess these modifications from a global and untargeted perspective, the effects of the UV-C radiation of the leaves of three different model plant species, Cissus antarctica Vent. (Vitaceae), Vitis vinifera L. (Vitaceae) and Cannabis sativa L. (Cannabaceae), were evaluated by an LC-HRMS-based metabolomic approach. The approach enabled the detection of significant metabolite modifications in the three species studied. For all species, clear modifications of phenylpropanoid metabolism were detected that led to an increased level of stilbene derivatives. Interestingly, resveratrol and piceid levels were strongly induced by the UV-C treatment of C. antarctica leaves. In contrast, both flavonoids and stilbene polymers were upregulated in UV-C-treated Vitis leaves. In Cannabis, important changes in cinnamic acid amides and stilbene-related compounds were also detected. Overall, our results highlighted phytoalexin induction upon UV-C radiation. To evaluate whether UV-C stress radiation could enhance the biosynthesis of bioactive compounds, the antioxidant activity of extracts from control and UV-C-treated leaves was measured. The results showed increased antioxidant activity in UV-C-treated V. vinifera extracts. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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5565 KiB  
Article
Effects of Endogenous Signals and Fusarium oxysporum on the Mechanism Regulating Genistein Synthesis and Accumulation in Yellow Lupine and Their Impact on Plant Cell Cytoskeleton
by Magda Formela, Sławomir Samardakiewicz, Łukasz Marczak, Witold Nowak, Dorota Narożna, Waldemar Bednarski, Anna Kasprowicz-Maluśki and Iwona Morkunas
Molecules 2014, 19(9), 13392-13421; https://doi.org/10.3390/molecules190913392 - 29 Aug 2014
Cited by 29 | Viewed by 8064
Abstract
The aim of the study was to examine cross-talk interactions of soluble sugars (sucrose, glucose and fructose) and infection caused by Fusarium oxysporum f.sp. lupini on the synthesis of genistein in embryo axes of Lupinus luteus L.cv. Juno. Genistein is a free aglycone, [...] Read more.
The aim of the study was to examine cross-talk interactions of soluble sugars (sucrose, glucose and fructose) and infection caused by Fusarium oxysporum f.sp. lupini on the synthesis of genistein in embryo axes of Lupinus luteus L.cv. Juno. Genistein is a free aglycone, highly reactive and with the potential to inhibit fungal infection and development of plant diseases. As signal molecules, sugars strongly stimulated accumulation of isoflavones, including genistein, and the expression of the isoflavonoid biosynthetic genes. Infection significantly enhanced the synthesis of genistein and other isoflavone aglycones in cells of embryo axes of yellow lupine with high endogenous sugar levels. The activity of β-glucosidase, the enzyme that releases free aglycones from their glucoside bindings, was higher in the infected tissues than in the control ones. At the same time, a very strong generation of the superoxide anion radical was observed in tissues with high sugar contents already in the initial stage of infection. During later stages after inoculation, a strong generation of semiquinone radicals was observed, which level was relatively higher in tissues deficient in sugars than in those with high sugar levels. Observations of actin and tubulin cytoskeletons in cells of infected embryo axes cultured on the medium with sucrose, as well as the medium without sugar, showed significant differences in their organization. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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666 KiB  
Article
Effectiveness of Phenolic Compounds against Citrus Green Mould
by Simona M. Sanzani, Leonardo Schena and Antonio Ippolito
Molecules 2014, 19(8), 12500-12508; https://doi.org/10.3390/molecules190812500 - 18 Aug 2014
Cited by 45 | Viewed by 6907
Abstract
Stored citrus fruit suffer huge losses because of the development of green mould caused by Penicillium digitatum. Usually synthetic fungicides are employed to control this disease, but their use is facing some obstacles, such public concern about possible adverse effects on human [...] Read more.
Stored citrus fruit suffer huge losses because of the development of green mould caused by Penicillium digitatum. Usually synthetic fungicides are employed to control this disease, but their use is facing some obstacles, such public concern about possible adverse effects on human and environmental health and the development of resistant pathogen populations. In the present study quercetin, scopoletin and scoparone—phenolic compounds present in several agricultural commodities and associated with response to stresses—were firstly tested in vitro against P. digitatum and then applied in vivo on oranges cv. Navelina. Fruits were wound-treated (100 µg), pathogen-inoculated, stored and surveyed for disease incidence and severity. Although only a minor (≤13%) control effect on P. digitatum growth was recorded in vitro, the in vivo trial results were encouraging. In fact, on phenolic-treated oranges, symptoms appeared at 6 days post-inoculation (DPI), i.e., with a 2 day-delay as compared to the untreated control. Moreover, at 8 DPI, quercetin, scopoletin, and scoparone significantly reduced disease incidence and severity by 69%–40% and 85%–70%, respectively, as compared to the control. At 14 DPI, scoparone was the most active molecule. Based on the results, these compounds might represent an interesting alternative to synthetic fungicides. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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3475 KiB  
Article
Analysis on Blast Fungus-Responsive Characters of a Flavonoid Phytoalexin Sakuranetin; Accumulation in Infected Rice Leaves, Antifungal Activity and Detoxification by Fungus
by Morifumi Hasegawa, Ichiro Mitsuhara, Shigemi Seo, Kazunori Okada, Hisakazu Yamane, Takayoshi Iwai and Yuko Ohashi
Molecules 2014, 19(8), 11404-11418; https://doi.org/10.3390/molecules190811404 - 04 Aug 2014
Cited by 65 | Viewed by 8986
Abstract
To understand the role of the rice flavonoid phytoalexin (PA) sakuranetin for blast resistance, the fungus-responsive characteristics were studied. Young rice leaves in a resistant line exhibited hypersensitive reaction (HR) within 3 days post inoculation (dpi) of a spore suspension, and an increase [...] Read more.
To understand the role of the rice flavonoid phytoalexin (PA) sakuranetin for blast resistance, the fungus-responsive characteristics were studied. Young rice leaves in a resistant line exhibited hypersensitive reaction (HR) within 3 days post inoculation (dpi) of a spore suspension, and an increase in sakuranetin was detected at 3 dpi, increasing to 4-fold at 4 dpi. In the susceptible line, increased sakuranetin was detected at 4 dpi, but not at 3 dpi, by which a large fungus mass has accumulated without HR. Induced expression of a PA biosynthesis gene OsNOMT for naringenin 7-O-methyltransferase was found before accumulation of sakuranetin in both cultivars. The antifungal activity of sakuranetin was considerably higher than that of the major rice diterpenoid PA momilactone A in vitro and in vivo under similar experimental conditions. The decrease and detoxification of sakuranetin were detected in both solid and liquid mycelium cultures, and they took place slower than those of momilactone A. Estimated local concentration of sakuranetin at HR lesions was thought to be effective for fungus restriction, while that at enlarged lesions in susceptible rice was insufficient. These results indicate possible involvement of sakuranetin in blast resistance and its specific relation to blast fungus. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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3727 KiB  
Article
ROS-Dependent Antiproliferative Effect of Brassinin Derivative Homobrassinin in Human Colorectal Cancer Caco2 Cells
by Martin Kello, David Drutovic, Martina Chripkova, Martina Pilatova, Mariana Budovska, Lucia Kulikova, Peter Urdzik and Jan Mojzis
Molecules 2014, 19(8), 10877-10897; https://doi.org/10.3390/molecules190810877 - 25 Jul 2014
Cited by 41 | Viewed by 8884
Abstract
This study was designed to examine the in vitro antiproliferative effect of brassinin and its derivatives on human cancer cell lines. Among seven tested compounds, homobrassinin (K1; N-[2-(indol-3-yl)ethyl]-S-methyldithiocarbamate) exhibited the most potent activity with IC50 = 8.0 μM in human [...] Read more.
This study was designed to examine the in vitro antiproliferative effect of brassinin and its derivatives on human cancer cell lines. Among seven tested compounds, homobrassinin (K1; N-[2-(indol-3-yl)ethyl]-S-methyldithiocarbamate) exhibited the most potent activity with IC50 = 8.0 μM in human colorectal Caco2 cells and was selected for further studies. The flow cytometric analysis revealed a K1-induced increase in the G2/M phase associated with dysregulation of α-tubulin, α1-tubulin and β5-tubulin expression. These findings suggest that the inhibitory effect of K1 can be mediated via inhibition of microtubule formation. Furthermore, simultaneously with G2/M arrest, K1 also increased population of cells with sub-G1 DNA content which is considered to be a marker of apoptotic cell death. Apoptosis was also confirmed by annexin V/PI double staining, DNA fragmentation assay and chromatin condensation assay. The apoptosis was associated with the loss of mitochondrial membrane potential (MMP), caspase-3 activation as well as intracellular reactive oxygen species (ROS) production. Moreover, the antioxidant Trolox blocked ROS production, changes in MMP and decreased K1 cytotoxicity, which confirmed the important role of ROS in cell apoptosis. Taken together, our data demonstrate that K1 induces ROS-dependent apoptosis in Caco2 cells and provide the rationale for further in vivo anticancer investigation. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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1167 KiB  
Article
Transcriptional Responses of the Bdtf1-Deletion Mutant to the Phytoalexin Brassinin in the Necrotrophic Fungus Alternaria brassicicola
by Yangrae Cho, Robin A. Ohm, Rakshit Devappa, Hyang Burm Lee, Igor V. Grigoriev, Bo Yeon Kim and Jong Seog Ahn
Molecules 2014, 19(8), 10717-10732; https://doi.org/10.3390/molecules190810717 - 24 Jul 2014
Cited by 11 | Viewed by 5664
Abstract
Brassica species produce the antifungal indolyl compounds brassinin and its derivatives, during microbial infection. The fungal pathogen Alternaria brassicicola detoxifies brassinin and possibly its derivatives. This ability is an important property for the successful infection of brassicaceous plants. Previously, we identified a transcription [...] Read more.
Brassica species produce the antifungal indolyl compounds brassinin and its derivatives, during microbial infection. The fungal pathogen Alternaria brassicicola detoxifies brassinin and possibly its derivatives. This ability is an important property for the successful infection of brassicaceous plants. Previously, we identified a transcription factor, Bdtf1, essential for the detoxification of brassinin and full virulence. To discover genes that encode putative brassinin-digesting enzymes, we compared gene expression profiles between a mutant strain of the transcription factor and wild-type A. brassicicola under two different experimental conditions. A total of 170 and 388 genes were expressed at higher levels in the mutants than the wild type during the infection of host plants and saprophytic growth in the presence of brassinin, respectively. In contrast, 93 and 560 genes were expressed, respectively, at lower levels in the mutant than the wild type under the two conditions. Fifteen of these genes were expressed at lower levels in the mutant than in the wild type under both conditions. These genes were assumed to be important for the detoxification of brassinin and included Bdtf1 and 10 putative enzymes. This list of genes provides a resource for the discovery of enzyme-coding genes important in the chemical modification of brassinin. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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739 KiB  
Article
MALDI Mass Spectrometry Imaging for the Simultaneous Location of Resveratrol, Pterostilbene and Viniferins on Grapevine Leaves
by Loïc Becker, Vincent Carré, Anne Poutaraud, Didier Merdinoglu and Patrick Chaimbault
Molecules 2014, 19(7), 10587-10600; https://doi.org/10.3390/molecules190710587 - 21 Jul 2014
Cited by 36 | Viewed by 14092
Abstract
To investigate the in-situ response to a stress, grapevine leaves have been subjected to mass spectrometry imaging (MSI) experiments. The Matrix Assisted Laser Desorption/Ionisation (MALDI) approach using different matrices has been evaluated. Among all the tested matrices, the 2,5-dihydroxybenzoic acid (DHB) was found [...] Read more.
To investigate the in-situ response to a stress, grapevine leaves have been subjected to mass spectrometry imaging (MSI) experiments. The Matrix Assisted Laser Desorption/Ionisation (MALDI) approach using different matrices has been evaluated. Among all the tested matrices, the 2,5-dihydroxybenzoic acid (DHB) was found to be the most efficient matrix allowing a broader range of detected stilbene phytoalexins. Resveratrol, but also more toxic compounds against fungi such as pterostilbene and viniferins, were identified and mapped. Their spatial distributions on grapevine leaves irradiated by UV show their specific colocation around the veins. Moreover, MALDI MSI reveals that resveratrol (and piceids) and viniferins are not specifically located on the same area when leaves are infected by Plasmopara viticola. Results obtained by MALDI mass spectrometry imaging demonstrate that this technique would be essential to improve the level of knowledge concerning the role of the stilbene phytoalexins involved in a stress event. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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552 KiB  
Article
Inhibition of Cancer Derived Cell Lines Proliferation by Synthesized Hydroxylated Stilbenes and New Ferrocenyl-Stilbene Analogs. Comparison with Resveratrol
by Malik Chalal, Dominique Delmas, Philippe Meunier, Norbert Latruffe and Dominique Vervandier-Fasseur
Molecules 2014, 19(6), 7850-7868; https://doi.org/10.3390/molecules19067850 - 11 Jun 2014
Cited by 25 | Viewed by 7377
Abstract
Further advances in understanding the mechanism of action of resveratrol and its application require new analogs to identify the structural determinants for the cell proliferation inhibition potency. Therefore, we synthesized new trans-resveratrol derivatives by using the Wittig and Heck methods, thus modifying [...] Read more.
Further advances in understanding the mechanism of action of resveratrol and its application require new analogs to identify the structural determinants for the cell proliferation inhibition potency. Therefore, we synthesized new trans-resveratrol derivatives by using the Wittig and Heck methods, thus modifying the hydroxylation and methoxylation patterns of the parent molecule. Moreover, we also synthesized new ferrocenylstilbene analogs by using an original protective group in the Wittig procedure. By performing cell proliferation assays we observed that the resveratrol derivatives show inhibition on the human colorectal tumor SW480 cell line. On the other hand, cell viability/cytotoxicity assays showed a weaker effects on the human hepatoblastoma HepG2 cell line. Importantly, the lack of effect on non-tumor cells (IEC18 intestinal epithelium cells) demonstrates the selectivity of these molecules for cancer cells. Here, we show that the numbers and positions of hydroxy and methoxy groups are crucial for the inhibition efficacy. In addition, the presence of at least one phenolic group is essential for the antitumoral activity. Moreover, in the series of ferrocenylstilbene analogs, the presence of a hidden phenolic function allows for a better solubilization in the cellular environment and significantly increases the antitumoral activity. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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519 KiB  
Article
Antimicrobial Activity of Resveratrol Analogues
by Malik Chalal, Agnès Klinguer, Abdelwahad Echairi, Philippe Meunier, Dominique Vervandier-Fasseur and Marielle Adrian
Molecules 2014, 19(6), 7679-7688; https://doi.org/10.3390/molecules19067679 - 10 Jun 2014
Cited by 63 | Viewed by 10070
Abstract
Stilbenes, especially resveratrol and its derivatives, have become famous for their positive effects on a wide range of medical disorders, as indicated by a huge number of published studies. A less investigated area of research is their antimicrobial properties. A series of 13 [...] Read more.
Stilbenes, especially resveratrol and its derivatives, have become famous for their positive effects on a wide range of medical disorders, as indicated by a huge number of published studies. A less investigated area of research is their antimicrobial properties. A series of 13 trans-resveratrol analogues was synthesized via Wittig or Heck reactions, and their antimicrobial activity assessed on two different grapevine pathogens responsible for severe diseases in the vineyard. The entire series, together with resveratrol, was first evaluated on the zoospore mobility and sporulation level of Plasmopara viticola (the oomycete responsible for downy mildew). Stilbenes displayed a spectrum of activity ranging from low to high. Six of them, including the most active ones, were subsequently tested on the development of Botrytis cinerea (fungus responsible for grey mold). The results obtained allowed us to identify the most active stilbenes against both grapevine pathogens, to compare the antimicrobial activity of the evaluated series of stilbenes, and to discuss the relationship between their chemical structure (number and position of methoxy and hydroxy groups) and antimicrobial activity. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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458 KiB  
Article
Regulation of Plant Immunity through Modulation of Phytoalexin Synthesis
by Olga V. Zernova, Anatoli V. Lygin, Michelle L. Pawlowski, Curtis B. Hill, Glen L. Hartman, Jack M. Widholm and Vera V. Lozovaya
Molecules 2014, 19(6), 7480-7496; https://doi.org/10.3390/molecules19067480 - 06 Jun 2014
Cited by 27 | Viewed by 8410
Abstract
Soybean hairy roots transformed with the resveratrol synthase and resveratrol oxymethyl transferase genes driven by constitutive Arabidopsis actin and CsVMV promoters were characterized. Transformed hairy roots accumulated glycoside conjugates of the stilbenic compound resveratrol and the related compound pterostilbene, which are normally not [...] Read more.
Soybean hairy roots transformed with the resveratrol synthase and resveratrol oxymethyl transferase genes driven by constitutive Arabidopsis actin and CsVMV promoters were characterized. Transformed hairy roots accumulated glycoside conjugates of the stilbenic compound resveratrol and the related compound pterostilbene, which are normally not synthesized by soybean plants. Expression of the non-native stilbenic phytoalexin synthesis in soybean hairy roots increased their resistance to the soybean pathogen Rhizoctonia solani. The expression of the AhRS3 gene resulted in 20% to 50% decreased root necrosis compared to that of untransformed hairy roots. The expression of two genes, the AhRS3 and ROMT, required for pterostilbene synthesis in soybean, resulted in significantly lower root necrosis (ranging from 0% to 7%) in transgenic roots than in untransformed hairy roots that had about 84% necrosis. Overexpression of the soybean prenyltransferase (dimethylallyltransferase) G4DT gene in soybean hairy roots increased accumulation of the native phytoalexin glyceollin resulting in decreased root necrosis. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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2117 KiB  
Article
Camalexin-Induced Apoptosis in Prostate Cancer Cells Involves Alterations of Expression and Activity of Lysosomal Protease Cathepsin D
by Basil Smith, Diandra Randle, Roman Mezencev, LeeShawn Thomas, Cimona Hinton and Valerie Odero-Marah
Molecules 2014, 19(4), 3988-4005; https://doi.org/10.3390/molecules19043988 - 02 Apr 2014
Cited by 18 | Viewed by 7991
Abstract
Camalexin, the phytoalexin produced in the model plant Arabidopsis thaliana, possesses antiproliferative and cancer chemopreventive effects. We have demonstrated that the cytostatic/cytotoxic effects of camalexin on several prostate cancer (PCa) cells are due to oxidative stress. Lysosomes are vulnerable organelles to Reactive [...] Read more.
Camalexin, the phytoalexin produced in the model plant Arabidopsis thaliana, possesses antiproliferative and cancer chemopreventive effects. We have demonstrated that the cytostatic/cytotoxic effects of camalexin on several prostate cancer (PCa) cells are due to oxidative stress. Lysosomes are vulnerable organelles to Reactive Oxygen Species (ROS)-induced injuries, with the potential to initiate and or facilitate apoptosis subsequent to release of proteases such as cathepsin D (CD) into the cytosol. We therefore hypothesized that camalexin reduces cell viability in PCa cells via alterations in expression and activity of CD. Cell viability was evaluated by MTS cell proliferation assay in LNCaP and ARCaP Epithelial (E) cells, and their respective aggressive sublines C4-2 and ARCaP Mesenchymal (M) cells, whereby the more aggressive PCa cells (C4-2 and ARCaPM) displayed greater sensitivity to camalexin treatments than the lesser aggressive cells (LNCaP and ARCaPE). Immunocytochemical analysis revealed CD relocalization from the lysosome to the cytosol subsequent to camalexin treatments, which was associated with increased protein expression of mature CD; p53, a transcriptional activator of CD; BAX, a downstream effector of CD, and cleaved PARP, a hallmark for apoptosis. Therefore, camalexin reduces cell viability via CD and may present as a novel therapeutic agent for treatment of metastatic prostate cancer cells. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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Review

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304 KiB  
Review
Deciphering the Role of Phytoalexins in Plant-Microorganism Interactions and Human Health
by Philippe Jeandet, Claire Hébrard, Marie-Alice Deville, Sylvain Cordelier, Stéphan Dorey, Aziz Aziz and Jérôme Crouzet
Molecules 2014, 19(11), 18033-18056; https://doi.org/10.3390/molecules191118033 - 05 Nov 2014
Cited by 148 | Viewed by 13355
Abstract
Phytoalexins are low molecular weight antimicrobial compounds that are produced by plants as a response to biotic and abiotic stresses. As such they take part in an intricate defense system which enables plants to control invading microorganisms. In this review we present the [...] Read more.
Phytoalexins are low molecular weight antimicrobial compounds that are produced by plants as a response to biotic and abiotic stresses. As such they take part in an intricate defense system which enables plants to control invading microorganisms. In this review we present the key features of this diverse group of molecules, namely their chemical structures, biosynthesis, regulatory mechanisms, biological activities, metabolism and molecular engineering. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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475 KiB  
Review
Maslinic Acid, a Natural Phytoalexin-Type Triterpene from Olives — A Promising Nutraceutical?
by Glòria Lozano-Mena, Marta Sánchez-González, M. Emília Juan and Joana M. Planas
Molecules 2014, 19(8), 11538-11559; https://doi.org/10.3390/molecules190811538 - 04 Aug 2014
Cited by 109 | Viewed by 12751
Abstract
Maslinic acid is a pentacyclic triterpene found in a variety of natural sources, ranging from herbal remedies used in traditional Asian medicine to edible vegetables and fruits present in the Mediterranean diet. In recent years, several studies have proved that maslinic acid exerts [...] Read more.
Maslinic acid is a pentacyclic triterpene found in a variety of natural sources, ranging from herbal remedies used in traditional Asian medicine to edible vegetables and fruits present in the Mediterranean diet. In recent years, several studies have proved that maslinic acid exerts a wide range of biological activities, i.e. antitumor, antidiabetic, antioxidant, cardioprotective, neuroprotective, antiparasitic and growth-stimulating. Experimental models used for the assessment of maslinic acid effects include established cell lines, which have been often used to elucidate the underlying mechanisms of action, and also animal models of different disorders, which have confirmed the effects of the triterpene in vivo. Overall, and supported by the lack of adverse effects in mice, the results provide evidence of the potential of maslinic acid as a nutraceutical, not only for health promotion, but also as a therapeutic adjuvant in the treatment of several disorders. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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1077 KiB  
Review
Red Card for Pathogens: Phytoalexins in Sorghum and Maize
by Alana Poloni and Jan Schirawski
Molecules 2014, 19(7), 9114-9133; https://doi.org/10.3390/molecules19079114 - 30 Jun 2014
Cited by 43 | Viewed by 10447
Abstract
Cereal crop plants such as maize and sorghum are constantly being attacked by a great variety of pathogens that cause large economic losses. Plants protect themselves against pathogens by synthesizing antimicrobial compounds, which include phytoalexins. In this review we summarize the current knowledge [...] Read more.
Cereal crop plants such as maize and sorghum are constantly being attacked by a great variety of pathogens that cause large economic losses. Plants protect themselves against pathogens by synthesizing antimicrobial compounds, which include phytoalexins. In this review we summarize the current knowledge on phytoalexins produced by sorghum (luteolinidin, apigeninidin) and maize (zealexin, kauralexin, DIMBOA and HDMBOA). For these molecules, we highlight biosynthetic pathways, known intermediates, proposed enzymes, and mechanisms of elicitation. Finally, we discuss the involvement of phytoalexins in plant resistance and their possible application in technology, medicine and agriculture. For those whose world is round we tried to set the scene in the context of a hypothetical football game in which pathogens fight with phytoalexins on the different playing fields provided by maize and sorghum. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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250 KiB  
Review
Resveratrol and Calcium Signaling: Molecular Mechanisms and Clinical Relevance
by Audrey E. McCalley, Simon Kaja, Andrew J. Payne and Peter Koulen
Molecules 2014, 19(6), 7327-7340; https://doi.org/10.3390/molecules19067327 - 05 Jun 2014
Cited by 57 | Viewed by 9854
Abstract
Resveratrol is a naturally occurring compound contributing to cellular defense mechanisms in plants. Its use as a nutritional component and/or supplement in a number of diseases, disorders, and syndromes such as chronic diseases of the central nervous system, cancer, inflammatory diseases, diabetes, and [...] Read more.
Resveratrol is a naturally occurring compound contributing to cellular defense mechanisms in plants. Its use as a nutritional component and/or supplement in a number of diseases, disorders, and syndromes such as chronic diseases of the central nervous system, cancer, inflammatory diseases, diabetes, and cardiovascular diseases has prompted great interest in the underlying molecular mechanisms of action. The present review focuses on resveratrol, specifically its isomer trans-resveratrol, and its effects on intracellular calcium signaling mechanisms. As resveratrol’s mechanisms of action are likely pleiotropic, its effects and interactions with key signaling proteins controlling cellular calcium homeostasis are reviewed and discussed. The clinical relevance of resveratrol’s actions on excitable cells, transformed or cancer cells, immune cells and retinal pigment epithelial cells are contrasted with a review of the molecular mechanisms affecting calcium signaling proteins on the plasma membrane, cytoplasm, endoplasmic reticulum, and mitochondria. The present review emphasizes the correlation between molecular mechanisms of action that have recently been identified for resveratrol and their clinical implications. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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541 KiB  
Review
Natural Products from the Genus Tephrosia
by Yinning Chen, Tao Yan, Chenghai Gao, Wenhao Cao and Riming Huang
Molecules 2014, 19(2), 1432-1458; https://doi.org/10.3390/molecules19021432 - 27 Jan 2014
Cited by 42 | Viewed by 10517
Abstract
The genus Tephrosia, belonging to the Leguminosae family, is a large pantropical genus of more than 350 species, many of which have important traditional uses in agriculture. This review not only outlines the source, chemistry and biological evaluations of natural products from [...] Read more.
The genus Tephrosia, belonging to the Leguminosae family, is a large pantropical genus of more than 350 species, many of which have important traditional uses in agriculture. This review not only outlines the source, chemistry and biological evaluations of natural products from the genus Tephrosia worldwide that have appeared in literature from 1910 to December 2013, but also covers work related to proposed biosynthetic pathways and synthesis of some natural products from the genus Tephrosia, with 105 citations and 168 new compounds. Full article
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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