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Glycoalkaloids

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https://www.readbyqxmd.com/read/28576466/are-additive-effects-of-dietary-surfactants-on-intestinal-tight-junction-integrity-an-overlooked-human-health-risk-a-mixture-study-on-caco-2-monolayers
#1
Anders Glynn, Annachiara Malin Igra, Salomon Sand, Nils Gunnar Ilbäck, Karl Erik Hellenäs, Johan Rosén, Bitte Aspenström-Fagerlund
Surfactants may cause dysfunction of intestinal tight junctions (TJs), which is a common feature of intestinal autoimmune diseases. Effects of dietary surfactants on TJ integrity, measured as trans-epithelial resistance (TEER), were studied in Caco-2 cell monolayers. Cytotoxicity was assessed as apical LDH leakage. Monolayers were apically exposed for 60 min to the dietary surfactants solanine and chaconine (SC, potato glycoalkaloids, 0-0.25 mM), perfluorooctane sulfonic acid (PFOS, industrial contaminant, 0-0...
May 30, 2017: Food and Chemical Toxicology
https://www.readbyqxmd.com/read/28554842/jasmonate-induced-biosynthesis-of-steroidal-glycoalkaloids-depends-on-coi1-proteins-in-tomato
#2
Ayman Abdelkareem, Chonprakun Thagun, Masaru Nakayasu, Masaharu Mizutani, Takashi Hashimoto, Tsubasa Shoji
In tomato, perception of jasmonates by a receptor complex, which includes the F-box protein CORONATINE INSENSITIVE 1 (COI1), elicits biosynthesis of defensive steroidal glycoalkaloids (SGAs) via a jasmonate-responsive ERF transcription factor, JRE4/GAME9. Although JRE4 is upregulated by jasmonate and induces the expression of many metabolic genes involved in SGA biosynthesis, it is not known whether JRE4 alone is sufficient for increased SGA biosynthesis upon activation of jasmonate signaling. Here, we show that application of methyl jasmonate induces the expression of JRE4 and SGA biosynthesis genes in leaves and hairy roots of wild-type tomato, but not in jasmonic acid insensitive 1 (jai1), a loss-of-function mutant allele of the tomato COI1 gene...
May 26, 2017: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/28510502/the-impact-of-steroidal-glycoalkaloids-on-the-physiology-of-phytophthora-infestans-the-causative-agent-of-potato-late-blight
#3
Paul Dahlin, Marion C Müller, Sophia Ekengren, Lauren S McKee, Vincent Bulone
Steroidal glycoalkaloids (SGAs) are plant secondary metabolites known to be toxic to animals and humans and that have putative roles in defense against pests. The proposed mechanisms of SGA toxicity are sterol-mediated disruption of membranes and inhibition of cholinesterase activity in neurons. It has been suggested that phytopathogenic microorganisms can overcome SGA toxicity by enzymatic deglycosylation of SGAs. Here, we have explored SGA-mediated toxicity toward the invasive oomycete Phytophthora infestans, the causative agent of the late blight disease in potato and tomato, as well as the potential for SGA deglycosylation by this species...
July 2017: Molecular Plant-microbe Interactions: MPMI
https://www.readbyqxmd.com/read/28283413/solasodine-inhibits-invasion-of-human-lung-cancer-cell-through-downregulation-of-mir-21-and-mmps-expression
#4
Kun-Hung Shen, Jui-Hsiang Hung, Chia-Wei Chang, Yu-Ting Weng, Ming-Jiuan Wu, Pin-Shern Chen
Solasodine, a naturally occurring aglycone of glycoalkaloid in eggplant (Solanum melongena), was found to inhibit proliferation in various tumor cells. However, the effect of solasodine on cancer cell metastasis remains unclear. This study investigates the suppression mechanism of solasodine on motility of human lung cancer cell A549 in vitro. Results show that solasodine reduces viability of A549 cells. Treatment with non-toxic doses of solasodine suppresses markedly cell invasion. Solasodine reduces the mRNA level of matrix metalloproteinase-2 (MMP-2), MMP-9 and extracellular inducer of matrix metalloproteinase (EMMPRIN), but increases the expression of reversion-inducing cysteine-rich protein with kazal motifs (RECK), as well as tissue inhibitor of metalloproteinase-1 (TIMP-1) and TIMP-2...
April 25, 2017: Chemico-biological Interactions
https://www.readbyqxmd.com/read/28256633/transcript-profiling-of-two-potato-cultivars-during-glycoalkaloid-inducing-treatments-shows-differential-expression-of-genes-in-sterol-and-glycoalkaloid-metabolism
#5
Nurun Nahar, Erik Westerberg, Usman Arif, Alexandre Huchelmann, Alexandra Olarte Guasca, Lisa Beste, Kerstin Dalman, Paresh C Dutta, Lisbeth Jonsson, Folke Sitbon
Steroidal glycoalkaloids (SGA) are sterol-derived neurotoxic defence substances present in several members of the Solanaceae. In the potato (Solanum tuberosum), high SGA levels may render tubers harmful for consumption. Tuber SGA levels depend on genetic factors, and can increase as a response to certain stresses and environmental conditions. To identify genes underlying the cultivar variation in tuber SGA levels, we investigated two potato cultivars differing in their SGA accumulation during wounding or light exposure; two known SGA-inducing treatments...
March 3, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28215419/comparative-metabolite-and-genome-analysis-of-tuber-bearing-potato-species
#6
Riccardo Aversano, Felice Contaldi, Maria Grazia Adelfi, Vincenzo D'Amelia, Gianfranco Diretto, Nunziatina De Tommasi, Carmen Vaccaro, Antonio Vassallo, Domenico Carputo
The cultivated potato Solanum tuberosum is unrivalled among crop plants for its wild relatives, which potentially represent an important source of genetic diversity to improve the nutritional value of potato varieties and understand metabolism regulation. The main aim of this research was to profile human health-related metabolites in a number of clones from 13 Solanum species. Results from HPLC-DAD and LC-ESI-MS analyses highlighted a high interspecific variability in the level of metabolites analysed. Ascorbic acid was confirmed to be the most abundant antioxidant in potato and chlorogenic acid the primary polyphenol...
May 2017: Phytochemistry
https://www.readbyqxmd.com/read/28005066/plant-cholesterol-biosynthetic-pathway-overlaps-with-phytosterol-metabolism
#7
Prashant D Sonawane, Jacob Pollier, Sayantan Panda, Jedrzej Szymanski, Hassan Massalha, Meital Yona, Tamar Unger, Sergey Malitsky, Philipp Arendt, Laurens Pauwels, Efrat Almekias-Siegl, Ilana Rogachev, Sagit Meir, Pablo D Cárdenas, Athar Masri, Marina Petrikov, Hubert Schaller, Arthur A Schaffer, Avinash Kamble, Ashok P Giri, Alain Goossens, Asaph Aharoni
The amount of cholesterol made by many plants is not negligible. Whereas cholesterogenesis in animals was elucidated decades ago, the plant pathway has remained enigmatic. Among other roles, cholesterol is a key precursor for thousands of bioactive plant metabolites, including the well-known Solanum steroidal glycoalkaloids. Integrating tomato transcript and protein co-expression data revealed candidate genes putatively associated with cholesterol biosynthesis. A combination of functional assays including gene silencing, examination of recombinant enzyme activity and yeast mutant complementation suggests the cholesterol pathway comprises 12 enzymes acting in 10 steps...
December 22, 2016: Nature Plants
https://www.readbyqxmd.com/read/27934291/antiprotozoal-effects-of-the-tomato-tetrasaccharide-glycoalkaloid-tomatine-and-the-aglycone-tomatidine-on-mucosal-trichomonads
#8
Jenny Liu, Sierra Kanetake, Yun-Hsuan Wu, Christina Tam, Luisa W Cheng, Kirkwood M Land, Mendel Friedman
The present study investigated the inhibitory effects of the commercial tetrasaccharide tomato glycoalkaloid tomatine and the aglycone tomatidine on three mucosal pathogenic protozoa that are reported to infect humans, cattle, and cats, respectively: Trichomonas vaginalis strain G3, Tritrichomonas foetus strain D1, and Tritrichomonas foetus strain C1. A preliminary screen showed that tomatine at 100 μM concentration completely inhibited the growth of all three trichomonads. In contrast, the inhibition of all three pathogens by tomatidine was much lower, suggesting the involvement of the lycotetraose carbohydrate side chain in the mechanism of inhibition...
November 23, 2016: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/27933363/spatially-resolved-metabolic-distribution-for-unraveling-the-physiological-change-and-responses-in-tomato-fruit-using-matrix-assisted-laser-desorption-ionization-mass-spectrometry-imaging-maldi-msi
#9
Junya Nakamura, Tomomi Morikawa-Ichinose, Yoshinori Fujimura, Eisuke Hayakawa, Katsutoshi Takahashi, Takanori Ishii, Daisuke Miura, Hiroyuki Wariishi
Information on spatiotemporal metabolic behavior is indispensable for a precise understanding of physiological changes and responses, including those of ripening processes and wounding stress, in fruit, but such information is still limited. Here, we visualized the spatial distribution of metabolites within tissue sections of tomato (Solanum lycopersicum L.) fruit using a matrix-assisted laser desorption/ionization-mass spectrometry imaging (MALDI-MSI) technique combined with a matrix sublimation/recrystallization method...
February 2017: Analytical and Bioanalytical Chemistry
https://www.readbyqxmd.com/read/27889865/does-plant-cultivar-difference-modify-the-bottom-up-effects-of-resource-limitation-on-plant-insect-herbivore-interactions
#10
Peng Han, Nicolas Desneux, Thomas Michel, Jacques Le Bot, Aurelie Seassau, Eric Wajnberg, Edwige Amiens-Desneux, Anne-Violette Lavoir
Variation in resource input to plants triggers bottom-up effects on plant-insect herbivore interactions. However, variation in plant intrinsic traits in response to resource availability may modify the bottom-up effects. Furthermore, the consequences also may depend on the feeding strategy of insect herbivores belonging to different feeding guilds. We evaluated the performance of two insect herbivores from distinct feeding guilds, the leaf miner Tuta absoluta and the phloem feeder Bemisia tabaci. We offered the insects two tomato cultivars growing under optimal nitrogen input vs...
December 2016: Journal of Chemical Ecology
https://www.readbyqxmd.com/read/27862922/mismatch-repair-deficiency-increases-the-transfer-of-antibiosis-and-antixenosis-properties-against-colorado-potato-beetle-in-somatic-hybrids-of-solanum-tuberosum-s-chacoense
#11
Imola Molnár, Enikő Besenyei, Ramona Thieme, Thomas Thieme, Adriana Aurori, Andreea Baricz, Horia Leonard Banciu, Elena Rakosy-Tican
BACKGROUND: Colorado potato beetle (CPB) has become the biggest enemy of cultivated potato worldwide. One of the most effective sources of resistance to CPB is Solanum chacoense, an accession with a high leptine glycoalkaloid content. The aim of our study was to assay the repellence and toxicity of S. chacoense, its somatic hybrids (SHs) and their backcross progenies (BC1 ) with potato for CPB adults and larvae. Transgenic S. chacoense, deficient in DNA mismatch repair (MMR), was also used to produce SHs, in order to increase homeologous recombination and hence introgression of wild-species DNA into the potato gene pool...
November 8, 2016: Pest Management Science
https://www.readbyqxmd.com/read/27855898/isolation-and-chemoenzymatic-treatment-of-glycoalkaloids-from-green-sprouting-and-rotting-solanum-tuberosum-potatoes-for-solanidine-recovery
#12
Grokoré Yvonne Koffi, Magali Remaud-Simeon, Ahipo Edmond Due, Didier Combes
The estimation of glycoalkaloids in the flesh of different types of decayed potatoes was evaluated. The results showed that turned green and also sprouting or rotting potato flesh contain high amounts of toxic solanine and chaconine, exceeding by 2-5-fold the recommended limit, and ranging from 2578±86mg/kg to 5063±230mg/kg of dry weight potato flesh. For safety consideration, these decayed potatoes should be systematically set aside. To avoid a net economic loss and encourage the removal of this hazardous food, a recycling process was investigated to generate added-value compounds from the toxic glycoalkaloids...
April 1, 2017: Food Chemistry
https://www.readbyqxmd.com/read/27754442/solasonine-a-natural-glycoalkaloid-compound-inhibits-gli-mediated-transcriptional-activity
#13
Jun Yang, Wenjing Huang, Wenfu Tan
The major obstacle limiting the efficacy of current Smoothened (Smo) inhibitors is the primary and acquired resistance mainly caused by Smo mutations and Gli amplification. In this context, developing Hh inhibitors targeting Gli, the final effector of this signaling pathway, may combat the resistance. In this study we found that solasonine, a natural glycoalkaloid compound, significantly inhibited the hedgehog (Hh) pathway activity. Meanwhile, solasonine may obviously inhibit the alkaline phosphatase (ALP) activity in C3H10T1/2 cells, concomitantly with reductions of the mRNA expression of Gli1 and Ptch1...
October 14, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/27726305/inhibition-of-prostate-cancer-growth-by-solanine-requires-the-suppression-of-cell-cycle-proteins-and-the-activation-of-ros-p38-signaling-pathway
#14
Bin Pan, Weifeng Zhong, Zhihai Deng, Caiyong Lai, Jing Chu, Genlong Jiao, Junfeng Liu, Qizhao Zhou
Solanine, a naturally steroidal glycoalkaloid in nightshade (Solanum nigrum Linn.), can inhibit proliferation and induce apoptosis of tumor cells. However, the mechanism of solanine-suppressing prostate cancer cell growth remains to be elucidated. This study investigates the inhibition mechanism of solanine on cancer development in vivo and in cultured human prostate cancer cell DU145 in vitro. Results show that solanine injection significantly suppresses the tumor cell growth in xenograft athymic nude mice...
November 2016: Cancer Medicine
https://www.readbyqxmd.com/read/27679507/integrated-rna-seq-and-srna-seq-analysis-reveals-mirna-effects-on-secondary-metabolism-in-solanum-tuberosum-l
#15
Yan Qiao, Jinjin Zhang, Jinwen Zhang, Zhiwei Wang, An Ran, Haixia Guo, Di Wang, Junlian Zhang
Light is a major environmental factor that affects metabolic pathways and stimulates the production of secondary metabolites in potato. However, adaptive changes in potato metabolic pathways and physiological functions triggered by light are partly explained by gene expression changes. Regulation of secondary metabolic pathways in potato has been extensively studied at transcriptional level, but little is known about the mechanisms of post-transcriptional regulation by miRNAs. To identify light-responsive miRNAs/mRNAs and construct putative metabolism pathways regulated by the miRNA-mRNA pairs, an integrated omics (sRNAome and transcriptome) analysis was performed to potato under light stimulus...
February 2017: Molecular Genetics and Genomics: MGG
https://www.readbyqxmd.com/read/27619473/increased-water-salinity-applied-to-tomato-plants-accelerates-the-development-of-the-leaf-miner-tuta-absoluta-through-bottom-up-effects
#16
Peng Han, Zhi-Jian Wang, Anne-Violette Lavoir, Thomas Michel, Aurélie Seassau, Wen-Yan Zheng, Chang-Ying Niu, Nicolas Desneux
Variation in resource inputs to plants may trigger bottom-up effects on herbivorous insects. We examined the effects of water input: optimal water vs. limited water; water salinity: with vs. without addition of 100 mM NaCl; and their interactions on tomato plants (Solanum lycopersicum), and consequently, the bottom-up effects on the tomato leaf miner, Tuta absoluta (Meytick) (Lepidoptera: Gelechiidae). Plant growth was significantly impeded by limited water input and NaCl addition. In terms of leaf chemical defense, the production of tomatidine significantly increased with limited water and NaCl addition, and a similar but non-significant trend was observed for the other glycoalkaloids...
2016: Scientific Reports
https://www.readbyqxmd.com/read/27593526/fragmentation-study-of-major-spirosolane-type-glycoalkaloids-by-collision-induced-dissociation-linear-ion-trap-and-infrared-multiphoton-dissociation-fourier-transform-ion-cyclotron-resonance-mass-spectrometry
#17
F Lelario, C Labella, G Napolitano, L Scrano, S A Bufo
RATIONALE: Glycoalkaloids play a key role in the plant protection system against phytopathogens including fungi, viruses, bacteria, insects and worms. They can be toxic to humans if consumed in high concentrations causing gastrointestinal disturbances. METHODS: The structural characterization of the major spirosolane glycoalkaloids, solasonine, solamargine, α-tomatine and dehydrotomatine, were investigated by positive electrospray ionization (ESI) coupled with a hybrid linear ion trap (LIT) and Fourier transform ion cyclotron resonance (FTICR) mass spectrometer...
November 30, 2016: Rapid Communications in Mass Spectrometry: RCM
https://www.readbyqxmd.com/read/27588073/inhibitory-effect-of-%C3%AE-solanine-on-esophageal-carcinoma-in-vitro
#18
Lei Wang, Qian-Qian Sun, Shi-Jie Zhang, Yu-Wen Du, Yuan-Yuan Wang, Wen-Qiao Zang, Xiao-Nan Chen, Guo-Qiang Zhao
α-solanine, a bioactive component and one of the major steroidal glycoalkaloids in potatoes, has been observed to inhibit growth and induce apoptosis in cancer cells. However, the antitumor efficacy of α-solanine on esophageal carcinoma has yet to be fully elucidated. In the present study, the antitumor efficacy of α-solanine against human esophageal carcinoma cells was investigated. It was determined that α-solanine inhibited the growth and proliferation of human esophageal EC9706 and Eca109 cancer cells in a dose-dependent manner, as well as the cell migration and invasion...
September 2016: Experimental and Therapeutic Medicine
https://www.readbyqxmd.com/read/27536892/%C3%AE-solanine-modulates-the-radiosensitivity-of-esophageal-cancer-cells-by-inducing-microrna-138-expression
#19
Yuanyuan Wang, Jianbo Wu, Wei Guo, Qianqian Sun, Xiaonan Chen, Wenqiao Zang, Ziming Dong, Guoqiang Zhao
BACKGROUND: Esophageal cancer (EC) is one of the most common malignant tumors in the world. Due to difficulties with performing the operation, most patients choose to have palliative treatment instead. Radiotherapy is one of the main palliative treatments of EC. However, the clinical efficacy of radiotherapy is not satisfactory α-Solanine is a bioactive component of steroidal glycoalkaloids which has been demonstrated to exhibit anti-metastasis activity in different cancers. In the present study, we determined the effect of α-solanine on the radiosensitivity of EC cells and priliminarily explored the underlying molecular mechanisms...
2016: Cellular Physiology and Biochemistry
https://www.readbyqxmd.com/read/27318495/spiralosides-a-c-three-new-c27-steroidal-glycoalkaloids-from-the-fruits-of-solanum-spirale
#20
Dan Li, Yun-Li Zhao, Xu-Jie Qin, Lu Liu, Xing-Wei Yang, Ying-Ying Chen, Bei Wang, Xin Wei, Ya-Ping Liu, Xiao-Dong Luo
Three new C27-steroidal glycoalkaloids, spiralosides A-C (1-3), were obtained from the total alkaloids of Solanum spirale by chromatographic methods. On the basis of spectroscopic evidence, spiralosides A-C were elucidated as (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl (1), (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (2), (22R,25S)-22,26-epiminocholest-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (3), respectively...
August 2016: Natural Products and Bioprospecting
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