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Glycoalkaloids

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https://www.readbyqxmd.com/read/28979674/solasonine-inhibits-glioma-growth-through-anti-inflammatory-pathways
#1
Xun Wang, Shuang Zou, Yu-Long Lan, Jin-Shan Xing, Xiao-Qiang Lan, Bo Zhang
The global burden of malignant glioma is expected to increase and new therapy approaches are urgently required. Solasonine is a natural glycoalkaloid compound that has been used in cancer treatment for many years; however the precise mechanisms are poorly understood. Here we seek to explore the potential roles of solasonine in glioma that could add to the development of newer therapeutic approaches for the treatment of malignant glioma. Cell proliferation of glioma cells was determined by MTT assay, and the biological functions of solasonine were investigated by migration, colony formation, apoptosis assays and cell cycle analysis in glioma cells...
2017: American Journal of Translational Research
https://www.readbyqxmd.com/read/28867954/evaluation-of-solasonine-content-and-expression-patterns-%C3%A2-of-sgt1-gene-in-different-tissues-of-two-iranian-eggplant-solanum-melongena-l-genotypes
#2
Mahmoud Bagheri, Ali Akbar Shahnejat Bushehri, Mohammad Reza Hassandokht, Mohammad Reza Naghavi
Eggplant (Solanum melongena L.) is one of the most consumed vegetables in the world. The eggplant glycoalkaloids (GAs) are toxic secondary metabolites that may have detrimental effects on human health, particularly if the magnitudes of GAs are higher than the recommended food safety level (200 mg per kg of fresh mass). In this study, the content of solasonine compound and the expression patterns of solasodine galactosyltransferase (SGT1) gene were assessed in different tissues (mature leaves, flower buds, young, mature, and physiologically ripe fruits) of two Iranian eggplant genotypes (D1 and J10) under field conditions...
June 2017: Food Technology and Biotechnology
https://www.readbyqxmd.com/read/28838234/structural-characterization-of-intact-glycoconjugates-by-tandem-mass-spectrometry-using-electron-induced-dissociation
#3
Y L Elaine Wong, Xiangfeng Chen, Ri Wu, Y L Winnie Hung, T-W Dominic Chan
Characterizing the structures of glycoconjungates is important because of glycan heterogeneity and structural complexity of aglycon. The presence of relatively weak glycosidic linkages leads to preferential cleavages that limit the acquisition of structural information under typical mass spectrometry dissociation conditions, such as collision-induced dissociation (CID) and infrared multiphoton dissociation. In this paper, we explored the dissociation behaviors of different members of glycoconjugates, including glycopeptides, glycoalkaloids, and glycolipids, under electron-induced dissociation (EID) conditions...
September 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28828630/lanosterol-synthase-like-is-involved-with-differential-accumulation-of-steroidal-glycoalkaloids-in-potato
#4
Akhilesh Kumar, Edna Fogelman, Mira Weissberg, Zachariah Tanami, Richard E Veilleux, Idit Ginzberg
Phytosterol homeostasis may be maintained in leaves through diversion of intermediates into glycoalkaloid biosynthesis, whereas in tuber flesh, excess intermediates are catalyzed by tuber-specific StLAS - like , resulting in low tuber glycoalkaloids. Lanosterol synthase (LAS) and cycloartenol synthase (CAS) are phylogenetically related enzymes. Cycloartenol is the accepted precursor leading to cholesterol and phytosterols, and in potato, to steroidal glycoalkaloid (SGA) biosynthesis. LAS was also shown to synthesize some plant sterols, albeit at trace amounts, questioning its role in sterol homeostasis...
December 2017: Planta
https://www.readbyqxmd.com/read/28795489/plasma-metabolomics-reveals-steroidal-alkaloids-as-novel-biomarkers-of-tomato-intake-in-mice
#5
Morgan J Cichon, Ken M Riedl, Lei Wan, Jennifer M Thomas-Ahner, David M Francis, Steven K Clinton, Steven J Schwartz
SCOPE: Diets rich in tomato products are associated with a reduced risk of various chronic disease processes. The carotenoid lycopene is most intensely studied as the bioactive mediating health effects, yet tomatoes contain an array of phytochemicals. We conducted an untargeted metabolomics study on blood plasma to identify novel markers of tomato consumption absorbed from the diet and released into the bloodstream in mice. METHODS AND RESULTS: Male mice were fed a control AIN-93G diet or the same diet supplemented with 0...
August 9, 2017: Molecular Nutrition & Food Research
https://www.readbyqxmd.com/read/28754839/a-dioxygenase-catalyzes-steroid-16%C3%AE-hydroxylation-in-steroidal-glycoalkaloid-biosynthesis
#6
Masaru Nakayasu, Naoyuki Umemoto, Kiyoshi Ohyama, Yoshinori Fujimoto, Hyoung Jae Lee, Bunta Watanabe, Toshiya Muranaka, Kazuki Saito, Yukihiro Sugimoto, Masaharu Mizutani
Steroidal glycoalkaloids (SGAs) are toxic specialized metabolites that are found in the Solanaceae. Potato (Solanum tuberosum) contains the SGAs α-solanine and α-chaconine, while tomato (Solanum lycopersicum) contains α-tomatine, all of which are biosynthesized from cholesterol. However, although two cytochrome P450 monooxygenases that catalyze the 22- and 26-hydroxylation of cholesterol have been identified, the 16-hydroxylase remains unknown. Feeding with deuterium-labeled cholesterol indicated that the 16α- and 16β-hydrogen atoms of cholesterol were eliminated to form α-solanine and α-chaconine in potato, while only the 16α-hydrogen atom was eliminated in α-tomatine biosynthesis, suggesting that a single oxidation at C-16 takes place during tomato SGA biosynthesis while a two-step oxidation occurs in potato...
September 2017: Plant Physiology
https://www.readbyqxmd.com/read/28704260/%C3%AE-solanine-reverses-pulmonary-vascular-remodeling-and-vascular-angiogenesis-in-experimental-pulmonary-artery-hypertension
#7
Xiaowei Nie, Youai Dai, Jianxin Tan, Yuan Chen, Guowei Qin, Wenjun Mao, Jian Zou, Yanhua Chang, Qian Wang, Jingyu Chen
OBJECTIVE: Similar to cancer, pulmonary arterial hypertension (PAH) is characterized by vascular remodeling, which leads to obliteration of the small pulmonary arteriole, with marked proliferation of pulmonary artery smooth muscle cells (PASMC) and/or endothelial cells dysfunction. Aberrant expression of tumor suppressor genes is closely associated with susceptibility to PAH. We hypothesized that α-solanine, a glycoalkaloid found in members of the nightshade family known to have antitumor activity in different cancers, reverses experimental PAH by activating the tumor suppressor-axis inhibition protein 2 (AXIN2)...
July 12, 2017: Journal of Hypertension
https://www.readbyqxmd.com/read/28698610/tomatoes-protect-against-development-of-uv-induced-keratinocyte-carcinoma-via-metabolomic-alterations
#8
Jessica L Cooperstone, Kathleen L Tober, Ken M Riedl, Matthew D Teegarden, Morgan J Cichon, David M Francis, Steven J Schwartz, Tatiana M Oberyszyn
Prolonged tomato consumption can mitigate ultraviolet (UV) light induced sunburn via unknown mechanisms. Dietary carotenoids distributed to skin are hypothesized to protect skin against UV-induced damage, although other phytochemicals may play a role. We hypothesize that tomato consumption would protect against skin cancer. SKH-1 hairless and immunocompetent mice (n = 180) were fed AIN-93G or AIN-93G + 10% tangerine or red tomato powder for 35 weeks. From weeks 11-20, mice (n = 120) were exposed to 2240 J/m(2) UV-B light, 3x/week, and tumors were tracked weekly...
July 11, 2017: Scientific Reports
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
#9
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...
August 2017: Food and Chemical Toxicology
https://www.readbyqxmd.com/read/28554842/jasmonate-induced-biosynthesis-of-steroidal-glycoalkaloids-depends-on-coi1-proteins-in-tomato
#10
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...
July 22, 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
#11
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
#12
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
#13
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
#14
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
#15
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
#16
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
#17
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
#18
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
#19
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
#20
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
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