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1.
Int J Biol Macromol ; 242(Pt 1): 124682, 2023 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-37164133

RESUMO

Glycoalkaloids (GAs), including α-solanine and α-chaconine, are secondary metabolites found in potato, which are toxic to higher animals. In a previous study, Alkalihalobacillus clausii PA21 showed the capacity to degrade GAs. Herein, the transcriptome response of PA21 to α-solanine or α-chaconine was evaluated. In total, 3170 and 2783 differential expressed genes (DEGs) were found in α-solanine- and α-chaconine-treated groups, respectively, with most DEGs upregulated. Moreover, GAs activated transmembrane transport, carbohydrate metabolism, transcription, quorum sensing, and bacterial chemotaxis in PA21 to withstand GA-induced stress and promote GAs degradation. Furthermore, qRT-PCR analysis confirmed the upregulation of degrading enzymes and components involved in GA degradation in PA21. In addition, the GAs-degrading enzymes were heterologous expressed, purified, and incubated with GAs to analyze the degradation products. The results showed that α-solanine was degraded to ß1-solanine, ß2-solanine, γ-solanine, and solanidine by ß-glucosidase, α-rhamnosidase, and ß-galactosidase. Meanwhile, α-chaconine was degraded to ß1-chaconine, ß2-chaconine, γ-chaconine, and solanidine by ß-glucosidase and α-rhamnosidase. Overall, the molecular mechanism underlying GAs degradation by PA21 was revealed by RNAseq combined with protein expression and function studies, thus providing the basis for the development of engineered bacteria that can efficiently degrade GAs to promote their application in the control of GAs in potatoes.


Assuntos
Celulases , Solanina , Solanum tuberosum , Animais , Solanina/análise , Solanina/metabolismo , Solanina/farmacologia , Solanum tuberosum/genética , Solanum tuberosum/metabolismo , Bactérias/metabolismo , Perfilação da Expressão Gênica , Redes e Vias Metabólicas , Celulases/metabolismo
2.
Sci Rep ; 11(1): 20029, 2021 10 08.
Artigo em Inglês | MEDLINE | ID: mdl-34625595

RESUMO

Inhibiting sprouting of potatoes is an interesting subject needed for potato storage and industry. Sprouting degrades the quality of tuber along with releasing α-solanine and α-chaconine, which are harmful for health. Sprout suppressants, available in the market, are either costly or toxic to both health and environment. So, there is a need for developing countries to explore new sprouting suppressant compound which is cheap, non-toxic and reasonably efficient in comparison to commercial ones. We have established that simple maleic acid and L-tartaric acid are effective sprout suppressing agents. Both can hinder sprouting up to 6 weeks and 4 weeks post treatment respectively at room temperature in dark. These do not affect the quality parameters, retain the moisture content and maintain the stout appearance of the tubers along the total storage period. Thus maleic acid and L-tartaric acid would qualify as alternative, cheap, efficient sprout suppressant for potato storage and processing.


Assuntos
Armazenamento de Alimentos/métodos , Maleatos/farmacologia , Tubérculos/crescimento & desenvolvimento , Solanina/análogos & derivados , Solanum tuberosum/crescimento & desenvolvimento , Tartaratos/farmacologia , Tubérculos/efeitos dos fármacos , Tubérculos/metabolismo , Solanina/metabolismo , Solanum tuberosum/efeitos dos fármacos , Solanum tuberosum/metabolismo
3.
Plant J ; 108(1): 81-92, 2021 10.
Artigo em Inglês | MEDLINE | ID: mdl-34273198

RESUMO

Steroidal glycoalkaloids (SGAs) are toxic specialized metabolites found in members of the Solanaceae, such as Solanum tuberosum (potato) and Solanum lycopersicum (tomato). The major potato SGAs are α-solanine and α-chaconine, which are biosynthesized from cholesterol. Previously, we have characterized two cytochrome P450 monooxygenases and a 2-oxoglutarate-dependent dioxygenase that function in hydroxylation at the C-22, C-26 and C-16α positions, but the aminotransferase responsible for the introduction of a nitrogen moiety into the steroidal skeleton remains uncharacterized. Here, we show that PGA4 encoding a putative γ-aminobutyrate aminotransferase is involved in SGA biosynthesis in potatoes. The PGA4 transcript was expressed at high levels in tuber sprouts, in which SGAs are abundant. Silencing the PGA4 gene decreased potato SGA levels and instead caused the accumulation of furostanol saponins. Analysis of the tomato PGA4 ortholog, GAME12, essentially provided the same results. Recombinant PGA4 protein exhibited catalysis of transamination at the C-26 position of 22-hydroxy-26-oxocholesterol using γ-aminobutyric acid as an amino donor. Solanum stipuloideum (PI 498120), a tuber-bearing wild potato species lacking SGA, was found to have a defective PGA4 gene expressing the truncated transcripts, and transformation of PI 498120 with functional PGA4 resulted in the complementation of SGA production. These findings indicate that PGA4 is a key enzyme for transamination in SGA biosynthesis. The disruption of PGA4 function by genome editing will be a viable approach for accumulating valuable steroidal saponins in SGA-free potatoes.


Assuntos
4-Aminobutirato Transaminase/metabolismo , Solanina/análogos & derivados , Solanum tuberosum/genética , 4-Aminobutirato Transaminase/genética , Edição de Genes , Hidroxilação , Cetocolesteróis/biossíntese , Cetocolesteróis/química , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Tubérculos/enzimologia , Tubérculos/genética , Tubérculos/fisiologia , Saponinas/biossíntese , Saponinas/química , Solanina/química , Solanina/metabolismo , Solanum tuberosum/enzimologia , Solanum tuberosum/fisiologia
4.
Chemosphere ; 258: 127254, 2020 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-32559492

RESUMO

Glyphosate is the most used herbicide worldwide, targeting physiological pathways in plants. Recent studies have shown that glyphosate can also cause toxic effects in animals. We investigated the glyphosate-based herbicide (GBH)-induced changes in potato (Solanum tuberosum) plant chemistry and the effects of a GBH on the survival rate and oxidative status of the Colorado potato beetle (Leptinotarsa decemlineata). The beetles were reared on potato plants grown in pots containing soil treated with a GBH (Roundup Gold, 450 g/l) or untreated soil (water control). The 2nd instar larvae were introduced to the potato plants and then collected in 2 phases: as 4th instar larvae and as adults. The main glycoalkaloids of the potato plants, α-solanine and α-chaconine, were measured twice during the experiment. The α-solanine was reduced in potato plants grown in GBH-treated soil, which can be detrimental to plant defenses against herbivores. GBH treatment had no effect on the survival rate or body mass of the larvae or the adult beetles. In the larvae, total glutathione (tGSH) concentration and the enzyme activity of catalase (CAT), superoxide dismutase, and glutathione-S-transferase were increased in the GBH treatment group. In the adult beetles, CAT activity and tGSH levels were affected by the interactive effect of GBH treatment and the body mass. To conclude, environmentally relevant concentrations of a GBH can affect the potato plant's glycoalkaloid concentrations, but are not likely to directly affect the survival rate of the Colorado potato beetle, but instead, modify the antioxidant defense of the beetles via diet.


Assuntos
Besouros/efeitos dos fármacos , Glicina/análogos & derivados , Herbicidas/toxicidade , Estresse Oxidativo/efeitos dos fármacos , Solo/química , Solanum tuberosum/efeitos dos fármacos , Animais , Antioxidantes/metabolismo , Besouros/metabolismo , Glutationa Transferase/metabolismo , Glicina/toxicidade , Larva/efeitos dos fármacos , Larva/metabolismo , Oxirredução , Solanina/análogos & derivados , Solanina/metabolismo , Solanum tuberosum/crescimento & desenvolvimento , Solanum tuberosum/metabolismo
5.
J Agric Food Chem ; 68(5): 1390-1396, 2020 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-31935098

RESUMO

Potato juice is a byproduct of starch processing currently used as feed. However, potato proteins are an untapped source of high-protein food for human nutrition if harmful constituents notably glycoalkaloids (GAs) are detoxified. The two principle GAs found in potato are α-chaconine and α-solanine, both consisting of a solanidine aglycone with a carbohydrate side chain. The first step in the detoxification of these compounds is the removal of the trisaccharide. Whole-genome sequencing of a bacterial isolate, Arthrobacter sp. S41, capable of completely degrading α-chaconine and α-solanine, revealed the presence of a gene cluster possibly involved in the deglycosylation of GAs. Functional characterization confirmed the enzymatic activity of the gene cluster involved in the complete deglycosylation of both α-chaconine and α-solanine. The novel enzymes described here may find value in the bioconversion of feed proteins to food proteins suitable for human nutrition.


Assuntos
Arthrobacter/metabolismo , Proteínas de Bactérias/metabolismo , Família Multigênica , Solanina/análogos & derivados , Solanum tuberosum/toxicidade , Arthrobacter/classificação , Arthrobacter/enzimologia , Arthrobacter/genética , Proteínas de Bactérias/genética , Biotransformação , Glicosilação , Filogenia , Solanina/química , Solanina/metabolismo , Solanina/toxicidade , Solanum tuberosum/metabolismo
6.
Genes (Basel) ; 10(11)2019 11 11.
Artigo em Inglês | MEDLINE | ID: mdl-31718041

RESUMO

Steroidal glycoalkaloids (SGAs), which are widely produced by potato, even in other Solanaceae plants, are a class of potentially toxic compounds, but are beneficial to host resistance. However, changes of the other metabolic process along with SGA accumulation are still poorly understood and researched. Based on RNA sequencing (RNA-seq) and bioinformatics analysis, the global gene expression profiles of potato variety Helan 15 (Favorita) was investigated at four-time points during light exposure. The data was further verified by using quantitative Real-time PCR (qRT-PCR). When compared to the control group, 1288, 1592, 1737, and 1870 differentially expressed genes (DEGs) were detected at 6 h, 24 h, 48 h, and 8 d, respectively. The results of both RNAseq and qRT-PCR showed that SGA biosynthetic genes were up-regulated in the potato tuber under light exposure. Functional enrichment analysis revealed that genes related to PS light reaction and Protein degradation were significantly enriched in most time points of light exposure. Additionally, enriched Bins included Receptor kinases, Secondary metabolic process in flavonoids, Abiotic stress, and Biotic stress in the early stage of light exposure, but PS Calvin cycle, RNA regulation of transcription, and UDP glucosyl and glucoronyl transferases in the later stage. Most of the DEGs involved in PS light reaction and Abiotic stress were up-regulated at all four time points, whereas DEGs that participated in biotic stresses were mainly up-regulated at the later stage (48 h and 8 d). Cis-element prediction and co-expression assay were used to confirm the expressional correlation between genes that are responsible for SGA biosynthesis and disease resistance. In conclusion, the expressions of genes involved in PS light reaction, Abiotic stress, and Biotic stress were obviously aroused during the accumulation of SGAs induced by light exposure. Moreover, an increased defense response might contribute to the potato resistance to the infection by phytopathogenic microorganisms.


Assuntos
Regulação da Expressão Gênica de Plantas/efeitos da radiação , Luz , Solanina/análogos & derivados , Solanum tuberosum/fisiologia , Resistência à Doença/genética , Tubérculos/genética , Tubérculos/metabolismo , Tubérculos/efeitos da radiação , RNA-Seq , Metabolismo Secundário/genética , Solanina/metabolismo , Estresse Fisiológico/genética , Transcriptoma/efeitos da radiação , Sequenciamento do Exoma
7.
Food Chem ; 284: 254-258, 2019 Jun 30.
Artigo em Inglês | MEDLINE | ID: mdl-30744854

RESUMO

Effect of citronella essential oil (CEO) fumigation on sprout suppression and quality of potato tubers during storage was investigated. Potato tubers were treated under conditions of single-phase (30 µL L-1, 0-10 d) and dual-phase (30 µL L-1, 0-10 d; 30 µL L-1, 35-90 d) fumigation. Changes in germination rate, weight loss, starch, reducing sugar, gibberellins (GA3), and α-solanine were measured. The results showed that CEO fumigation could control sprouting and improve the quality of potato tubers during storage compared to the non-treated tubers. CEO treatments inhibited the degradation of starch and the increase of reducing sugar content. The production of gibberellins (GA3) was suppressed, and the levels of α-solanine in the skin and flesh of potato tubers were decreased by CEO fumigation. Dual-phase CEO fumigation had a better effect on sprout suppression than single-phase fumigation, and possesses potential for postharvest application.


Assuntos
Cymbopogon/metabolismo , Armazenamento de Alimentos , Germinação/efeitos dos fármacos , Óleos Voláteis/farmacologia , Solanum tuberosum/efeitos dos fármacos , Cymbopogon/química , Fumigação , Giberelinas/metabolismo , Tubérculos/crescimento & desenvolvimento , Tubérculos/metabolismo , Solanina/metabolismo , Solanum tuberosum/metabolismo , Amido/metabolismo
8.
Plant Physiol Biochem ; 131: 70-77, 2018 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-29735370

RESUMO

Potato (Solanum tuberosum) is a major food crop, while the most tissues of potato accumulates steroidal glycoalkaloids (SGAs) α-solanine and α-chaconine. Since SGAs confer a bitter taste on human and show the toxicity against various organisms, reducing the SGA content in the tubers is requisite for potato breeding. However, generation of SGA-free potato has not been achieved yet, although silencing of several SGA biosynthetic genes led a decrease in SGAs. Here, we show that the knockout of St16DOX encoding a steroid 16α-hydroxylase in SGA biosynthesis causes the complete abolition of the SGA accumulation in potato hairy roots. Nine candidate guide RNA (gRNA) target sequences were selected from St16DOX by in silico analysis, and the two or three gRNAs were introduced into a CRISPR/Cas9 vector designated as pMgP237-2A-GFP that can express multiplex gRNAs based on the pre-tRNA processing system. To establish rapid screening of the candidate gRNAs that can efficiently mutate the St16DOX gene, we used a potato hairy root culture system for the introduction of the pMgP237 vectors. Among the transgenic hairy roots, two independent lines showed no detectable SGAs but accumulated the glycosides of 22,26-dihydroxycholesterol, which is the substrate of St16DOX. Analysis of the two lines with sequencing exhibited the mutated sequences of St16DOX with no wild-type sequences. Thus, generation of SGA-free hairy roots of tetraploid potato was achieved by the combination of the hairy root culture and the pMgP237-2A-GFP vector. This experimental system is useful to evaluate the efficacy of candidate gRNA target sequences in the short-term.


Assuntos
Sistemas CRISPR-Cas/genética , Edição de Genes/métodos , Genes de Plantas/genética , Raízes de Plantas/genética , Solanina/metabolismo , Solanum tuberosum/genética , Esteroide 16-alfa-Hidroxilase/genética , Técnicas de Inativação de Genes/métodos , Raízes de Plantas/metabolismo , Plantas Geneticamente Modificadas/genética , Plantas Geneticamente Modificadas/metabolismo , Análise de Sequência de DNA , Solanum tuberosum/metabolismo , Esteroide 16-alfa-Hidroxilase/metabolismo
9.
Planta ; 246(6): 1189-1202, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-28828630

RESUMO

MAIN CONCLUSION: 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. Presently, a potato LAS-related gene (StLAS-like) was identified and its activity verified in a yeast complementation assay. A transgenic approach with targeted gene expression and metabolic profiling of sterols and SGAs was used. Analyses of StLAS-like transcript levels and StLAS-like-promoter::GUS reporter assays indicated specific expression in tuber flesh tissue. Overexpression of Arabidopsis AtLAS in leaves where the endogenic StLAS-like is not expressed, resulted with increased SGA level and reduced phytosterol level, while in the tuber flesh SGA level was reduced. StLAS-like expression only in tuber flesh may explain the differential accumulation of SGAs in commercial cultivars-low in tubers, high in leaves. In leaves, to maintain phytosterol homeostasis, an excess of intermediates may be diverted into SGA biosynthesis, whereas in tuber flesh these intermediates are catalyzed by tuber-specific StLAS-like instead, resulting in low levels of SGA.


Assuntos
Arabidopsis/enzimologia , Transferases Intramoleculares/metabolismo , Fitosteróis/metabolismo , Solanina/metabolismo , Solanum tuberosum/enzimologia , Triterpenos/metabolismo , Sequência de Aminoácidos , Arabidopsis/genética , Vias Biossintéticas , Genes Reporter , Transferases Intramoleculares/genética , Plantas Geneticamente Modificadas , Alinhamento de Sequência , Solanum tuberosum/genética
10.
Plant Physiol ; 171(4): 2458-67, 2016 08.
Artigo em Inglês | MEDLINE | ID: mdl-27307258

RESUMO

α-Solanine and α-chaconine, steroidal glycoalkaloids (SGAs) found in potato (Solanum tuberosum), are among the best-known secondary metabolites in food crops. At low concentrations in potato tubers, SGAs are distasteful; however, at high concentrations, SGAs are harmful to humans and animals. Here, we show that POTATO GLYCOALKALOID BIOSYNTHESIS1 (PGA1) and PGA2, two genes that encode cytochrome P450 monooxygenases (CYP72A208 and CYP72A188), are involved in the SGA biosynthetic pathway, respectively. The knockdown plants of either PGA1 or PGA2 contained very little SGA, yet vegetative growth and tuber production were not affected. Analyzing metabolites that accumulated in the plants and produced by in vitro enzyme assays revealed that PGA1 and PGA2 catalyzed the 26- and 22-hydroxylation steps, respectively, in the SGA biosynthetic pathway. The PGA-knockdown plants had two unique phenotypic characteristics: The plants were sterile and tubers of these knockdown plants did not sprout during storage. Functional analyses of PGA1 and PGA2 have provided clues for controlling both potato glycoalkaloid biosynthesis and tuber sprouting, two traits that can significantly impact potato breeding and the industry.


Assuntos
Sistema Enzimático do Citocromo P-450/metabolismo , Solanina/análogos & derivados , Solanum tuberosum/enzimologia , Vias Biossintéticas , Cruzamento , Produtos Agrícolas , Sistema Enzimático do Citocromo P-450/genética , Inativação Gênica , Hidroxilação , Fenótipo , Fitosteróis/química , Fitosteróis/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Tubérculos/enzimologia , Tubérculos/genética , Tubérculos/crescimento & desenvolvimento , Solanina/química , Solanina/metabolismo , Solanum tuberosum/genética , Solanum tuberosum/crescimento & desenvolvimento
11.
J Appl Microbiol ; 120(4): 955-65, 2016 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-26786886

RESUMO

AIMS: To study the antifungal effects of the potato secondary metabolites α-solanine, α-chaconine, solanidine and caffeic acid, alone or combined. METHODS AND RESULTS: Resistance to glycoalkaloids varied among the fungal species tested, as derived from minimum inhibitory concentrations assays. Synergistic antifungal activity between glycoalkaloids and phenolic compounds was found. Changes in the fluidity of fungal membranes caused by potato secondary plant metabolites were determined by calculation of the generalized polarization values. The results partially explained the synergistic effect between caffeic acid and α-chaconine and supported findings on membrane disruption mechanisms from previous studies on artificial membranes. LC/MS analysis was used to determine variability and relative amounts of sterols in the different fungal species. Results suggested that the sterol pattern of fungi is related to their resistance to potato glycoalkaloids and to their taxonomy. CONCLUSION: Fungal resistance to α-chaconine and possibly other glycoalkaloids is species dependent. α-Chaconine and caffeic acid show synergistic antifungal activity. The taxonomic classification and the sterol pattern play a role in fungal resistance to glycoalkaloids. SIGNIFICANCE AND IMPACT OF THE STUDY: Results improve the understanding of the antifungal mode of action of potato secondary metabolites, which is essential for their potential utilization as antifungal agents in nonfood systems.


Assuntos
Antifúngicos/farmacologia , Diosgenina/farmacologia , Fungos/efeitos dos fármacos , Solanina/análogos & derivados , Antifúngicos/isolamento & purificação , Antifúngicos/metabolismo , Ácidos Cafeicos/isolamento & purificação , Ácidos Cafeicos/metabolismo , Ácidos Cafeicos/farmacologia , Diosgenina/isolamento & purificação , Diosgenina/metabolismo , Testes de Sensibilidade Microbiana , Fenóis/metabolismo , Solanina/isolamento & purificação , Solanina/metabolismo , Solanina/farmacologia , Solanum tuberosum/metabolismo
12.
J Agric Food Chem ; 64(4): 988-96, 2016 Feb 03.
Artigo em Inglês | MEDLINE | ID: mdl-26768994

RESUMO

Before commercial release, new potato (Solanum tuberosum) varieties must be evaluated for content of toxic compounds such as glycoalkaloids (GAs), which are potent poisons. GA biosynthesis proceeds via the cholesterol pathway to α-chaconine and α-solanine. The goal of this study was to evaluate the relationship between total glycoalkaloid (TGA) content and the expression of GAME, SGT1, and SGT3 genes in potato tubers. TGA content was measured by HPLC-MS, and reverse transcription quantitative polymerase chain reactions were performed to determine the relative expression of GAME, SGT1, and SGT3 genes. We searched for cis-elements of the transcription start site using the PlantPAN database. There was a relationship between TGA content and the relative expression of GAME, SGT1, and SGT3 genes in potato tubers. Putative promoter regions showed the presence of several cis-elements related to biotic and abiotic stresses and light. These findings provide an important step toward understanding TGA regulation and variation in potato tubers.


Assuntos
Alcaloides/biossíntese , Proteínas de Plantas/genética , Solanum tuberosum/genética , Solanum tuberosum/metabolismo , Transcrição Gênica , Alcaloides/toxicidade , Vias Biossintéticas , Proteínas de Plantas/metabolismo , Tubérculos/química , Tubérculos/genética , Tubérculos/metabolismo , Regiões Promotoras Genéticas , Solanina/análogos & derivados , Solanina/metabolismo , Solanina/toxicidade
13.
Molecules ; 20(5): 8560-73, 2015 May 13.
Artigo em Inglês | MEDLINE | ID: mdl-25985357

RESUMO

A higher yield of glycoalkaloids was recovered from potato peels using pressurized liquid extraction (1.92 mg/g dried potato peels) compared to conventional solid-liquid extraction (0.981 mg/g dried potato peels). Response surface methodology deduced the optimal temperature and extracting solvent (methanol) for the pressurized liquid extraction (PLE) of glycoalkaloids as 80 °C in 89% methanol. Using these two optimum PLE conditions, levels of individual steroidal alkaloids obtained were of 597, 873, 374 and 75 µg/g dried potato peel for α-solanine, α-chaconine, solanidine and demissidine respectively. Corresponding values for solid liquid extraction were 59%, 46%, 40% and 52% lower for α-solanine, α-chaconine, solanidine and demissidine respectively.


Assuntos
Alcaloides/metabolismo , Compostos Fitoquímicos/metabolismo , Solanum tuberosum/metabolismo , Extração em Fase Sólida/métodos , Diosgenina/metabolismo , Metanol/química , Alcaloides de Solanáceas/metabolismo , Solanina/análogos & derivados , Solanina/metabolismo
14.
J Am Soc Mass Spectrom ; 26(4): 641-8, 2015 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-25510927

RESUMO

The response of plants to microbial pathogens is based on the production of secondary metabolites. The complexity of plant-pathogen interactions makes their understanding a challenging task for metabolomic studies requiring powerful analytical approaches. In this paper, the ability of ambient mass spectrometry to provide a snapshot of plant metabolic response to pathogen invasion was tested. The fluctuations of glycoalkaloids present in sprouted potatoes infected by the phytopathogen Pythium ultimum were monitored by imprint imaging desorption electrospray ionization mass spectrometry (DESI-MS). After 8 d from the inoculation, a decrease of the relative abundance of potato glycoalkaloids α-solanine (m/z 706) and α-chaconine (m/z 722) was observed, whereas the relative intensity of solanidine (m/z 398), solasodenone (m/z 412), solanaviol (m/z 430), solasodiene (m/z 396), solaspiralidine (m/z 428), γ-solanine/γ-chaconine (m/z 560) , ß-solanine (m/z 706), and ß-chaconine (m/z 722) increased. The progression of the disease, expressed by the development of brown necrotic lesions on the potato, led to the further decrease of all the glycoalkaloid metabolites. Therefore, the applicability of imprint imaging DESI-MS in studying the plant metabolic changes in a simple pathosystem was demonstrated with minimal sample preparation.


Assuntos
Imagem Molecular/métodos , Raízes de Plantas/metabolismo , Raízes de Plantas/parasitologia , Solanum tuberosum/metabolismo , Solanum tuberosum/parasitologia , Espectrometria de Massas por Ionização por Electrospray/métodos , Raízes de Plantas/química , Pythium , Solanina/análogos & derivados , Solanina/análise , Solanina/química , Solanina/metabolismo , Solanum tuberosum/química
15.
J Agric Food Chem ; 62(36): 9043-55, 2014 Sep 10.
Artigo em Inglês | MEDLINE | ID: mdl-25144460

RESUMO

The Colorado potato beetle Leptinotarsa decemlineata (Say) (CPB) is a coleopteran herbivore that feeds on the foliage on Solanum species, in particular, potato. Six resistant wild Solanum species were identified, and two of these species had low levels of glycoalkaloids. Comparative analysis of the untargeted metabolite profiles of the foliage using UPLC-qTOF-MS was done to find metabolites shared between the wild species but not with Solanum tuberosum (L.) to identify resistance-related metabolites. It was found that only S. tuberosum produced the triose glycoalkaloids solanine and chaconine. Instead, the six wild species produced glycoalkaloids that shared in common tetrose sugar side chains. Additionally, there were non-glycoalkaloid metabolites associated with resistance including hydroxycoumarin and a phenylpropanoid, which were produced in all wild species but not in S. tuberosum.


Assuntos
Alcaloides/farmacologia , Besouros/efeitos dos fármacos , Folhas de Planta/química , Folhas de Planta/metabolismo , Solanum tuberosum/metabolismo , Solanum/metabolismo , Alcaloides/análise , Alcaloides/metabolismo , Animais , Besouros/fisiologia , Glicosídeos/metabolismo , Metabolômica , Doenças das Plantas , Alcaloides de Solanáceas/metabolismo , Solanina/metabolismo , Solanina/farmacologia , Solanum/crescimento & desenvolvimento , Solanum tuberosum/crescimento & desenvolvimento , Tomatina/metabolismo
16.
J Food Sci ; 79(5): T1039-48, 2014 May.
Artigo em Inglês | MEDLINE | ID: mdl-24697731

RESUMO

UNLABELLED: Potatoes accumulate toxic steroidal compounds that could be harmful for humans if consumed in high quantities and must be controlled. In this study, we were interested in assessing the levels and variation of glycoalkaloid content in 60 varieties of potato planted in 2 trial sites over 2 y. Total glycoalkaloid levels ranged from 4 to 957 mg/kg of dry weight in the flesh and from 150 to 8133 mg/kg in the skin, with the latter accumulating generally more α-chaconine than α-solanine. Contents in the flesh were below the safe limit for all varieties, but were generally above in the skin. Maximum values in each site and year of cultivation were found for varieties "Beauty of Hebron," "May Queen," and "Arran Pilot" in the skin and "Beauty of Hebron," "International Kidney," and "Congo" in the flesh. Year of cultivation had a significant effect on total glycoalkaloid content (P < 0.0001), with interactions between variety and site of cultivation and variety and year of cultivation also significant (P < 0.0001), implying that environmental effects seem to act differentially and could induce high levels in genetically predisposed varieties. PRACTICAL APPLICATION: This paper reports the levels of toxic glycoalkaloids in 60 varieties of potato. Dietary intake and safety of consumers is discussed and varieties used by the potato processing industry are assessed in terms of safety and potential use of waste peel as raw material.


Assuntos
Agricultura , Dieta , Meio Ambiente , Inocuidade dos Alimentos , Genótipo , Solanina/metabolismo , Solanum tuberosum/genética , Humanos , Tubérculos/metabolismo , Solanina/análogos & derivados , Solanum tuberosum/metabolismo
17.
J Agric Food Chem ; 61(24): 5893-902, 2013 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-23692427

RESUMO

Potato tubers naturally contain a number of defense substances, some of which are of major concern for food safety. Among these substances are the glycoalkaloids and calystegines. We have here analyzed levels of glycoalkaloids (α-chaconine and α-solanine) and calystegines (A3, B2, and B4) in potato tubers subjected to mechanical wounding, light exposure, or elevated temperature: stress treatments that are known or anticipated to induce glycoalkaloid levels. Basal glycoalkaloid levels in tubers varied between potato cultivars. Wounding and light exposure, but not heat, increased tuber glycoalkaloid levels, and the relative response differed among the cultivars. Also, calystegine levels varied between cultivars, with calystegine B4 showing the most marked variation. However, the total calystegine level was not affected by wounding or light exposure. The results demonstrate a strong variation among potato cultivars with regard to postharvest glycoalkaloid increases, and they suggest that the biosynthesis of glycoalkaloids and calystegines occurs independently of each other.


Assuntos
Produtos Agrícolas/química , Manipulação de Alimentos , Qualidade dos Alimentos , Nortropanos/análise , Tubérculos/química , Alcaloides de Solanáceas/análise , Solanum tuberosum/química , Produtos Agrícolas/metabolismo , Produtos Agrícolas/efeitos da radiação , Glicosilação , Temperatura Alta/efeitos adversos , Luz/efeitos adversos , Fenômenos Mecânicos , Nortropanos/química , Nortropanos/metabolismo , Tubérculos/metabolismo , Tubérculos/efeitos da radiação , Alcaloides de Solanáceas/biossíntese , Alcaloides de Solanáceas/química , Alcaloides de Solanáceas/metabolismo , Solanina/análogos & derivados , Solanina/análise , Solanina/química , Solanina/metabolismo , Solanum tuberosum/metabolismo , Solanum tuberosum/efeitos da radiação , Especificidade da Espécie , Estereoisomerismo , Suécia , Regulação para Cima
18.
Toxins (Basel) ; 5(4): 743-75, 2013 Apr 23.
Artigo em Inglês | MEDLINE | ID: mdl-23612750

RESUMO

There is a need to develop food-compatible conditions to alter the structures of fungal, bacterial, and plant toxins, thus transforming toxins to nontoxic molecules. The term 'chemical genetics' has been used to describe this approach. This overview attempts to survey and consolidate the widely scattered literature on the inhibition by natural compounds and plant extracts of the biological (toxicological) activity of the following food-related toxins: aflatoxin B1, fumonisins, and ochratoxin A produced by fungi; cholera toxin produced by Vibrio cholerae bacteria; Shiga toxins produced by E. coli bacteria; staphylococcal enterotoxins produced by Staphylococcus aureus bacteria; ricin produced by seeds of the castor plant Ricinus communis; and the glycoalkaloid α-chaconine synthesized in potato tubers and leaves. The reduction of biological activity has been achieved by one or more of the following approaches: inhibition of the release of the toxin into the environment, especially food; an alteration of the structural integrity of the toxin molecules; changes in the optimum microenvironment, especially pH, for toxin activity; and protection against adverse effects of the toxins in cells, animals, and humans (chemoprevention). The results show that food-compatible and safe compounds with anti-toxin properties can be used to reduce the toxic potential of these toxins. Practical applications and research needs are suggested that may further facilitate reducing the toxic burden of the diet. Researchers are challenged to (a) apply the available methods without adversely affecting the nutritional quality, safety, and sensory attributes of animal feed and human food and (b) educate food producers and processors and the public about available approaches to mitigating the undesirable effects of natural toxins that may present in the diet.


Assuntos
Toxinas Bacterianas/antagonistas & inibidores , Contaminação de Alimentos/prevenção & controle , Micotoxinas/antagonistas & inibidores , Ricina/antagonistas & inibidores , Solanina/antagonistas & inibidores , Animais , Antitoxinas/farmacologia , Antitoxinas/uso terapêutico , Toxinas Bacterianas/metabolismo , Toxinas Bacterianas/toxicidade , Descoberta de Drogas , Aditivos Alimentares/química , Aditivos Alimentares/metabolismo , Aditivos Alimentares/farmacologia , Doenças Transmitidas por Alimentos/tratamento farmacológico , Doenças Transmitidas por Alimentos/prevenção & controle , Doenças Transmitidas por Alimentos/terapia , Doenças Transmitidas por Alimentos/veterinária , Humanos , Micotoxinas/metabolismo , Micotoxinas/toxicidade , Ricina/metabolismo , Ricina/toxicidade , Solanina/metabolismo , Solanina/toxicidade
19.
Arch Insect Biochem Physiol ; 83(1): 15-24, 2013 May.
Artigo em Inglês | MEDLINE | ID: mdl-23494897

RESUMO

Plant allelochemicals are nonnutritional chemicals that interfere with the biology of herbivores. We posed the hypothesis that ingestion of a glycoalkaloid allelochemical, α-solanine, impairs biological parameters of greater wax moths Galleria mellonella. To test this idea, we reared wax moths on artificial diets with 0.015, 0.15, or 1.5 mg/100 g diet of α-solanine. Addition of α-solanine to the diet affected survival of seventh-instar larvae, pupae, and adults; and female fecundity and fertility. The diet containing the highest α-solanine concentration led to decreased survivorship, fecundity, and fertility. The diets supplemented with α-solanine led to increased malondialdehyde and protein carbonyl contents in midgut and fat body and the effect was dose-dependent. Dietary α-solanine led to increased midgut glutathione S-transferase activity and to decreased fat body glutathione S-transferase activitiy. We infer from these findings that α-solanine influences life history parameters and antioxidative enzyme activities in the midgut and fat body of G. mellonella.


Assuntos
Corpo Adiposo/metabolismo , Mariposas/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Solanina/farmacologia , Animais , Feminino , Fertilidade/efeitos dos fármacos , Trato Gastrointestinal/metabolismo , Glutationa Transferase/metabolismo , Masculino , Malondialdeído/metabolismo , Mariposas/metabolismo , Carbonilação Proteica/efeitos dos fármacos , Solanina/metabolismo
20.
Phytochemistry ; 85: 72-81, 2013 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-23122773

RESUMO

Guatemalan potato moth, Tecia solanivora, lay eggs in the soil nearby potato Solanum spp. and larvae feed on the tubers. We investigated the oviposition behaviour of T. solanivora females and the survival of larval offspring on healthy vs. stressed, i.e. light exposed and/or damaged potato tubers. In choice tests, females laid significantly more eggs in response to potato odour of healthy tubers and female oviposition preference correlated with higher larval survival. Survival of larvae was negatively correlated with the tuber content of the steroid glycoalkaloids α-solanine and α-chaconine: healthy potatoes contained lower amounts than stressed tubers, ranging from 25 to 500 µg g⁻¹ and from 30 to 600 µg g⁻¹, respectively. Analysis of volatile compounds emitted by potato tubers revealed that stressed tubers could clearly be distinguished from healthy tubers by the composition of their volatile profiles. Compounds that contributed to this difference were e.g. decanal, nonanal, isopropyl myristate, phenylacetaldehyde, benzothiazole, heptadecane, octadecane, myristicin, E,E-α-farnesene and verbenone. Oviposition assays, when female moths were not in contact with the tubers, clearly demonstrated that volatiles guide the females to lay fewer eggs on stressed tubers that are of inferior quality for the larvae. We propose that volatiles, such as sesquiterpenes and aldehydes, mediate oviposition behaviour and are correlated with biosynthetically related, non-volatile compounds, such as steroidal glycoalkaloids, which influence larval survival. We conclude that the oviposition response and larval survival of T. solanivora on healthy vs. stressed tubers supports the preference performance hypothesis for insect herbivores.


Assuntos
Mariposas/fisiologia , Odorantes , Solanina/metabolismo , Solanum tuberosum/metabolismo , Solanum/química , Animais , Feminino , Oviposição/fisiologia , Fenóis/metabolismo
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