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1.
J Nat Prod ; 86(5): 1274-1283, 2023 May 26.
Artigo em Inglês | MEDLINE | ID: mdl-37133415

RESUMO

Phenolamides are abundant specialized metabolites found in nature and consist of hydroxycinnamic acids mono- or polyconjugated with polyamines. Their participation in flower development is well-documented, and their presence in pollen raises the question of their role in pollen/pollinator interactions. The structural characterization of phenolamides is complicated by the presence of positional isomers and stereoisomers. Liquid chromatography coupled to tandem mass spectrometry in the positive ionization mode is becoming very popular in phenolamide structural characterization. However, collision-induced transamidation processes that cause the swapping of side chains have been detected, making it difficult to distinguish regioisomers with this technique. In the present report, we explore the dissociation processes undergone by the [M - H]- ions of spermidine-based phenolamides as model compounds. We describe two original competitive dissociation routes, namely, the phenolate and imidate pathways, to account for the observed fragmentation reactions undergone by collisional activated standard phenolamide anions. Whereas the phenolate pathway is regioselective at the central position for spermidine, the imidate pathway, requiring a deprotonated amide, only occurs at the extremities. Tandem mass spectrometry experiments on negatively charged phenolamide ions may then outperform their positive ionization mode counterparts for the distinction between phenolamide regioisomers and globally for the identification of phenolamides in natural extracts.


Assuntos
Espermidina , Espectrometria de Massas em Tandem , Espectrometria de Massas em Tandem/métodos , Íons , Cromatografia Líquida , Imidoésteres , Espectrometria de Massas por Ionização por Electrospray/métodos
2.
J Org Chem ; 87(23): 16063-16073, 2022 Dec 02.
Artigo em Inglês | MEDLINE | ID: mdl-36372967

RESUMO

Ph3P-I2-mediated condensation reactions of isatoic anhydrides and o-phenylenediamines have been developed for the regioselective syntheses of a wide range of linearly and angularly fused benzoimidazoquinazolinones. The selectivity of the products relies on the generation of either highly electrophilic oxyphosphonium or less reactive imidate intermediates. A direct amine attack at the C-2 position of the oxyphosphonium intermediate presumably drives the reaction toward the linearly fused products, whereas an attack of the diamine at the C-4 position of the in situ generated cyclic imidate leads to the angularly fused derivatives. This strategy serves as a practical handle for the efficient synthesis of other related heterocycles.


Assuntos
Aminas , Anidridos , Imidoésteres
3.
Org Lett ; 24(41): 7696-7700, 2022 10 21.
Artigo em Inglês | MEDLINE | ID: mdl-36214750

RESUMO

The rapid and facile generation of 4'-carbon radicals from oxime imidates of nucleosides via 1,5-hydrogen atom transfer induced by iminyl radicals was developed. The cyclization of 4'-carbon radicals with olefins, followed by the hydrolysis of imidate residues, provided various 2'-O,4'-C- and 3'-O,4'-C-bridged nucleosides. This operationally simple approach can be applied to the few-step syntheses of 6'S-methyl-2'-O,4'-C-ethylene-bridged 5-methyluridine (6'S-Me-ENA-T) and S-constrained ethyl-bridged 5-methyluridine (S-cEt-T).


Assuntos
Hidrogênio , Nucleosídeos , Carbono , Etilenos/química , Alcenos , Oximas , Imidoésteres
4.
DNA Cell Biol ; 41(11): 987-995, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36251737

RESUMO

An aberrant immunologic mechanism and mitochondrial biogenesis have been suggested to be involved in the pathogenesis of endometriosis. Genetic alterations in the vitamin D receptor (VDR) gene and peroxisome proliferator-activated receptor-gamma coactivator 1α (PGC-1α) may lead to important defects in gene activation, which principally affect immune function and normal mitochondrial function. Therefore, we hypothesized a possible role of VDR and PGC-1α genes in the pathogenesis of endometriosis and analyzed the association of genetic variants ApaI A/C (rs7975232) and TaqI T/C (rs731236) of VDR and rs8192678 (G/A), rs13131226 (T/C), and rs2970856 (T/C) of PGC-1α gene. This study included a total of 425 reproductive-age women (cases = 200 and controls = 225). Detection of VDR and PGC-1α gene polymorphism was performed using polymerase chain reaction-restriction fragment length polymorphism and sequencing analysis. The chi-square test was used to compare allele and genotype frequencies between groups, and a p-value of <0.05 was considered statistically significant. The genotype and allele distribution of both the gene polymorphisms did not show statistically significant association with endometriosis. Our result indicated ApaI A and TaqI T of VDR and GTT of PGC-1α gene as the most common haplotype in Indian women. The data suggest that VDR and PGC-1α gene polymorphisms did not play an important role in the pathogenesis of endometriosis in Indian women studied.


Assuntos
Endometriose , Coativador 1-alfa do Receptor gama Ativado por Proliferador de Peroxissomo , Receptores de Calcitriol , Feminino , Humanos , Povo Asiático , Endometriose/genética , Predisposição Genética para Doença/genética , Genótipo , Imidoésteres , Polimorfismo Genético , Polimorfismo de Nucleotídeo Único , Receptores de Calcitriol/genética , Coativador 1-alfa do Receptor gama Ativado por Proliferador de Peroxissomo/genética
5.
J Org Chem ; 87(21): 14514-14522, 2022 Nov 04.
Artigo em Inglês | MEDLINE | ID: mdl-36264227

RESUMO

A base-mediated (3 + 2) cycloaddition of trifluoroacetohydrazonoyl chlorides with imidates for the construction of 3-trifluoromethyl-1,2,4-triazoles has been described. This reaction is characterized by readily starting materials, simple reaction conditions, good yields, a broad substrate scope, and excellent regioselectivity. The utility of this protocol has been validated by the synthesis of a drug-like molecule.


Assuntos
Cloretos , Triazóis , Reação de Cicloadição , Triazóis/química , Cloretos/química , Imidoésteres
6.
Nutrients ; 14(16)2022 Aug 10.
Artigo em Inglês | MEDLINE | ID: mdl-36014767

RESUMO

Diets rich in cruciferous vegetables have been associated with a lower risk of incidence and progression of prostate cancer. Sulforaphane, an isothiocyanate derived from 4-methylsulphinylbutyl glucosinolate (glucoraphanin) that accumulates in certain of these vegetables, notably broccoli, has been implicated in their protective effects. Likewise, the consumption of garlic and its sulphur-containing compounds such as alliin have been associated with a reduction in risk of prostate cancer. In this study, we tested whether consuming glucoraphanin derived from broccoli seeds and alliin derived from garlic resulted in the occurrence of these potential bioactive compounds in the prostate, which may contribute to our understanding of the putative protective effects of these dietary components. We recruited 42 men scheduled for a trans-perineal prostate biopsy into a randomised, double-blinded, 2 × 2-factorial dietary supplement four-week intervention study, and 39 completed the study. The two active interventions were supplements providing glucoraphanin from broccoli (BroccoMax®) and alliin from garlic (Kwai Heartcare®). Following the intervention, prostate biopsy tissue was analysed for the presence of sulforaphane and its thiol conjugates and for alliin and associated metabolites. Sulforaphane occurred in significantly higher levels in the prostate tissue (both within the transition and peripheral zone) of men consuming the glucoraphanin containing supplements (p < 0.0001) compared to men not consuming these supplements. However, while alliin and alliin-derived metabolites were detected within the prostate, there was no significant difference in the concentrations of these compounds in the prostate of men consuming supplements derived from garlic compared to men not consuming these supplements.


Assuntos
Allium , Brassica , Neoplasias da Próstata , Antioxidantes/metabolismo , Brassica/metabolismo , Cisteína/análogos & derivados , Glucosinolatos/metabolismo , Humanos , Imidoésteres/metabolismo , Isotiocianatos/metabolismo , Masculino , Próstata/metabolismo , Neoplasias da Próstata/metabolismo , Neoplasias da Próstata/prevenção & controle , Sulfóxidos
7.
Immunol Res ; 70(6): 781-792, 2022 12.
Artigo em Inglês | MEDLINE | ID: mdl-35849257

RESUMO

OBJECTIVE: The aim of this study was to investigate whether the gene polymorphisms of vitamin D receptor (VDR) had a genetic effect on the susceptibility of Behcet's disease (BD). MATERIAL AND METHODS: We conducted a meta-analysis emphasizing the association between the VDR gene polymorphisms and the risk of BD. The strength of the association in five genetic models was assessed by pooled odds ratios (OR) with a corresponding 95%confidence interval (CI). RESULTS: A total of seven independent comparisons with 478 cases and 666 healthy controls were included in this meta-analysis. The overall results suggested that a significant association between ApaI polymorphism and BD risk was found in allele comparison, recessive model, and homozygote model among total populations. Subgroup analysis indicated that a significant association of ApaI polymorphism in the development of BD existed under the allelic model among Africans, while for Caucasians, a similar link was identified in the recessive model and homozygote model. Regarding Bsml polymorphism, an obvious relationship was detected to be significant in allele comparison and recessive model in the Caucasian population. Interestingly, the Fokl variant decreased the risk of BD in Africans under five genetic models, while it increased the risk in Caucasians across the recessive model and homozygote model. CONCLUSION: The results of this meta-analysis provide evidence of the link between the four widely studied polymorphisms in the VDR gene and BD, indicating a robust estimate of the genetic risk.


Assuntos
Síndrome de Behçet , Humanos , Síndrome de Behçet/genética , Predisposição Genética para Doença , Imidoésteres , Polimorfismo Genético , Receptores de Calcitriol/genética
8.
Angew Chem Int Ed Engl ; 61(42): e202210145, 2022 10 17.
Artigo em Inglês | MEDLINE | ID: mdl-35900908

RESUMO

The catalytic allylic substitution is one of the most important tools in asymmetric synthesis to form C-C bonds in an enantioselective way. While high efficiency was previously accomplished in terms of enantio- and regiocontrol using different catalyst types, a strong general limitation is a very pronounced preference for the formation of allylic substitution products with (E)-configured C=C double bonds. Herein, we report that with a planar chiral palladacycle catalyst a diastereospecific reaction outcome is achieved using isoxazolinones and allylic imidates as substrates, thus maintaining the C=C double bond geometry of the allylic substrates in the highly enantioenriched products. DFT calculations show that the reactions proceed via an SN 2 mechanism and not via π-allyl Pd complexes. Crucial for the high control is the stabilization of the allylic fragment in the SN 2 transition state by π-interactions with the phenyl substituents of the pentaphenylferrocenyl catalyst core.


Assuntos
Imidoésteres , Paládio , Catálise , Paládio/química , Estereoisomerismo
9.
J Phys Chem A ; 126(26): 4176-4184, 2022 Jul 07.
Artigo em Inglês | MEDLINE | ID: mdl-35737507

RESUMO

Arylene diimide compounds exhibit thermally activated delayed fluorescence (TADF), but its mechanism remains elusive. Herein we studied the TADF mechanism of a carbazole-substituted pyromellitic diimide derivative (CzPhPmDI) in poly(methyl methacrylate) (PMMA) film by using DFT, TD-DFT, and MS-CASPT2 methods within the QM/MM framework. We found that the TADF mechanism involves three electronic states (i.e., S0, S1, and T1), but the T2 state is not involved because its energy is higher than the S1 state by 6.9 kcal/mol. By contrast, the T1 state is only 3.2 kcal/mol lower than the S1 state and such small energy difference benefits the reverse intersystem crossing (rISC) process from T1 to S1 thereto TADF. This point is seconded by relevant radiative and nonradiative rates calculated. At room temperature, the ISC rate from S1 to T1 is calculated to be 6.1 × 106 s-1, which is larger than the fluorescence emission rate, 2.2 × 105 s-1; thus, the dominant S1 population converts to the T1 state. However, in the T1 state, the rISC process (1.8 × 104 s-1) becomes the most important channel because of the negligible phosphorescence emission rate (3.5 × 10-2 s-1). So, the T1 population is still converted back to the S1 state to fluoresce enabling TADF. Unfortunately, the rISC process is blocked in low temperature. Besides, we found that relevant Huang-Rhys factors have dominant contribution from low-frequency vibrational motion related to the torsional motion of functional groups. These gained insights could provide useful information for the design of organic TADF materials with excellent luminescence efficiency.


Assuntos
Eletrônica , Imidoésteres , Teoria da Densidade Funcional , Fluorescência
10.
PLoS One ; 17(6): e0269692, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-35700171

RESUMO

The reference sequence of structurally complex regions can only be obtained through a highly accurate clone-based approach that we call Single-Haplotype Iterative Mapping and Sequencing (SHIMS). In recent years, improvements to SHIMS have reduced the cost and time required by two orders of magnitude, but internally repetitive clones still require extensive manual effort to transform draft assemblies into reference-quality finished sequences. Here we describe SHIMS 3.0, using ultra-long nanopore reads to augment the Illumina data from SHIMS 2.0 assemblies and resolve internally repetitive structures. This greatly minimizes the need for manual finishing of Illumina-based draft assemblies, allowing a small team with no prior finishing experience to sequence challenging targets with high accuracy. This protocol proceeds from clone-picking to finished assemblies in 2 weeks for about $80 (USD) per clone. We recently used this protocol to produce reference sequence of structurally complex palindromes on chimpanzee and rhesus macaque X chromosomes. Our protocol provides access to structurally complex regions that would otherwise be inaccessible from whole-genome shotgun data or require an impractical amount of manual effort to generate an accurate assembly.


Assuntos
Nanoporos , Animais , Haplótipos , Sequenciamento de Nucleotídeos em Larga Escala/métodos , Imidoésteres , Macaca mulatta , Análise de Sequência de DNA/métodos
11.
ACS Synth Biol ; 11(5): 1865-1873, 2022 05 20.
Artigo em Inglês | MEDLINE | ID: mdl-35438493

RESUMO

Glucoraphanin is a plant specialized metabolite found in cruciferous vegetables that has long been a target for production in a heterologous host because it can subsequently be hydrolyzed to form the chemopreventive compound sulforaphane before and during consumption. However, previous studies have only been able to produce small amounts of glucoraphanin in heterologous plant and microbial systems compared to the levels found in glucoraphanin-producing plants, suggesting that there may be missing auxiliary genes that play a role in improving production in planta. In an effort to identify auxiliary genes required for high glucoraphanin production, we leveraged transient expression in Nicotiana benthamiana to screen a combination of previously uncharacterized coexpressed genes and rationally selected genes alongside the glucoraphanin biosynthetic pathway. This strategy alleviated metabolic bottlenecks, which improved glucoraphanin production by 4.74-fold. Our optimized glucoraphanin biosynthetic pathway provides a pathway amenable for high glucoraphanin production.


Assuntos
Glucosinolatos , Imidoésteres , Oximas , Sulfóxidos , Tabaco/genética
12.
Ultrason Sonochem ; 84: 105977, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-35279633

RESUMO

In this investigation, the combinations of exogenous pretreatment (melatonin or vitamin C) and contact ultrasound-assisted air drying were utilized to dry broccoli florets. To understand the influences of the studied dehydration methods on the conversion of glucoraphanin to bioactive sulforaphane in broccoli, various components (like glucoraphanin, sulforaphane, myrosinase, etc.) and factors (temperature and moisture) involved in the metabolism pathway were analyzed. The results showed that compared with direct air drying, the sequential exogenous pretreatment and contact ultrasound drying shortened the drying time by 19.0-22.7%. Meanwhile, contact sonication could promote the degradation of glucoraphanin. Both melatonin pretreatment and vitamin C pretreatment showed protective effects on the sulforaphane content and myrosinase activity during the subsequent drying process. At the end of drying, the sulforaphane content in samples dehydrated by the sequential melatonin (or vitamin C) pretreatment and ultrasound-intensified drying was 14.4% (or 26.5%) higher than only air-dried samples. The correlation analysis revealed that the exogenous pretreatment or ultrasound could affect the enzymatic degradation of glucoraphanin and the generation of sulforaphane through weakening the connections of sulforaphane-myrosinase, sulforaphane-VC, and VC-myrosinase. Overall, the reported results can enrich the biochemistry knowledge about the transformation of glucoraphanin to sulforaphane in cruciferous vegetables during drying, and the combined VC/melatonin pretreatment and ultrasound drying is conducive to protect bioactive sulforaphane in dehydrated broccoli.


Assuntos
Brassica , Brassica/química , Glucosinolatos/química , Imidoésteres , Redes e Vias Metabólicas , Oximas/metabolismo , Sulfóxidos/metabolismo
13.
J Agric Food Chem ; 70(7): 2303-2311, 2022 Feb 23.
Artigo em Inglês | MEDLINE | ID: mdl-35112855

RESUMO

Myrosinase is a biotechnological tool for the preparation of sulforaphane and sulforaphene with a variety of excellent biological activities. In this study, a gene encoding the novel glycoside hydrolase family 3 (GH3) myrosinase Rmyr from Rahnella inusitata was heterologously expressed in Escherichia coli BL21 (DE3). The purified Rmyr shows the highest activity at 40 °C and pH 7.0; meanwhile, its half-life at 30 °C reaches 12 days, indicating its excellent stability. Its sinigrin-, glucoraphenin-, and glucoraphanin-hydrolyzing activities were 12.73, 4.81, and 6.99 U/mg, respectively. Rmyr could efficiently degrade the radish seed-derived glucoraphenin and the broccoli seed-derived glucoraphanin into sulforaphene and sulforaphane within 10 min with the highest yields of 5.07 mg/g radish seeds and 9.56 mg/g broccoli seeds, respectively. The highest conversion efficiencies of sulforaphane from glucoraphanin and sulforaphene from glucoraphenin reached up to 92.48 and 97.84%, respectively. Therefore, Rmyr is a promising and potent biocatalyst for efficient and large-scale preparation of sulforaphane and sulforaphene.


Assuntos
Glucosinolatos , Imidoésteres , Glucosinolatos/metabolismo , Glicosídeo Hidrolases/genética , Glicosídeo Hidrolases/metabolismo , Imidoésteres/metabolismo , Isotiocianatos/química , Rahnella , Sulfóxidos
14.
J Org Chem ; 86(24): 17965-17974, 2021 12 17.
Artigo em Inglês | MEDLINE | ID: mdl-34843247

RESUMO

A regioselective synthesis of furanone-fused isoquinoline heterocycles is developed in a single step using a Rh(III) catalyst. In this reaction, a cascade C-H activation, regioselective annulation, and lactonization occur in one pot. A wide range of alkynoates was examined, which showed good regioselectivity. The regioselectivity was guided by steric bulk at the C4 position of the 4-hydroxy-2-alkynoates. The synthetic utility was exemplified, and the model reaction was scaled up to a 1 g scale.


Assuntos
Ródio , Catálise , Imidoésteres , Iminas , Isoquinolinas
15.
ACS Appl Mater Interfaces ; 13(34): 40401-40414, 2021 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-34405670

RESUMO

Resistance to antibiotics because of misuse and overuse is one of the greatest public health challenges worldwide. Despite the introduction of advanced nanotechnology in the production of antibiotics, the choice of appropriate medicines is limited due to side effects such as blood coagulation, toxicity, low efficacy, and low biocompatibility; therefore, novel nanomaterial composites are required to counter these repercussions. We first introduce a facile method for synthesizing a homobifunctional imidoester-coated nanospindle (HINS) zinc oxide composite for enhancement of antibiotic efficacy and reduction of toxicity and blood coagulation. The antibiotic efficacy of the composites is twice that of commercialized zinc nanoparticles; in addition, they have good biocompatibility, have increased surface charge and solubility owing to the covalent acylation groups of HI, and produce a large number of Zn+ ions and defensive reactive oxygen species (ROS) that effectively kill bacteria and fungi. The synergistic effect of a combination therapy with the HINS composite and itraconazole shows more than 90% destruction of fungi in treatments with low dosage with no cytotoxicity or coagulation evident in intravenous administration in in vitro and in vivo experiments. Thus, HINS composites are useful in reducing the effect of misuse and overuse of antibiotics in the medical field.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Imidoésteres/farmacologia , Nanopartículas Metálicas/química , Nanocompostos/química , Óxido de Zinco/farmacologia , Antibacterianos/química , Antibacterianos/toxicidade , Antifúngicos/química , Antifúngicos/toxicidade , Aspergillus fumigatus/efeitos dos fármacos , Sinergismo Farmacológico , Escherichia coli/efeitos dos fármacos , Imidoésteres/química , Imidoésteres/toxicidade , Itraconazol/farmacologia , Nanopartículas Metálicas/toxicidade , Testes de Sensibilidade Microbiana , Nanocompostos/toxicidade , Salmonella/efeitos dos fármacos , Óxido de Zinco/química , Óxido de Zinco/toxicidade
16.
Chem Commun (Camb) ; 57(65): 8075-8078, 2021 Aug 12.
Artigo em Inglês | MEDLINE | ID: mdl-34296709

RESUMO

Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.


Assuntos
Derivados de Benzeno/síntese química , Imidoésteres/química , Sulfetos/síntese química , Catálise , Complexos de Coordenação/química , Oxirredução , Rutênio/química
17.
Molecules ; 26(11)2021 May 28.
Artigo em Inglês | MEDLINE | ID: mdl-34071404

RESUMO

Broccoli microgreens have shown potential health benefits due to their high glucosinolate (GL) levels. Previously, we observed that postharvest UVB treatment did not have much effect on increasing GLs in broccoli microgreens. In this study, we investigated the influence of preharvest UVB irradiation on GL levels in broccoli microgreens. UHPLC-ESI/ITMS analysis showed that preharvest UVB treatments with UVB 0.09 and 0.27 Wh/m2 significantly increased the glucoraphanin (GLR), glucoerucin (GLE), and total aliphatic GL levels by 13.7 and 16.9%, respectively, in broccoli microgreens when measured on harvest day. The nutritional qualities of UVB-treated microgreens were stable during 21-day storage, with only small changes in their GL levels. Broccoli microgreens treated before harvest with UVB 0.27 Wh/m2 and 10 mM CaCl2 spray maintained their overall quality, and had the lowest tissue electrolyte leakage and off-odor values during the storage. Furthermore, preharvest UVB 0.27 Wh/m2 treatment significantly increased GL biosynthesis genes when evaluated before harvest, and reduced the expression level of myrosinase, a gene responsible for GL breakdown during postharvest storage. Overall, preharvest UVB treatment, together with calcium chloride spray, can increase and maintain health-beneficial compound levels such as GLs and prolong the postharvest quality of broccoli microgreens.


Assuntos
Brassica/metabolismo , Glucosinolatos/química , Raios Ultravioleta , Antioxidantes/química , Cálcio/química , Cloreto de Cálcio/química , Cromatografia Líquida de Alta Pressão , Glucose/análogos & derivados , Glucose/química , Imidoésteres/química , Valor Nutritivo , Estresse Oxidativo , Oximas/química , Fenol , Sementes , Espectrometria de Massas por Ionização por Electrospray , Sulfóxidos/química
18.
Food Chem ; 345: 128771, 2021 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-33601652

RESUMO

The isothiocyanate sulforaphane (SF) is one of the most potent naturally occurring Phase 2 enzymes inducers derived from brassica vegetables like broccoli, cabbage, brussel sprouts, etc. Ingestion of broccoli releases SF via hydrolysis of glucoraphanin (GRP) by plant myrosinase and/or intestinal microbiota. However, both SF and plant myrosinase are thermal-labile, and the epithiospecifier protein (ESP) directs the hydrolysis of GRP toward formation of sulforaphane nitrile instead of SF. In addition, bacterial myrosinase has low hydrolyzing efficiency. In this review, we discuss strategies that could be employed to improve the stability of SF, increase SF formation during thermal and non-thermal processing of broccoli, and enhance the myrosinase-like activity of the gut microbiota. Furthermore, new cooking methods or blanching technologies should be developed to maintain myrosinase activity, and novel thermostable myrosinase and/or microbes with high SF producing abilities should also be developed.


Assuntos
Brassica/química , Isotiocianatos/metabolismo , Bactérias/enzimologia , Proteínas de Bactérias/metabolismo , Brassica/metabolismo , Culinária , Estabilidade de Medicamentos , Glucosinolatos/química , Glucosinolatos/metabolismo , Glicosídeo Hidrolases/metabolismo , Hidrólise , Imidoésteres/química , Imidoésteres/metabolismo , Isotiocianatos/química , Oximas , Pressão , Sulfóxidos
19.
Food Chem ; 334: 127519, 2021 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-32721832

RESUMO

We aimed to characterize and quantify glucosinolate compounds and contents in broccoli, and a total of 80 genotypes and eight developmental organs were analyzed with UHPLC-Triple-TOF-MS. The method was validated in terms of performance, and the coefficients of determination (R2) were 0.97 and 0.99 for glucoraphanin and gluconapin, respectively. In 80 genotypes, twelve glucosinolates were found in broccoli florets ranging from 0.467 to 57.156 µmol/g DW, with the highest glucosinolate content being approximately 122-fold higher than the lowest value. The principal component of glucobrassicin, neoglucobrassicin and glucoraphanin explained 60.53% of the total variance. There were positive correlations among hydroxyglucobrassicin, methoxyglucobrassicin, glucobrassicin, glucoerucin, gluconasturtiin, glucoraphanin, and glucotropaeolin (P < 0.05). The root contained 43% of total glucosinolates in 80 genotypes, and glucoraphanin represented 29% of the total glucosinolate content in different organs. The mutant broccoli genotypes were found by analysis of gluconapin contents in different organs.


Assuntos
Brassica/metabolismo , Glucosinolatos/química , Espectrometria de Massas por Ionização por Electrospray/métodos , Brassica/genética , Cromatografia Líquida de Alta Pressão , Genótipo , Glucosinolatos/análise , Imidoésteres/análise , Indóis/análise , Oximas , Sulfóxidos
20.
Food Chem ; 334: 127520, 2021 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-32693332

RESUMO

CaCl2, Ca2+ chelator (EGTA) and Ca2+ channel blocker (verapamil) were used to investigate mechanism of glucoraphanin metabolism in broccoli sprouts under ZnSO4 stress. CaCl2 treatment promoted sprout growth, reduced MDA (malonaldehyde) content and electrolyte leakage in sprouts under ZnSO4 stress. The highest MDA content and electrolyte leakage were obtained in ZnSO4 plus verapamil-treated sprouts. In addition, ZnSO4 plus CaCl2 treatment significantly enhanced glucoraphanin content and sulforaphane formation, while an opposite result was observed after ZnSO4 plus EGTA treatment; which were further supported by expression of glucoraphanin biosynthetic and hydrolytic genes as well as myrosinase (MYR) and epithiospecifier protein (ESP) activities. These results indicated that exogenous and endogenous calcium promoted glucoraphanin biosynthesis and the conversion rate of glucoraphanin into sulforaphane. Verapamil treatment also stimulated glucoraphanin biosynthesis, but exerted an adverse influence on sulforaphane formation from the hydrolysis of glucoraphanin because of much higher ESP expression and ESP activity than ZnSO4 treatment.


Assuntos
Brassica/efeitos dos fármacos , Cloreto de Cálcio/farmacologia , Glucosinolatos/metabolismo , Imidoésteres/metabolismo , Sulfato de Zinco/farmacologia , Brassica/crescimento & desenvolvimento , Brassica/metabolismo , Ácido Egtázico/farmacologia , Glicosídeo Hidrolases/metabolismo , Hidrólise , Isotiocianatos/metabolismo , Malondialdeído/metabolismo , Oximas , Proteínas de Plantas/metabolismo , Plântula/efeitos dos fármacos , Plântula/metabolismo , Estresse Fisiológico , Sulfóxidos
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