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1.
J Sep Sci ; 47(11): e2400181, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38863110

RESUMO

Topotecan (TPT) is used in the treatment of retinoblastoma, the most common malignant intraocular tumor in children. TPT undergoes pH-dependent hydrolysis of the lactone ring to the ring-opened carboxylate form, with the lactone form showing antitumor activity. A selective, and highly sensitive ultra-high-performance liquid chromatography-tandem mass spectrometry method was developed for the determination of both forms of TPT in one mobile phase composition in plasma and vitreous humor matrices. The method showed an excellent linear range of 0.375-120 ng/mL for the lactone. For the carboxylate, the linear range was from 0.75 to 120 ng/mL. The matrix effect and the recovery for the lactone ranged from 98.5% to 106.0% in both matrices, for the carboxylate form, it ranged from 94.9% to 101.2%. The dynamics of the transition between TPT lactone and TPT carboxylate were evaluated at different pH environments. The stability of TPT forms was assessed in plasma and vitreous humor at 8 and 37°C and a very fast conversion of lactone to carboxylate form occurred at 37°C in both matrices. The method developed facilitates the investigation of TPT pharmacodynamics and the release kinetics in the development of the innovative local drug delivery systems.


Assuntos
Lactonas , Espectrometria de Massas em Tandem , Topotecan , Corpo Vítreo , Cromatografia Líquida de Alta Pressão , Lactonas/química , Lactonas/análise , Corpo Vítreo/química , Topotecan/química , Topotecan/análise , Humanos , Ácidos Carboxílicos/química , Ácidos Carboxílicos/análise , Estrutura Molecular
2.
Molecules ; 29(4)2024 Feb 09.
Artigo em Inglês | MEDLINE | ID: mdl-38398555

RESUMO

This research is an exploratory study on the sesquiterpenes and flavonoid present in the leaves of Artemisia tridentata subsp. tridentata. The leaf foliage was extracted with 100% chloroform. Thin-layer chromatography (TLC) analysis of the crude extract showed four bands. Each band was purified by column chromatography followed by recrystallization. Three sesquiterpene lactones (SLs) were isolated-leucodin, matricarin and desacetylmatricarin. Of these, desacetylmatricarin was the major component. In addition, a highly bio-active flavonoid, quercetagetin 3,6,4'-trimethyl ether (QTE), was also isolated. This is the first report on the isolation of this component from the leaves of Artemisia tridentata subsp. tridentata. All the components were identified and isolated by TLC, high-performance liquid chromatography (HPLC) and mass spectrometry (MS) techniques. Likewise, the structure and stereochemistry of the purified components were characterized by extensive spectroscopic analysis, including 1D and 2D nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy (FTIR) studies. The antioxidant activities of crude extract were analyzed, and their radical-scavenging ability was determined by Ferric reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The crude extract showed antioxidant activity of 18.99 ± 0.51 and 11.59 ± 0.38 µmol TEg-1 FW for FRAP and DPPH assay, respectively, whereas the activities of matricarin, leucodin, desacetylmatricarin and QTE were 13.22, 13.03, 14.90 and 15.02 µmol TEg-1 FW, respectively, for the FRAP assay. The antitumor properties were probed by submitting the four isolated compounds to the National Cancer Institute (NCI) for NCI-60 cancer cell line screening. Overall, the results of the one-dose assay for each SL were unremarkable. However, the flavonoid's one-dose mean graph demonstrated significant growth inhibition and lethality, which prompted an evaluation of this compound against the 60-cell panel at a five-dose assay. Tests from two separate dates indicate a lethality of approximately 75% and 98% at the log-4 concentration when tested against the melanoma cancer line SK-Mel 5. This warrants further testing and derivatization of the bioactive components from sagebrush as a potential source for anticancer properties.


Assuntos
Artemisia , Sesquiterpenos , Antioxidantes/química , Flavonoides/farmacologia , Flavonoides/análise , Sesquiterpenos/farmacologia , Sesquiterpenos/análise , Lactonas/farmacologia , Lactonas/análise , Compostos Fitoquímicos/análise , Extratos Vegetais/química , Folhas de Planta/química
3.
Zhongguo Zhong Yao Za Zhi ; 49(8): 2138-2146, 2024 Apr.
Artigo em Zh | MEDLINE | ID: mdl-38812229

RESUMO

In this study, four Atractylodes chinensis(A. chinensis) with different leaf shapes, such as the split leaf, long and narrow leaf, oval leaf, and large round leaf, were used as experimental materials to establish a method for simultaneously determining atractylodin, atractylenolide Ⅰ, ß-eudesmol, and atractylon in the rhizome of A. chinensis. The expression of key enzyme genes for biosynthesis of acetyl-CoA carboxylase(ACC), 3-hydroxy-3-methylglutaryl-CoA reductase(HMGR), and farnesyl pyrophosphate synthase(FPPS) was detected by real-time fluorescence quantitative polymerase chain reaction(qRT-PCR). High performance liquid chromatography(HPLC) was used to compare the difference in the content of four active components in A. chinensis with different leaf shapes, and the correlation between the content of active components and the expression of key enzyme genes in biosynthesis was discussed. The results show that there was good linearity among atractylodin, atractylenolide Ⅰ, ß-eudesmol, and atractylon in the range of 3.30-33.00 µg·mL~(-1)(r =0.999 7), 12.04-120.40 µg·mL~(-1)(r =0.999 5), 29.16-291.60 µg·mL~(-1)(r =0.999 5), and 14.20-142.00 µg·mL~(-1)(r =0.999 5), respectively. The average recoveries were 99.77%(RSD=2.1%), 98.56%(RSD=1.2%), 103.0%(RSD=1.2%), and 100.6%(RSD=1.5%), respectively. The method was accurate and had good reproducibility, which could be used to simultaneously detect atractylodin, atractylenolide Ⅰ, ß-eudesmol, and atractylon. The results showed that there were significant differences in the content of four active components in A. chinensis with different leaf shapes. The content of atractylodin, atractylenolide Ⅰ, and ß-eudesmol in A. chinensis with split leaves was the highest, which were 1.341 9, 5.237 2, and 12.084 3 mg·g~(-1), respectively. The content of atractylon in A. chinensis with long and narrow leaves was the highest(5.470 1 mg·g~(-1)). The content of atractylodin, atractylenolide Ⅰ, ß-eudesmol, and atractylon in A. chinensis with oval leaves was the lowest. The total content of the four effective components in descending order was A. chinensis with split leaves > A. chinensis with long and narrow leaves > A. chinensis with large round leaves > A. chinensis with oval leaves. The gene expression levels of key enzymes ACC, HMGR, and FPPS in A. chinensis with split leaves were the highest(P < 0.05), and the gene expression levels of key enzymes ACC and HMGR in A. chinensis with oval leaves were the lowest(P < 0.05). The gene expression level of key enzyme FPPS in A. chinensis with large round leaves was the lowest. In A. chinensis with different leaf shapes, the key enzyme gene ACC was significantly positively correlated with the polyacetylene component, namely atractylodin(P < 0.01), and the key enzyme genes HMGR and FPPS were positively correlated with the sesquiterpene components, namely atractylenolide Ⅰ, ß-eudesmol, and atractylon. In summary, the quality of A. chinensis with split leaves is the best, and the biosynthesis of atractylodin is significantly correlated with the gene expression of key enzyme ACC, which provides a theoretical basis for screening and optimizing the germplasm resources of A. chinensis and improving the quality of medicinal materials.


Assuntos
Atractylodes , Lactonas , Folhas de Planta , Sesquiterpenos , Atractylodes/genética , Atractylodes/química , Atractylodes/metabolismo , Folhas de Planta/genética , Folhas de Planta/metabolismo , Folhas de Planta/química , Sesquiterpenos/metabolismo , Sesquiterpenos/análise , Lactonas/metabolismo , Lactonas/análise , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Furanos/metabolismo , Medicamentos de Ervas Chinesas , Regulação da Expressão Gênica de Plantas , Rizoma/genética , Rizoma/química , Rizoma/metabolismo , Sesquiterpenos de Eudesmano
4.
Pak J Pharm Sci ; 37(1(Special)): 205-213, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38747271

RESUMO

In this study, a sensitive high-performance liquid chromatography detector was established and validated for the simultaneous determination of geniposide, ellagic acid, piperine, costunolide and dehydrocostuslactone in Liuwei Muxiang Capsules. The analysis was achieved on CHANIN 100-5-C18-H column (5µm, 250 mm×4.6 mm) with the temperature of 30oC. Gradient elution was applied using 0.1% phosphoric acid solution-methanol-acetonitrile (50:50) as mobile phase at the flow rate of 1.0 mL/min. The determination was performed at the wavelength of 225 nm (detecting geniposide), 254 nm (detecting ellagic acid), 343 nm (detecting piperine) and 225 nm (detecting costunolide and dehydrocostuslactone) along with the sample volume of 10µL. The linear ranges of geniposide, ellagic acid, piperine, costunolide and dehydrocostuslactone demonstrated good linear relationships within their respective determination ranges. The average recoveries were 100.04%, 99.86%, 99.79%, 100.17% and 100.41%, respectively. RSD% was 1.3%, 1.2%, 1.2%, 1.2%, 1.5%, respectively. The developed method was proved to be simple, accurate and sensitive, which can provide a quantitative analysis method for the content determination of geniposide, ellagic acid, piperine, costunolide and dehydrocostuslactone in Liuwei Muxiang capsules.


Assuntos
Alcaloides , Benzodioxóis , Cápsulas , Medicamentos de Ervas Chinesas , Ácido Elágico , Iridoides , Lactonas , Piperidinas , Alcamidas Poli-Insaturadas , Cromatografia Líquida de Alta Pressão/métodos , Benzodioxóis/análise , Alcamidas Poli-Insaturadas/análise , Piperidinas/análise , Piperidinas/química , Alcaloides/análise , Lactonas/análise , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/análise , Iridoides/análise , Ácido Elágico/análise , Reprodutibilidade dos Testes , Sesquiterpenos/análise
5.
J Sci Food Agric ; 103(14): 6861-6870, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37288717

RESUMO

BACKGROUND: Alternaria can infest pears to produce metabolites, which can contaminate pears and their processed products. Pear paste, one of the most important pear-based products, is popular among Chinese consumers especially for its cough relieving and phlegm removal properties. Although people are concerned about the risk of Alternaria toxins in many agro-foods and their products, little is known about the toxins in pear paste. RESULTS: A method was developed for the determination of tenuazonic acid, alternariol, alternariol menomethyl ether, altenuene and tentoxin in pear paste by ultra-performance liquid chromatography tandem mass spectrometry with saturated sodium sulphate dissolution and acidified acetonitrile extraction. The mean recoveries of the five toxins were 75.3-113.8% with relative standard deviations of 2.8-12.2% at spiked levels of 1.0-100 µg kg-1 . Alternaria toxins were detected in 53 out of 76 samples, with a detection rate of 71.4%. Tenuazonic acid (67.1%), alternariol (35.5%), tentoxin (23.7%) and alternariol monomethyl ether (7.9%) were detected in all samples at concentrations of < limit of quantification (LOQ)-105.0 µg kg-1 , < LOQ-32.1 µg kg-1 , < LOQ-74.2 µg kg-1 and < LOQ-15.1 µg kg-1 , respectively. Altenuene was never found in pear paste samples. Tenuazonic acid, alternariol, tentoxin and alternariol menomethyl ether should be focused on due to their toxicity and detection rates. CONCLUSION: To the best of our knowledge, this is the first report on the detection method and residue levels of Alternaria toxins in pear paste. The proposed method and research data can provide technical support for the Chinese government to continuously monitor and control Alternaria toxins in pear paste, especially tenuazonic acid. It can also provide a useful reference for related researchers. © 2023 Society of Chemical Industry.


Assuntos
Micotoxinas , Pyrus , Humanos , Cromatografia Líquida , Espectrometria de Massas em Tandem/métodos , Ácido Tenuazônico/análise , Micotoxinas/metabolismo , Pyrus/metabolismo , Cromatografia Líquida de Alta Pressão/métodos , Alternaria/metabolismo , Solubilidade , Lactonas/análise , Extração Líquido-Líquido , Éteres/análise , Éteres/metabolismo , Contaminação de Alimentos/análise
6.
Plant J ; 105(2): 542-557, 2021 01.
Artigo em Inglês | MEDLINE | ID: mdl-33231903

RESUMO

Plant hormones play important roles in plant growth and development and physiology, and in acclimation to environmental changes. The hormone signaling networks are highly complex and interconnected. It is thus important to not only know where the hormones are produced, how they are transported and how and where they are perceived, but also to monitor their distribution quantitatively, ideally in a non-invasive manner. Here we summarize the diverse set of tools available for quantifying and visualizing hormone distribution and dynamics. We provide an overview over the tools that are currently available, including transcriptional reporters, degradation sensors, and luciferase and fluorescent sensors, and compare the tools and their suitability for different purposes.


Assuntos
Técnicas Biossensoriais , Reguladores de Crescimento de Plantas/análise , Ácido Abscísico/análise , Ácido Abscísico/metabolismo , Técnicas Biossensoriais/métodos , Brassinosteroides/análise , Brassinosteroides/metabolismo , Ciclopentanos/análise , Ciclopentanos/metabolismo , Citocininas/análise , Citocininas/metabolismo , Etilenos/análise , Etilenos/metabolismo , Corantes Fluorescentes , Giberelinas/análise , Giberelinas/metabolismo , Compostos Heterocíclicos com 3 Anéis/análise , Compostos Heterocíclicos com 3 Anéis/metabolismo , Ácidos Indolacéticos/análise , Ácidos Indolacéticos/metabolismo , Lactonas/análise , Lactonas/metabolismo , Oxilipinas/análise , Oxilipinas/metabolismo , Reguladores de Crescimento de Plantas/fisiologia , Plantas/química , Plantas/metabolismo
7.
Molecules ; 27(18)2022 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-36144486

RESUMO

Secoatractylohexone A (1), an unprecedented secoguaiane lactone glycoside featuring 6/7 cores and dihydroxy-9-guaine-3-one 11-O-ß-d-glucopyranoside (2), a 9,10-unsaturated guaiene-type glycoside possessing an uncommon scaffold, were isolated from the water-soluble portion of the ethanolic extract of Atractylodes lancea rhizomes together with five known compounds (3-7). The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic data and application of the CD technique. The potential biological activities of secoatractylohexone A were predicted by network pharmacology in silico, the result of which indicated that secoatractylohexone A may be used to treat type II diabetes.


Assuntos
Atractylodes , Diabetes Mellitus Tipo 2 , Sesquiterpenos , Atractylodes/química , Glicosídeos/química , Lactonas/análise , Extratos Vegetais/química , Rizoma/química , Sesquiterpenos/química , Água/análise
8.
Molecules ; 27(10)2022 May 12.
Artigo em Inglês | MEDLINE | ID: mdl-35630575

RESUMO

Three isopimarane diterpenes [fladins B (1), C (2), and D (3)] were isolated from the twigs and leaves of Chinese folk medicine, Isodon flavidus. The chemical structures were determined by the analysis of the comprehensive spectroscopic data, and the absolute configuration was confirmed by X-ray crystallographic analysis. The structures of 1-3 were formed from isopimaranes through the rearrangement of ring A by the bond break at C-3 and C-4 to form a new δ-lactone ring system between C-3 and C-9. This structure type represents the first discovery of a natural isopimarane diterpene with an unusual lactone moiety at C-9 and C-10. In the crystal of 1, molecules are linked to each other by intermolecular O-H···O bonds, forming chains along the b axis. Compounds 1-3 were evaluated for their bioactivities against different diseases. None of these compounds displayed cytotoxic activities against HCT116 and A549 cancer cell lines, antifungal activities against Trichophyton rubrum and T. mentagrophytes, or antiviral activities against HIV entry at 20 µg/mL (62.9-66.7) µM. Compounds 1 and 3 did not show antiviral activities against Ebola entry at 20 µg/mL either; only 2 was found to show an 81% inhibitory effect against Ebola entry activity at 20 µg/mL (66.7 µM). The bioactivity evidence suggested that this type of compound could be a valuable antiviral lead for further structure modification to improve the antiviral potential.


Assuntos
Diterpenos , Doença pelo Vírus Ebola , Isodon , Abietanos/análise , Abietanos/farmacologia , Antivirais/análise , Diterpenos/química , Isodon/química , Lactonas/análise , Folhas de Planta/química
9.
J Sci Food Agric ; 102(14): 6687-6695, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-35620803

RESUMO

BACKGROUND: After the harvest, green coffee beans are dried on the farm using several methods: the wet process, natural process, pulped natural process, or mechanical demucilaging. This study evaluated how the choice of a specific processing method influenced the volatile organic compounds of the coffee beans, before and after roasting, and the sensory characteristics of the beverage. Coffea arabica beans of two varieties (cv. Mundo Novo and cv. Catuai Vermelho) were subjected to these four processing methods on a single farm in the Cerrado area of Brazil. RESULTS: Analysis by gas chromatography-mass spectrometry headspace solid-phase microextraction identified 40 volatile organic compounds in green coffee beans and 37 in roasted beans. The main difference between post-harvest treatments was that naturally processed green beans of both varieties contained a different profile of alcohols, acids, and lactones. In medium-roasted beans, those differences were not observed. The coffee beverages had similar taste attributes but distinct flavor profiles. Some of the treatments resulted in specialty-grade coffee, whereas others did not. CONCLUSION: The choice of a specific post-harvest processing method influences the volatile compounds found in green beans, the final beverage's flavor profile, and the cupping score, which can have a significant impact on the profitability of coffee farms' operations. © 2022 Society of Chemical Industry.


Assuntos
Coffea , Compostos Orgânicos Voláteis , Coffea/química , Manipulação de Alimentos/métodos , Lactonas/análise , Sementes/química , Compostos Orgânicos Voláteis/química
10.
Zhongguo Zhong Yao Za Zhi ; 47(5): 1293-1299, 2022 Mar.
Artigo em Zh | MEDLINE | ID: mdl-35343157

RESUMO

This study established a method for rapid quantification of terpene lactone, bilobalide, ginkgolide C, ginkgolide A and ginkgolide B in the chromatographic process of Ginkgo Folium based on near infrared spectroscopy(NIRS). The effects of competitive adaptive reweighting sampling(CARS), random frog(RF), and synergy interval partial least squares(siPLS) on the performance of partial least squares regression(PLSR) model were compared to the reference values measured by HPLC. Among them, the correlation coefficients of prediction(Rp) of validation sets of terpene lactone, bilobalide, and ginkgolide C were all higher than 0.98, and the relative standard errors of prediction(RSEPs) were 5.87%, 6.90% and 6.63%, respectively. Aiming at ginkgolide A and ginkgolide B with relatively low content, the genetic algorithm joint extreme learning machine(GA-ELM) was used to establish the optimized quantitative analysis model. Compared with CARS-PLSR model, the CARS-GA-ELM models of ginkgolide A and ginkgolide B exhibited a reduction in RSEP from 15.65% to 8.52% and from 21.28% to 10.84%, respectively, which met the needs of quantitative ana-lysis. It has been proved that NIRS can be used for the rapid detection of various lactone components in the chromatographic process of Ginkgo Folium.


Assuntos
Ginkgo biloba , Espectroscopia de Luz Próxima ao Infravermelho , Cromatografia Líquida de Alta Pressão , Lactonas/análise , Análise dos Mínimos Quadrados , Espectroscopia de Luz Próxima ao Infravermelho/métodos
11.
Zhongguo Zhong Yao Za Zhi ; 47(15): 4055-4065, 2022 Aug.
Artigo em Zh | MEDLINE | ID: mdl-36046895

RESUMO

The content of total flavonol glycosides in Ginkgo Folium in the planting bases was determined by high performance liquid chromatography(HPLC).The samples were extracted by reflux with methanol-25% hydrochloric acid.The HPLC conditions were as follows: Agilent ZORBAX SB-C_(18) column(4.6 mm×250 mm, 5 µm), isocratic elution with mobile phase of 0.4% phosphoric acid solution-methanol(45∶55), flow rate of 1 mL·min~(-1), column temperature of 30 ℃, detection wavelength of 360 nm, and injection vo-lume of 10 µL.A method for the determination of terpene lactones in Ginkgo Folium was established based on ultra-high performance liquid chromatograph-triple-quadrupole/linear ion-trap tandem mass spectrometry(UPLC-QTRAP-MS/MS).The UPLC conditions were as below: gradient elution with acetonitrile-0.1% formic acid, flow rate of 0.2 mL·min~(-1), column temperature of 30 ℃, sample chamber temperature of 10 ℃, and injection volume of 10 µL.The ESI~+and multiple reaction monitoring(MRM) were adopted for the MS.The above methods were used to determine the content of total flavonol glycosides and terpene lactones in 99 batches of Ginkgo Folium from 6 planting bases, and the results were statistically analyzed.The content of flavonoids and terpene lactones in Ginkgo Folium from different origins, from trees of different ages, harvested at different time, from trees of different genders, and processed with different methods was compared.The results showed that the content of total flavonol glucosides in 99 Ginkgo Folium samples ranged from 0.38% to 2.08%, and the total content of the four terpene lactones was in the range of 0.03%-0.87%.The method established in this study is simple and reliable, which can be used for the quantitative analysis of Ginkgo Folium.The research results lay a basis for the quality control of Ginkgo Folium.


Assuntos
Flavonoides , Ginkgo biloba , Cromatografia Líquida de Alta Pressão/métodos , Flavonoides/análise , Flavonóis , Glicosídeos/análise , Lactonas/análise , Metanol , Folhas de Planta/química , Espectrometria de Massas em Tandem/métodos , Terpenos/análise , Árvores
12.
Bioorg Med Chem Lett ; 53: 128414, 2021 12 01.
Artigo em Inglês | MEDLINE | ID: mdl-34666187

RESUMO

S-Palmitoylation is a reversible post-translational lipid modification that regulates protein trafficking and signaling. The enzymatic depalmitoylation of proteins is inhibited by the beta-lactones Palmostatin M and B, which have been found to target several serine hydrolases. In efforts to better understand the mechanism of action of Palmostatin M, we describe herein the synthesis, chemical proteomic analysis, and functional characterization of analogs of this compound. We identify Palmostatin M analogs that maintain inhibitory activity in N-Ras depalmitoylation assays while displaying complementary reactivity across the serine hydrolase class as measured by activity-based protein profiling. Active Palmostatin M analogs inhibit the recently characterized ABHD17 subfamily of depalmitoylating enzymes, while sparing other candidate depalmitoylases such as LYPLA1 and LYPLA2. These findings improve our understanding of the structure-activity relationship of Palmostatin M and refine the set of serine hydrolase targets relevant to the compound's effects on N-Ras palmitoylation dynamics.


Assuntos
Lactonas/análise , Propiolactona/análogos & derivados , Proteômica , Sulfonas/análise , Proteínas ras/metabolismo , Humanos , Lactonas/metabolismo , Lactonas/farmacologia , Estrutura Molecular , Propiolactona/análise , Propiolactona/metabolismo , Propiolactona/farmacologia , Sulfonas/metabolismo , Sulfonas/farmacologia , Proteínas ras/antagonistas & inibidores , Proteínas ras/química
13.
J Appl Microbiol ; 131(2): 833-843, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-33420735

RESUMO

AIMS: Alternaria alternata is a major contaminant of wine grapes, meaning a health risk for wine consumers due to the accumulation of toxic metabolites. To develop a successful biofungicide, the effectiveness of epiphytic wine grape yeasts against A. alternata growth and toxin production was assessed in vitro under temperature and aW conditions that simulate those present in the field. METHODS AND RESULTS: The effect of 14 antagonistic yeasts was evaluated on growth and alternariol (AOH), alternariol monomethyl ether (AME) and tenuazonic acid (TA) production by three A. alternata strains in a synthetic medium with composition similar to grape (SN) at three temperatures (15, 25 and 30°C). All Metschnikowia sp. yeast strains evaluated completely prevented A. alternata growth and mycotoxin production at all temperatures in SN medium. Meanwhile, the growth inhibition exerted by Starmerella bacillaris yeast strains was higher at 30°C, followed by 25 and 15°C, being able to show a stimulating or inhibiting effect. Hanseniaspora uvarum yeast strains showed a growth promoting activity higher at 15°C, followed by 25 and 30°C. Even at conditions where A. alternata growth was stimulated by the S. bacillaris and H. uvarum yeasts, high inhibitions of mycotoxin production (AOH, AME and TA) were observed, indicating a complex interaction between growth and mycotoxin production. CONCLUSION: There is a significant influence of temperature on the effectiveness of biocontrol against A. alternata growth and mycotoxin production. Metschnikowia sp. strains are good candidates to compose a biofungicide against A. alternata. SIGNIFICANCE AND IMPACT OF THE STUDY: Among the different antagonistic yeasts evaluated, only Metschnikowia sp. strains were equally effective reducing A. alternata growth and mycotoxin at different temperatures underlining the importance of considering environmental factors in the selection of the antagonists.


Assuntos
Antibiose , Micotoxinas , Vitis , Leveduras/fisiologia , Alternaria/patogenicidade , Frutas/microbiologia , Hanseniaspora , Lactonas/análise , Micotoxinas/análise , Saccharomycetales , Vitis/microbiologia , Vinho
14.
J Sep Sci ; 44(14): 2705-2716, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33951745

RESUMO

Kava, the rhizomes and roots of Piper methysticum Forst, is a popular edible medicinal herb traditionally used to prepare beverages for anxiety reduction. Since the German kava ban has been lifted by the court, the quality evaluation is particularly important for its application, especially the flavokawains which were believed to be responsible for hepatotoxicity. Now, by employing two different standard references and four different methods to calculate the relative correction factors, eight different quantitative analyses of multicomponents by single-marker methods have been developed for the simultaneous determination of eight major kavalactones and flavokawains in kava. The low standard method difference on quantitative measurement of the compounds among the external standard method and ours confirmed the reliability of the mentioned methods. A radar plot clearly illustrated that the contents of dihydrokavain and kavain were higher, whereas flavokawains A and B were lower in different kava samples. Only one of eight samples did not detect flavokawains that may be related to hepatotoxicity. In summary, by using different agents as an internal standard reference, the developed methods were believed as a powerful analytical tool not only for the qualitative and quantitative of kava constituents but also for the other multicomponents when authentic standard substances were unavailable.


Assuntos
Chalcona/análogos & derivados , Kava/química , Pironas , Chalcona/análise , Chalcona/química , Cromatografia Líquida de Alta Pressão/métodos , Suplementos Nutricionais , Lactonas/análise , Lactonas/química , Fitoterapia , Extratos Vegetais/análise , Extratos Vegetais/química , Raízes de Plantas/química , Plantas Medicinais , Pironas/análise , Pironas/química
15.
Biomed Chromatogr ; 35(10): e5170, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-33982313

RESUMO

Previously reported HPLC-evaporative light scattering detection methods for terpene trilactone determination in Ginkgo biloba leaf extract (EGBL) have complicated sample preparation steps and are time-consuming. Thus, in this work, an HPLC-MS method for the determination of terpene trilactones in EGBL was developed with a novel analytical quality by design approach to provide robust and simple measurements. For this purpose, analytical target profiles and systematic risk analyses were performed to identify potential critical method attributes and critical method parameters. After screening experiments, a Box-Behnken design approach was utilized to investigate the relationships between critical method attributes and critical method parameters. A hypercube design space obtained by a Monte Carlo method was used for choosing the analytical control strategy. Then, verification experiments were performed within the design space, and the models were found to be accurate. After that, the optimized method was verified and successfully used for quality control analysis of EGBL from different manufacturers, and the results were almost the same as those determined by HPLC-evaporative light scattering detection. To our knowledge, this is the first study to establish a robust HPLC-MS method for determination of terpene trilactones in EGBL based on a novel analytical quality by design concept, which can improve the quality control of commercial EGBL.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Lactonas/análise , Espectrometria de Massas/métodos , Extratos Vegetais/química , Terpenos/análise , Ginkgo biloba , Projetos de Pesquisa
16.
Int J Mol Sci ; 22(16)2021 Aug 13.
Artigo em Inglês | MEDLINE | ID: mdl-34445400

RESUMO

Alternariol (AOH) is an emerging mycotoxin produced by Alternaria molds. It occurs as a contaminant e.g., in oilseeds, cereals, grapes, and tomatoes. Chronic exposure to AOH may cause genotoxic and endocrine disruptor effects. Our recent studies demonstrated that the fluorescence signal of AOH can be strongly affected by the environmental pH as well as by the presence of serum albumin or cyclodextrins. In the current study, we aimed to characterize the most optimal circumstances regarding the highly sensitive fluorescent detection of AOH. Therefore, the further detailed investigation of the microenvironment on the fluorescence signal of the mycotoxin has been performed, including the effects of different buffers, organic solvents, detergents, and cations. Organic solvents (acetonitrile and methanol) caused only slight increase in the emission signal of AOH, while detergents (sodium dodecyl sulfate and Triton-X100) and Ca2+ induced considerably higher enhancement in the fluorescence of the mycotoxin. In addition, Mg2+ proved to be a superior fluorescence enhancer of the AOH. Spectroscopic and modeling studies suggest the formation of low-affinity AOH-Mg2+ complexes. The effect of Mg2+ was also tested in two HPLC assays: Our results show that Mg2+ can considerably increase the fluorescence signal of AOH even in a chromatographic system.


Assuntos
Alternaria/química , Lactonas/análise , Magnésio/química , Acetonitrilas/química , Cromatografia Líquida de Alta Pressão , Concentração de Íons de Hidrogênio , Lactonas/química , Metanol/química , Conformação Molecular , Estrutura Molecular , Octoxinol/química , Dodecilsulfato de Sódio/química , Espectrometria de Fluorescência
17.
Molecules ; 26(15)2021 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-34361835

RESUMO

The present study compared the effects of natural senescence and methyl jasmonate (JA-Me) treatment on the levels of terpene trilactones (TTLs; ginkgolides and bilobalide), phenolic acids, and flavonoids in the primary organs of Ginkgo biloba leaves, leaf blades, and petioles. Levels of the major TTLs, ginkgolides B and C, were significantly higher in the leaf blades of naturally senesced yellow leaves harvested on 20 October compared with green leaves harvested on 9 September. In petioles, a similar effect was found, although the levels of these compounds were almost half as high. These facts indicate the importance of the senescence process on TTL accumulation. Some flavonoids and phenolic acids also showed changes in content related to maturation or senescence. Generally, the application of JA-Me slightly but substantially increased the levels of TTLs in leaf blades irrespective of the difference in its application side on the leaves. Of the flavonoids analyzed, levels of quercetin, rutin, quercetin-4-glucoside, apigenin, and luteolin were dependent on the JA-Me application site, whereas levels of (+) catechin and (-) epicatechin were not. Application of JA-Me increased ferulic acid and p-coumaric acid esters in the petiole but decreased the levels of these compounds in the leaf blade. The content of p-coumaric acid glycosides and caffeic acid esters was only slightly modified by JA-Me. In general, JA-Me application affected leaf senescence by modifying the accumulation of ginkogolides, flavonoids, and phenolic acids. These effects were also found to be different in leaf blades and petioles. Based on JA-Me- and aging-related metabolic changes in endogenous levels of the secondary metabolites in G. biloba leaves, we discussed the results of study in the context of basic research and possible practical application.


Assuntos
Senescência Celular , Ciclopentanos/farmacologia , Flavonoides/metabolismo , Ginkgo biloba/metabolismo , Hidroxibenzoatos/metabolismo , Lactonas/metabolismo , Oxilipinas/farmacologia , Folhas de Planta/metabolismo , Flavonoides/análise , Ginkgo biloba/efeitos dos fármacos , Ginkgo biloba/crescimento & desenvolvimento , Hidroxibenzoatos/análise , Lactonas/análise , Reguladores de Crescimento de Plantas/farmacologia , Folhas de Planta/efeitos dos fármacos , Folhas de Planta/crescimento & desenvolvimento , Terpenos/análise , Terpenos/metabolismo
18.
J Sci Food Agric ; 101(9): 3732-3741, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33301191

RESUMO

BACKGROUND: Rice flour does not contain gluten and lacks cohesion and extensibility, which is responsible for the poor texture of rice noodles. Different technologies have been used to mitigate this challenge, including hydrothermal treatments of rice flour, direct addition of protein in noodles, use of additives such as hydrocolloids and alginates, and microbial transglutaminase (MTG). Recently, the inclusion of soy protein isolate (SPI), MTG, and glucono-δ-lactone (GDL) in the rice noodles system yielded rice noodles with improved texture and more compact microstructure, hence the need to optimize the addition of SPI, MTG, and GDL to make quality rice noodles. RESULTS: Numerical optimization showed that rice noodles prepared with SPI, 68.32 (g kg-1 of rice flour), MTG, 5.06 (g kg-1 of rice flour) and GDL, 5.0 (g kg-1 of rice flour) gave the best response variables; hardness (53.19 N), springiness (0.76), chewiness (20.28 J), tensile strength (60.35 kPa), and cooking time (5.15 min). The pH, sensory, and microstructure results showed that the optimized rice noodles had a more compact microstructure with fewer hollows, optimum pH for MTG action, and overall sensory panelists also showed the highest preference for the optimized formulation, compared to other samples selected from the numerical optimization and desirability tests. CONCLUSION: Optimization of the levels of SPI, MTG, and GDL yielded quality noodles with improved textural, mechanical, sensory, and microstructural properties. This was partly due to the favourable pH value of the optimized noodles that provided the most suitable conditions for MTG crosslinking and balanced electrostatic interaction of proteins. © 2020 Society of Chemical Industry.


Assuntos
Proteínas de Bactérias/análise , Aditivos Alimentares/análise , Manipulação de Alimentos/métodos , Gluconatos/análise , Lactonas/análise , Oryza/química , Proteínas de Soja/análise , Transglutaminases/análise , Culinária , Dieta Livre de Glúten , Farinha/análise , Dureza , Resistência à Tração
19.
J Sci Food Agric ; 101(7): 3071-3077, 2021 May.
Artigo em Inglês | MEDLINE | ID: mdl-33124688

RESUMO

BACKGROUND: Wheat is one of three major food crops in China. Alternaria species can cause spoilage of wheat with consequent mycotoxin accumulation. Alternariol (AOH), alternariol monomethyl ether (AME), and tenuazonic acid (TeA) are the most common and frequently studied mycotoxins. There are limited regulations placed on Alternaria mycotoxin concentrations worldwide due to the lack of toxicity data available. More data on the levels of mycotoxin contamination are also needed. It is also important to reduce the risks of Alternaria mycotoxins. RESULTS: One hundred and thirty-two wheat samples were collected from Hebei Province, China, and analyzed for AOH, AME, and TeA. Tenuazonic acid was found to be the predominant Alternaria mycotoxin, especially in flour samples. Studying Alternaria species that cause black-point disease of wheat indicated that Alternaria alternata and Alternaria tenuissima were the dominant species. Most of the Alternaria strains studied produced more than one mycotoxin and TeA was produced at the highest concentration, which may have resulted in the high level of TeA contamination in the wheat samples. Furthermore, magnolol displayed obvious antifungal and antimycotoxigenic activity against Alternaria. This is the first report on the antimycotoxigenic activity of magnolol against Alternaria species. CONCLUSION: The Alternaria mycotoxin contamination levels in wheat and wheat products from Hebei Province, China, were correlated with the toxigenic capacity of the Alternaria strains colonizing the wheat. Considering its safety, magnolol could be developed as a natural fungicide in wheat, or as a natural alternative food preservative based on its strong antifungal and antimycotoxigenic activity against Alternaria strains. © 2020 Society of Chemical Industry.


Assuntos
Alternaria/efeitos dos fármacos , Compostos de Bifenilo/farmacologia , Fungicidas Industriais/farmacologia , Lignanas/farmacologia , Triticum/microbiologia , Alternaria/metabolismo , China , Farinha/análise , Farinha/microbiologia , Contaminação de Alimentos/análise , Lactonas/análise , Lactonas/metabolismo , Doenças das Plantas/microbiologia , Doenças das Plantas/prevenção & controle , Ácido Tenuazônico/análise , Ácido Tenuazônico/metabolismo , Triticum/química
20.
J Environ Sci Health B ; 56(5): 467-476, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33852377

RESUMO

Different technologies to prepare long term pesticide forms include polymer coating, preparing composites and encapsulating pesticides in nanoparticles. A simple and low-cost method was proposed to obtain slow-release formulations by co-extrusion of a pesticide with a biodegradable polymer at a temperature above the melting points of both components. A herbicide metribuzin and low-melting polyester poly-ε-caprolactone were chosen for this work. Formulations containing 10%, 20%, and 40% herbicide were prepared. During 7 days of their exposition in water, it was released from 81% to 96% of initially loaded metribuzin; the highest release was detected for 40%-loaded forms. Biodegradation of the constructs and pesticide release were further studied in the model soil. Degradation rates of the specimens increased with an increase in pesticide content, from 9% to 20% over 14 weeks for the 10%/20%-loaded and the 40%-loaded specimens, respectively. The release of metribuzin reached, respectively, 37-38% and 55%. The herbicide content in soil was lower due to its partial degradation in soil; it reached 23-25% and 33%, respectively, from initially loaded into the polymer matrix. Release kinetics of metribuzin in water as in soil best fitted the First-order model. The used approach is promising for obtaining long-term release formulations for soil applications.


Assuntos
Caproatos/química , Herbicidas/química , Lactonas/química , Poliésteres/química , Poluentes do Solo/química , Triazinas/química , Biodegradação Ambiental , Caproatos/análise , Caproatos/farmacocinética , Preparações de Ação Retardada , Composição de Medicamentos , Herbicidas/análise , Herbicidas/farmacocinética , Cinética , Lactonas/análise , Lactonas/farmacocinética , Poliésteres/análise , Poliésteres/farmacocinética , Solo/química , Poluentes do Solo/análise , Poluentes do Solo/farmacocinética , Triazinas/análise , Triazinas/farmacocinética
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