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1.
Phytochemistry ; 173: 112326, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-32120117

RESUMO

Four undescribed alkaloids, 7-ethoxy-6-methoxy-2-methylisoquinolin-1(2H)-one, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, and 5,6-dihydroxy-N-methylphthalimide, were obtained from the root bark of Hernanadia nymphaeifolia, along with fourteen known compounds. The structures of these compounds were determined through spectroscopic and MS analyses. 7,8-Dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, 5,6-dihydroxy-N-methylphthalimide, oxohernagine, hernandonine, and N-trans-feruloylmethoxytyramine inhibited the superoxide anion (O2-) production (IC50 values ≤ 6.23 µg/mL) by neutrophils stimulated with formyl-L-methionyl-L-leuckyl-L-phenyl-alanine/cytochalasin B (fMLP/CB). Furthermore, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, 5,6-dihydroxy-N-methylphthalimide, oxohernagine, and N-trans-feruloylmethoxytyramine inhibited fMLP/CB-induced elastase release with IC50 values ≤ 7.41 µg/mL. In addition, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, oxohernagine, and N-trans-feruloylmethoxytyramine showed potent inhibition with IC50 values ≤ 28.55 µM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation.


Assuntos
Alcaloides , Hernandiaceae , Anti-Inflamatórios , N-Formilmetionina Leucil-Fenilalanina , Neutrófilos , Elastase Pancreática , Casca de Planta , Superóxidos
2.
Phytochemistry ; 173: 112314, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-32120118

RESUMO

The genus Ocotea is one of the largest and most economically explored in the Lauraceae family. However, its current industrial use is limited by the difficult identification of Ocotea species. At present, the genus is botanically considered a complex since accurate classification is very difficult to achieve based on taxonomic characteristics. As chemophenetics can aid in Ocotea species identification processes, we propose to evaluate the chemical data in several studies of Lauraceae species published between 1906 and 2019 in order to provide insights of the identification issue of matrix which DNA material or full morphological characteristics may not be readily available. Several alkaloids and lignoids have been found to be specifically synthesized by Ocotea species, enabling their usage in species identification by targeted and untargeted metabolomic approaches. The multivariate analysis of alkaloid, lignoid and flavonoid profiles allowed the characterization of subsets of species, the differentiation of chemical profile based on plant parts (leaves and branches), and to elucidate specific biomarkers for species. The previous chemophenetic model was contradicted by our data using statistical tools, such as HCPC, which allowed clustering adjustments based not only in the presence or absence of two single chemical classes. Chemophenetic study has proved to be a reliable tool in the enhancement of the identification and comprehension of this genus and the family. Here, the current status, pitfalls and future perspectives in Ocotea species metabolomic characterization will be presented.


Assuntos
Alcaloides , Lauraceae , Ocotea , Extratos Vegetais , Folhas de Planta
3.
Acta Cir Bras ; 34(12): e201901205, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32049185

RESUMO

PURPOSE: To investigate the effects of huperzine A (HupA) on hippocampal inflammatory response and neurotrophic factors in aged rats after anesthesia. METHODS: Thirty-six Sprague Dawley rats (20-22 months old) were randomly divided into control, isofluran, and isoflurane+HupA groups; 12 rats in each group. The isoflurane+HupA group was intraperitoneally injected with 0.2 mg/kg of HupA. After 30 min, isoflurane inhalation anesthesia was performed in the isoflurane and isoflurane+HupA groups. After 24 h from anesthesia, Morris water maze experiment and open-field test were performed. Hippocampal inflammatory and neurotrophic factors were determined. RESULTS: Compared with isoflurane group, in isofluran+HupA group the escape latency of rats was significantly decreased (P < 0.05), the original platform quadrant residence time and traversing times were significantly increased (P < 0.05), the central area residence time was significantly increased (P < 0.05), the hippocampal tumor necrosis factor α, interleukin 6 and interleukin 1ß levels were significantly decreased (P < 0.05), and the hippocampal nerve growth factor, brain derived neurotrophic factor and neurotrophin-3 levels were significantly increased (P < 0.05). CONCLUSION: HupA may alleviate the cognitive impairment in rats after isoflurane anesthesia by decreasing inflammatory factors and increasing hippocampal neurotrophic factors in hippocampus tissue.


Assuntos
Alcaloides/farmacologia , Anestésicos Inalatórios/efeitos adversos , Hipocampo/efeitos dos fármacos , Isoflurano/efeitos adversos , Fatores de Crescimento Neural/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Sesquiterpenos/farmacologia , Anestesia/efeitos adversos , Animais , Ensaio de Imunoadsorção Enzimática , Hipocampo/metabolismo , Humanos , Interleucina-1beta/análise , Interleucina-6/análise , Masculino , Aprendizagem em Labirinto , Fatores de Crescimento Neural/análise , Distribuição Aleatória , Ratos Sprague-Dawley , Reprodutibilidade dos Testes , Fatores de Tempo , Resultado do Tratamento , Fator de Necrose Tumoral alfa/análise
4.
J Agric Food Chem ; 68(10): 3140-3148, 2020 Mar 11.
Artigo em Inglês | MEDLINE | ID: mdl-32053361

RESUMO

3-O-Cinnamoylepicatechin (1) was synthesized along with four flavoalkaloids, (-)-6-(5‴S)-N-ethyl-2-pyrrolidinone-3-O-cinnamoylepicatechin (2), (-)-6-(5‴R)-N-ethyl-2-pyrrolidinone-3-O-cinnamoylepicatechin (3), (-)-8-(5‴S)-N-ethyl-2-pyrrolidinone-3-O-cinnamoylepicatechin (4), and (-)-8-(5‴R)-N-ethyl-2-pyrrolidinone-3-O-cinnamoylepicatechin (5) via esterification of epicatechin followed by phenolic Mannich reaction of 1 with theanine in the presence of heat. The new compounds 1-5 were detected in leaves of three tea cultivars, Fuding-Dabai, Huangjingui, and Zimudan with the help of ultra-performance liquid chromatography hyphenated with a photodiode array detector and electrospray ionization high-resolution mass spectrometry (UPLC-PDA-ESI-HRMS), suggesting that they are naturally occurring in tea leaves. The structures of the novel natural products were characterized by one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) and mass spectroscopy. Compounds 1-5 were then evaluated for their acetylcholinesterase (AChE) inhibitory effect (IC50 = 0.12-1.02 µM). The availability of the synthesized epicatechin derivatives 1-5 via a synthetic route enabled the first unequivocal identification of these derivatives as tea secondary metabolites and made it possible to determine their content in the tea material as well as the diverse bioactivities.


Assuntos
Alcaloides/química , Camellia sinensis/química , Inibidores da Colinesterase/química , Extratos Vegetais/química , Acetilcolinesterase/química , Cromatografia Líquida de Alta Pressão , Folhas de Planta/química , Espectrometria de Massas por Ionização por Electrospray
5.
Alkaloids Chem Biol ; 83: 1-112, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32098648

RESUMO

Lamellarins are marine alkaloids containing fused 14-phenyl-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinoline or non-fused 3,4-diarylpyrrole-2-carboxylate ring systems. To date, more than 50 lamellarins have been isolated from a variety of marine organisms, such as mollusks, tunicates, and sponges. Many of them, especially fused type I lamellarins, exhibit impressive biological activity, such as potent cytotoxicity, topoisomerase I inhibition, protein kinases inhibition, and anti-HIV-1 activity. Due to their useful biological activity and limited availability from natural sources, a number of synthetic methods have been developed. In this chapter, we present an updated and comprehensive review on lamellarin alkaloids summarizing their isolation, synthesis, and biological activity.


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Fármacos Anti-HIV/farmacologia , Antineoplásicos/farmacologia , Inibidores de Proteínas Quinases/farmacologia , Pirróis/isolamento & purificação , Pirróis/farmacologia , Inibidores da Topoisomerase I/farmacologia , Alcaloides/síntese química , Alcaloides/química , Animais , Fármacos Anti-HIV/síntese química , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Antineoplásicos/síntese química , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Humanos , Inibidores de Proteínas Quinases/síntese química , Inibidores de Proteínas Quinases/química , Inibidores de Proteínas Quinases/isolamento & purificação , Pirróis/síntese química , Pirróis/química , Inibidores da Topoisomerase I/síntese química , Inibidores da Topoisomerase I/química , Inibidores da Topoisomerase I/isolamento & purificação
6.
J Agric Food Chem ; 68(8): 2406-2417, 2020 Feb 26.
Artigo em Inglês | MEDLINE | ID: mdl-32031370

RESUMO

Black pepper (Piper nigrum L.) has been commonly utilized in food preparation and traditional medicine in several countries. Seven new amide alkaloids, pipernigramides A-G (3, 10, 38, and 41-44), a new piperic ester, pipernigrester A (48), along with 47 known compounds were isolated from the EtOH extract of P. nigrum. The inhibitory effects on nitric oxide (NO) of all compounds were then evaluated. Among the tested compounds, three of them (42-44) significantly inhibited inducible nitric oxide synthase (iNOS)-mediated NO (IC50 = 4.74 ± 0.18, 4.08 ± 0.19, and 3.71 ± 0.32 µM, respectively), and IL-1ß, IL-6, TNF-α, and PGE2 release in RAW 264.7 cells stimulated by lipopolysaccharide. Moreover, 42-44 suppressed IκB degradation and further inhibited the cytosol-nucleus translocation of the p65 subunit by targeting IKK-ß. In the carrageenan-induced paw edema test, 42-44 demonstrated anti-inflammatory effects as well. These results indicate that all three compounds from P.nigrum have the potential anti-inflammatory effects.


Assuntos
Alcaloides/farmacologia , Anti-Inflamatórios/farmacologia , Macrófagos/efeitos dos fármacos , NF-kappa B/imunologia , Piper nigrum/química , Extratos Vegetais/farmacologia , Alcaloides/química , Animais , Anti-Inflamatórios/química , Dinoprostona/imunologia , Interleucina-6/genética , Interleucina-6/imunologia , Macrófagos/imunologia , Camundongos , Estrutura Molecular , NF-kappa B/genética , Óxido Nítrico Sintase Tipo II/genética , Óxido Nítrico Sintase Tipo II/imunologia , Extratos Vegetais/química , Células RAW 264.7
8.
Top Curr Chem (Cham) ; 378(2): 22, 2020 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-32030596

RESUMO

Heterocyclic compounds having a nitrogen atom in the ring exhibit very interesting biological activities. Indole is the core structure of many bioactive compounds owing to its high affinity to bind with most biological targets. Indole is an electron-rich compound and generally prefers electrophilic rather than nucleophilic substitution. Hence, many important indole derivatives are difficult to synthesize through the conventional reactivity of indole. This limitation can be avoided by using the umpolung, from the German word meaning polarity inversion. In umpolung, the indole molecule, especially the C2 and C3 positions, behave as an electrophile. As C2-functionalized indoles have substantial importance in synthetic and pharmaceutical chemistry, this review focuses on the C2 umpolung of indoles via the indirect approach which is less explored. Unlike direct approaches of indole umpolung, indirect methods have several advantages and therefore a number of research articles have been published in this field. But no review is available up till now. This is the first review on this topic and we believe that it will surely motivate the readers to work in this area further.


Assuntos
Carbono/química , Indóis/química , Alcaloides/síntese química , Alcaloides/química , Catálise , Ciclização , Iodo/química , Quinolinas/síntese química , Quinolinas/química , Ácidos Sulfínicos/química
9.
Chem Pharm Bull (Tokyo) ; 68(2): 103-116, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32009077

RESUMO

The merits of biogenetic considerations in the chemical syntheses of natural products have been emphasized by describing the total syntheses of Lycopodium alkaloids; lycodine, flabellidine, lycopodine, and flabelliformine, as well as monoterpenoid indole alkaloids; C-mavacurine, kopsiyunnanine K, koumine, and 11-methoxy-19R-hydroxygelselegine.


Assuntos
Alcaloides/síntese química , Produtos Biológicos/síntese química , Técnicas de Química Sintética/métodos , Lycopodium/química , Alcaloides de Triptamina e Secologanina/síntese química , Alcaloides/química , Produtos Biológicos/química , Alcaloides de Triptamina e Secologanina/química
10.
Chem Pharm Bull (Tokyo) ; 68(2): 140-149, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32009081

RESUMO

Previously, we reported that the c-Met inhibitory effect of Ephedra Herb extract (EHE) is derived from ingredients besides ephedrine alkaloids. Moreover, analgesic and anti-influenza activities of EHE and ephedrine alkaloids-free Ephedra Herb extract (EFE) have been reported recently. In this study, we examined the fractions containing c-Met kinase inhibitory activity from EHE and the fractions with analgesic and anti-influenza activities from EFE, and elucidated the structural characteristics of the active fractions. Significant c-Met kinase activity was observed in 30, 40, and 50% methanol (MeOH) eluate fractions obtained from water extract of EHE using Diaion HP-20 column chromatography. Similarly, 20 and 40% MeOH, and MeOH eluate fractions obtained from water extract of EFE were found to display analgesic and anti-influenza activities. Reversed phase-HPLC analysis of the active fractions commonly showed broad peaks characteristic of high-molecular mass condensed tannin. The active fractions were analyzed using 13C-NMR and decomposition reactions; the deduced structures of active components were high-molecular mass condensed tannins, which were mainly procyanidin B-type and partly procyanidin A-type, including pyrogallol- and catechol-type flavan 3-ols as extension and terminal units. HPLC and gel permeation chromatography (GPC) analyses estimated that the ratio of pyrogallol- and catechol-type was approximately 9 : 2, and the weight-average molecular weight based on the polystyrene standard was >45000. Furthermore, GPC-based analysis was proposed as the quality evaluation method for high-molecular mass condensed tannin in EHE and EFE.


Assuntos
Ephedra/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Alcaloides/química , Alcaloides/farmacologia , Analgésicos/química , Analgésicos/farmacologia , Animais , Antivirais/química , Antivirais/farmacologia , Biflavonoides/química , Biflavonoides/farmacologia , Catequina/química , Catequina/farmacologia , Linhagem Celular Tumoral , Cães , Efedrina/química , Efedrina/farmacologia , Humanos , Células Madin Darby de Rim Canino , Masculino , Camundongos , Proantocianidinas/química , Proantocianidinas/farmacologia , Inibidores de Proteínas Quinases/química , Inibidores de Proteínas Quinases/farmacologia , Proteínas Proto-Oncogênicas c-met/antagonistas & inibidores
11.
Anticancer Res ; 40(2): 689-694, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-32014909

RESUMO

BACKGROUND/AIM: Piperine, a major alkaloid of the fruit of black pepper plants, selectively inhibits the growth of triple-negative breast cancer cells but its lipophilicity restricts possible clinical application. This study therefore determined the feasibility of encapsulating piperine in nanoparticles (NPs) to increase its solubility in an aqueous environment. MATERIALS AND METHODS: Piperine-loaded biodegradable methoxy poly(ethylene glycol)-poly(lactic-co-glycolic) acid copolymer-based NPs were produced by single emulsion solvent extraction and thin-film hydration. Growth and viability of triple-negative breast cancer (TNBC) cells were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and Annexin-V-FLUOS/propidium iodide staining, respectively. RESULTS: Thin-film hydration was superior to single emulsion solvent extraction, yielding piperine-loaded NPs with an average size of 50 nm. Piperine-loaded NPs inhibited TNBC cell growth and induced apoptosis while sparing normal fibroblasts. CONCLUSION: It is feasible to deliver a cytotoxic concentration of piperine to TNBC cells via NPs with the potential for improved bioavailability and solubility in biological fluids.


Assuntos
Alcaloides/administração & dosagem , Benzodioxóis/administração & dosagem , Nanopartículas/administração & dosagem , Piperidinas/administração & dosagem , Alcamidas Poli-Insaturadas/administração & dosagem , Neoplasias de Mama Triplo Negativas/tratamento farmacológico , Alcaloides/química , Antineoplásicos Fitogênicos/administração & dosagem , Antineoplásicos Fitogênicos/química , Apoptose/efeitos dos fármacos , Benzodioxóis/química , Linhagem Celular Tumoral , Emulsões/administração & dosagem , Emulsões/química , Feminino , Humanos , Nanopartículas/química , Piperidinas/química , Poliésteres/administração & dosagem , Poliésteres/química , Polietilenoglicóis/administração & dosagem , Polietilenoglicóis/química , Alcamidas Poli-Insaturadas/química , Neoplasias de Mama Triplo Negativas/patologia
12.
Phytochemistry ; 173: 112296, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-32087436

RESUMO

The first phytochemical examination of extracts from leaves and stem bark of Palicourea luxurians (Rusby) Borhidi yielded two undescribed and one known alstrostine derivative together with the oxindole alkaloid javaniside as well as with 5α-carboxystrictosidine. Additionally, five iridoids and four secologanin derived isolation artifacts have been isolated. Lack of strictosidine and its follow-up metabolization products suggested that the Pictet-Spenglerase in P. luxurians does barely or not catalyze the formation of strictosidine. Against this background the biosynthesis of javaniside and 5α-carboxystrictosidine is discussed with regard to possible reaction mechanisms. Similarly, P. luxurians used an independent biosynthetic pathway to produce alstrostine type structures from secologanin and tryptamine in a 2:1 ratio. The structure of isoalstrostine A, which was isolated for the first time, allowed the refinement of a previously reported pathway to the alstrostine type carbon skeleton as well as to some follow-up metabolization products. In spite of various biosynthetic pathways incorporating secologanin to gain different types of tryptophan- and tryptamine-iridoid alkaloids, P. luxurians accumulates this compound as well a couple of further metabolized iridoids deriving from loganin and secologanin.


Assuntos
Alcaloides , Rubiaceae , Alcaloides de Triptamina e Secologanina , Glucosídeos Iridoides , Iridoides , Triptaminas , Triptofano , Alcaloides de Vinca
13.
Ecotoxicol Environ Saf ; 190: 110134, 2020 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-31901541

RESUMO

The widely distributed ß-carboline alkaloids exhibit promising psychopharmacological and biochemical effects. Harmine, a natural ß-carboline, can inhibit insect growth and development with unclear mechanisms. In this study, harmine (at 0-200 mg/L) showed a dose-dependent inhibitory effect on the pupal weight, length, height, pupation rate and eclosion rate of fruit flies Drosophila melanogaster, which was similar to the inhibition induced by the well-known botanical insect growth regulator azadirachtin. Moreover, the expression levels of major regulators from the developmental signaling network were down-regulated during the pupal stage except Numb, Fringe, Yorkie and Pten. The Notch, Wnt, Hedgehog and TGF-ß pathways mainly played vital roles in coping with harmine exposure in pupae stage, while the Hippo, Hedgehog and TGF-ß elements were involved in the sex differences. Notch, Hippo, Hedgehog, Dpp and Armadillo were proved to be suppressed in the developmental inhibition with fly mutants, while Numb and Punt were increased by harmine. In conclusion, harmine significantly inhibited the development of Drosophila by negatively affecting their developmental signaling network during different stages. Our results establish a preliminary understanding of the developmental signaling network subjected to botanical component-induced growth inhibition and lay the groundwork for further application.


Assuntos
Alcaloides/metabolismo , Drosophila melanogaster/fisiologia , Harmina/metabolismo , Animais , Carbolinas , Regulação para Baixo/efeitos dos fármacos , Proteínas de Drosophila/genética , Drosophila melanogaster/metabolismo , Drosophilidae , Hormônios Juvenis , Limoninas , Proteínas Nucleares , Pupa/metabolismo , Transativadores
14.
J Agric Food Chem ; 68(5): 1169-1185, 2020 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-31922733

RESUMO

Epichloë endophytes in forage grasses have attracted widespread attention and interest of chemistry researchers as a result of the various unique chemical structures and interesting biological activities of their secondary metabolites. This review describes the diversity of unique chemical structures of taxa from Epichloë endophytes and grass infected with Epichloë endophytes and demonstrates their reported biological activities. Until now, nearly 160 secondary metabolites (alkaloids, peptides, indole derivatives, pyrimidines, sesquiterpenoids, flavonoids, phenol and phenolic acid derivatives, aliphatic metabolites, sterols, amines and amides, and others) have been reported from Epichloë endophytes and grass infected with Epichloë endophytes. Among these, non-alkaloids account for half of the population of total metabolites, indicating that they also play an important role in Epichloë endophytes and grass infected with Epichloë endophytes. Also, a diverse array of secondary metabolites isolated from Epichloë endophytes and symbionts is a rich source for developing new pesticides and drugs. Bioassays disclose that, in addition to toxic alkaloids, the other metabolites isolated from Epichloë endophytes and symbionts have notable biological activities, such as antifungal, anti-insect, and phytotoxic activities. Accordingly, the biological functions of non-alkaloids should not be neglected in the future investigation of Epichloë endophytes and symbionts.


Assuntos
Alcaloides/metabolismo , Endófitos/química , Epichloe/química , Poaceae/microbiologia , Simbiose , Alcaloides/química , Alcaloides/toxicidade , Animais , Endófitos/fisiologia , Epichloe/metabolismo , Insetos/efeitos dos fármacos , Gado/metabolismo , Poaceae/fisiologia
15.
Food Chem ; 312: 126030, 2020 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-31911353

RESUMO

This study developed comprehensive quantification methods for major nutritive and antinutritive phytochemical aglycones in edible African nightshade leaves, an underutilized food resource in the sub-Saharan area. A simultaneous hydrolysis and extraction method was developed using methanol with 2 M sulfuric acid with incubation at 65 °C for 60 min. UHPLC-QqQ-MS/MS methods were developed and validated for hydrolysis optimization and for quantification of eight major aglycones of polyphenols, alkaloids and sapogenins in 20 differently sourced nightshade leaves, comprising two African species Solanum scabrum and S. nigrum, and from two distinct cultivation sites, one in New Jersey, US and the other in Kenya Eldoret. Variation in species, accessions and cultivation environment played an important role in affecting the phytochemical profile. Total antinutritive alkaloids and sapogenins in all nightshade leaves were evaluated and found to be safe for consumption. This work provides evidence that the consumption of African nightshade leaves as a nutrient rich leafy green vegetable is safe and can contribute to food security and nutritional improvement in the sub-Saharan area.


Assuntos
Alcaloides/análise , Polifenóis/análise , Saponinas/análise , Solanum/química , Cromatografia Líquida de Alta Pressão/métodos , Glicosilação , Hidrólise , Quênia , Análise Multivariada , Folhas de Planta/química , Espectrometria de Massas em Tandem
16.
Plant Mol Biol ; 102(4-5): 477-499, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31902069

RESUMO

KEY MESSAGE: The study carry out comprehensive transcriptome analysis of C. deltoidea and exploration of BIAs biosynthesis and accumulation based on UHPLC-MS/MS and combined sequencing platforms. Coptis deltoidea is an important medicinal plant with a long history of medicinal use, which is rich in benzylisoquinoline alkaloids (BIAs). In this study, Ultra performance liquid chromatography-electrospray ionization tandem mass spectrometry (UHPLC-ESI-MS/MS) and combined sequencing platforms were performed for exploration of BIAs biosynthesis, accumulation and comprehensive transcriptome analysis of C. deltoidea. By metabolism profiling, the accumulation of ten BIAs was analyzed using UHPLC-MS/MS and different contents were observed in different organs. From transcriptome sequencing result, we applied single-molecule real-time (SMRT) sequencing to C. deltoidea and generated a total of 75,438 full-length transcripts. We proposed the candidate biosynthetic pathway of tyrosine, precursor of BIAs, and identified 64 full length-transcripts encoding enzymes putatively involved in BIAs biosynthesis. RNA-Seq data indicated that the majority of genes exhibited relatively high expression level in roots. Transport of BIAs was also important for their accumulation. Here, 9 ABC transporters and 2 MATE transporters highly homologous to known alkaloid transporters related with BIAs transport in roots and rhizomes were identified. These findings based on the combined sequencing platforms provide valuable genetic information for C. deltoidea and the results of transcriptome combined with metabolome analysis can help us better understand BIAs biosynthesis and transport in this medicinal plant. The information will be critical for further characterization of C. deltoidea transcriptome and molecular-assisted breeding for this medicinal plant with scarce resources.


Assuntos
Alcaloides/biossíntese , Benzilisoquinolinas/química , Coptis/genética , Coptis/metabolismo , Transcriptoma , Cromatografia Líquida de Alta Pressão , Perfilação da Expressão Gênica , Regulação da Expressão Gênica de Plantas , Filogenia , Folhas de Planta/metabolismo , Raízes de Plantas/metabolismo , Plantas Medicinais/metabolismo , Rizoma/metabolismo , Análise de Sequência de DNA , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em Tandem
17.
Forensic Sci Int ; 307: 110105, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31915111

RESUMO

The main psychoactive compound in Khat is cathinone which consists of two enantiomers, S-(-)-cathinone being more stimulant than its R antipode. This study aimed to the enantioseparation and determination of these two stereoisomers in different parts of fresh Catha edulis. The samples were solvent extracted and cathinone was derivatized with menthyl chloroformate. The separation of the two diastereomeric derivatives was carried out by gas chromatography and showed an excellent resolution, while their structure was confirmed by mass spectrometry. The quantitative determination of both enantiomers showed a different distribution in various investigated parts of the plant, as shown in their enantiomeric excess. Unlike the results published in some previous articles, the current study confirmed the presence of both S and R cathinone in all parts of the fresh plant. The concentration of S-cathinone was higher in stems while its values were lower in leaves. The obtained concentrations were in the ranges 0.081-0.290 and 0.087-0.211 mg/g for S and R antipodes, respectively. Also, S-cathinone which is the most psychoactive stereoisomer showed an increasing concentration from lower to upper stems of the plant. The present study is the first quantitative investigation of the two cathinone enantiomers in different parts of fresh Catha edulis.


Assuntos
Alcaloides/análise , Catha/química , Cromatografia Gasosa-Espectrometria de Massas , Extratos Vegetais/química , Folhas de Planta/química , Estereoisomerismo
18.
Food Chem ; 312: 126068, 2020 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-31918364

RESUMO

The present study aimed at the identification of novel imidazole alkaloids derived from histamine or histidinol and generally investigating the occurrence of suchlike alkaloids in a variety of foodstuffs. Herein, N-caprylhistamine was synthesized and the glucosidic derivative N-caprylhistamine-ß-glucoside was isolated from ripe tomato fruits and structurally characterized. The obtained reference standards were used for the extension of an established LC-MS/MS-based method for the quantitation of several imidazole alkaloids in tomato products. After validation for the two additional analytes and demonstrating the applicability of the method to nine other food matrices, 104 food items were screened for the occurrence of the described imidazole alkaloids. Remarkably, all of the investigated alkaloids were only quantifiable in tomato-based products and the occurrence of N-caprylhistamine and N-caprylhistamine-ß-glucoside was reported for the first time. These imidazole alkaloids could thus be applicable as specific intake biomarkers for tomatoes and their biological activities as well as metabolic fate should be investigated in future research.


Assuntos
Glucosídeos/química , Lycopersicon esculentum/química , Alcaloides/química , Cromatografia Líquida/métodos , Frutas/química , Imidazóis/química , Espectrometria de Massas em Tandem/métodos
19.
Anticancer Res ; 40(1): 323-333, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31892583

RESUMO

BACKGROUND/AIM: Despite the Warburg effect, mitochondria play an essential role in the survival and maintenance of cancer cells. Thus, mitochondria have been considered a target for anticancer agents. Here, we identified a mitochondria-targeting anticancer agent from natural products. MATERIALS AND METHODS: Morphological and functional changes in mitochondria were determined by a fluorescence-based High Content Imaging System. Using human non-small cell lung cancer (NSCLC) cell lines (H1299, H226B, and A549), cell viability and colony formation assays, cell cycle analysis, and immunoblotting were performed to determine cytotoxic and proapoptotic effects of papuamine. RESULTS: Using a natural product chemical library, we identified papuamine as an active compound to inhibit viability and ATP production of NSCLC cells. Papuamine depleted intracellular ATP by causing mitochondrial dysfunction, as indicated by the loss of the mitochondrial membrane potential and increased mitochondrial superoxide generation. Papuamine significantly inhibited viability and colony formation of NSCLC cells by inducing apoptosis. CONCLUSION: Papuamine has a potential as a novel mitochondria-targeting anticancer agent.


Assuntos
Alcaloides/uso terapêutico , Carcinoma Pulmonar de Células não Pequenas/tratamento farmacológico , Neoplasias Pulmonares/tratamento farmacológico , Mitocôndrias/patologia , Células A549 , Trifosfato de Adenosina/metabolismo , Adenilato Quinase/metabolismo , Alcaloides/química , Alcaloides/farmacologia , Carcinoma Pulmonar de Células não Pequenas/patologia , Sobrevivência Celular/efeitos dos fármacos , Humanos , Neoplasias Pulmonares/patologia , Mitocôndrias/efeitos dos fármacos , Ensaio Tumoral de Célula-Tronco , Regulação para Cima/efeitos dos fármacos
20.
Phytochemistry ; 172: 112260, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-31982646

RESUMO

Six undescribed quinoline alkaloids, named dasycarines A-E, and 18 known ones were isolated from the root bark of Dictamnus dasycarpus. All the structures were elucidated on the basis of comprehensive analysis of UV, IR, NMR, and HRMS spectroscopic data, and the absolute configurations were assigned via comparison of the calculated and experimental ECD data. (+)-Dasycarine A (1a) and (-)-Dasycarine A (1b) are a pair of enantiomers of dimeric furoquinoline alkaloid, which are the first dimeric via [2 + 2] cycloaddition of furan. The structure and absolute configuration of (-)-dasycarine A was determined via X-ray crystallography. Additionally, all the isolated compounds were tested for their inhibitory effects on NO production stimulated by LPS in BV-2 microglial cells. Three compounds showed strong inhibition with IC50 values below 5.0 µM; nine compounds exhibited inhibition with IC50 values in the range of 7.8-28.4 µM. Furthermore, we demonstrated that preskimmianine suppressed the levels of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and nuclear factor kappa B (NF-κB) in LPS-induced BV-2 microglial cells.


Assuntos
Alcaloides , Dictamnus , Quinolinas , Anti-Inflamatórios , Casca de Planta
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