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1.
Zhongguo Zhong Yao Za Zhi ; 45(14): 3422-3431, 2020 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-32726058

RESUMO

In this study, based on the transcriptome database of suspension cells of Arnebia euchroma, we explored two candidate cytochrome P450 enzyme genes that might relate to the shikonin biosynthesis downstream pathway when CYP76B74 sequence was referenced. We constructed interference-type hairy roots of candidate genes and cultured them. We measured the fresh weight, dry weight, total naphthoquinone content, shikonin and its derivatives content and expression levels of key enzyme genes involved in shikonin biosynthesis pathway. The effects of candidate genes on the growth and shikonin production of A. euchroma hairy roots were discussed, and the possible regulatory mechanisms that candidate genes affected shikonin synthesis were discussed. Through local Blast and phylogenetic analysis, two candidate CYP450 genes(CYP76B75 and CYP76B100) with high homology to CYP76B74 in A. euchroma were screened, and corresponding interference hairy roots were constructed. Compared with the control(RNAi-control), the fresh weight of CYP76B75 interfered hairy root(RNAi-CYP76B75) and CYP76B100 interfered hairy root(RNAi-CYP76B100) were significantly reduced, while dry weight were not affected, so the dry rate increased significantly. Except for ß-acetoxyisovalerylalkannin, which is high in three groups of hairy roots, the contents of shikonin, deoxyshikonin, acetylshikonin, ß,ß'-dimethacrylicalkannin, ß-hydroxyisovalerylshikonin,ß-hydroxyisovalerylshikonin, isobutyrylshikonin and total naphthoquinones showed a consistent pattern: RNAi-CYP76B75>RNAi-CYP76B100>RNAi-control. Among them, the synthesis of ß-hydroxyisovalerylshikonin was most significantly promoted by interfering with the expression of CYP76B75. The content of ß-hydroxyisovalerylshikonin in RNAi-CYP76B75 was 11.7 times that of RNAi-control. RESULTS:: of real-time qPCR analysis showed that compared to RNAi-control, the expression levels of AePGT gene in RNAi-CYP76B75 and RNAi-CYP76B100 were not changed significantly, and the expression levels of CYP76B74 and AeHMGR were up-regulated. In addition, the expression level of CYP76B100 in RNAi-CYP76B75 was down-regulated, whereas in RNAi-CYP76B100, the expression of CYP76B75 was significantly up-regulated. Therefore, this study confirmed that when the expression of CYP76B75 and CYP76B100 were interrupted, the growth of hairy roots were suppressed, but the synthesis of shikonin were promoted. They might increase the shikonin biosynthesis by up-regulating the expression of CYP76B74 in the hairy roots of A. euchroma.


Assuntos
Boraginaceae/genética , Naftoquinonas , Sistema Enzimático do Citocromo P-450 , Filogenia , Raízes de Plantas , RNA , Interferência de RNA
2.
PLoS One ; 15(6): e0233516, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32479498

RESUMO

The Balkans endemic species Alkanna primuliflora Griseb., A. stribrnyi Velen., and A. graeca Boiss. & Spruner have limited distribution in the Balkan Peninsula and a large variation in the morphological characteristics. The populations of the three Alkanna species in the Bulgarian flora are small and fragmented. There are no previous reports on the chemical profile or on the embryology of these species. The hypothesis was that the limited distribution of A. primuliflora, A. stribrnyi, and A. graeca was due to their reproductive capacity and genetic diversity. Furthermore, we hypothesized that the three species will contain pyrrolizidine alkaloids (PAs), as other species of the genus Alkanna (Boraginaceae), but they would have differential alkaloids composition. The population genetic structure and differentiation showed a clear distinction between species and revealed average levels of genetic diversity among the natural populations of the three Alkanna species. The embryological investigation observed stability of the processes in the male and female generative spheres and high viability of mature pollen and embryo of the three species. The normal formation of male and female gametophytes without deviations or degenerative processes, and observed levels of genetic diversity between Alkanna individuals are important in maintaining the size and resilience of the Alkanna populations. Eight alkaloids were identified by GC-MS in A. primuliflora and A. graeca and six alkaloids in A. stribrnyi. The main pyrrolizidine alkaloids (PAs) in all investigated species was triangularine. A. primuliflora and A. graeca showed similar chemical composition that comprised 9-angeloylretronecine, 7-tigloylretronecine, 9-tigloylretronecine, triangularicine, dihydroxytriangularine, dihydroxytriangularicine, whereas, in A. stribrnyi 9-tigloylretronecine, triangularicine and dihydroxytriangularicine were not found. This is the first report on the presence of PAs in A. primuliflora, A. stribrnyi and A. graeca. Besides, this is the first report on the embryology of these endemic species. The results contribute to the knowledge of the three endemic Alkanna species and will facilitate policy-making and defining new strategies for their conservation.


Assuntos
Boraginaceae/química , Boraginaceae/genética , Alcaloides/análise , Península Balcânica , Boraginaceae/metabolismo , Bulgária , Cromatografia Líquida de Alta Pressão/métodos , Cromatografia Gasosa-Espectrometria de Massas/métodos , Variação Genética/genética , Extratos Vegetais/química , Alcaloides de Pirrolizidina/química , Reprodução/fisiologia , Especificidade da Espécie
3.
Am J Bot ; 107(3): 445-455, 2020 03.
Artigo em Inglês | MEDLINE | ID: mdl-32086803

RESUMO

PREMISE: Flowering time may influence pollination success and seed set through a variety of mechanisms, including seasonal changes in total pollinator visitation or the composition and effectiveness of pollinator visitors. METHODS: We investigated mechanisms by which changes in flowering phenology influence pollination and reproductive success of Mertensia ciliata (Boraginaceae). We manipulated flowering onset of potted plants and assessed the frequency and composition of pollinator visitors, as well as seed set. We tested whether floral visitors differed in their effectiveness as pollinators by measuring pollen receipt and seed set resulting from single visits to virgin flowers. RESULTS: Despite a five-fold decrease in pollinator visitation over four weeks, we detected no significant difference in seed set among plants blooming at different times. On a per-visit basis, each bumblebee transferred more conspecific pollen than did a solitary bee or a fly. The proportion of visits by bumblebees increased over the season, countering the decrease in visitation rate so that flowering time had little net effect on seed set. CONCLUSIONS: This work illustrates the need to consider pollinator effectiveness, along with changes in pollinator visitation and species composition to understand the mechanisms by which phenology affects levels of pollination.


Assuntos
Boraginaceae , Polinização , Animais , Abelhas , Flores , Pólen , Reprodução
4.
J Biotechnol ; 308: 130-140, 2020 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-31843519

RESUMO

Buglossoides arvensis seed oil is the richest natural source of stearidonic acid (SDA), an ω-3 fatty acid with nutraceutical potential superior to α-linolenic acid (ALA). The molecular basis of polyunsaturated fatty acid synthesis in B. arvensis is unknown. Here, we describe the identification of B. arvensis fatty acid desaturase2 (BaFAD2), fatty acid desaturase3 (BaFAD3), and Delta-6-desaturase (BaD6D-1 and BaD6D-2) genes by mining the transcriptome of developing seeds and their functional characterization by heterologous expression in Saccharomyces cerevisiae. In silico analysis of their encoded protein sequences showed conserved histidine-boxes and signature motifs essential for desaturase activity. Expression profiling of these genes showed higher transcript abundance in reproductive tissues than in vegetative tissues, and their expression varied with temperature stress treatments. Yeast expressing BaFAD2 was found to desaturate both oleic acid and palmitoleic acid into linoleic acid (LA) and hexadecadienoic acid, respectively. Fatty acid supplementation studies in yeast expressing BaFAD3 and BaD6D-1 genes revealed that the encoded enzyme activities of BaFAD3 efficiently converted LA to ALA, and BaD6D-1 converted LA to γ-linolenic acid and ALA to SDA, but with an apparent preference to LA. BaD6D-2 did not show the encoded enzyme activity and is not a functional D6D. Our results provide an insight into SDA biosynthesis in B. arvensis and expand the repository of fatty acid desaturase targets available for biotechnological production of SDA in traditional oilseed crops.


Assuntos
Vias Biossintéticas , Boraginaceae/genética , Ácidos Graxos Insaturados/metabolismo , Perfilação da Expressão Gênica/métodos , Boraginaceae/metabolismo , Simulação por Computador , Ácidos Graxos Dessaturases/genética , Ácidos Graxos Dessaturases/metabolismo , Regulação Enzimológica da Expressão Gênica , Regulação da Expressão Gênica de Plantas , Linoleoil-CoA Desaturase/genética , Linoleoil-CoA Desaturase/metabolismo , Microssomos/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Sementes/genética , Sementes/metabolismo , Estresse Fisiológico , Temperatura
5.
J Ethnopharmacol ; 248: 112317, 2020 Feb 10.
Artigo em Inglês | MEDLINE | ID: mdl-31629862

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Arnebiae Radix, a common herbal medicine in China, is often utilized to treat blood-heat syndrome and has been reported to exert an effect on the heart. AIM OF THE STUDY: The combination of acetylcholine (Ach) and CaCl2 has been widely used to induce atrial fibrillation (AF) in animals. However, whether Arnebiae Radix displays any preventive action on Ach-CaCl2 induced AF in rats remains uncertain. In our study, we attempted to investigate the protective effects of Arnebiae Radix on Ach-CaCl2 induced AF compared to amiodarone, which was employed as the positive control. MATERIALS AND METHODS: To establish the AF model, SD rats were treated with a mixture of 0.1 mL/100 g Ach-CaCl2 (60 µg/mL Ach and 10 mg/mL CaCl2) by tail vein injection for 7 days. Rats were also given a gavage of Arnebiae Radix (0.18 g/mL) one week before or concurrently with the establishment of the AF model. At the end of the experimental period, the induction, duration and timing of AF were monitored using electrocardiogram recordings. Left atrial tissues were stained to observe the level of fibrosis. Electrophysiological measurements were used to examine atrial size and function. RESULTS: In Ach-CaCl2-induced AF rats, Arnebiae Radix decreased AF induction, duration and susceptibility to AF. In addition, Arnebiae Radix significantly reduced atrial fibrosis and inhibited atrial enlargement induced by Ach-CaCl2. Moreover, there was an apparent improvement in cardiac function in the Arnebiae Radix-treated group. CONCLUSIONS: Our findings indicate that Arnebiae Radix treatment can attenuate Ach-CaCl2-induced atrial injury and serve as an effective therapeutic strategy for the treatment of AF in the future.


Assuntos
Antiarrítmicos/farmacologia , Fibrilação Atrial/prevenção & controle , Função do Átrio Esquerdo/efeitos dos fármacos , Remodelamento Atrial/efeitos dos fármacos , Boraginaceae , Frequência Cardíaca/efeitos dos fármacos , Extratos Vegetais/farmacologia , Acetilcolina , Animais , Antiarrítmicos/isolamento & purificação , Fibrilação Atrial/induzido quimicamente , Fibrilação Atrial/fisiopatologia , Boraginaceae/química , Cloreto de Cálcio , Modelos Animais de Doenças , Fibrose , Masculino , Extratos Vegetais/isolamento & purificação , Ratos Sprague-Dawley , Função Ventricular Esquerda/efeitos dos fármacos , Remodelação Ventricular/efeitos dos fármacos
6.
Drug Des Devel Ther ; 13: 4195-4205, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31849451

RESUMO

Background: Cancer is one of the chronic health conditions worldwide. Various therapeutically active compounds from medicinal plants were the current focus of this research in order to uncover a treatment regimen for cancer. Anchusa arvensis (A. anchusa) (L.) M.Bieb. contains many biologically active compounds. Methods: In the current study, new ester 3-hydroxyoctyl -5- trans-docosenoate (compound-1) was isolated from the chloroform soluble fraction of A. anchusa using column chromatography. Using MTT assay, the anticancer effect of the compound was determined in human hepatocellular carcinoma cells (HepG-2) compared with normal epithelial cell line (Vero). DPPH and ABTS radical scavenging assays were performed to assess the antioxidant potential. The Molecular Operating Environment (MOE-2016) tool was used against tyrosine kinase. Results: The structure of the compound was elucidated based on IR, EI, and NMR spectroscopy technique. It exhibited a considerable cytotoxic effect against HepG-2 cell lines with IC50 value of 6.50 ± 0.70 µg/mL in comparison to positive control (doxorubicin) which showed IC50 value of 1.3±0.21 µg/mL. The compound did not show a cytotoxic effect against normal epithelial cell line (Vero). The compound also exhibited significant DPHH scavenging ability with IC50 value of 12 ± 0.80 µg/mL, whereas ascorbic acid, used as positive control, demonstrated activity with IC50 = 05 ± 0.15 µg/mL. Similarly, it showed ABTS radical scavenging ability (IC50 = 130 ± 0.20 µg/mL) compared with the value obtained for ascorbic acid (06 ± 0.85 µg/mL). In docking studies using MOE-2016 tool, it was observed that compound-1 was highly bound to tyrosine kinase by having two hydrogen bonds at the hinge region. This good bonding network by the compound might be one of the reasons for showing significant activity against this enzyme. Conclusion: Our findings led to the isolation of a new compound from A. anchusa which has significant cytotoxic activity against HepG-2 cell lines with marked antioxidant potential.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Boraginaceae/química , Ésteres/farmacologia , Ácidos Graxos Monoinsaturados/farmacologia , Picratos/antagonistas & inibidores , Ácidos Sulfônicos/antagonistas & inibidores , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Chlorocebus aethiops , Simulação por Computador , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Ésteres/química , Ésteres/isolamento & purificação , Ácidos Graxos Monoinsaturados/química , Ácidos Graxos Monoinsaturados/isolamento & purificação , Células Hep G2 , Humanos , Simulação de Acoplamento Molecular , Estrutura Molecular , Plantas Medicinais , Relação Estrutura-Atividade , Células Vero
7.
Zootaxa ; 4685(1): zootaxa.4685.1.1, 2019 Oct 11.
Artigo em Inglês | MEDLINE | ID: mdl-31719371

RESUMO

A taxonomic revision of the tribe Ceroptresini (Hymenoptera: Cynipidae) is conducted for the first time. Prior to this study, the total number of valid species of Ceroptres, the only genus within Ceroptresini to date, was 23. As a result of this revision, 15 Ceroptres species are retained as valid and one species, Amblynotus ensiger Walsh, 1864, is desynonymized from Ceroptres petiolicola (Osten-Sacken, 1861), being considered here as a valid Ceroptres species: C. ensiger (Walsh, 1864) status verified and comb. nov. An additional five new species are described from Mexico: Ceroptres junquerasi Lobato-Vila Pujade-Villar sp. nov.; C. lenis Lobato-Vila Pujade-Villar sp. nov.; C. mexicanus Lobato-Vila Pujade-Villar sp. nov.; C. nigricrus Lobato-Vila Pujade-Villar sp. nov.; C. quadratifacies Lobato-Vila Pujade-Villar sp. nov., increasing the total number of valid Ceroptres species to 21. Ceroptres masudai Abe, 1997 is synonymized with C. kovalevi Belizin, 1973. Ceroptres niger Fullaway, 1911 is transferred to Andricus (Andricus confusus Lobato-Vila Pujade-Villar comb. nov. and nom. nov.). Five species (Amblynotus inermis Walsh, 1864; Cynips quercusarbos Fitch, 1859; Cynips querficus Fitch, 1859; Cynips quercuspisum Fitch, 1859; and Cynips quercustuber Fitch, 1859) are not considered as valid Ceroptres. The status of Ceroptres quereicola (Shinji, 1938), previously classified as an unplaced species, is commented on. In addition, a Nearctic species from the USA, Ceroptres politus Ashmead, 1896, is here proposed as the type species of a new genus within Ceroptresini: Buffingtonella Lobato-Vila Pujade-Villar gen. nov. Redescriptions, biological and distribution data, illustrations and keys to genera and species within Ceroptresini are provided. The diagnostic morphological traits of Ceroptresini, Ceroptres and the new genus are discussed.


Assuntos
Asteraceae , Boraginaceae , Himenópteros , Animais , México , Fenótipo
8.
Curr Top Med Chem ; 19(30): 2805-2813, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31702502

RESUMO

BACKGROUND: Liver cancer is a devastating cancer with increasing incidence and mortality rates worldwide. Plants possess numerous therapeutic properties, therefore the search for novel, naturally occurring cytotoxic compounds is urgently needed. METHODS: The anticancer activity of plant extracts and isolated compounds from Anchusa arvensis (A. arvensis) were studied against the cell culture of HepG-2 (human hepatocellular carcinoma cell lines) using 3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazoliumbromide (MTT) assay. Apoptosis was investigated by performing Acridine orange -ethidium bromide staining, styox green assay and DNA interaction study. We also used tools for computational chemistry studies of isolated compounds with the tyrosine kinase. RESULTS: In MTT assay, the crude extract caused a significant cytotoxic effect with IC50 of 34.14 ± 0.9 µg/ml against HepG-2 cell lines. Upon fractionation, chloroform fraction (Aa.Chm) exhibited the highest antiproliferative activity with IC50 6.55 ± 1.2 µg/ml followed by ethyl acetate (Aa.Et) fraction (IC50, 24.59 ± 0.85 µg/ml) and n-hexane (Aa.Hex) fraction (IC50 29.53 ± 1.5µg/ml). However, the aqueous (Aa.Aq) fraction did not show any anti-proliferative activity. Bioactivity-guided isolation led to the isolation of two compounds which were characterized as para-methoxycatechol (1) and decane (2) through various spectroscopic techniques. Against HepG-2 cells, compound 1 showed marked potency with IC50 6.03 ± 0.75 µg/ml followed by 2 with IC50 18.52 ± 1.9 µg/ml. DMSO was used as a negative control and doxorubicin as a reference standard (IC50 1.3 ± 0.21 µg/ml). It was observed that compounds 1-2 caused apoptotic cell death evaluated by Acridine orange -ethidium bromide staining, styox green assay and DNA interaction study, therefore both compounds were tested for molecular docking studies against tyrosine kinase to support cytotoxic activity. CONCLUSION: This study revealed that the plant extracts and isolated compounds possess promising antiproliferative activity against HepG-2 cell lines via apoptotic cell death.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Boraginaceae/química , Extratos Vegetais/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Células Hep G2 , Humanos , Simulação de Acoplamento Molecular
9.
Pak J Pharm Sci ; 32(4): 1477-1484, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31608865

RESUMO

This study investigates the pharmacological potential of Adiantum incisum, Alternanthera pungens and Trichodesma indicum. Biological activities of plant extracts (aqueous, methanolic and n-hexane extracts of whole plants) were screened by antitumor potato disc assay (10000, 1000, 100, 10 ppm doses), antifungal tube dilution assay (50, 25, 12.5, 6.25mg/ml) and antioxidant DPPH/reducing power assays (250, 200, 150, 100, 50µg/ml). Significant amount of alkaloids (230.83±30.20mg/g) in Adiantum incisum with lowest amount of phenolics in Alternanthera pungens (43.45 ±14.22µg/mg) were detected. Significant antitumor potential (p<0.05) was revealed by Trichodesma indicum n-hexane extract (85% tumor inhibition; IC50 <10ppm). Moderate to significant antifungal activity (50.73%-78.3%) was shown against Aspergillus niger by Adiantum incisum extracts. Hexane extract of Trichodesma indicum revealed significant antifungal activity (98.9% inhibition) against Mucor specie. Methanolic extracts of all plants displayed significant DPPH radical scavenging potential (96.72%-60.33%; IC50 <50µg/ml) and Ferric power reducing ability with absorbance values (0.164-0.942) very close to standard ascorbic acid. Present study supports the extensive use of these plants in folk medicine and also promotes elaborative in-vivo investigations, isolation of pure therapeutic compounds and formulation of plant-based drugs.


Assuntos
Antifúngicos/farmacologia , Antioxidantes/farmacologia , Extratos Vegetais/farmacologia , Plantas Medicinais/química , Adiantum/química , Amaranthaceae/química , Antifúngicos/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/química , Boraginaceae/química , Avaliação Pré-Clínica de Medicamentos , Ensaios de Seleção de Medicamentos Antitumorais , Medicina Tradicional , Paquistão , Compostos Fitoquímicos/análise , Extratos Vegetais/química
10.
Mol Phylogenet Evol ; 141: 106626, 2019 12.
Artigo em Inglês | MEDLINE | ID: mdl-31526848

RESUMO

Studies about the drivers of angiosperm clade diversifications have revealed how the environment continuously alters the species chances to adapt or to go extinct. This process depends on complex interactions between abiotic and biotic factors, conditioned to the geological and tectonic settings, the genetic variability of species and the rate at which speciation occurs. In this study, we aim to elucidate the timing of diversification of the Lithospermeae, the second largest tribe within Boraginaceae, and to identify the possible morphological and ecological characters associated with shifts in diversification rates of the most species-rich clades. Lithospermeae includes ca. 470 species and 26 genera, among which are some of the largest genera of the family such as Onosma (150 spp.), Echium (60 spp.), and Lithospermum (80 spp.). An exhaustive study of the whole clade is not available to date and its evolutionary history and diversification rates are incompletely known. In the present study, we provide the most comprehensive phylogeny of the group so far, sampling 242 species and all 26 genera. We found that crown-groups and diversification rates of Lithospermeae largely date back to the Mid-Miocene, with high diversification rates in the largest genera, though only significantly high in Onosma. Our analysis fails to associate any of the functional or morphological traits considered with significant shifts in diversification rates. The timing of the diversification of the species-rich clades corresponds with Miocene tectonic events and global climate changes increasing aridity across Eurasia and western North America. These results suggest a causal link between known ecological features of Lithospermeae (i.e., pre-adaptation to arid, open habitats, and mineral soils) and their diversification. Future studies should expand the sampling of individual subclades and detailed functional analyses to identify the contribution of adaptations to arid conditions and pollinator shifts.


Assuntos
Biodiversidade , Boraginaceae/classificação , Filogenia , Filogeografia , Sequência de Bases , Boraginaceae/anatomia & histologia , DNA de Cloroplastos/genética , DNA Espaçador Ribossômico/genética , América do Norte , Especificidade da Espécie , Fatores de Tempo
11.
Curr Pharm Des ; 25(16): 1861-1865, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31333091

RESUMO

Overcoming the antibiotic resistance is nowadays a challenge. There is still no clear strategy to combat this problem. Therefore, the urgent need to find new sources of antibacterial agents exists. According to some literature, substances of plant origin are able to overcome bacterial resistance against antibiotics. Alkanna species plants are among the valuable producers of these metabolites. But there is a problem of obtaining the standardized product. So, this review is focused on the discussion of the possibilities of biotechnological production of antimicrobial agents from Alkanna genus species against some microorganisms including antibiotic resistant bacterial strains.


Assuntos
Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Boraginaceae/química , Extratos Vegetais/farmacologia , Farmacorresistência Bacteriana , Testes de Sensibilidade Microbiana
12.
Food Funct ; 10(7): 4280-4290, 2019 Jul 17.
Artigo em Inglês | MEDLINE | ID: mdl-31264668

RESUMO

The present study aimed to determine the chemical composition, antioxidant effects and antitumor properties of a methanol extract of Anchusa azurea Mill. (Boraginaceae) aerial parts against four tumour cell lines (MCF-7, MDA-MB-231, RKO, and R2C). The antioxidant effects were assessed by using ß-carotene bleaching, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and ferric reducing ability power (FRAP) tests. HPLC analyses revealed chlorogenic acid, catechin, caffeic acid, and astragalin as the most abundant compounds. Interesting results were obtained in the ß-carotene bleaching test with IC50 values of 7.6 and 27.5 µg mL-1 after 30 and 60 min of incubation, respectively. Furthermore, the A. azurea extract protects 3T3-L1 mouse cells from oxidative stress induced by menadione and exhibits good antitumor activity, with very low toxicity. Our data indicate that the antitumor properties are due to the ability to induce programmed cancer cell death through caspase 3/7 and 9 activation and interference with the cytoskeleton dynamics.


Assuntos
Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Boraginaceae/química , Citoesqueleto/efeitos dos fármacos , Componentes Aéreos da Planta/química , Extratos Vegetais/farmacologia , Animais , Antioxidantes/farmacologia , Benzotiazóis , Compostos de Bifenilo , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Camundongos , Estresse Oxidativo/efeitos dos fármacos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Picratos , Espécies Reativas de Oxigênio , Ácidos Sulfônicos
13.
Molecules ; 24(13)2019 Jun 26.
Artigo em Inglês | MEDLINE | ID: mdl-31248041

RESUMO

Three polyisoprenoid alcohols were isolated from the leaves of Tournefortia hirsutissima by a bioassay-guided phytochemical investigation. The compounds were identified as 16-hydroxy-lycopersene (Compound 1), (Z8,E3,ω)-dodecaprenol (Compound 2) and (Z9,E3,ω)-tridecaprenol (Compound 3). Compound 1, an unusual polyisoprenoid, was characterized by 1D and 2D NMR. We also determined the absolute configuration at C-16 by the modified Mosher's method. The in vitro antiproliferative and anti-inflammatory activities of the isolated compounds were evaluated. Among isolates, Compound 1 moderately inhibited the nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. On the other hand, Compound 1 displayed selective antiproliferative activity against HeLa, PC3, HepG2 and Hep3B cancer cells and was less potent against IHH non-cancerous cells. Compound 1 in Hep3B cells showed significant inhibition of cell cycle progression increasing the sub-G1 phase, suggesting cell death. Acridine orange/ethidium bromide staining and Annexin V-FITC/PI staining demonstrated that cell death induced by Compound 1 in cells Hep3B was by apoptosis. Further study showed that apoptosis induced by Compound 1 in Hep3b cells is associated with the increase of the ratio of Bax/Bcl-2, and caspase 3/7 activation. These results suggest that Compound 1 induce apoptotic cell death by the mitochondrial pathway. To our knowledge, this is the first report about the presence of polyprenol Compounds 1-3 in T. hirsutissima, and the apoptotic and anti-inflammatory action of Compound 1.


Assuntos
Apoptose/efeitos dos fármacos , Boraginaceae/química , Óxido Nítrico/biossíntese , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Terpenos/química , Terpenos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Humanos , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Extratos Vegetais/isolamento & purificação , Células RAW 264.7 , Terpenos/isolamento & purificação
14.
Pharm Biol ; 57(1): 412-423, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31230505

RESUMO

Context: Shikonins, a series of natural occurring naphthoquinones extracted from Arnebia euchroma (Royle) Jonst. (Boraginaceae), have antitumor activities and low toxicity. Objective: To illuminate potential activity and mechanism of shikonins against colorectal cancer (CRC). Materials and methods: Five shikonins were isolated from A. euchroma, and elucidated by extensive spectroscopic analysis. Anti-proliferative activities of shikonins (0-100 µg/mL) on human colorectal cells were evaluated by MTT and CCK-8 for 24 or 48 h. Cell apoptosis and cycle distribution were examined by FCM analysis. The expression of PI3K/Akt/mTOR pathway mRNAs and proteins was analysed by RT-PCR and Western blot, respectively. Cell viability, cell apoptosis, cell cycle and protein expression were measured, when co-treated with PI3K/Akt/mTOR pathway inhibitors. The in vivo activity of deoxyshikonin was evaluated using xenograft tumour model. Results: Deoxyshikonin and another four shikonins were isolated and identified. Deoxyshikonin exhibited anti-proliferative activity with IC50 of 10.97 µM against HT29 cells. Moreover, the percentage of early apoptotic cells and G0/G1 cells increased from 1 to 29% and 44 to 67% with 0-50 µg/mL deoxyshikonin, respectively. Deoxyshikonin also down-regulated the expression of PI3K, p-PI3K, Akt, p-Akt308 and mTOR proteins in HT29 and DLD-1 cells. Moreover, LY294002, NVP-BEZ235 and MK-2206 can make deoxyshikonin more cell proliferation inhibited, cell cycle arrested at G0/G1 and apoptosis promoted. In vivo study, the weight of tumour tissues at deoxyshikonin groups was significantly reduced compared with the control group, and PI3K, p-PI3K, Akt, p-Akt308 and mTOR expression was decreased. Discussion and conclusions: We can conclude that deoxyshikonin isolated from Arnebia euchroma inhibited CRC through the PI3K/Akt/mTOR pathway.


Assuntos
Neoplasias do Colo/tratamento farmacológico , Neoplasias do Colo/metabolismo , Neoplasias Colorretais/tratamento farmacológico , Naftoquinonas/farmacologia , Fosfatidilinositol 3-Quinases/metabolismo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Serina-Treonina Quinases TOR/metabolismo , Animais , Apoptose/efeitos dos fármacos , Boraginaceae/química , Células CACO-2 , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Neoplasias do Colo/patologia , Neoplasias Colorretais/metabolismo , Neoplasias Colorretais/patologia , Regulação para Baixo , Células HCT116 , Células HT29 , Humanos , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Naftoquinonas/química , Naftoquinonas/isolamento & purificação , Distribuição Aleatória , Transdução de Sinais/efeitos dos fármacos , Ensaios Antitumorais Modelo de Xenoenxerto
15.
Molecules ; 24(12)2019 Jun 18.
Artigo em Inglês | MEDLINE | ID: mdl-31216776

RESUMO

Symphytum species belongs to the Boraginaceae family and have been used for centuries for bone breakages, sprains and rheumatism, liver problems, gastritis, ulcers, skin problems, joint pain and contusions, wounds, gout, hematomas and thrombophlebitis. Considering the innumerable potentialities of the Symphytum species and their widespread use in the world, it is extremely important to provide data compiling the available literature to identify the areas of intense research and the main gaps in order to design future studies. The present review aims at summarizing the main data on the therapeutic indications of the Symphytum species based on the current evidence, also emphasizing data on both the efficacy and adverse effects. The present review was carried out by consulting PubMed (Medline), Web of Science, Embase, Scopus, Cochrane Database, Science Direct and Google Scholar (as a search engine) databases to retrieve the most updated articles on this topic. All articles were carefully analyzed by the authors to assess their strengths and weaknesses, and to select the most useful ones for the purpose of review, prioritizing articles published from 1956 to 2018. The pharmacological effects of the Symphytum species are attributed to several chemical compounds, among them allantoin, phenolic compounds, glycopeptides, polysaccharides and some toxic pyrrolizidine alkaloids. Not less important to highlight are the risks associated with its use. In fact, there is increasing consumption of over-the-counter drugs, which when associated with conventional drugs can cause serious and even fatal adverse events. Although clinical trials sustain the folk topical application of Symphytum species in musculoskeletal and blunt injuries, with minor adverse effects, its antimicrobial potency was still poorly investigated. Further studies are needed to assess the antimicrobial spectrum of Symphytum species and to characterize the active molecules both in vitro and in vivo.


Assuntos
Boraginaceae/química , Boraginaceae/fisiologia , Animais , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Ecossistema , Conservação de Alimentos , Humanos , Doenças Musculoesqueléticas/tratamento farmacológico , Doenças Musculoesqueléticas/etiologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Resultado do Tratamento , Cicatrização/efeitos dos fármacos
16.
J Appl Microbiol ; 127(1): 208-218, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30985950

RESUMO

AIMS: The aim of this study was to evaluate the persistence of Pseudomonas fluorescens LBUM677 in the rhizosphere of Buglossoides arvensis under agricultural field conditions and determine if B. arvensis intraspecific genetic variations affect the capacity of LBUM677 to colonize its rhizosphere and increase seed oil and stearidonic acid (SDA) accumulation. METHODS AND RESULTS: Two field experiments were performed to: (i) study the persistence of various concentrations of LBUM677 inoculated in the rhizosphere of B. arvensis and determine a minimum inoculation threshold required to maximize biological activity; and (ii) study the impact of B. arvensis intraspecific genetic variations on LBUM677 rhizosphere colonization and seed oil and SDA accumulation. In order to track LBUM677 populations in soil over time, a specific quantitative polymerase chain reaction assay was developed. Inoculation with a minimum of 109 LBUM677 bacterial cells per plant was determined as a threshold to promote maximum B. arvensis rhizosphere colonization and seed oil and SDA accumulation. Buglossoides arvensis intraspecific genetic variations had an impact on rhizosphere colonization, B. arvensis seed oil and SDA accumulation, where two cultivars benefited more than others from LBUM677 inoculation. CONCLUSIONS: LBUM677 can colonize the rhizosphere and increase seed oil and SDA yields in B. arvensis plants in a cultivar-dependant manner. SIGNIFICANCE AND IMPACT OF THE STUDY: LBUM677 shows potential to be used as a biofertilizer to specifically increase seed oil and SDA yields in B. arvensis. This will in turn promote the development of an economically viable agricultural-based approach as an alternative for producing high-quality polyunsaturated fatty acids.


Assuntos
Boraginaceae/microbiologia , Ácidos Graxos Ômega-3/metabolismo , Óleos Vegetais/metabolismo , Pseudomonas fluorescens/crescimento & desenvolvimento , Rizosfera , Microbiologia do Solo , Boraginaceae/genética , Boraginaceae/metabolismo , Variação Genética , Raízes de Plantas/microbiologia , Sementes/metabolismo , Sementes/microbiologia
17.
Am J Bot ; 106(5): 713-721, 2019 05.
Artigo em Inglês | MEDLINE | ID: mdl-31002744

RESUMO

PREMISE: Outcrossing species depend on pollen from conspecific individuals that may not be exposed to the same abiotic conditions as maternal plants. Additionally, many flowers receive heterospecific pollen, which can also influence seed production. Studies aimed to understand how abiotic conditions influence seed production tend to focus on maternal conditions and leave unexplored the effect of abiotic conditions experienced by pollen donors. We tested how water availability to pollen donors, both conspecific and heterospecific, influenced the seed production of recipient plants exposed to different water availability regimes. METHODS: In a greenhouse setting we manipulated the water availability (low- or high-water treatment) to potted recipient plants (Phacelia parryi), to conspecific pollen donors, and to heterospecific pollen donors (Brassica nigra). We hand pollinated recipient plants with different pollen mixes that represented all combinations of conspecific pollen mixed with heterospecific pollen. From these hand pollinations we determined the amount of pollen that was transferred, pollen volume, pollen shape, and seed production. RESULTS: Higher water availability to conspecific pollen donors led to higher seed production. Under low water availability to heterospecific pollen donors, seed production was unaffected by recipient or conspecific pollen donor treatment. Under high water availability to heterospecific pollen donors, seed production was highest when conspecific pollen donors and pollen recipients also received the high-water treatment. CONCLUSIONS: Environmental conditions of pollen donors can influence the seed production of maternal plants. These results illustrate potential impacts of environmental heterogeneity on post-pollination events that lead to seed production and thus impact a pollinator's contribution to plant fitness.


Assuntos
Boraginaceae/fisiologia , Secas , Mostardeira/fisiologia , Polinização , Água/metabolismo , Sementes/fisiologia
18.
Environ Sci Pollut Res Int ; 26(16): 16303-16315, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30977009

RESUMO

The effects of crude ethanol derived leaf extract Trichodesma indicum (Linn) (Ex-Ti) and their chief derivatives were accessed on the survival and development of the dengue mosquito Ae. aegypti also their non-toxic activity against mosquito predator. T. indicum is recognized to be the vital weed plant and a promising herb in the traditional ayurvedic medicine. In this study, the GC-MS chromatogram of Ex-Ti showed higher peak area percentage for cis-10-Heptadecenoic acid (21.83%) followed by cycloheptadecanone (14.32%). The Ex-Ti displayed predominant mortality in larvae with 96.45 and 93.31% at the prominent dosage (200 ppm) against III and IV instar. Correspondingly, sub-lethal dosage against the enzymatic profile of III and IV instar showed downregulation of α,ß-carboxylesterase and SOD protein profiles at the maximum concentration of 100 ppm. However, enzyme level of GST as well as CYP450 increased significantly dependent on sub-lethal concentration. Likewise, fecundity and hatchability of egg rate of dengue mosquito decreased to the sub-lethal concentration of Ex-Ti. Repellent assay illustrates that Ex-Ti concentration had greater protection time up to 210 min at 100 ppm. Also, activity of Ex-Ti on adult mosquito displayed 100% mortality at the maximum dosage of 600, 500 and 400 ppm within the period of 50, 60 and 70 min, respectively. Photomicrography screening showed that lethal dosage of Ex-Ti (100 ppm) produced severe morphological changes with dysregulation in their body parts as matched to the control. Effects of Ex-Ti on the Toxorhynchites splendens IV instar larvae showed less mortality (43.47%) even at the maximum dosage of 1500 ppm as matched to the chemical pesticide Temephos. Overall, the present research adds a toxicological valuation on the Ex-Ti and their active constituents as a larvicidal, repellent and adulticidal agents against the global burdening dengue mosquito.


Assuntos
Aedes/efeitos dos fármacos , Boraginaceae/química , Repelentes de Insetos/farmacologia , Mosquitos Vetores/efeitos dos fármacos , Extratos Vegetais/farmacologia , Animais , Carboxilesterase , Culicidae/efeitos dos fármacos , Dengue/prevenção & controle , Feminino , Fertilidade/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Larva/efeitos dos fármacos , Praguicidas/farmacologia , Extratos Vegetais/análise , Folhas de Planta/química
19.
Molecules ; 24(7)2019 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-30978970

RESUMO

The aim of this study was to investigate anti-aging molecules from Onosma bracteatum Wall, a traditional medicinal plant used in the Unani and Ayurvedic systems of medicine. During bioassay-guided isolation, two known benzoquinones, allomicrophyllone (1) and ehretiquinone (2) along with three novel benzoquinones designated as ehretiquinones B-D (3-5) were isolated from O. bracteatum. Their structures were characterized by spectroscopic analysis through 1D and 2D NMR, by MS spectroscopic analysis and comparing with those reported in the literatures. The anti-aging potential of the isolated benzoquinones was evaluated through a yeast lifespan assay, and the results indicated that 1, 2, 4 and 5 significantly extended the replicative lifespan of K6001 yeast, indicating that these benzoquinones obtained from O. brateatum have the ability to be employed as a potential therapeutic agent against age-related diseases.


Assuntos
Envelhecimento/efeitos dos fármacos , Benzoquinonas/química , Boraginaceae/química , Longevidade/efeitos dos fármacos , Envelhecimento/fisiologia , Benzoquinonas/isolamento & purificação , Humanos , Medicina Ayurvédica , Estrutura Molecular , Plantas Medicinais/química , Saccharomyces cerevisiae/efeitos dos fármacos
20.
Am J Bot ; 106(3): 438-452, 2019 03.
Artigo em Inglês | MEDLINE | ID: mdl-30861101

RESUMO

PREMISE OF THE STUDY: Long-distance dispersal (LDD) syndromes, especially endozoochory, facilitate plant colonization of new territories that trigger diversification. However, few studies have analyzed how epizoochorous fruits influence both range distribution and diversification rates. We examined the evolutionary history of a hyperdiverse clade of Boraginaceae (subfamily Cynoglossoideae, eight tribes, ~60 genera, ~1100 species) and the evolution of fruit traits. We evaluated the evolutionary history of diaspore syndromes correlated with geographic distribution and diversification rates over time. METHODS: Plastid DNA regions and morphological traits associated with dispersal syndromes were analyzed for 71 genera (226 species). We employed trait-dependent diversification analysis (HiSSE) and biogeographic reconstruction (Lagrange) using a time-calibrated phylogeny. KEY RESULTS: Our results indicate that (1) the earliest divergence events in Cynoglossoideae occurred in the central-northeastern Palearctic during the Paleogene (early to middle Eocene); (2) an epizoochorous trait (specialized hooks named glochids) is ancestral and has been maintained long term; and (3) glochids are correlated with increased diversification rates in two distantly related clades (Rochelieae and Cynoglossinae). Rapid speciation occurred for these two groups in the same area (central-eastern Palearctic) and same period (Oligocene-Miocene: Rochelieae, 30.82-13.69 mya; Cynoglossinae, 33.10-15.21 mya). Lower diversification rates were inferred for the remaining four glochid-bearing clades. CONCLUSIONS: One more example of "biogeographic congruence" in angiosperms is supported by a shared geographic (central-northeastern Palearctic) and temporal (28.60-21.59 mya, late Oligocene) opportunity window for two main clades' diversification. Epizoochorous traits (fruit glochids) had an effect in higher diversification rates only with the joint effect of other unmeasured factors.


Assuntos
Evolução Biológica , Boraginaceae/fisiologia , Traços de História de Vida , Dispersão Vegetal , Especiação Genética
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