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1.
BMC Plant Biol ; 21(1): 414, 2021 Sep 09.
Artigo em Inglês | MEDLINE | ID: mdl-34503445

RESUMO

BACKGROUND: Adventitious root formation is considered a major developmental step during the propagation of difficult to root plants, especially in horticultural crops. Recently, adventitious roots induced through plant tissue culture methods have also been used for production of phytochemicals such as flavonoids, anthocyanins and anthraquinones. It is rather well understood which horticultural species will easily form adventitious roots, but the factors affecting this process at molecular level or regulating the induction process in in vitro conditions are far less known. The present study was conducted to identify transcripts involved in in vitro induction and formation of adventitious roots using Arnebia euchroma leaves at different time points (intact leaf (control), 3 h, 12 h, 24 h, 3 d, 7 d, 10 d and 15 d). A. euchroma is an endangered medicinal Himalayan herb whose root contains red naphthoquinone pigments. These phytoconstituents are widely used as an herbal ingredient in Asian traditional medicine as well as natural colouring agent in food and cosmetics. RESULTS: A total of 137.93 to 293.76 million raw reads were generated and assembled to 54,587 transcripts with average length of 1512.27 bps and N50 of 2193 bps, respectively. In addition, 50,107 differentially expressed genes were identified and found to be involved in plant hormone signal transduction, cell wall modification and wound induced mitogen activated protein kinase signalling. The data exhibited dominance of auxin responsive (AUXIN RESPONSE FACTOR8, IAA13, GRETCHEN HAGEN3.1) and sucrose translocation (BETA-31 FRUCTOFURANOSIDASE and MONOSACCHARIDE-SENSING protein1) genes during induction phase. In the initiation phase, the expression of LATERAL ORGAN BOUNDARIES DOMAIN16, EXPANSIN-B15, ENDOGLUCANASE25 and LEUCINE-rich repeat EXTENSION-like proteins was increased. During the expression phase, the same transcripts, with exception of LATERAL ORGAN BOUNDARIES DOMAIN16 were identified. Overall, the transcriptomic analysis revealed a similar patterns of genes, however, their expression level varied in subsequent phases of in vitro adventitious root formation in A. euchroma. CONCLUSION: The results presented here will be helpful in understanding key regulators of in vitro adventitious root development in Arnebia species, which may be deployed in the future for phytochemical production at a commercial scale.


Assuntos
Boraginaceae/genética , Folhas de Planta , Proteínas de Plantas/genética , Raízes de Plantas/crescimento & desenvolvimento , Raízes de Plantas/genética , Boraginaceae/crescimento & desenvolvimento , Perfilação da Expressão Gênica , Regulação da Expressão Gênica de Plantas , Indóis/farmacologia , Anotação de Sequência Molecular , Folhas de Planta/efeitos dos fármacos , Folhas de Planta/genética , Plantas Medicinais/genética , Plantas Medicinais/crescimento & desenvolvimento , Análise de Sequência de RNA , Técnicas de Cultura de Tecidos/métodos
2.
J Pharm Biomed Anal ; 204: 114283, 2021 Sep 10.
Artigo em Inglês | MEDLINE | ID: mdl-34329923

RESUMO

This study was aimed at providing a comprehensive phytochemical characterization and multi-biological assessment of Symphytum officinale L., a medicinal plant with a noteworthy traditional use, and Anchusa ochroleuca M. Bieb., a Boraginaceae species from the Romanian flora. The dichloromethane, methanol and 65 % ethanol extracts obtained from the roots and aerial parts of both plants revealed the presence of numerous phenolic acids, oxygenated fatty acids, pyrrolizidine alkaloids (PAs) and flavonoids, as assessed by LC-HRMS/MS analysis. Consistent with their higher total phenolic content, the polar aerial part extracts of S. officinale and root extracts of A. ochroleuca showed the most significant antioxidant activities, as evaluated by DPPH (173.22-216.98 mg TE/g) and ABTS (219.41-311.97 mg TE/g) radical scavenging, CUPRAC (387.18-626.40 mg TE/g), FRAP (199.36-299.86 mg TE/g) and total antioxidant capacity (2.28-2.68 mmol TE/g). Furthermore, both plants exhibited good tyrosinase (19.11-43.89 mg KAE/g) and α-glucosidase (2.45-12.54 mmol ACAE/g) inhibitory effects. The orthogonal projections to latent structures discriminant analysis (OPLS-DA) allowed the objective differentiation between the roots and aerial parts of the two investigated species based on their phytochemical and biological profiles. The partial least square (PLS) analysis showed that several individual phenolic acids, such as danshensu, rabdosiin and rosmarinic acid, significantly contributed to the antioxidant potential of both Boraginaceae species, whilst the relative levels of sucrose were positively correlated with the anti-enzymatic properties. Overall, S. officinale and A. ochroleuca could be regarded as rich sources of bioactive phytochemicals that could further lead to developing novel phyto-pharmaceutical commodities.


Assuntos
Boraginaceae , Confrei , Antioxidantes/farmacologia , Cromatografia Líquida , Compostos Fitoquímicos , Extratos Vegetais/farmacologia
3.
Molecules ; 26(12)2021 Jun 08.
Artigo em Inglês | MEDLINE | ID: mdl-34201193

RESUMO

Ehretia laevis Roxb. (Boraginaceae) has been extensively used as a traditional remedy for the treatment of a diverse range of ailments related to the respiratory system, the gastrointestinal tract, the reproductive system, and against several infections. This review critically assesses and documents, for the first time, the fragmented information on E. laevis, including its botanical description, folklore uses, bioactive phyto metabolites and pharmacological activities. The goal is to explore this plant therapeutically. Ethnomedicinal surveys reveal that E. laevis has been used by tribal communities in Asian countries for the treatment of various disorders. Quantitative and qualitative phytochemical investigations of E. laevis showed the presence of important phytoconstituents such as pentacyclic triterpenoids, phenolic acids, flavonoids, fatty acids, steroids, alkaloids, aliphatic alcohols, hydrocarbons, amino acids, carbohydrates, vitamins and minerals. Fresh plant parts, crude extracts, fractions and isolated compounds have been reported to exhibit broad spectrum of therapeutic activities viz., antioxidant, antiarthritic, antidiabetic, anti-inflammatory, antiulcer, antidiarrheal, antidysenteric, wound healing and anti-infective activities. E. laevis is shown to be an excellent potential source of drugs for the mitigation of jaundice, asthma, dysentery, ulcers, diarrhea, ringworm, eczema, diabetes, fissure, syphilis, cuts and wounds, inflammation, liver problems, venereal and infectious disorders. Although few investigations authenticated its traditional uses but employed uncharacterized crude extracts of the plant, the major concerns raised are reproducibility of therapeutic efficacy and safety of plant material. The outcomes of limited pharmacological screening and reported bioactive compounds of E. laevis suggest that there is an urgent need for in-depth pharmacological investigations of the plant.


Assuntos
Boraginaceae/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Ásia , Etnofarmacologia/métodos , Humanos , Medicina Tradicional/métodos , Reprodutibilidade dos Testes
4.
Molecules ; 26(14)2021 Jul 12.
Artigo em Inglês | MEDLINE | ID: mdl-34299514

RESUMO

Aspergillus is one of the most diverse genera, and it is chemically profound and known to produce many biologically active secondary metabolites. In the present study, a new aspochalasin H1 (1), together with nine known compounds (2-10), were isolated from a Hawaiian plant-associated endophytic fungus Aspergillus sp. FT1307. The structures were elucidated using nuclear magnetic resonance (NMR) (1H, 1H-1H COSY, HSQC, HMBC, ROESY and 1D NOE), high-resolution electrospray ionization mass spectroscopy (HRESIMS), and comparisons with the reported literature. The absolute configuration of the new compound was established by electronic circular dichroism (ECD) in combination with NMR calculations. The new compound contains an epoxide moiety and an adjacent trans-diol, which has not been reported before in the aspochalasin family. The antibacterial screening of the isolated compounds was carried out against pathogenic bacteria (Staphylococcus aureus, Methicillin-resistant S. aureus and Bacillus subtilis). The antiproliferative activity of compounds 1-10 was evaluated against human breast cancer cell lines (MCF-7 and T46D) and ovarian cancer cell lines (A2780).


Assuntos
Aspergillus/metabolismo , Boraginaceae/microbiologia , Citocalasinas/farmacologia , Antibacterianos/farmacologia , Antineoplásicos/farmacologia , Neoplasias da Mama/tratamento farmacológico , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Dicroísmo Circular , Feminino , Hawaii , Humanos , Células MCF-7 , Espectroscopia de Ressonância Magnética/métodos , Neoplasias Ovarianas/tratamento farmacológico
5.
Molecules ; 26(10)2021 May 18.
Artigo em Inglês | MEDLINE | ID: mdl-34069766

RESUMO

The aim of this study was to investigate the chemical composition, antioxidant and enzyme inhibitory activities of methanol (MeOH) extracts from Onosma bourgaei (Boiss.) and O. trachytricha (Boiss.). In addition, the interactions between phytochemicals found in extracts in high amounts and the target enzymes in question were revealed at the molecular scale by performing in silico molecular docking simulations. While the total amount of flavonoid compounds was higher in O. bourgaei, O. trachytricha was richer in phenolics. Chromatographic analysis showed that the major compounds of the extracts were luteolin 7-glucoside, apigenin 7-glucoside and rosmarinic acid. With the exception of the ferrous ion chelating assay, O. trachytricha exhibited higher antioxidant activity than O. bourgaei. O. bourgaei exhibited also slightly higher activity on digestive enzymes. The inhibitory activities of the Onosma species on tyrosinase were almost equal. In addition, the inhibitory activities of the extracts on acetylcholinesterase (AChE) were stronger than the activity on butyrylcholinesterase (BChE). Molecular docking simulations revealed that luteolin 7-glucoside and apigenin 7-glucoside have particularly strong binding affinities against ChEs, tyrosinase, α-amylase and α-glucosidase when compared with co-crystallized inhibitors. Therefore, it was concluded that the compounds in question could act as effective inhibitors on cholinesterases, tyrosinase and digestive enzymes.


Assuntos
Antioxidantes/farmacologia , Boraginaceae/química , Inibidores Enzimáticos/farmacologia , Simulação de Acoplamento Molecular , Inibidores Enzimáticos/química , Sequestradores de Radicais Livres/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Termodinâmica
6.
J Ethnopharmacol ; 277: 114222, 2021 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-34033901

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: There have been different methods proposed to prevent the sexual transmission of HIV-1 and many of them have centered on the use of anti-retrovirals as microbicides. Given that a large section of the African population still relies on herbal medicine, Lobostemon trigonus (L. trigonus), a traditionally used medicinal plant in South Africa to treat HIV-1 was further investigated for its potential as a natural microbicide to prevent the sexual transmission of HIV-1. METHODS: The aerial parts of L. trigonus were oven-dried at 80 °C, ground, extracted with boiling water for 30 min and then filtered. The aqueous extract produced was then bioassayed using different HIV-1 inhibition assays. The active components were purified and chemically profiled using ultra-performance liquid chromatography/quadrupole time-of flight mass spectrometry (UPLC-qTOF-MS). The mechanism of HIV-1 inhibition was determined by fusion arrest assay and time of addition assay. Molecular modelling and molecular dynamic simulations, using Schrödinger, were used to better understand the molecule's mechanism of entry inhibition by evaluating their docking affinity and stability against the gp120 of HIV-1. RESULTS: The aqueous extract of this plant had a broad spectrum of activity against different subtypes of the virus; neutralizing subtype A, B and C in the TZM-bl cells, with IC50 values ranging from 0.10 to 7.21 µg/mL. The extract was also inhibitory to the virus induced cytopathic effects in CEM-SS cells with an EC50 of 8.9 µg/mL. In addition, it inhibited infection in peripheral blood mononuclear cells (PBMC) and macrophages with IC50 values of 0.97 and 4.4 µg/mL, respectively. In the presence of vaginal and seminal simulants, and in human semen it retained its inhibitory activity albeit with a decrease in efficiency, by about 3-fold. Studies of the mode of action suggested that the extract blocked HIV-1 attachment to target cells. No toxicity was observed when the Lactobacilli strains, L. acidophilus, L. jensenii, and L. crispatus that populate the female genital tract were cultured in the presence of L. trigonus extract. UPLC-qTOF-MS analyses of the purified fraction of the extract, confirmed the presence of six compounds of which four were identified as rosmarinic acid, salvianolic acids B and C and lithospermic acid. The additional molecular dynamic simulations provided further insight into the entry inhibitory characteristics of salvianolic acid B against the HIV-1 gp120, with a stable pose being found within the CD4 binding site. CONCLUSION: The data suggests that the inhibitory effect of L. trigonus may be due to the presence of organic acids which are known to possess anti-HIV-1 properties. The molecules salvianolic acids B and C have been identified for the first time in L. trigonus species. Our study also showed that the L. trigonus extract blocked HIV-1 attachment to target cells, and that it has a broad spectrum of activity against different subtypes of the virus; thus, justifying further investigation as a HIV-1 microbicide.


Assuntos
Boraginaceae/química , HIV-1/efeitos dos fármacos , Extratos Vegetais/farmacologia , Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Cromatografia Líquida de Alta Pressão , Feminino , Humanos , Leucócitos Mononucleares/efeitos dos fármacos , Leucócitos Mononucleares/virologia , Masculino , Modelos Moleculares , Simulação de Dinâmica Molecular , Componentes Aéreos da Planta , África do Sul
7.
Zhongguo Zhong Yao Za Zhi ; 46(9): 2182-2189, 2021 May.
Artigo em Chinês | MEDLINE | ID: mdl-34047119

RESUMO

Carboxyl CoA ligases(CCLs) is an important branch of adenylate synthetase gene family, which mainly has two-step catalytic reactions. Firstly, in the presence of adenosine triphosphate, it can catalyze the pyrophosphorylation of carboxylateswith diffe-rent structures to form corresponding acyl adenosine monophosphate intermediates. Secondly, adenosine monophosphate was replaced by free electrons in the mercaptan group of enzyme A or other acyl receptors by nucleophilic attack to form thioesters. In this study, on the basis of the transcriptome database of Arnebia euchroma, two genes were selected, named AeCCL5(XP_019237476.1) and AeCCL7(XP_019237476.1). Bioinformatics analysis showed that their relative molecular weights were 60.569 kDa and 60.928 kDa, theoretical PI were 8.59 and 8.92, respectively. They both have transmembrane domains but without signal peptide. By multiple sequence alignment and phylogenetic tree analysis, we found that the similarity between AeCCLs and other plant homologous proteins was not high, and the substrate binding sites of AeCCLs were not highly conserved. The reasons might be that the sequence and structure need to adapt to the changes of new substrates in the process of evolution. In this study, the full-length of AeCCL5 and AecCCL7 were cloned into the expression vector pCDFDuet-1. The proteins of AeCCL5 and AeCCL7 with His-tag were expressed in Escherichia coli. The proteins of AeCCL5 and AeCCL7 were purified by nickel column. In vitro enzymatic reactions proved that both AeCCL5 and AeCCL7 can participate in the upstream phenylpropane pathway of shikonin biosynthesisby catalyzing 4-coumaric acid to produce 4-coumarin-CoA, and then to synthesis p-hydroxybenzoic acid, which is an important precursor of shikonin biosynthesis in A. euchroma.


Assuntos
Boraginaceae , Coenzima A Ligases , Boraginaceae/genética , Clonagem Molecular , Coenzima A , Coenzima A Ligases/genética , Ligases , Filogenia
8.
Vet Med Sci ; 7(4): 1417-1425, 2021 07.
Artigo em Inglês | MEDLINE | ID: mdl-33939304

RESUMO

BACKGROUND: Rheumatoid arthritis (RA) is a systemic chronic disease with synovial membrane, tendon and articular tissue inflammation. Current treatments of RA have many side effects and are quite expensive. Today, new treatments procedures and inexpensive herbal drugs are developed. Marham-Mafasel is mainly made out of two traditional herbs (Arnebia euchroma and Martricaria chamomilla). OBJECTIVE: In this study, for the first time, the impact of Marham-Mafasel on joint inflammation, histopathological changes and IL-1ß gene expression was evaluated in RA animal model. METHODS: The RA was induced by a single s.c. injection of 0.1 ml Freund's complete adjuvant into the left hind footpad. In continuous, 15 RA male Wistar rats were used in three groups: I: Control; II: Treatment I (Piroxicam) and III: Treatment II (Marham-Mafasel). The volume of the hind paw was measured every day from 0 to 19 using water changed volume approach. The inflammation in the joint was evaluated using histopathology assay and gene expression of IL-1ß was evaluated with use of Real-Time PCR. RESULTS: Hind paw swelling of Marham-Mafasel at days 10th and 19th was reduced compared with the control group (p < 0.05). There was no statistically difference in histological degrading and changes index in three groups (p ≥ 0.05). Relative expression of IL-1ß in Marham-Mafasel group was significantly decreased compared with other groups. CONCLUSION: The co-administration of M. Chamomile and A. euchroma, called Marham-Mafasel, decreases IL-1ß gene expression that leads to a reduction in inflammation in rheumatoid arthritis (RA) animal model.


Assuntos
Anti-Inflamatórios/farmacologia , Artrite Reumatoide/tratamento farmacológico , Boraginaceae/química , Inflamação/tratamento farmacológico , Interleucina-1beta/metabolismo , Matricaria/química , Animais , Masculino , Medicina Tradicional , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Ratos , Ratos Wistar
9.
Syst Appl Microbiol ; 44(3): 126206, 2021 May.
Artigo em Inglês | MEDLINE | ID: mdl-33945925

RESUMO

Two Gram-negative, aerobic, rod-shaped and yellow-orange pigmented bacterial strains (LMG 31523T and LMG 31524) were isolated from roots of wild-growing Alkanna tinctoria plants collected near Thessaloniki, Greece. Analysis of their 16S rRNA gene sequences revealed that they form a separate cluster related to the genus Roseomonas. A comparative whole genome analysis of the two strains and the type strains of related Roseomonas species revealed average nucleotide identity values from 78.84 and 80.32%. The G + C contents of the genomic DNA of strains LMG 31523T and LMG 31524 were 69.69% and 69.74%, respectively. Combined data from phenotypic, phylogenetic and chemotaxonomic studies indicated that the strains LMG 31523T and LMG 31524 represent a novel species of the genus Roseomonas. Genome analysis of the new strains showed a number of genes involved in survival in the rhizosphere environment and in plant colonization and confirmed the endophytic characteristics of LMG 31523T and LMG 31524. Since the strains LMG 31523T and LMG 31524 were isolated from a plant collected in Greece the name Roseomonas hellenica sp. nov. is proposed. The type strain is LMG 31523T (=CECT 30032T).


Assuntos
Boraginaceae , Methylobacteriaceae , Filogenia , Técnicas de Tipagem Bacteriana , Composição de Bases , Boraginaceae/microbiologia , DNA Bacteriano/genética , Endófitos , Grécia , Methylobacteriaceae/classificação , Methylobacteriaceae/isolamento & purificação , Pigmentação , Raízes de Plantas/microbiologia , RNA Ribossômico 16S/genética , Análise de Sequência de DNA
10.
Molecules ; 26(6)2021 Mar 10.
Artigo em Inglês | MEDLINE | ID: mdl-33801907

RESUMO

Comfrey (Symphytum officinale) is a medicinal plant with anti-inflammatory, analgesic, and proliferative properties. However, its pharmaceutical application is hampered by the co-occurrence of toxic pyrrolizidine alkaloids (PAs) in its tissues. Using a CRISPR/Cas9-based approach, we introduced detrimental mutations into the hss gene encoding homospermidine synthase (HSS), the first pathway-specific enzyme of PA biosynthesis. The resulting hairy root (HR) lines were analyzed for the type of gene-editing effect that they exhibited and for their homospermidine and PA content. Inactivation of only one of the two hss alleles resulted in HRs with significantly reduced levels of homospermidine and PAs, whereas no alkaloids were detectable in HRs with two inactivated hss alleles. PAs were detectable once again after the HSS-deficient HRs were fed homospermidine confirming that the inability of these roots to produce PAs was only attributable to the inactivated HSS and not to any unidentified off-target effect of the CRISPR/Cas9 approach. Further analyses showed that PA-free HRs possessed, at least in traces, detectable amounts of homospermidine, and that the PA patterns of manipulated HRs were different from those of control lines. These observations are discussed with regard to the potential use of such a CRISPR/Cas9-mediated approach for the economical exploitation of in vitro systems in a medicinal plant and for further studies of PA biosynthesis in non-model plants.


Assuntos
Alquil e Aril Transferases/genética , Confrei/genética , Alcaloides de Pirrolizidina/metabolismo , Alquil e Aril Transferases/metabolismo , Boraginaceae/genética , Boraginaceae/metabolismo , Sistemas CRISPR-Cas/genética , Confrei/metabolismo , Edição de Genes/métodos , Regulação da Expressão Gênica de Plantas/genética , Raízes de Plantas/genética , Plantas Medicinais/genética , Alcaloides de Pirrolizidina/química
11.
Molecules ; 26(7)2021 Apr 02.
Artigo em Inglês | MEDLINE | ID: mdl-33918531

RESUMO

Admittedly, the disastrous emergence of drug resistance in prokaryotic and eukaryotic human pathogens has created an urgent need to develop novel chemotherapeutic agents. Onosma chitralicum is a source of traditional medicine with cooling, laxative, and anthelmintic effects. The objective of the current research was to analyze the biological potential of Onosma chitralicum, and to isolate and characterize the chemical constituents of the plant. The crude extracts of the plant prepared with different solvents, such as aqueous, hexane, chloroform, ethyl acetate, and butanol, were subjected to antimicrobial activities. Results corroborate that crude (methanol), EtoAc, and n-C6H14 fractions were more active against bacterial strains. Among these fractions, the EtoAc fraction was found more potent. The EtoAc fraction was the most active against the selected microbes, which was subjected to successive column chromatography, and the resultant compounds 1 to 7 were isolated. Different techniques, such as UV, IR, and NMR, were used to characterize the structures of the isolated compounds 1-7. All the isolated pure compounds (1-7) were tested for their antimicrobial potential. Compounds 1 (4',8-dimethoxy-7-hydroxyisoflavone), 6 (5,3',3-trihydroxy-7,4'-dimethoxyflavanone), and 7 (5',7,8-trihydroxy-6,3',4'-trimethoxyflavanone) were found to be more active against Staphylococcus aureus and Salmonella Typhi. Compound 1 inhibited S. typhi and S. aureus to 10 ± 0.21 mm and 10 ± 0.45 mm, whereas compound 6 showed inhibition to 10 ± 0.77 mm and 9 ± 0.20 mm, respectively. Compound 7 inhibited S. aureus to 6 ± 0.36 mm. Compounds 6 and 7 showed significant antibacterial potential, and the structure-activity relationship also justifies their binding to the bacterial enzymes, i.e., beta-hydroxyacyl dehydratase (HadAB complex) and tyrosyl-tRNA synthetase. Both bacterial enzymes are potential drug targets. Further, the isolated compounds were found to be active against the tested fungal strains. Whereas docking identified compound 7, the best binder to the lanosterol 14α-demethylase (an essential fungal cell membrane synthesizing enzyme), reported as an antifungal fluconazole binding enzyme. Based on our isolation-linked preliminary structure-activity relationship (SAR) data, we conclude that O. chitralicum can be a good source of natural compounds for drug development against some potential enzyme targets.


Assuntos
Proteínas de Bactérias/antagonistas & inibidores , Boraginaceae/química , Simulação por Computador , Farmacorresistência Bacteriana , Flavonoides/química , Flavonoides/isolamento & purificação , Salmonella typhi/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos , Antifúngicos/química , Antifúngicos/farmacologia , Proteínas de Bactérias/química , Proteínas de Bactérias/metabolismo , Sítios de Ligação , Avaliação Pré-Clínica de Medicamentos , Farmacorresistência Bacteriana/efeitos dos fármacos , Flavonoides/farmacologia , Testes de Sensibilidade Microbiana , Simulação de Acoplamento Molecular , Salmonella typhi/metabolismo , Staphylococcus aureus/metabolismo , Relação Estrutura-Atividade
12.
Nutrients ; 13(4)2021 Mar 31.
Artigo em Inglês | MEDLINE | ID: mdl-33807148

RESUMO

Antitumor effects of shikonins on chronic lymphocytic leukemia (CLL) and B-cell prolymphocytic leukemia (B-PLL) are mostly unexplored. The antitumor activity of shikonins, isolated from Onosma visianii Clem (Boraginaceae), in BCL1, mouse CLL cells and JVM-13, human B-PLL cells was explored in this study. The cytotoxicity of shikonin derivatives was measured by an MTT test. Cell death, proliferation, cell cycle, and expression of molecules that control these processes were analyzed by flow cytometry. Expression of STAT3-regulated genes was analyzed by real-time q-RT-PCR (Quantitative Real-Time Polymerase Chain Reaction). The antitumor effects of shikonin derivatives in vivo were analyzed, using flow cytometry, by detection of leukemia cells in the peripheral blood and spleens of mice intravenously injected with BCL1 cells. The two most potent derivatives, isobutyrylshikonin (IBS) and α-methylbutyrylshikonin (MBS), induced cell cycle disturbances and apoptosis, inhibited proliferation, and decreased expression of phospho-STAT3 and downstream-regulated molecules in BCL1 and JVM-13 cells. IBS and MBS decreased the percentage of leukemia cells in vivo. The link between the decrease in phosphorylated STAT3 by MBS and IBS and BCL1 cell death was confirmed by detection of enhanced cell death after addition of AG490, an inhibitor of Jak2 kinase. It seems that IBS and MBS, by decreasing STAT3 phosphorylation, trigger apoptosis, inhibit cell proliferation, and attenuate leukemia cell stemness.


Assuntos
Boraginaceae/química , Leucemia/metabolismo , Naftoquinonas/química , Fator de Transcrição STAT3/metabolismo , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Apoptose , Linhagem Celular , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Masculino , Proteínas de Membrana , Camundongos , Camundongos Endogâmicos BALB C , Fosfoproteínas , Fator de Transcrição STAT3/genética
13.
Zhongguo Zhong Yao Za Zhi ; 46(1): 86-93, 2021 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-33645056

RESUMO

Caffeic acid and its oligomers are the main water-soluble active constituents of the traditional Chinese medicine(TCM) Arnebiae Radix. These compounds possess multiple biological activities such as antimicrobial, antioxidant, cardiovascular protective, liver protective, anti-liver fibrosis, antiviral and anticancer activities. The phenylpropanoid pathway in plants is responsible for the biosynthesis of caffeic acid and its oligomers. Glycosylation can change phenylpropanoid solubility, stability and toxic potential, as well as influencing compartmentalization and biological activity. In view of the important role played by de-glycosylation in the regulation of phenylpropanoid homeostasis, the biosynthesis of caffeic acid and its oligomers are supposed to be under the control of relative UDP-glycosyltransferases(UGTs). Through the data mining of Arnebia euchroma transcriptome, we cloned 15 full-length putative UGT genes. After recombinant expression using the prokaryotic system, the crude enzyme solution of the putative UGTs was examined for the glycosylation activities towards caffeic acid and rosmarinic acid in vitro. AeUGT_01, AeUGT_02, AeUGT_03, AeUGT_04 and AeUGT_10 were able to glycosylate caffeic acid and/or rosmarinic acid resulting in different mono-and/or di-glycosylated products in the UPLC-MS analyses. The characterized UGTs were distantly related to each other and divided into different clades of the phylogenetic tree. Based on the observation that each characterized UGT exhibited substrate or catalytic similarity with the members in their own clade, we supposed the glycosylation abilities towards caffeic acid and/or rosmarinic acid were evolved independently in different clades. The identification of caffeic acid and rosmarinic acid UGTs from A. euchroma could lead to deeper understanding of the caffeic acid oligomers biosynthesis and its regulation. Furthermore, these UGTs might be used for regiospecific glycosylation of caffeic acid and rosmarinic acid to produce bioactive compounds for potential therapeutic applications.


Assuntos
Boraginaceae , Glicosiltransferases , Boraginaceae/genética , Ácidos Cafeicos , Cromatografia Líquida , Cinamatos , Clonagem Molecular , Depsídeos , Glicosiltransferases/genética , Filogenia , Espectrometria de Massas em Tandem
14.
Org Lett ; 23(7): 2455-2459, 2021 04 02.
Artigo em Inglês | MEDLINE | ID: mdl-33728922

RESUMO

Shikonin and S-enantiomer alkannin are important naphthoquinone derivatives present in many Boraginaceae species. We report that cytochrome P450 monooxygenases (CYPs) from a new CYP82AR subfamily catalyzed hydroxylations of deoxyshikonin at C-1' position of isoprenoid side chain. Two homologues were discovered from each species of the four Boraginaceae plants. One CYP preferred converting deoxyshikonin into shikonin, and the other stereoselectively hydroxylated deoxyshikonin into alkannin. The discovery might be a general feature of shikonin/alkannin-producing Boraginaceae plants.


Assuntos
Boraginaceae/metabolismo , Sistema Enzimático do Citocromo P-450/metabolismo , Naftoquinonas/química , Boraginaceae/química , Catálise , Sistema Enzimático do Citocromo P-450/química , Hidroxilação , Estrutura Molecular , Naftoquinonas/metabolismo , Extratos Vegetais , Terpenos/química
15.
J Ethnopharmacol ; 271: 113896, 2021 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-33524510

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: The present study has indicated phytochemical composition, distribution and ethno-medicinal uses of Arnebia euchroma (Royle) I.M. Johnst, which is commonly known as "Ratanjot" in the Indian subcontinent. It has widely been used in the traditional systems of the Unani, Ayurvedic and Chinese medicines recipes due to its anti-fungal and anti-microbial properties. Instead, the gap of earlier studies is well defined that will be helpful for researchers to carry out more analysis and increase medicinal importance of this plant. AIM OF STUDY: The main aim of this review study is to demonstrate the phytochemical composition and traditional ethno-medicinal uses of A. euchroma all over the world. Earlier studies related to this plant have been discussed in the present study and on that basis, future perspective of A. euchroma is also proposed. MATERIALS AND METHODS: The information of A. euchroma has been gathered from various electronic database, reference books and available literature. RESULTS: The study has indicated that Arnebia euchroma owing to anti-microbial and anti-inflammatory properties is used in the traditional medicines and pharmaceutical industries for the treatment of hair problems, remitting, chronic diseases, burnt limbs, cough and cold, etc., and besides as a vegetable colorant and dyeing of cloths. The important phytochemical constituents viz., shikonin, acetyl-shikonin, iso-butyryl-shikonin, ß,ß-di-methylacryl-shikonin, isovaleryl-shikonin, ß-hydroxy-isovaleryl-shikonin, deoxy-shikonin, isobutyl-shikonin, arnebinone, arnebin-7, stigmasterol, etc., isolated from the roots of Arnebia euchroma are used for curing various harmful diseases. CONCLUSIONS: The earlier studies have confirmed that Arnebia euchroma is having wound healing, anti-microbial and anti-bacterial properties and thus used for the treatment of several diseases. Although, a little works is done on the experimental study regarding anti-HIV, anti-cancer diseases, etc., so there is a requirement of more exploration via analytical studies on phytochemical compounds to treat such diseases. Moreover, the information of its clinical and pharmacokinetics uses is also limited. Therefore, further research is needed to understand bioavailability and pharmacokinetics of this species. In-situ and ex-situ conservations for the management of this endangered species are also lacking in the Himalayan perspective. Such studies will emphasize to explore the possibilities for its conservation and development of agro-technological protocol.


Assuntos
Boraginaceae/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/uso terapêutico , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Animais , Etnofarmacologia , Humanos , Medicina Tradicional , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/toxicidade , Extratos Vegetais/farmacologia , Extratos Vegetais/toxicidade , Raízes de Plantas/química
16.
Z Naturforsch C J Biosci ; 76(5-6): 205-212, 2021 May 26.
Artigo em Inglês | MEDLINE | ID: mdl-33544998

RESUMO

In the current study the pyrrolizidine alkaloid profiles of the species Echium sabulicola ssp. decipiens (Pomel) Klotz and Solenanthus lanatus DC were studied in various extracts. In addition, a chemotaxonomic study within the genus and the family was carried out. The analysis was carried out by using gas chromatography coupled to mass spectrometry and by comparing the Kovats Indices and molecular and fragment ions with literature data. Twenty-three alkaloids were tentatively identified. The results showed the presence of already reported compounds as well as previously unreported ones leading both to a confirmation of the botanical classification of the two studied species and to a brand new path in the chemotaxonomy of Boraginaceae family. The presence of some pyrrolizidine alkaloids sets limits for the usage of these plants for medicinal purposes. The identified compounds confirm the botanical classification of the studied species as members of the Boraginaceae family and their presence advices against their use in the ethnopharmacological field.


Assuntos
Boraginaceae/química , Alcaloides de Pirrolizidina/química , Argélia , Boraginaceae/metabolismo , Frutas/química , Frutas/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Conformação Molecular , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Alcaloides de Pirrolizidina/isolamento & purificação
17.
Oxid Med Cell Longev ; 2021: 5469849, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33510837

RESUMO

The antiaging benzoquinone-type molecule ehretiquinone was isolated in a previous study as a leading compound from the herbal medicine Onosma bracteatum wall. This paper reports the antiaging effect and mechanism of ehretiquinone by using yeasts, mammal cells, and mice. Ehretiquinone extends not only the replicative lifespan but also the chronological lifespan of yeast and the yeast-like chronological lifespan of mammal cells. Moreover, ehretiquinone increases glutathione peroxidase, catalase, and superoxide dismutase activity and reduces reactive oxygen species and malondialdehyde (MDA) levels, contributing to the lifespan extension of the yeasts. Furthermore, ehretiquinone does not extend the replicative lifespan of Δsod1, Δsod2, Δuth1, Δskn7, Δgpx, Δcat, Δatg2, and Δatg32 mutants of yeast. Crucially, ehretiquinone induces autophagy in yeasts and mice, thereby providing significant evidence on the antiaging effects of the molecule in the mammalian level. Concomitantly, the silent information regulator 2 gene, which is known for its contributions in prolonging replicative lifespan, was confirmed to be involved in the chronological lifespan of yeasts and participates in the antiaging activity of ehretiquinone. These findings suggest that ehretiquinone shows an antiaging effect through antioxidative stress, autophagy, and histone deacetylase Sir2 regulation. Therefore, ehretiquinone is a promising molecule that could be developed as an antiaging drug or healthcare product.


Assuntos
Autofagia/efeitos dos fármacos , Benzoquinonas/farmacologia , Boraginaceae/química , Estresse Oxidativo/efeitos dos fármacos , Saccharomyces cerevisiae/metabolismo , Animais , Autofagia/genética , Benzoquinonas/química , Benzoquinonas/isolamento & purificação , Estresse Oxidativo/genética , Células PC12 , Ratos , Saccharomyces cerevisiae/genética
18.
J Food Sci ; 86(2): 357-365, 2021 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-32984979

RESUMO

In this study, besides isovaleryl shikonin, another shikonin derivative, tigloylshikonin, was also isolated from the roots of Onosma hookeri Clarke. var. longiforum Duthie as a main naphthoquinone constituent for the first time. Then optimization of the ultrasonic-assisted extraction was done by Box-Behnken design-response surface methodology on the basis of single-factor experiments. The optimized conditions were 72% (v/v) ethanol and the material to solution ratio was 1:37(g/mL) at 52 °C for 77 min. Under these conditions, the extraction yield of ethanol extract was 36.74 ± 0.32%, the contents of isovaleryl shikonin and tigloylshikonin reached 0.094 ± 0.003% and 0.223 ± 0.006%, respectively. Notably, in that optimized condition, the yield of isovaleryl shikonin increased by approximately 7.64-fold than the previous report. In the in vitro antioxidant activity assay, the optimal ethanol extract exhibited similar 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity as butylated hydroxy toluene (BHT), but slightly weaker 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS) scavenging activity and total antioxidant capacity than that of BHT. However, the active polar fraction, the ethyl acetate fraction, which is enriched with naphthoquinone constituents, performs as a better antioxidant agent than BHT. Therefore, both of them could be considered as a naturally sourced antioxidants compared to commercially available synthetic drugs. PRACTICAL APPLICATION: Onosma hookeri Clarke. var. longiforum Duthie, a traditional Chinese medicine and food item, has been in use since a long time. A systematic determination of the main naphthoquinones, and antioxidant capacity of the naphthoquinones-enriched ethanol extract and different polar fractions, was carried out in the present study. The results may provide theoretical basis for the claim that naphthoquinones-enriched ethanol extract and ethyl acetate fraction from the roots of Onosma hookeri Clarke. var. longiforum Duthie could be used as potential natural antioxidants in the pharmaceutical, food, and cosmetic industries.


Assuntos
Boraginaceae/química , Naftoquinonas/análise , Naftoquinonas/isolamento & purificação , Extratos Vegetais/química , Antioxidantes/química , Sequestradores de Radicais Livres/química , Naftoquinonas/química , Ácidos Pentanoicos/isolamento & purificação , Raízes de Plantas/química , Ultrassom
19.
Braz J Biol ; 81(3): 650-656, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-32876169

RESUMO

Light is considered a factor that influences the seed germination of many weed species, and it can signal whether the environmental conditions are favorable or are not favorable for germination. We aimed to study if there is an influence of light quality and dormancy overcoming in seed germination of Echium plantagineum L. We carried out a 2 x 6 factorial experiment, with and without dormancy overcoming with potassium nitrate followed by immersion in gibberellic acid; six light qualities, obtained through the light filters: blue, green, red, far-red, white light and absence of light. The evaluations performed were germination speed index (GSI), average germination time (AGT), germination at the four and 14 days after seeding (DAS), accumulated germination and relative frequency of germination. We observed significant interaction among the light qualities and seed dormancy overcoming or not for the studied variables. There was no significant effect of light qualities, in the evaluated variables, when performing dormancy overcoming, presenting germination above 90% in all the light qualities. However, without dormancy overcoming, we observed greater GSI, germination at four and 14 DAS for the red light filter with 5, 4, 29 and 45%, respectively. When the seeds were submitted to the absence of light, and without dormancy overcoming, there was only 7% of germination at 14 DAS. The seeds of E. plantagineum presented greater germination under incidence of red light, without dormancy overcoming, being classified as preferably positively photoblastics, provided that the dormancy is not overcome.


Assuntos
Boraginaceae , Echium , Germinação , Dormência de Plantas , Sementes
20.
Environ Sci Pollut Res Int ; 28(12): 14983-15004, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33222070

RESUMO

Onosma bracteata Wall. (Boraginaceae), commonly known as "gaozaban" is a highly valuable medicinal herb, useful in the treatment of body swellings, abdominal pain, eye-related problems, fever, and urinary calculi. The present study was performed to investigate the antioxidant properties of extract/fractions, viz. ethanol (Obeth) extract, hexane (Obhex) fraction, chloroform (Obcl) fraction, ethyl acetate (Obea) fraction, butanol (Obbu) fraction, and aqueous (Obaq) fraction isolated from O. bracteata. Obea fraction showed stronger free radical quenching ability in various antioxidant assays, as compared to the other fractions. Obea fraction with effective free radical-scavenging properties was further evaluated for the antiproliferative activity against human osteosarcoma MG-63, human neuroblastoma IMR-32, and human lung cancer A549 cell lines using MTT assay. Obea fraction showed strong cytotoxicity with GI50 value of 88.56, 101.61, and 112.7 µg/ml towards MG-63, IMR-32, and A549 cells respectively. Mechanistic studies revealed that Obea fraction in osteosarcoma MG-63 cells increased reactive oxygen species (ROS) level and reduced mitochondrial membrane potential. In the presence of Obea, the cells were found to be arrested in the G0/G1 phase in a dose-dependent manner which is also confirmed by the enhancement in the early apoptotic cell population in flow cytometer analysis. Western blotting demonstrated the decrease in expression of p-NFκB, COX-2, p-Akt, and Bcl-xL, whereas upregulation was observed in the expression of GSK-3ß, p53, caspase-3, and caspase-9 proteins. RT-qPCR studies revealed downregulation of Bcl-2, cyclin E, CDK2, and mortalin gene expression and upregulation in the expression of p53 genes. The antioxidant and cytotoxic potential of Obea was attributed to the presence of catechin, kaempferol, onosmin A, and epicatechin, as revealed by HPLC analysis. This is the first report regarding the antiproliferative potential of O. bracteata against osteosarcoma.


Assuntos
Boraginaceae , Osteossarcoma , Apoptose , Linhagem Celular Tumoral , Ciclina E , Glicogênio Sintase Quinase 3 beta , Humanos , Osteossarcoma/tratamento farmacológico , Extratos Vegetais/farmacologia , Proteínas Proto-Oncogênicas c-akt , Espécies Reativas de Oxigênio
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