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1.
Sci Rep ; 12(1): 7194, 2022 May 03.
Artigo em Inglês | MEDLINE | ID: mdl-35505005

RESUMO

The basic helix-loop-helix (bHLH) transcription factors are involved in several biological processes both in plant development and stress responses. Agarwood, a major active and economical product, is only induced and accumulated when the roots, stems, or branches are wounded in Aquilaria sinensis. Although genome-wide comprehensive analyses of the bHLH family have been identified in many plants, no systematic study of the genes in this family has been conducted in A. sinensis. In this study, 105 bHLH genes were identified in A. sinensis through genome-wide analysis and named according to their chromosomal locations. Based on a phylogenetic tree, AsbHLH family proteins were classified into 18 subfamilies. Most of them were distributed on eight chromosomes, with the exception of two genes. Based on the tissue-specific expression characteristics and expression patterns in response to methyl jasmonate (MeJA) treatment, seven AsbHLH genes were likely involved in wound-induced agarwood formation. The results provide comprehensive information on AsbHLHs that can be used to elucidate the molecular functions and physiological roles of these proteins in A. sinensis.


Assuntos
Fatores de Transcrição Hélice-Alça-Hélice Básicos , Thymelaeaceae , Fatores de Transcrição Hélice-Alça-Hélice Básicos/metabolismo , Genoma de Planta , Família Multigênica , Filogenia , Thymelaeaceae/genética , Thymelaeaceae/metabolismo
2.
J Tradit Chin Med ; 42(2): 187-193, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35473338

RESUMO

OBJECTIVE: To observe the effects of the flower of Edgeworthia gardneri (Wall.) Meisn (EWM) on glucose and lipid metabolism in KK/upj-Ay/J (KKAy) mice and investigate the possible mechanism of EWM in the liver of KKAy mice by transcriptome analysis. METHODS: Forty KKAy mice were fed a high-sugar and high-fat diet for 3 weeks to establish the animal model of metabolic syndrome. After 5 weeks of continuous administration of EWM, serum high-density lipoprotein (HDL), low-density lipoprotein (LDL), triglycerides (TG), total cholesterol (TC), and free fatty acids (FFA) were detected by radioimmunoassay. Serum fasting insulin (Fins) and adiponectin levels were measured by enzyme-linked immunosorbent assay. Liver tissue fixed with paraformaldehyde was stained with hematoxylin-eosin and oil red O. Transcriptome analysis was used to evaluate the liver tissue. The expressions of lipoprotein lipase (LPL), peroxisome proliferator-activated receptor-γ (PPARγ), adenosine 5'-monophosphate-activated protein kinase (AMPK), sterol regulatory element binding protein-1c (SREBP-1c), and fatty acid synthase (Fas) mRNA and protein in liver tissue were detected by reverse transcription-polymerase chain reaction (RT-PCR) and Western blot analysis. RESULTS: EWM slightly reduced FBG and Fins in KKAy mice. Furthermore, EWM was able to downregulate serum LDL, TG, TC, and FFA and upregulate the expression of serum HDL and adiponectin. Transcriptome analysis revealed the following differential pathways: the peroxisome proliferator-activated receptor (PPAR) signaling pathway and the AMPK signaling pathway. RT-PCR and western blot analysis detected the associated genes and proteins. In addition, EWM was able to upregulate the expression of AMPK and downregulate the expression of PPARγ, SREBP1c, and Fas mRNA and protein and upregulate the expression of LPL mRNA. CONCLUSIONS: EWM can alleviate lipid metabolism disorders and to some extent improve glucose metabolism disorders in KKAy mice. These effects may be related to regulating PPARγ/LPL and activating the AMPK/SREBP1c/Fas pathway.


Assuntos
Metabolismo dos Lipídeos , Thymelaeaceae , Proteínas Quinases Ativadas por AMP/metabolismo , Adiponectina/metabolismo , Animais , Flores , Glucose , Humanos , Camundongos , PPAR gama/genética , RNA Mensageiro/metabolismo , Proteína de Ligação a Elemento Regulador de Esterol 1/genética , Proteína de Ligação a Elemento Regulador de Esterol 1/metabolismo , Thymelaeaceae/metabolismo , Triglicerídeos
3.
Molecules ; 27(3)2022 Jan 19.
Artigo em Inglês | MEDLINE | ID: mdl-35163893

RESUMO

Aquilaria sinensis (Lour.) Spreng is known for its resinous secretion (agarwood), often secreted in defense against injuries. We investigated the effects of A. sinensis flower extract (AF) on peroxisome proliferator-activated receptors alpha and gamma (PPARα and PPARγ), liver X receptor (LXR), glucose uptake, and lipid accumulation (adipogenesis). Activation of PPARα, PPARγ and LXR was determined in hepatic (HepG2) cells by reporter gene assays. Glucose uptake was determined in differentiated muscle (C2C12) cells using 2-NBDG (2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose). Adipogenesis was determined in adipocytes (3T3-L1 cells) by Oil red O staining. At a concentration of 50 µg/mL, AF caused 12.2-fold activation of PPARα and 5.7-fold activation of PPARγ, while the activation of LXR was only 1.7-fold. AF inhibited (28%) the adipogenic effect induced by rosiglitazone in adipocytes and increased glucose uptake (32.8%) in muscle cells at 50 µg/mL. It was concluded that AF acted as a PPARα/γ dual agonist without the undesired effect of adipogenesis and exhibited the property of enhancing glucose uptake. This is the first report to reveal the PPARα/γ dual agonistic action and glucose uptake enhancing property of AF along with its antiadipogenic effect, indicating its potential in ameliorating the symptoms of metabolic syndrome.


Assuntos
Síndrome Metabólica , Thymelaeaceae , Células 3T3-L1 , Adipogenia , Animais , Flores/metabolismo , Síndrome Metabólica/tratamento farmacológico , Camundongos , PPAR gama/metabolismo , Extratos Vegetais/farmacologia , Thymelaeaceae/metabolismo
4.
BMC Plant Biol ; 21(1): 591, 2021 Dec 13.
Artigo em Inglês | MEDLINE | ID: mdl-34903180

RESUMO

BACKGROUND: Agarwood is a highly sought-after resinous wood for uses in medicine, incense, and perfume production. To overcome challenges associated with agarwood production in Aquilaria sinensis, several artificial agarwood-induction treatments have been developed. However, the effects of these techniques on the metabolome of the treated wood samples are unknown. Therefore, the present study was conducted to evaluate the effects of four treatments: fire drill treatment (F), fire drill + brine treatment (FS), cold drill treatment (D) and cold drill + brine treatment (DS)) on ethanol-extracted oil content and metabolome profiles of treated wood samples from A. sinensis. RESULTS: The ethanol-extracted oil content obtained from the four treatments differed significantly (F < D < DS < FS). A total of 712 metabolites composed mostly of alkaloids, amino acids and derivatives, flavonoids, lipids, phenolic acids, organic acids, nucleotides and derivatives, and terpenoids were detected. In pairwise comparisons, 302, 155, 271 and 363 differentially accumulated metabolites (DAM) were detected in F_vs_FS, D_vs_DS, F_vs_D and FS_vs_DS, respectively. The DAMs were enriched in flavonoid/flavone and flavonol biosynthesis, sesquiterpenoid and triterpenoid biosynthesis. Generally, addition of brine to either fire or cold drill treatments reduced the abundance of most of the metabolites. CONCLUSION: The results from this study offer valuable insights into synthetically-induced agarwood production in A. sinensis.


Assuntos
Metaboloma , Óleos Vegetais/química , Thymelaeaceae/metabolismo , Madeira/metabolismo , Alcaloides/metabolismo , Aminoácidos/metabolismo , Ácidos Carboxílicos/metabolismo , Temperatura Baixa , Etanol , Incêndios , Flavonas/metabolismo , Flavonoides/metabolismo , Hidroxibenzoatos/metabolismo , Metabolismo dos Lipídeos , Nucleotídeos/metabolismo , Sais/farmacologia , Terpenos/metabolismo , Thymelaeaceae/química , Thymelaeaceae/efeitos dos fármacos , Madeira/química , Madeira/efeitos dos fármacos
5.
Xenobiotica ; 51(6): 728-736, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-33874851

RESUMO

Although Edgeworthia gardneri (Wall.) Meisn and its main component tiliroside (TIL) show good bioactivity, its intestinal absorption data supporting its low bioavailability have not been reported.The evaluation results of three absorption models in vitro and in vivo indicated that the results of the Ussing chamber model were basically consistent with the results of in vivo experiments. It was thus applied to investigate the characteristics of TIL across various intestinal regions and the interaction between TIL and adenosine triphosphate (ATP)-binding cassette family proteins (ABC) including, P-glycoprotein (P-gp), multidrug resistance-associated protein 2 (MRP2), and breast cancer resistance protein (BCRP).The data of the bi-directional transport showed that the ileum had the higher apparent permeability coefficient (Papp) of TIL than duodenum and jejunum, suggesting the best absorption of TIL in the ileum.In the presence of the MRP2 inhibitor, the absorption of TIL from water extracts of E. gardneri (Wall.) Meisn (WAE) was improved, indicating that MRP2 other than P-gp and BCRP affected the absorption of TIL and might be responsible for its low bioavailability. This study laid the foundation for enhancing the bioavailability of TIL and highlighted the influences of efflux transporters on bioavailability.


Assuntos
Proteínas de Neoplasias , Thymelaeaceae , Membro 2 da Subfamília G de Transportadores de Cassetes de Ligação de ATP , Flavonoides , Absorção Intestinal , Proteínas Associadas à Resistência a Múltiplos Medicamentos/metabolismo , Proteínas de Neoplasias/metabolismo , Thymelaeaceae/metabolismo
6.
Nat Prod Rep ; 38(3): 528-565, 2021 03 01.
Artigo em Inglês | MEDLINE | ID: mdl-32990292

RESUMO

Covering: Up to the end of 2019.Agarwood is a resinous portion of Aquilaria trees, which is formed in response to environmental stress factors such as physical injury or microbial attack. It is very sought-after among the natural incenses, as well as for its medicinal properties in traditional Chinese and Ayurvedic medicine. Interestingly, the chemical constituents of agarwood and healthy Aquilaria trees are quite different. Sesquiterpenes and 2-(2-phenethyl)chromones with diverse scaffolds commonly accumulate in agarwood. Similar structures have rarely been reported from the original trees that mainly contain flavonoids, benzophenones, xanthones, lignans, simple phenolic compounds, megastigmanes, diterpenoids, triterpenoids, steroids, alkaloids, etc. This review summarizes the chemical constituents and biological activities both in agarwood and Aquilaria trees, and their biosynthesis is discussed in order to give a comprehensive overview of the research progress on agarwood.


Assuntos
Produtos Biológicos/química , Produtos Biológicos/farmacologia , Thymelaeaceae/química , Madeira/química , Alcaloides/química , Alcaloides/farmacologia , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Produtos Biológicos/metabolismo , Flavonoides/química , Flavonoides/farmacologia , Humanos , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Fenóis/química , Fenóis/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Thymelaeaceae/metabolismo , Madeira/metabolismo
7.
Sci Rep ; 10(1): 3018, 2020 02 20.
Artigo em Inglês | MEDLINE | ID: mdl-32080225

RESUMO

The WRKY proteins are a superfamily of transcription factor that regulate diverse developmental and physiological processes in plants. Completion of the whole-genome sequencing of Aquilaria sinensis allowed us to perform a genome-wide investigation for WRKY proteins. Here, we predicted 70 WRKY genes from the A. sinensis genome and undertaken a comprehensive bioinformatic analysis. Due to their diverse structural features, the 70 AsWRKY genes are classified into three main groups (group I-III), with five subgroups (IIa-IIe) in group II, except two belong to none of them. Distinct expression profiles of AsWRKYs with RNA sequencing data revealed their diverse expression patterns among different tissues and in the process of whole-tree-inducing agarwood formation. Based on the expression characteristics, we predict some AsWRKYs are pseudogenes, and some may be involved in the biosynthesis of agarwood sesquiterpenes as activators or repressors. Among the tested genes treated with MeJA and H2O2, most of them are induced by H2O2, but downregulated by MeJA, implying the complexity of their involvement in signal transduction regulation. Our results not only provide a basic platform for functional identification of WRKYs in A. sinensis but important clues for further analysis their regulation role in agarwood formation.


Assuntos
Genoma de Planta , Thymelaeaceae/genética , Thymelaeaceae/metabolismo , Fatores de Transcrição/metabolismo , Acetatos/farmacologia , Cromossomos de Plantas/genética , Sequência Conservada/genética , Ciclopentanos/farmacologia , Regulação da Expressão Gênica de Plantas/efeitos dos fármacos , Genes de Plantas , Peróxido de Hidrogênio/farmacologia , Motivos de Nucleotídeos/genética , Especificidade de Órgãos/efeitos dos fármacos , Especificidade de Órgãos/genética , Oxilipinas/farmacologia , Filogenia , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Thymelaeaceae/efeitos dos fármacos , Madeira/genética
8.
J Exp Bot ; 71(3): 1128-1138, 2020 01 23.
Artigo em Inglês | MEDLINE | ID: mdl-31639819

RESUMO

Agarwood is derived from wounds in Aquilaria trees and is widely used in traditional medicine, incense, and perfume. Sesquiterpenes are one of the main active components in agarwood and are known to be induced by wounding or injury; However, the molecular mechanisms by which wounding leads to sesquiterpene formation remain largely unknown. Agarwood sesquiterpene synthase 1 (ASS1) is one of key enzymes responsible for the biosynthesis of sesquiterpenes and is a crucial jasmonate (JA)-responsive wound-inducible synthase. However, it is not known why ASS1 is not expressed in healthy trees and how its expression is induced as a result of wounding. Here, we report that ASS1 is a wound-induced gene with a promoter in which a 242-bp region (-973 to -731bp) is identified as the core sequence for responding to wound signals. AsWRKY44 binds directly to this region and represses ASS1 promoter activity. Down-regulation or disruption of AsWRKY44 can relieve the inhibition and activate ASS1 expression. In addition, AsWRKY44 is degraded and the expression of ASS1 is significantly up-regulated in response to exogenous application of methyl jasmonate. Thus, AsWRKY44 is a crucial negative regulator of wound-induced ASS1 transcription, and is central to the mechanism of sesquiterpene biosynthesis in agarwood.


Assuntos
Sesquiterpenos/metabolismo , Thymelaeaceae/metabolismo , Fatores de Transcrição/metabolismo , Regulação da Expressão Gênica de Plantas , Regiões Promotoras Genéticas , Thymelaeaceae/genética
9.
J Plant Physiol ; 234-235: 167-175, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-30818186

RESUMO

Agarwood, a non-timber fragrant wood, is produced in wounded Aquilaria trees and widely used in perfume, incense, and medicine. Sesquiterpene is one of its main active compounds. It has been demonstrated that hydrogen peroxide (H2O2) plays a role in promoting agarwood sesquiterpene biosynthesis, but little is known about its signaling pathway. In this study, the pruning of actively growing saplings of A. sinensis resulted in an H2O2 burst and the accumulation of jasmonic acid (JA), salicylic acid (SA), and ethylene (ET), which was followed by the up-regulation of sesquiterpene synthase and the production of sesquiterpene in the pruned stems. This process could be enhanced by absorbed H2O2 and inhibited by an H2O2 scavenger (ascorbate, AsA) in pruned stems, although the concentration of ET and transcription of ET-related synthase genes remained unaffected. These results confirmed that the H2O2 burst in wounded stems triggered JA and SA accumulation to promote agarwood sesquiterpene biosynthesis. ET was also activated by injury that was independent with H2O2. All results excavated a full-scale signaling transduction nets among multiple stress signals during wound-induced agarwood production in A. sinensis and provide a new insight into improving the artificial technology of agarwood production.


Assuntos
Ciclopentanos/metabolismo , Peróxido de Hidrogênio/metabolismo , Oxilipinas/metabolismo , Ácido Salicílico/metabolismo , Sesquiterpenos/metabolismo , Thymelaeaceae/metabolismo , Etilenos/metabolismo
10.
Proteomics ; 18(20): e1800023, 2018 10.
Artigo em Inglês | MEDLINE | ID: mdl-30035352

RESUMO

Agarwood is a precious traditional Chinese medicine with a variety of pharmacological effects. Although efforts have been made in elucidating the mechanism of agarwood formation, little progress is obtained till now. Therefore, the molecular mechanism of agarwood formation needs to be further explored using different biological approaches. In this study, the quantitative proteomic analysis using iTRAQ technology combined with transcriptomic and metabolomic analyses on chemically induced Aquilaria sinensis is performed to elucidate the agarwood formation mechanism by formic acid stimulus. Data are available via ProteomeXchange with identifier PXD007586; 1884 proteins are detected, 504 differential proteins that show at least twofold differences in their expression levels are selected based on GO annotations, KEGG, STRING analysis, and quantitative RT-PCR analysis. The results indicate that sesquiterpene synthase, germin-like protein, pathogenesis-related protein, 6-phosphogluconate dehydrogenase, lipoyl synthase, and superoxide dismutase play important roles in the agarwood formation, suggesting that the proteins related to the plant defensive response, the removal of peroxide, the disease-resistance, the biosythesis of glycan, fatty acids, and sesquiterpene are crucial for agarwood formation.


Assuntos
Formiatos/farmacologia , Metaboloma , Proteínas de Plantas/análise , Proteoma , Thymelaeaceae/metabolismo , Transcriptoma , Madeira/metabolismo , Regulação da Expressão Gênica de Plantas , Thymelaeaceae/efeitos dos fármacos , Thymelaeaceae/genética , Thymelaeaceae/crescimento & desenvolvimento , Madeira/química
11.
PLoS One ; 13(6): e0198111, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-29856792

RESUMO

Only when Aquilaria spp. or Gyrinops spp. trees are wounded, due to insect attack, or microbial invasion, agarwood can be successfully induced. In the present study, a fungus which can induce agarwood formation efficiently was isolated and a suitable method for its application to induce agarwood formation was developed. Rigidoporus vinctus was isolated from the inner layers from infectious A. sinensis trees. When the fermentation liquid of fungi inoculated back to A. sinensis tree, agarwood was found to be induced. In addition, a novel method called trunk surface agarwood-inducing technique (Agar-Sit) was developed to produce agarwood with R. vinctus. The alcohol soluble extract content of the agarwood, up to 38.9%, far higher than the requirement (10%) in Chinese Pharmacopoeia and the six characteristic compounds of agarwood used as Chinese Medicinal Materials were all detected. Their relative percentages of the sesquiterpenes in the essential oil were 22.76%. This is the first report of the Agar-Sit and also the application of R. vinctus in agarwood induction. According to the results, when the combination of Agar-Sit and R. vinctus is used agarwood can be induced with high yield and good quality.


Assuntos
Polyporales/fisiologia , Resinas Vegetais/metabolismo , Thymelaeaceae/microbiologia , Cromatografia Líquida de Alta Pressão , Cromatografia em Camada Delgada , Medicamentos de Ervas Chinesas/análise , Medicamentos de Ervas Chinesas/isolamento & purificação , Fermentação , Fungos/isolamento & purificação , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Caules de Planta/metabolismo , Caules de Planta/microbiologia , Polyporales/química , Polyporales/isolamento & purificação , Resinas Vegetais/química , Sesquiterpenos/análise , Thymelaeaceae/metabolismo
12.
Molecules ; 23(6)2018 May 25.
Artigo em Inglês | MEDLINE | ID: mdl-29799457

RESUMO

Agarwood is highly valued for its uses as incense, perfume, and medicine. However, systematic analyses of dynamic changes of secondary metabolites during the process of agarwood formation have not yet been reported. In this study, agarwood was produced by transfusing the agarwood inducer into the trunk of Aquilaria sinensis, and changing patterns of chemical constituents, especially 2-(2-phenylethyl)chromones (PECs), in wood samples collected from the 1st to 12th month, were analyzed by GC-EI-MS and UPLC-ESI-MS/MS methods. Aromatic compounds, steroids, fatty acids/esters, sesquiterpenoids, and PECs were detected by GC-MS, in which PECs were the major constituents. Following this, UPLC-MS was used for further comprehensive analysis of PECs, from which we found that 2-(2-phenylethyl)chromones of flindersia type (FTPECs) were the most abundant, while PECs with epoxidated chromone moiety were detected with limited numbers and relatively low content. Speculation on the formation of major FTPECs was fully elucidated in our context. The key step of FTPECs biosynthesis is possibly catalyzed by type III polyketide synthases (PKSs) which condensate dihydro-cinnamoyl-CoA analogues and malonyl-CoA with 2-hydroxy-benzoyl-CoA to produce 2-(2-phenyethyl)chromone scaffold, or with 2,5-dihydroxybenzoyl-CoA to form FTPECS with 6-hydroxy group, which may serve as precursors for further reactions catalyzed by hydroxylase or O-methyltransferase (OMT) to produce FTPECs with diverse substitution patterns. It is the first report that systematically analyzed dynamic changes of secondary metabolites during the process of agarwood formation and fully discussed the biosynthetic pathway of PECs.


Assuntos
Catecóis/isolamento & purificação , Cromonas/isolamento & purificação , Flavonoides/isolamento & purificação , Odorantes/análise , Sesquiterpenos/isolamento & purificação , Thymelaeaceae/química , Catecóis/química , Catecóis/metabolismo , Cromonas/química , Cromonas/metabolismo , Flavonoides/biossíntese , Flavonoides/química , Cromatografia Gasosa-Espectrometria de Massas , Phialophora/fisiologia , Doenças das Plantas/microbiologia , Sesquiterpenos/química , Sesquiterpenos/metabolismo , Espectrometria de Massas por Ionização por Electrospray , Thymelaeaceae/metabolismo , Thymelaeaceae/microbiologia , Fatores de Tempo
13.
Plant Cell Physiol ; 58(11): 1924-1933, 2017 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-29016977

RESUMO

Sesquiterpenes are one of the most important defensive secondary metabolite components of agarwood. Agarwood, which is a product of the Aquilaria sinensis response to external damage, is a fragrant and resinous wood that is widely used in traditional medicines, incense and perfume. We previously reported that jasmonic acid (JA) plays an important role in promoting agarwood sesquiterpene biosynthesis and induces expression of the sesquiterpene synthase ASS1, which is a key enzyme that is responsible for the biosynthesis of agarwood sesquiterpenes in A. sinensis. However, little is known about this molecular regulation mechanism. Here, we characterized a basic helix-loop-helix transcription factor, AsMYC2, from A. sinensis as an activator of ASS1 expression. AsMYC2 is an immediate-early jasmonate-responsive gene and is co-induced with ASS1. Using a combination of yeast one-hybrid assays and chromatin immunoprecipitation analyses, we showed that AsMYC2 bound the promoter of ASS1 containing a G-box motif. AsMYC2 activated expression of ASS1 in tobacco epidermis cells and up-regulated expression of sesquiterpene synthase genes (TPS21 and TPS11) in Arabidopsis, which was also promoted by methyl jasmonate. Our results suggest that AsMYC2 participates in the regulation of agarwood sesquiterpene biosynthesis in A. sinensis by controlling the expression of ASS1 through the JA signaling pathway.


Assuntos
Proteínas de Plantas/metabolismo , Sesquiterpenos/metabolismo , Thymelaeaceae/metabolismo , Fatores de Transcrição/metabolismo , Acetatos/metabolismo , Acetatos/farmacologia , Alquil e Aril Transferases/genética , Alquil e Aril Transferases/metabolismo , Arabidopsis/genética , Ciclopentanos/metabolismo , Ciclopentanos/farmacologia , Regulação da Expressão Gênica de Plantas , Sequências Hélice-Alça-Hélice , Oxilipinas/metabolismo , Oxilipinas/farmacologia , Proteínas de Plantas/genética , Plantas Geneticamente Modificadas , Regiões Promotoras Genéticas , Thymelaeaceae/efeitos dos fármacos , Thymelaeaceae/genética , Fatores de Transcrição/genética
14.
Molecules ; 22(10)2017 Sep 25.
Artigo em Inglês | MEDLINE | ID: mdl-28946701

RESUMO

Gaharu (agarwood, Aquilaria malaccensis Lamk.) is a valuable tropical rainforest product traded internationally for its distinctive fragrance. It is not only popular as incense and in perfumery, but also favored in traditional medicine due to its sedative, carminative, cardioprotective and analgesic effects. The current study addresses the chemical differences and similarities between gaharu samples of different grades, obtained commercially, using ¹H-NMR-based metabolomics. Two classification models: partial least squares-discriminant analysis (PLS-DA) and Random Forests were developed to classify the gaharu samples on the basis of their chemical constituents. The gaharu samples could be reclassified into a 'high grade' group (samples A, B and D), characterized by high contents of kusunol, jinkohol, and 10-epi-γ-eudesmol; an 'intermediate grade' group (samples C, F and G), dominated by fatty acid and vanillic acid; and a 'low grade' group (sample E and H), which had higher contents of aquilarone derivatives and phenylethyl chromones. The results showed that ¹H- NMR-based metabolomics can be a potential method to grade the quality of gaharu samples on the basis of their chemical constituents.


Assuntos
Metabolômica/métodos , Espectroscopia de Prótons por Ressonância Magnética/métodos , Thymelaeaceae/metabolismo , Espectroscopia de Ressonância Magnética
15.
Nat Prod Res ; 31(17): 2032-2041, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28105861

RESUMO

A new compound (microphybenzimidazole, 7) along with the six known compounds matairesinol (1), prestegane B (2), umbelliferone (3), daphnoretin (4), microphynolide A (5) and microphynolide B (6) were isolated from Thymelaea microphylla. The structures of the pure compounds were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR, and HPLC-TOF/MS. Compounds 2 and 4, as well as three fractions (F6, F6-C5, and F6-W42) obtained from a 50% (v:v) CH2Cl2:MeOH extract exhibited a selective activity against rat brain glioma cells (C6). Moreover, compound 1 and other fractions obtained from 50% (v:v) CH2Cl2:MeOH and 70% (v:v) MeOH:H2O extracts exhibited dose- and time-dependent effects on human cervical cancer cell (HeLa), as measured by xCELLigence assay. Compound 2 (IC50 = 14.0 ± 0.2 µg/mL) and fraction F5 (IC50 = 12.4 ± 0.1 µg/mL) showed higher radical scavenging ability than the synthetic agent butylated hydroxytoluene (BHT, IC50 = 22.7 ± 0.6 µg/mL).


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Benzimidazóis/química , Thymelaeaceae/química , 4-Butirolactona/análogos & derivados , 4-Butirolactona/química , 4-Butirolactona/farmacologia , Animais , Antineoplásicos Fitogênicos/química , Antioxidantes/química , Benzimidazóis/farmacologia , Hidroxitolueno Butilado/farmacologia , Linhagem Celular Tumoral , Cromatografia Líquida de Alta Pressão , Cumarínicos/química , Cumarínicos/farmacologia , Relação Dose-Resposta a Droga , Furanos/química , Furanos/farmacologia , Células HeLa , Humanos , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Ratos , Metabolismo Secundário , Thymelaeaceae/metabolismo
16.
J Photochem Photobiol B ; 160: 260-70, 2016 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-27152674

RESUMO

This study reports a green process for the fabrication of Ag@AgCl (silver@silver chloride) nanoparticles by using Aquilaria agallocha (AA) leaves juice without using any external reagents. The effect of various reaction parameters, such as reaction temperature, reaction time and concentration of Aquilaria agallocha leaves juice in the formation of nanoparticles have also been investigated. From the FTIR spectra of leaves juice and phytochemicals test, it was found that flavonoids present in the leaves are responsible for the reduction of Ag(+) ions to Ag(0) species and leads to the formation of Ag@AgCl NPs. The synthesized Ag@AgCl NPs were utilized for the removal of toxic and hazardous dyes, such as Victoria Blue B from aqueous phase. Approximately, 99.46% degradation of Victoria Blue B dye were observed with Ag@AgCl NPs. Furthermore, the photocatalytic activity of the Ag@AgCl nanoparticles was unchanged after 5cycles of operation.


Assuntos
Nanopartículas Metálicas/química , Corantes de Rosanilina/química , Compostos de Prata/química , Prata/química , Catálise , Corantes/química , Química Verde , Luz , Nanopartículas Metálicas/ultraestrutura , Microscopia Eletrônica de Transmissão , Oxirredução , Fotólise/efeitos da radiação , Folhas de Planta/química , Folhas de Planta/metabolismo , Espectrometria por Raios X , Espectroscopia de Infravermelho com Transformada de Fourier , Temperatura , Thymelaeaceae/química , Thymelaeaceae/metabolismo , Água/química , Difração de Raios X
17.
BMC Plant Biol ; 16(1): 119, 2016 05 26.
Artigo em Inglês | MEDLINE | ID: mdl-27230436

RESUMO

BACKGROUND: Agarwood, is a resinous portion derived from Aquilaria sinensis, has been widely used in traditional medicine and incense. 2-(2-phenylethyl)chromones are principal components responsible for the quality of agarwood. However, the molecular basis of 2-(2-phenylethyl)chromones biosynthesis and regulation remains almost unknown. Our research indicated that salt stress induced production of several of 2-(2-phenylethyl)chromones in A. sinensis calli. Transcriptome analysis of A. sinensis calli treated with NaCl is required to further facilitate the multiple signal pathways in response to salt stress and to understand the mechanism of 2-(2-phenylethyl)chromones biosynthesis. RESULTS: Forty one 2-(2-phenylethyl)chromones were identified from NaCl-treated A. sinensis calli. 93 041 unigenes with an average length of 1562 nt were generated from the control and salt-treated calli by Illmunina sequencing after assembly, and the unigenes were annotated by comparing with the public databases including NR, Swiss-Prot, KEGG, COG, and GO database. In total, 18 069 differentially expressed transcripts were identified by the transcriptome comparisons on the control calli and calli induced by 24 h or 120 h salinity stress. Numerous genes involved in signal transduction pathways including the genes responsible for hormone signal transduction, receptor-like kinases, MAPK cascades, Ca(2+) signal transduction, and transcription factors showed clear differences between the control calli and NaCl-treated calli. Furthermore, our data suggested that the genes annotated as chalcone synthases and O-methyltransferases may contribute to the biosynthesis of 2-(2-phenylethyl)chromones. CONCLUSIONS: Salinity stress could induce the production of 41 2-(2-phenylethyl)chromones in A. sinensis calli. We conducted the first deep-sequencing transcriptome profiling of A. sinensis under salt stress and observed a large number of differentially expressed genes in response to salinity stress. Moreover, salt stress induced dynamic changes in transcript abundance for novel classes of responsive genes involved in signal transduction, including the genes responsible for hormone signal transduction, receptor-like kinases, MAPK cascades, Ca(2+) signal transduction, and transcription factors. This study will aid in selecting the target genes to genetically regulate A. sinensis salt-stress signal transduction and elucidating the biosynthesis of 2-(2-phenylethyl)chromones under salinity stress.


Assuntos
Cromonas/metabolismo , Proteínas de Plantas/genética , Salinidade , Transdução de Sinais/genética , Estresse Fisiológico/genética , Thymelaeaceae/genética , Células do Mesofilo , Imunidade Vegetal , Proteínas de Plantas/metabolismo , Cloreto de Sódio/farmacologia , Thymelaeaceae/efeitos dos fármacos , Thymelaeaceae/metabolismo
18.
Sci Rep ; 6: 21843, 2016 Feb 23.
Artigo em Inglês | MEDLINE | ID: mdl-26902148

RESUMO

Agarwood, a highly valuable resinous and fragrant heartwood of Aquilaria plants, is widely used in traditional medicines, incense and perfume. Only when Aquilaria trees are wounded by external stimuli do they form agarwood sesquiterpene defensive compounds. Therefore, understanding the signaling pathway of wound-induced agarwood formation is important. Jasmonic acid (JA) is a well-characterized molecule that mediates a plant's defense response and secondary metabolism. However, little is known about the function of endogenous JA in agarwood sesquiterpene biosynthesis. Here, we report that heat shock can up-regulate the expression of genes in JA signaling pathway, induce JA production and the accumulation of agarwood sesquiterpene in A. sinensis cell suspension cultures. A specific inhibitor of JA, nordihydroguaiaretic acid (NDGA), could block the JA signaling pathway and reduce the accumulation of sesquiterpene compounds. Additionally, compared to SA and H2O2, exogenously supplied methyl jasmonate has the strongest stimulation effect on the production of sesquiterpene compounds. These results clearly demonstrate the central induction role of JA in heat-shock-induced sesquiterpene production in A. sinensis.


Assuntos
Ciclopentanos/metabolismo , Regulação da Expressão Gênica de Plantas , Proteínas de Choque Térmico/genética , Oxilipinas/metabolismo , Proteínas de Plantas/genética , Sesquiterpenos/metabolismo , Thymelaeaceae/metabolismo , Acetatos/farmacologia , Técnicas de Cultura de Células , Ciclopentanos/antagonistas & inibidores , Ciclopentanos/farmacologia , Proteínas de Choque Térmico/metabolismo , Resposta ao Choque Térmico/efeitos dos fármacos , Resposta ao Choque Térmico/genética , Temperatura Alta , Masoprocol/farmacologia , Oxilipinas/antagonistas & inibidores , Oxilipinas/farmacologia , Células Vegetais/efeitos dos fármacos , Células Vegetais/metabolismo , Proteínas de Plantas/metabolismo , Metabolismo Secundário , Sesquiterpenos/antagonistas & inibidores , Transdução de Sinais , Thymelaeaceae/efeitos dos fármacos , Thymelaeaceae/genética
19.
Artigo em Inglês | MEDLINE | ID: mdl-26655105

RESUMO

In this study, an ultra performance liquid chromatography tandem mass spectrometry method (UPLC-MS/MS) was developed for simultaneous determination of umbelliferone, apigenin, daphnoretin and genkwanin in total (free and conjugated) forms in rat plasma using psoralen as internal standard. Plasma samples were protein precipitated with acetonitrile followed by liquid-liquid extracted with ethyl acetate. Four ingredients were separated on an Acquity UPLC(®) BEH C18 column using gradient elution with the mobile phase consisting of 0.1% formic acid aqueous solution and acetonitrile, and detected by positive ion electrospray ionization (ESI) in multiple reaction monitoring mode (MRM). The method was linear for all analytes over investigated ranges with all correlation coefficients greater than 0.99. The validated lower limit of quantification was 3ng/mL for umbelliferone, 3ng/mL for apigenin, 12ng/mL for daphnoretin and 2ng/mL for genkwanin, respectively. Intra- and inter-day precisions (RSD%) were less than 15% and accuracy (RE%) ranged from -1.1% to 15%. The mean absolute extraction recoveries of analytes and IS from rat plasma were all more than 75%. The validated method was firstly and successfully applied to investigate the pharmacokinetics of four chemical ingredients after oral administration of Wikstroemia indica extract (WIE) to rats.


Assuntos
Cromatografia Líquida/métodos , Cumarínicos/sangue , Flavonoides/sangue , Extratos Vegetais/análise , Espectrometria de Massas em Tandem/métodos , Thymelaeaceae/metabolismo , Animais , Ratos
20.
Int J Pharm ; 496(2): 440-7, 2015 Dec 30.
Artigo em Inglês | MEDLINE | ID: mdl-26475967

RESUMO

Chamaechromone and neochamaejasmin B (NCB) are the most abundant components in the dried roots of the toxic perennial herb Stellera chamaejasme L. and have pharmacological activities. The objective of this study was to investigate the transport mechanism of these two components in vivo and in vitro. The transport and cellular accumulation studies in Madin-Darby canine kidney (MDCK) cells overexpressing human multidrug resistance protein 2 (MRP2) or P-gp and LLC-PK1 cells overexpressing human breast cancer resistance protein (BCRP) were performed. The results showed that chamaechromone was a good substrate of MRP2 and BCRP but not a substrate of P-gp. NCB was found to be a MRP2 inhibitor in transfected cells and significantly enhanced the cellular accumulation of chamaechromone in MDCK cells overexpressing MRP2. Similar results were obtained in LLC-PK1-BCRP cells. In addition, the influence of NCB on the bioavailability of chamaechromone following their co-administration was also determined in rats. The results showed that the area under the plasma concentration-time curve and maximal plasma concentration of chamaechromone in rats were increased by 48.9% and 81.9%, respectively. The mechanism of improving the oral bioavailability of chamaechromone was attributable to the inhibition of the BCRP and MRP2-mediated efflux of chamaechromone by NCB.


Assuntos
Transportadores de Cassetes de Ligação de ATP/antagonistas & inibidores , Biflavonoides/farmacologia , Flavonas/farmacocinética , Proteínas Associadas à Resistência a Múltiplos Medicamentos/antagonistas & inibidores , Proteínas de Neoplasias/antagonistas & inibidores , Thymelaeaceae/metabolismo , Membro 2 da Subfamília G de Transportadores de Cassetes de Ligação de ATP , Transportadores de Cassetes de Ligação de ATP/fisiologia , Animais , Disponibilidade Biológica , Cães , Fluoresceínas/farmacocinética , Humanos , Células LLC-PK1 , Células Madin Darby de Rim Canino , Masculino , Proteínas Associadas à Resistência a Múltiplos Medicamentos/fisiologia , Proteínas de Neoplasias/fisiologia , Ratos , Ratos Sprague-Dawley , Suínos , Espectrometria de Massas em Tandem
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