RESUMO
Chemical investigation on the leaves of Michelia champaca L. (Magnoliaceae) led to the isolation of five previously undescribed phenylethanoid glycosides (PhGs), 4-O-ß-d-glucopyranosyl-acteoside (1), 4â´-O-(6-O-E-caffeoyl)-ß-d-glucopyranosyl-acteoside (2), 4â´-O-(6-O-E-caffeoyl)-ß-d-glucopyranosyl-isoacteoside (3), 6""-O-E-feruloyl-echinacoside (4), and 6""-O-p-E-coumaroyl-echinacoside (5), together with eighteen known PhGs. Their structures were determined by spectroscopic and chemical methods. All the known PhGs except acteoside (8) were not previously reported in the genus. Twenty-one PhGs exhibited more potent DPPH radical scavenging activity and FRAP than l-ascorbic acid (l-AA), and twenty-two PhGs showed better ABTS radical cation scavenging activity than l-AA. In addition, twelve PhGs displayed more potent cellular reactive oxygen species scavenging activity than curcumin. The results revealed that the leaves of M. champaca are a rich source of phenylethanoid glycosides and antioxidants.
Assuntos
Glicosídeos , Folhas de Planta , Folhas de Planta/química , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Estrutura Molecular , Compostos de Bifenilo/antagonistas & inibidores , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Picratos/antagonistas & inibidores , Magnoliaceae/química , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Glucosídeos/isolamento & purificação , Glucosídeos/química , PolifenóisRESUMO
Michelia champaca L. (Magnoliaceae) was cultivated in large scale for flowers as cosmetic raw materials, whereas the value of its leaves remains to be discovered. Our chemical study on the leaves yielded four new flavonol diglycosides, champaflavosides A-D (1-4), together with twenty-three known flavonoid glycosides (5-27). Their structures were determined by spectroscopic and chemical methods. Compounds 5-21 and 23-27 were not previously reported from the genus Michelia, and kaempferol 3-O-rutinoside (22) was obtained from this species for the first time. All the compounds were evaluated for antioxidant activity by four in vitro assays. Compounds 3-12 and 20 showed more potent 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity than l-ascorbic acid (l-AA). Compounds 2-23, 25, and 27 exhibited 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation scavenging activity superior to l-AA. The ferric reducing antioxidant powers (FRAP) of compounds 2-13, 17, and 19 were higher than l-AA. Further, eighteen compounds demonstrated cellular reactive oxygen species (ROS) scavenging activity, of which champaflavoside D (4), rhamnetin 3-O-neohesperidoside (8), quercetin 3-O-(6-O-E-p-coumaroyl)-neohesperidoside (9), and liquiritin (27) were more potent than curcumin. The results revealed that the renewable leaves of M. champaca are a rich source of flavonoids and antioxidants.
Assuntos
Antioxidantes , Flavonoides , Glicosídeos , Folhas de Planta , Folhas de Planta/química , Glicosídeos/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/química , Flavonoides/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/química , Estrutura Molecular , Antioxidantes/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/química , Magnoliaceae/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , China , Quempferóis/farmacologia , Quempferóis/isolamento & purificação , Quempferóis/químicaRESUMO
Essential oils (EOs) of Clausena indica fruits, Zanthoxylum rhetsa fruits, and Michelia tonkinensis seeds were analyzed for their phytochemical profiles and biological activities, including anti-diabetes, anti-gout, and anti-leukemia properties. Sixty-six volatile compounds were identified by gas chromatography-mass spectrometry (GC-MS), in which, myristicin (68.3%), limonene (44.2%), and linalool (49.3%) were the most prominent components of EOs extracted from C. indica, Z. rhetsa, and M. tonkinensis, respectively. In addition, only EOs from C. indica inhibited the activities of all tested enzymes comprising α-amylase (IC50 = 7.73 mg/mL), α-glucosidase (IC50 = 0.84 mg/mL), and xanthine oxidase (IC50 = 0.88 mg/mL), which are related to type 2 diabetes and gout. Remarkably, all EOs from C. indica, Z. rhetsa (IC50 = 0.73 mg/mL), and M. tonkinensis (IC50 = 1.46 mg/mL) showed a stronger anti-α-glucosidase ability than acarbose (IC50 = 2.69 mg/mL), a known anti-diabetic agent. Moreover, the growth of leukemia cell Meg-01 was significantly suppressed by all EOs, of which, the IC50 values were recorded as 0.32, 0.64, and 0.31 mg/mL for EOs from C. indica, Z. rhetsa, and M. tonkinensis, respectively. As it stands, this is the first report about the inhibitory effects of EOs from C. indica and Z. rhetsa fruits, and M. tonkinensis seeds on the human leukemia cell line Meg-01 and key enzymes linked to diabetes and gout. In conclusion, the present study suggests that EOs from these natural spices may be promising candidates for pharmaceutical industries to develop nature-based drugs to treat diabetes mellitus or gout, as well as malignant hematological diseases such as leukemia.
Assuntos
Antineoplásicos/uso terapêutico , Clausena/química , Supressores da Gota/uso terapêutico , Hipoglicemiantes/uso terapêutico , Leucemia/tratamento farmacológico , Magnoliaceae/química , Óleos Voláteis/uso terapêutico , Zanthoxylum/química , Humanos , Óleos Voláteis/químicaRESUMO
In this study, Magnolia citrata Noot and Chalermglin (Magnoliaceae) essential oil (MCEO) was evaluated for insecticidal activity against the yellow fever mosquito Aedes aegypti and attractant activity for the Mediterranean fruit fly Ceratitis capitata. The leaves of Magnolia citrata (Gioi chanh) were collected from northwestern Vietnam, and the water-distilled MCEO was analyzed by gas-chromatography and mass spectrometry (GC-MS). The major constituents of MCEO were identified as linalool 19%, geranial 16%, citronellal 14%, neral 14%, and sabinene 12%. MCEO showed 100% mortality at 1 µg/µL against 1st instar larvae of Ae. aegypti (Orlando strain, ORL), and the oil exhibited 54% (ORL) and 68% (Puerto Rico strain) mortality at 5 µg/mosquito against Ae. aegypti adult females. Initial screens showed that MCEO had weak insecticidal activity compared to the positive control permethrin. In bioassays with sterile male C. capitata, MCEO exhibited moderately strong attraction, comparable to that observed with a positive control, Tetradenia riparia essential oil (TREO). Herein, the insecticidal and attractant activities of MCEO are reported for the first time.
Assuntos
Cromatografia Gasosa-Espectrometria de Massas/métodos , Inseticidas/farmacologia , Magnolia/química , Aedes/efeitos dos fármacos , Animais , Ceratitis capitata/efeitos dos fármacos , Magnoliaceae/química , Óleos Voláteis/farmacologiaRESUMO
Natural products have been fundamental materials in drug discovery. Traditional strategies for observing natural products with novel structure and/or biological activity are challenging due to large cost and time consumption. Implementation of the MS/MS-based molecular networking strategy with the in silico annotation tool is expected to expedite the dereplication of secondary metabolites. In this study, using this tool, two new dilignans with a 2-phenyl-3-chromanol motif, obovatolins A (1) and B (2), were discovered from the stem barks of Magnolia obovata Thunb. along with six known compounds (3-8), expanding chemical diversity of lignan skeletons in this natural source. Their structures and configurations were elucidated using spectroscopic data. All isolates were evaluated for their PCSK9 mRNA expression inhibitory activity. Obovatolins A (1) and B (2), and magnolol (3) showed potent lipid controlling activities. To identify transcriptionally controlled genes by 1 along with downregulation of PCSK9, using small set of genes (42 genes) related to lipid metabolism selected from the database, focused bioinformatic analysis was carried out. As a result, it showed the correlations between gene expression under presence of 1, which led to detailed insight of the lipid metabolism caused by 1.
Assuntos
Magnolia/química , Magnoliaceae/química , Pró-Proteína Convertase 9/metabolismo , Western Blotting , Células Hep G2 , Humanos , Metabolismo dos Lipídeos/efeitos dos fármacos , Estrutura Molecular , Casca de Planta/química , Caules de Planta/química , Pró-Proteína Convertase 9/genética , Reação em Cadeia da Polimerase Via Transcriptase Reversa , Espectrometria de Massas em TandemRESUMO
The nanoencapsulation of essential oils for biodegradable films functionalization is a viable alternative for the production of active food packaging. In this study, the Cinnamodendron dinisii Schwanke essential oil was nanoencapsulated using zein as wall material, and applied in chitosan matrix to produce an active nanocomposite film packaging for food conservation. The chemical composition of the Cinnamodendron dinisii Schwanke essential oil showed a variety of unexplored bioactive compounds, and 1,8-cineole was the major compound. The oil nanoencapsulation produced stable and homogeneous nanoparticles with zeta potential close to 30 mV and polydispersity index lower than 0.2. The nanoparticles size showed a size variation between 70 and 110 nm. The chitosan films obtained functionalized with nanoparticles demonstrated antioxidant activity and antimicrobial activity. The active packaging containing zein nanoparticles was efficient in the conservation of ground beef, stabilizing the deterioration reactions and preserving the color.
Assuntos
Quitosana/química , Magnoliaceae/química , Zeína/química , Anti-Infecciosos/química , Antioxidantes/química , Embalagem de Alimentos/métodos , Magnoliaceae/metabolismo , Magnoliopsida/química , Magnoliopsida/metabolismo , Nanocompostos/química , Nanopartículas/química , Óleos Voláteis/químicaRESUMO
Magnoliae Flos is a commonly used traditional medicinal material in Asia. It is used to treat sinusitis, nasal congestion, and hypersensitive skin. Because Magonlia Flos was described as an aromatic material in ancient Chinese texts, we hypothesized that its essential oil may be used to treat immune disorders. Dendritic cells (DCs), regarded as a major target of immunomodulators to control immune responses, play a critical role in the adaptive immune response. In this study, Magnoliae Flos essential oil (MFEO) decreased the production of the cytokines TNF-α, IL-6, and IL-12p70 in lipopolysaccharide (LPS)-stimulated DCs. It also suppressed the surface markers MHC II, CD80, and CD86 in LPS-stimulated DCs. Animal models demonstrated that the 2,4-Dinitro-1-fluorobenzene (DNFB) inducing a contact hypersensitivity response was inhibited following treatment with MFEO. In addition, MFEO inhibited the infiltration of T cells in the ears of DNFB-induced mice. To explore its bioactive compounds, the components of MFEO were analyzed using gas chromatography (GC) and GC-mass spectrometry. The results revealed that the major compounds in MFEO are camphor and 1,8-cineole. Additional DC bioassays confirmed that these compounds substantially suppressed cytokine production in LPS-induced DCs. Therefore, we demonstrated that MFEO exhibits an immunosuppressive effect both in vivo and in vitro, and camphor and 1,8-cineole may be the major components responsible for its immunosuppressive ability. The findings indicate that MFEO has the potential to be developed as a new immunosuppressant for excessive diseases.
Assuntos
Imunidade Adaptativa/efeitos dos fármacos , Células Dendríticas/imunologia , Dermatite de Contato/tratamento farmacológico , Dermatite de Contato/imunologia , Imunossupressores , Magnoliaceae/química , Óleos Voláteis/farmacologia , Óleos Voláteis/uso terapêutico , Fitoterapia , Animais , Cânfora/análise , Cânfora/isolamento & purificação , Células Cultivadas , Citocinas/metabolismo , Células Dendríticas/metabolismo , Modelos Animais de Doenças , Eucaliptol/análise , Eucaliptol/isolamento & purificação , Camundongos , Óleos Voláteis/química , Linfócitos T/imunologiaRESUMO
Menyanthes trifoliata L. is a valuable medical plant found in Europe, North America, and Asia, which grows on peat bogs and swamps. It has long been used in folk medicine as a remedy for various ailments. This is the first report to demonstrate the protective antioxidant and anti-inflammatory properties of aqueous methanolic extracts derived from the aerial parts (MtAPV) and roots (MtRV) of in vitro grown plants on human umbilical vein endothelial cells (HUVECs). It describes the influence of the tested extracts on the expression of antioxidant (HO-1, NQO1, NRF2, kEAP1, and GCLC) and inflammation-related genes (IL-1α, IL-1ß, IL-6, TNF-α, and IFN-γ) in cells stimulated with H2O2 or LPS, respectively. In addition, M. trifoliata extracts were found to moderately affect the growth of certain bacterial and fungal pathogens, with the strongest antibacterial effect found against Pseudomonas aeruginosa and Enterococcus faecalis. M. trifoliata extracts demonstrated protective effects against mitochondrial DNA (mtDNA) and nuclear DNA (nDNA) damage caused by ROS, decreasing the numbers of mtDNA lesions in the ND1 and ND2 genes and nDNA damage in the TP53 and HPRT1 genes and reducing cleavage in PARP1- and γ-H2A.X-positive cells. The root extract of in vitro M. trifoliata (MtRV) appears to have better anti-inflammatory, antioxidant, antimicrobial, and protective properties than the extract from the aerial part (MtAPV). These differences in biological properties may result from the higher content of selected phenolic compounds and betulinic acid in the MtRV than in the MtAPV extract.
Assuntos
Anti-Infecciosos/farmacologia , Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , DNA Mitocondrial/fisiologia , Endotélio Vascular/efeitos dos fármacos , Enterococcus faecalis/fisiologia , Inibidores do Crescimento/farmacologia , Magnoliaceae/química , Extratos Vegetais/farmacologia , Pseudomonas aeruginosa/fisiologia , Citocinas/metabolismo , Endotélio Vascular/patologia , Enterococcus faecalis/efeitos dos fármacos , Inibidores do Crescimento/química , Células Endoteliais da Veia Umbilical Humana , Humanos , Oxirredução , Extratos Vegetais/química , Raízes de Plantas , Pseudomonas aeruginosa/efeitos dos fármacos , Proteína Supressora de Tumor p53/genéticaRESUMO
Chinese herbs such as Flos magnoliae (FM) and Centipeda minima (CM) can be effective in treating allergic rhinitis (AR). However, there is little research on the therapeutic mechanism of these two drugs acting on AR at the same time. In order to systematically understand the mechanism of action of two drugs acting on AR at the same time, we searched various databases to obtain 31 components and 289 target proteins of FM, 25 components and 465 target proteins of CM. The interaction networks of FM, CM, and AR proteins were constructed by Cytoscape-v3.2.1 software. The core protein of two network intersections was obtained by using Venny 2.1.0. The R platform was used for the core target protein gene ontology (GO) comment analysis and KEGG (Kyoto Encyclopedia of Genes and Genomes) pathway analysis. Thirteen common targets and seven acting pathways were obtained. The results of animal experiments showed that FM and CM volatile oil could effectively improve the symptoms of AR by regulating the common targets. In summary, this study successfully explained the potential therapeutic mechanism of FM and CM in the treatment of AR. At the same time, it indicates that the two drugs can be compatible as a new application.
Assuntos
Asteraceae/química , Medicamentos de Ervas Chinesas/farmacologia , Magnoliaceae/química , Óleos Voláteis/farmacologia , Rinite Alérgica/tratamento farmacológico , Animais , Modelos Animais de Doenças , Avaliação Pré-Clínica de Medicamentos , Quimioterapia Combinada/métodos , Medicamentos de Ervas Chinesas/uso terapêutico , Humanos , Masculino , Mucosa Nasal/efeitos dos fármacos , Mucosa Nasal/imunologia , Mucosa Nasal/patologia , Óleos Voláteis/uso terapêutico , Ovalbumina/administração & dosagem , Ovalbumina/imunologia , Mapas de Interação de Proteínas/efeitos dos fármacos , Mapas de Interação de Proteínas/imunologia , Ratos , Rinite Alérgica/diagnóstico , Rinite Alérgica/imunologia , Rinite Alérgica/patologia , Resultado do TratamentoRESUMO
.This study aimed to investigate the hypolipidemic and antioxidant activities of volatile oils from Michelia martini Levl. The antioxidant property of volatile oils from Michelia martini in vitro was investigated by establishment of various systems. High fat diet induced rats were used to assess the hypolipidemic and antioxidant activities of Michelia martini volatile oils in vivo. The level of total cholesterol, triglycerides, high density lipoprotein cholesterol, low density lipoprotein cholesterol, alanine transaminase, aspartate aminotransferase, alkaline phosphatase and gamma-glutamyl transpeptidase in serum, and the activities of catalase, malondialdehyde, super oxide dismutase and glutathione in liver of rats were assayed by standard procedures. Our results showed that Michelia martini exhibits strong hypolipidemic and antioxidant activities both in vitro and vivo. Our data were also supplemented with histopathological studies on liver tissues and aorta sections of rats.
Assuntos
Antioxidantes/farmacologia , Hipolipemiantes/farmacologia , Magnoliaceae/química , Óleos Voláteis/farmacologia , Óleos de Plantas/farmacologia , Anfotericina B/toxicidade , Animais , Antioxidantes/isolamento & purificação , Compostos de Bifenilo/química , Células CHO , Cricetulus , Dieta Hiperlipídica/efeitos adversos , Relação Dose-Resposta a Droga , Hiperlipidemias/sangue , Hiperlipidemias/prevenção & controle , Hipolipemiantes/isolamento & purificação , Lipídeos/sangue , Masculino , Óleos Voláteis/isolamento & purificação , Picratos/química , Folhas de Planta/química , Óleos de Plantas/isolamento & purificação , Ratos Sprague-DawleyRESUMO
OBJECTIVE: To evaluate the efficacy and safety of Tongfu powder for external application on Shénquè (the umbilicus, hereafter, Tongfu powder) versus mosapride in acute pancreatitis (AP) patients with gastrointestinal dysfunction. METHODS: A total of 102 AP patients were diagnosed using the latest Atlanta Criterion and recruited at the Department of Infectious Disease, Beijing Friendship Hospital (Beijing, People's Republic of China) from August 2014 to December 2016. Patients were randomized into the Tongfu powder group and mosapride group using the random table. Information on scores (eg, the gastrointestinal function score) on days 1 and 7 of hospitalization, biochemical indicators (eg, interleukin [IL]-2 and IL-6), indicators for curative effects (eg, first defecation time, bowel sound recovery time, hospitalization costs, and duration) were collected and compared between the 2 groups. RESULTS: The gastrointestinal function score decreased significantly after treatment, and the changes were significantly different between the Tongfu powder group and the mosapride group (P<0.05). Significantly shorter time to first defecation and bowel sound recovery was observed in the Tongfu powder group versus the mosapride group (P<0.05). The improvements of IL-2, IL-4, intestinal fatty acid binding protein, motilin, and vasoactive intestinal peptide in the Tongfu powder group were higher than those in the mosapride group (P<0.05). There were no significant differences in hospital cost and length of hospital stay between the 2 groups. CONCLUSION: This study suggested that Tongfu powder for external application may improve gastrointestinal function for AP patients compared with mosapride.
Assuntos
Medicamentos de Ervas Chinesas/uso terapêutico , Gastroenteropatias/tratamento farmacológico , Pancreatite/tratamento farmacológico , Doença Aguda , China , Citrus/química , Medicamentos de Ervas Chinesas/administração & dosagem , Feminino , Gastroenteropatias/diagnóstico , Gastroenteropatias/metabolismo , Humanos , Magnoliaceae/química , Masculino , Medicina Tradicional Chinesa , Pessoa de Meia-Idade , Escores de Disfunção Orgânica , Pancreatite/diagnóstico , Pancreatite/metabolismo , Polygonaceae/química , PósRESUMO
A preliminary phytochemical investigation on the MeOH extract of the leaves and twigs of the endangered ornamental plant Michelia shiluensis led to the isolation of 16 sesquiterpenoids. The isolated compounds comprised germacrane- (1-4, 13, 14), guaiane- (5-9, 15), amorphane- (10), and eudesmane-type (11, 12, 16) sesquiterpenoids. The new structures (1-12) were elucidated by spectroscopic and computational methods, and their absolute configurations (except for 9) were assigned by single-crystal X-ray diffraction crystallographic data and/or electronic circular dichroism spectra. Shiluolides (A-D, 1-4) are unprecedented C16 or C17 homogermacranolides, and their putative biosynthetic pathways are briefly discussed. Shiluone D (8) is a rare 1,10- seco-guaiane sesquiterpenoid featuring a new ether-containing spirocyclic ring, whereas shiluone E (9) represents the first example of a 1,5-4,5-di- seco-guaiane with a rare 5,11 -lactone moiety. Shiluone F (10) is the first amorphane-type sesquiterpenoid possessing an oxetane ring bridging C-1 and C-7. Bioassay evaluations indicated that lipiferolide (13) showed noteworthy cytotoxicities toward human cancer cell lines MCF-7 and A-549, with IC50 values of 1.5 and 7.3 µM, respectively. Shiluone D (8) exerted inhibition against protein tyrosine phosphatase 1B (IC50: 46.3 µM).
Assuntos
Magnoliaceae/química , Sesquiterpenos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Espécies em Perigo de Extinção , Humanos , Estrutura Molecular , Extratos Vegetais/química , Folhas de Planta/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Difração de Raios XRESUMO
Magnoliae Flos (MF) is a traditional medicinal herb used for managing rhinitis, sinusitis and headache. The purpose of the present study was to determine the neuroprotective effect of MF against glutamate-induced oxidative stress and to assess the underlying mechanism. Glutamate is a major endogenous excitatory neurotransmitter in the brain and contributes to the development of neurodegenerative diseases by excessive activation. MF extract was subjected to a neuroprotective effect assay in HT22 mouse hippocampal cells. The mechanism underlying the neuroprotective effect of MF extract was evaluated by assaying reactive oxygen species (ROS) levels, intracellular Ca2+ levels, mitochondrial membrane potential, glutathione level and antioxidant enzyme activity in HT22 cells. MF extract significantly decreased glutamate-induced death of HT22 cells (80.83 ± 7.34% relative neuroprotection). MF extract reduced the intracellular ROS and Ca2+ levels and increased the glutathione level and glutathione reductase and glutathione peroxide activities. Moreover, MF extract attenuated the mitochondrial membrane potential in HT22 cells. These results suggested that MF extract exerts a neuroprotective effect against oxidative stress HT22 cells, which was mediated by its antioxidant activity.
Assuntos
Hipocampo/citologia , Magnoliaceae/química , Neurônios/efeitos dos fármacos , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/farmacologia , Animais , Apoptose/efeitos dos fármacos , Cálcio/metabolismo , Linhagem Celular , Glutationa/metabolismo , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Camundongos , Espécies Reativas de Oxigênio/metabolismoRESUMO
Four new lignans, a furofuran lignan medioresinol B (10) and three tetrahydrofuran lignans kobusinol C (16), 7'-methoxy magnostellin A (21), and mangnostellin D (23), along with 19 known lignans, were isolated from the flower buds of Magnolia biondii PAMP. The structures of the isolates were elucidated using spectroscopic analysis, mainly one- and two-dimensional NMR, high resolution-MS, and circular dichroism techniques as well as Mosher's esterification method. The anti-allergic effects of the isolated compounds were evaluated by analyzing the inhibition of interleukin-2 (IL-2) expression in Jurkat T-cells. Compounds 11-14 reduced IL-2 expression in a dose-dependent manner.
Assuntos
Interleucina-2/metabolismo , Lignanas/química , Magnoliaceae/química , Sobrevivência Celular/efeitos dos fármacos , Dicroísmo Circular , Análise Citogenética , Ensaio de Imunoadsorção Enzimática , Expressão Gênica/efeitos dos fármacos , Humanos , Interleucina-2/análise , Interleucina-2/antagonistas & inibidores , Células Jurkat , Lignanas/isolamento & purificação , Lignanas/farmacologia , Espectroscopia de Ressonância Magnética , Magnoliaceae/metabolismo , Espectrometria de MassasRESUMO
This chapter provides a comprehensive overview of recent achievements in the area of Galbulimima alkaloids. Following a discussion of the isolation of Galbulimima alkaloids and structural features of members of this fascinating family of secondary metabolites, biological properties of selected compounds are briefly discussed. Furthermore, the proposed biosynthetic routes toward Galbulimima alkaloids are outlined. The main section of the chapter is devoted to a detailed discussion and comparison of all total syntheses of Galbulimima alkaloids published to date.
Assuntos
Alcaloides/síntese química , Magnoliaceae/química , Alcaloides/biossíntese , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , HumanosRESUMO
The objective of the study was to optimise the encapsulation of Michelia alba D.C. (MAD) extract using octenyl succinic anhydride (OSA) starch. The MAD extract (5-10 g/100 g of dry starch) and the OSA starch (25-100 g/100 ml of water) was used in microcapsule preparation and analysed for the physicochemical and encapsulation properties. The optimised formula using the MAD extract and the OSA starch were 15.00 g/100 g of dry starch and 96.32 g/100 g water, which provided the highest in yield recovery (40.65% ± 0.99) and encapsulation efficiency (68.91% ± 1.50), with the lowest moisture content (3.19% ± 0.06) and water activity (0.236 ± 0.004). The aroma release from the optimum encapsulated powder in simulated artificial saliva fluid (SSF) suggested that linalool retention in microcapsules was higher than verbenone and 2-methyl butanoic acid. This study shows that the optimised formulation of MAD encapsulated flavour powder was found to be effective for controlling the aroma release.
Assuntos
Preparações de Ação Retardada/química , Aromatizantes/administração & dosagem , Magnoliaceae/química , Odorantes , Extratos Vegetais/administração & dosagem , Amido/análogos & derivados , Anidridos Succínicos/química , Aromatizantes/química , Odorantes/análise , Extratos Vegetais/químicaRESUMO
Tuberaria lignosa (Sweet) Samp. is found in European regions, and has antioxidant properties due to its composition in ascorbic acid and phenolic compounds. Given its traditional use and antioxidant properties, the tumor cell growth inhibitory potential of aqueous extracts from T. lignosa (prepared by infusion and decoction) was investigated in three human tumor cell lines: MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and HCT-15 (human colorectal adenocarcinoma). Both extracts inhibited the growth of these cell lines; the most potent one being the T. lignosa extract obtained by infusion in the NCI-H460 cells (GI50 of approximately 50 µg/mL). Further assays were carried out with this extract in NCI-H460 cells. At 100 µg/mL or 150 µg/mL it caused an increase in the percentage of cells in the G0/G1 phase and a decrease of cells in S phase of the cell cycle. Additionally, these concentrations caused an increase in the percentage of apoptotic cells. In agreement, a decrease in total poly (ADP-ribose) polymerase (PARP) and pro-caspase 3 levels was found. In conclusion, the T. lignosa extract obtained by infusion was more potent in NCI-H460 cells, altering the cell cycle progression and inducing apoptosis. This work highlights the importance of T. lignosa as a source of bioactive compounds with tumor cell growth inhibitory potential.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Ciclo Celular/efeitos dos fármacos , Magnoliaceae/química , Extratos Vegetais/farmacologia , Antineoplásicos Fitogênicos/química , Apoptose , Caspase 3/metabolismo , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Humanos , Células MCF-7 , Extratos Vegetais/química , Poli(ADP-Ribose) Polimerases/metabolismo , Transdução de Sinais/efeitos dos fármacosRESUMO
A new sesquiterpene manghookerins A (1) was isolated from the barks of Manglietia hookeri (Magnoliaceae) together with five known eudesmane-type sesquiterpenes. The structure of manghookerins A (1) was elucidated by physical and spectroscopic data analysis, including 1D and 2D NMR, HR-ESI-MS and X-ray diffraction. The structures of known sesquiterpenes were established by comparing their spectroscopic data with those in literatures.
Assuntos
Magnoliaceae/química , Sesquiterpenos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Casca de Planta/química , Sesquiterpenos/química , Difração de Raios XRESUMO
The previously proposed structure for a tetrahydrofuranol isolated from the leaves of Michelia compressa var. lanyuensis (Magnoliaceae) was synthesised in an enantiopure form using diethyl D-tartarate as the starting material. The synthetic sample showed spectroscopic data incompatible with those for the natural product and thus unequivocally disproved the previously assigned structure.
Assuntos
Furanos/química , Magnoliaceae/química , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Conformação Molecular , Folhas de Planta/química , EstereoisomerismoRESUMO
The comet assay-guided fractionation of the twigs of Manglietia hookeri resulted in the isolation of three sesquiterpene-neolignans, including a new one 5-allyl-2-(4-allyl-phenoxy)-3-[7-(1-hydroxy-1-methyl-ethyl)-1, 4a-dimethyl-decahydro-naphthalen-1-yloxy]-phenol (1), and eudesobovatol A (2) and eudesobovatol B (3), together with three lignans, obovatol (4), honokiol (5) and magnolol (6). Their structures were elucidated on the basis of spectral analysis and by comparison with related literature data. Compounds 1, 4-6 showed a protective effect on UV inductive DNA damage in mice lymphocyte cells, while compound 1 indicated the smallest Olive Tail Moment 7.34 ± 2.09 at 6 × 10(-6) µM.