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1.
Nat Prod Res ; 34(7): 935-942, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30587063

RESUMO

Phytochemical investigation on the leaves and twigs of Toona ciliata has led to the isolation of four new polyynes (1-4) and two knowns (5 and 6). Their structures were determined by extensive spectroscopic analysis (MS, UV, IR, and NMR) and Mosher's method. All compounds were evaluated for their inhibitory activities against HepG2 human tumor cell line but were inactive.


Assuntos
Meliaceae/química , Poli-Inos/isolamento & purificação , Linhagem Celular Tumoral , Células Hep G2/efeitos dos fármacos , Humanos , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Poli-Inos/química , Poli-Inos/farmacologia , Análise Espectral
2.
Fitoterapia ; 140: 104431, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31759031

RESUMO

Two novel heptanornemoralisin-type diterpenoids nornemoralisins A (1) and B (2), together with two known compounds nemoralisin (3) and nemoralisin A (4), were isolated from the stem bark and leaves of Aphanamixis polystachya (Wall.) R. Parker. Their structures were established through comprehensive analyses of NMR spectroscopic data and high resolution mass spectrometric (HR-ESI-MS) data. The absolute configurations of carbon stereocenters were elucidated by circular dichroism (CD) analyses. The four compounds were tested for their potential cytotoxic effects against ACHN, HeLa, SMMC-7721, and MCF-7 cell lines. Nornemoralisins A (1) and B (2) exhibited significant cytotoxicity on ACHN with an IC50 value of 13.9 ± 0.8 and 10.3 ± 0.4 µM, respectively, and other compounds failed to reveal obvious cytotoxicity on the tested cell lines, compared to positive control vinblastine (IC50, 28.0 ± 0.9 µM).


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Diterpenos/farmacologia , Meliaceae/química , Antineoplásicos Fitogênicos/isolamento & purificação , China , Diterpenos/isolamento & purificação , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Casca de Planta/química , Folhas de Planta/química
3.
Chem Biol Interact ; 316: 108920, 2020 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-31857088

RESUMO

Cedrelone is a limonoid isolated from the plant Trichilia catigua (Meliaceae). Previous studies have demonstrated that cedrelone (1) has several damaging effects on triple negative breast tumor (TNBC) cell line MDA-MB-231. In this work we investigated two new derivatives of cedrelone, the acetate (1a) and the mesylate (1b), to examine whether their effects are improved in comparison to the lead molecule. Cedrelone acetate (1a) was the most cytotoxic compound on TNBC cells and was chosen for additional analyses in traditional two-dimensional (2D) monolayer cultures and three-dimensional (3D) assays. In 2D, 1a induced cell cycle arrest, apoptosis and inhibited essential steps of the metastasis process of the MDA-MB-231 cells, in vitro. Moreover, 1a was able to revert the malignant phenotype of the T4-2 cells in 3D. These effects were concomitant with the downregulation of EGFR, ß1-integrin and phospho-Akt, which could have resulted in a decrease of NFκB levels and MMP9 activity. These results suggest that 1a could be used as an important model for the design of a new drug to be applied in cancer treatment and be further studied in vivo for its antitumor and antimetastatic effects.


Assuntos
Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Limoninas/química , Acetilação , Antineoplásicos/química , Neoplasias da Mama/metabolismo , Neoplasias da Mama/patologia , Técnicas de Cultura de Células , Pontos de Checagem do Ciclo Celular , Linhagem Celular Tumoral , Movimento Celular/efeitos dos fármacos , Regulação para Baixo/efeitos dos fármacos , Receptores ErbB/genética , Receptores ErbB/metabolismo , Feminino , Humanos , Integrina beta1/genética , Integrina beta1/metabolismo , Limoninas/farmacologia , Meliaceae/química , Meliaceae/metabolismo , Fenótipo
4.
Chin J Nat Med ; 17(12): 912-917, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31882045

RESUMO

Six new trichilin-type limonoids (1-6) with C-19/29 lactol or acetal bridge and a new ring intact limonoid (7) were isolated from the desiccative ripe fruits of Trichilia sinensis. Their structures were determined by extensive spectroscopic methods including 1H NMR, 13C NMR, HSQC, HMBC, ROESY experiments as well as HRESI-MS data. All isolated compounds were evaluated for toxicities against human pulmonary carcinoma A549 and Hela cell lines by sulforhodamine B (SRB) method. Compound 7 showed weak inhibitory activity in Hela cell line at 40 µmol·L-1.


Assuntos
Limoninas/química , Limoninas/isolamento & purificação , Meliaceae/química , Células A549 , China , Células HeLa , Humanos , Espectroscopia de Ressonância Magnética , Medicina Tradicional Chinesa
5.
Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi ; 35(9): 794-799, 2019 Sep.
Artigo em Chinês | MEDLINE | ID: mdl-31750820

RESUMO

Objective To explore the inhibitory effects of polyphenols from Toona sinensis seeds (PTSS) on neuroinflammation and the underlying mechanism in rats with Parkinson's disease (PD). Methods PD rat models were prepared by stereotaxic injection of 6-hydroxydopamine (6-OHDA) into one side of striatum of Sprague-Dawley male rats. Model rats were randomly divided into model group and PTSS group (n=10), and a normal control group was set as well (n=10). The rotational behavior of rats was induced by intraperitoneal injection of apomorphine (APO) after 30 days, and the behavioral changes of rats from each group were investigated. The morphological and quantity changes of DA neurons (tyrosine hydroxylase positive, TH-positive), microglia cells (ionized calcium binding adaptor molecule-1, Iba1-positive) and astrocytes (glial fibrillary acidic protein, GFAP-positive) in substantia nigra (SN) of rats from each group were examined by immunohistochemistry. Inducible nitric oxide synthase (iNOS), nuclear factor-κB p65 (NF-κBp65), p38 mitogen-activated protein kinase (p38MAPK) and phosphor-p38 mitogen-activated protein kinase (p-p38MAPK) levels were evaluated through immunohistochemical staining. The protein levels of TH, GFAP, p38MAPK and p-p38MAPK in SN were examined by Western blot analysis. Results The number of rotations in the rats of the PTSS group was significantly reduced compared with that in the model group. The number of TH-positive cells in the model group was much less than that in the control group. The number and protein levels of TH-positive cells were enhanced significantly by PTSS intervention. Compared with the control group, the protein levels of Iba1, GFAP, iNOS, NF-κB, p38MAPK and p-p38MAPK in the injured side of the model group significantly increased, which could be suppressed significantly by PTSS intervention. Conclusion PTSS demonstrates protective effects on DA neurons by inhibiting p38MAPK signaling pathway and reducing the expression of inflammatory factors in PD rats.


Assuntos
Neurônios Dopaminérgicos/efeitos dos fármacos , Sistema de Sinalização das MAP Quinases , Meliaceae/química , Doença de Parkinson/tratamento farmacológico , Polifenóis/farmacologia , Sementes/química , Animais , Masculino , Oxidopamina , Compostos Fitoquímicos/farmacologia , Ratos , Ratos Sprague-Dawley , Substância Negra
6.
J Agric Food Chem ; 67(36): 10107-10115, 2019 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-31434473

RESUMO

We examined the antiobesity effect of a limonoid 7-deacetoxy-7-oxogedunin, named CG-1, purified from the seeds of Carapa guianensis, Meliaceae, known as andiroba in high-fat-diet (HFD)-fed mice. C57BL/6 mice were fed a low-fat diet or an HFD and orally administered CG-1 (20 mg/kg) for 7 weeks. CG-1 lowered the body weight gain and improved the serum triglyceride level and insulin sensitivity in HFD-fed mice. The expression level of the adipogenesis-related genes was lowered by CG-1 in the visceral white adipose tissue (vWAT). The mRNA expression level of the macrophage-related genes decreased in vWAT following the administration of CG-1 to HFD-fed mice. It is noteworthy that CG-1 activated the brown adipose tissue (BAT) with enhanced expression of uncoupling protein 1 and increased the rectal temperature in HFD-fed mice. These results indicate that the limonoid CG-1 decreased body weight gain and ameliorated hypertriglyceridemia and insulin resistance with the activation of BAT in HFD-fed mice.


Assuntos
Tecido Adiposo Marrom/efeitos dos fármacos , Fármacos Antiobesidade/administração & dosagem , Resistência à Insulina , Limoninas/administração & dosagem , Meliaceae/química , Obesidade/tratamento farmacológico , Extratos Vegetais/administração & dosagem , Tecido Adiposo Marrom/metabolismo , Animais , Dieta Hiperlipídica/efeitos adversos , Humanos , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Obesidade/genética , Obesidade/metabolismo , Obesidade/fisiopatologia , Sementes/química , Triglicerídeos/sangue , Proteína Desacopladora 1/genética , Proteína Desacopladora 1/metabolismo , Ganho de Peso/efeitos dos fármacos
7.
Fitoterapia ; 137: 104269, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31323238

RESUMO

The genus Amoora belongs to the Meliaceae family comprising approximately 25-30 species. Many Amoora species have been used as folk medicines for the treatment of many diseases. This review focuses on diverse chemical constituents from Amoora species as well as significant pharmacological activities. Up to now, a total of 140 compounds including eight sesquiterpenoids, twenty-six diterpenoids, forty-two triterpenoids, twenty-two limonoids, seven steroids, seven alkaloids, seven rocaglamide derivatives, four flavonoids, four glycosides, two coumarins, nine phenols, and two organic acids and esters were reported from Amoora species. Triterpenoids are characteristic components for Amoora species. The extracts and chemical constituents of Amoora species exhibit a broad spectrum of pharmacological activities including cytotoxic, anti-inflammatory, antibacterial and antifungal activity. The present review may provide useful evidence for reasonable utilization of Amoora species as folk medicines and further research in drug discovery.


Assuntos
Meliaceae/química , Compostos Fitoquímicos/farmacologia , Plantas Medicinais/química , Medicina Tradicional
8.
Cell Physiol Biochem ; 53(1): 76-86, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31192545

RESUMO

BACKGROUND/AIMS: Diabetes causes damage to the enteric nervous system. The enteric nervous system consists of neurons and enteric glial cells (EGCs). The present study evaluated the effects of an ethyl-acetate fraction (EAF) from Trichilia catigua (T. catigua; 200 mg/kg) on the total population of enteric neurons (HuC/D-immunoreactive [IR]) and EGCs (S100-IR and glial fibrillary acidic protein [GFAP]-IR) in the total preparation and jejunal mucosa in diabetic rats. METHODS: The animals were distributed into four groups: normoglycemic rats (N), diabetic rats (D), normoglycemic rats that received the EAF (NC), and diabetic rats that received the EAF (DC). The jejunum was processed for immunohistochemistry to evaluate HuC/D, S100, and GFAP immunoreactivity. The expression of S100 and GFAP proteins was also quantified by Western blot. RESULTS: The D group exhibited a decrease in the number of neurons and EGCs, an increase in the area of cell bodies, an increase in S100 protein expression, a decrease in GFAP protein expression, and a decrease in S100-IR and GFAP-IR EGCs in the jejunal mucosa. The DC group exhibited a decrease in the number of neurons and EGCs, a decrease in the area of cell bodies, a decrease in S100 and GFAP protein expression, and a decrease in S100-IR and GFAP-IR EGCs in the jejunal mucosa. The NC group exhibited maintenance of the number of neurons and EGCs, an increase in the area of cell bodies, and a decrease in S100 and GFAP protein expression. CONCLUSION: The EAF from T. catigua partially conferred protection against diabetic neuropathy in the enteric nervous system.


Assuntos
Diabetes Mellitus Experimental/complicações , Neuropatias Diabéticas/prevenção & controle , Jejuno/inervação , Meliaceae/química , Neuroglia/efeitos dos fármacos , Neurônios/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Extratos Vegetais/farmacologia , Acetatos/química , Animais , Diabetes Mellitus Experimental/patologia , Neuropatias Diabéticas/etiologia , Neuropatias Diabéticas/patologia , Sistema Nervoso Entérico/efeitos dos fármacos , Proteína Glial Fibrilar Ácida/análise , Jejuno/efeitos dos fármacos , Jejuno/patologia , Masculino , Neuroglia/patologia , Neurônios/patologia , Neuroproteção/efeitos dos fármacos , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/uso terapêutico , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Ratos , Ratos Wistar , Proteínas S100/análise
9.
Molecules ; 24(9)2019 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-31035366

RESUMO

Limonoids are phytochemicals with a variety of biological properties. In the present study, we elucidated the molecular mechanism of suppression of adipogenesis in adipocytes by a limonoid, 7-deacetoxy-7-oxogedunin (CG-1) from Carapa guianensis (Meliaceae), known as andiroba. CG-1 reduced the accumulation of intracellular triglycerides in a concentration-dependent manner. The expression levels of the adipogenic, lipogenic, and lipolytic genes were decreased by CG-1 treatment, whereas the glycerol release level was not affected. When CG-1 was added into the medium during days 0-2 of 6-days-adipogenesis, the accumulation of intracellular lipids and the mRNA levels of the adipogenesis-related genes were decreased. In addition, the phosphorylation level of insulin receptor substrate-1 (IRS-1) and Akt in the early phase of adipocyte differentiation (within 1 day after initiating adipocyte differentiation) was reduced by CG-1. Furthermore, insulin-activated translocation of glucose transporter 4 to the plasma membranes in adipocytes was suppressed by CG-1, followed by decreased glucose uptake into the cells. These results indicate that an andiroba limonoid CG-1 suppressed the accumulation of intracellular lipids in the early phase of adipocyte differentiation through repression of IRS-1/Akt-mediated glucose uptake in adipocytes.


Assuntos
Adipócitos/efeitos dos fármacos , Adipócitos/metabolismo , Transportador de Glucose Tipo 4/genética , Glucose/metabolismo , Proteínas Substratos do Receptor de Insulina/metabolismo , Limoninas/farmacologia , Metabolismo dos Lipídeos/efeitos dos fármacos , Proteínas Proto-Oncogênicas c-akt/metabolismo , Células 3T3-L1 , Adipogenia/efeitos dos fármacos , Animais , Transportador de Glucose Tipo 4/metabolismo , Limoninas/química , Meliaceae/química , Camundongos , Estrutura Molecular
10.
J Nat Med ; 73(4): 727-734, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31104253

RESUMO

From the methanolic extract of the leaves of Lansium domesticum, three new onoceranoid-type triterpenoids, lansium acids X-XII and a new cycloartane-type triterpene, lansium acid XIII, were isolated. The chemical structures of the isolated new compounds were elucidated on the basis of chemical/physicochemical evidence. For new onoceranoid-type triterpenoids, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. The isolated onoceranoid-type triterpenoids showed antimutagenic effects in the Ames assay against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1).


Assuntos
Antimutagênicos/farmacologia , Meliaceae/química , Extratos Vegetais/química , Triterpenos/química , Estrutura Molecular , Folhas de Planta , Triterpenos/isolamento & purificação
11.
J Agric Food Chem ; 67(35): 9885-9894, 2019 Sep 04.
Artigo em Inglês | MEDLINE | ID: mdl-31090412

RESUMO

A systematic approach for the characterization of the key aroma-active compounds in sun-dried Toona sinensis (SDTS) and vacuum-dried T. sinensis (VDTS) was performed by means of the molecular sensory science concept. A total of 64 aroma-active compounds were identified via gas chromatography-olfactometry (GC-O) and gas chromatography-mass spectrometry (GC-MS). Aroma extract dilution analysis (AEDA) and static headspace dilution analysis revealed 39 odorants in SDTS and 32 odorants in VDTS with flavor dilution (FD) factors from 8 to 4096, with the highest for vanillin and eugenol in both samples. Stable isotope dilution analysis (SIDA) and an internal standard method were applied to quantitate 42 odorants, revealing 35 compounds in concentrations above their respective odor thresholds in SDTS and 29 compounds in VDTS, respectively. Calculation of odor activity values (OAVs) indicated 2-isopropyl-3-methoxypyrazine, eugenol, and ß-ionone with the highest OAVs in both samples. Recombination experiments of the overall aromas of SDTS and VDTS by mixing the odorants with OAVs ≥1 in their naturally occurring concentrations proved the successful identification and quantitation of the respective key odorants.


Assuntos
Aromatizantes/química , Meliaceae/química , Compostos Orgânicos Voláteis/química , Cromatografia Gasosa-Espectrometria de Massas , Odorantes/análise , Olfatometria
12.
Molecules ; 24(7)2019 Apr 02.
Artigo em Inglês | MEDLINE | ID: mdl-30987040

RESUMO

A phytochemical investigation of the roots of Swietenia macrophylla led to the isolation of seven polyacetylenes, including five new compounds (1-5) and two known ones (6-7). Their structures were elucidated by extensive spectroscopic analysis and detailed comparison with reported data. All the isolates were tested for their cytotoxicity against the human hepatocellular carcinoma cell line BEL-7402, human myeloid leukemia cell line K562, and human gastric carcinoma cell line SGC-7901. Compounds 1 and 6 showed moderate cytotoxicity against the above three human cancer cell lines with IC50 values ranging from 14.3 to 45.4 µM. Compound 4 displayed cytotoxicity against the K562 and SGC-7901 cancer cell lines with IC50 values of 26.2 ± 0.4 and 21.9 ± 0.3 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Meliaceae/química , Raízes de Plantas/química , Polímero Poliacetilênico/farmacologia , Antineoplásicos Fitogênicos/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Células K562 , Polímero Poliacetilênico/química
13.
Phytomedicine ; 58: 152891, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30901665

RESUMO

BACKGROUND: Swietenia humilis seeds are consumed in Mexico to treat type 2 diabetes; the antihyperglycemic effect of this species was previously demonstrated and related to the presence of tetranortriterpenoids of the mexicanolide class. PURPOSE AND STUDY DESIGN: The present investigation was conducted to determine the mechanism of action of selected mexicanolides, including 2-hydroxy-destigloyl-6-deoxyswietenine acetate (1), methyl-2-hydroxy-3-ß-tigloyloxy-1-oxomeliac-8(30)-enate (2) and humilinolide H (3), using in vivo experiments with hyperglycemic mice, and cell-based models. METHODS: Nicotinamide-streptozotocin hyperglycemic mice (50-130 mg/kg, i.p.) were used to build antihyperglycemic drug-response curves using an oral glucose tolerance test model. In vitro studies were carried out on INSE1, H4IIE and C2C12 cells to assess insulin secretion, glucose-6-phosphatase inhibition, glucose uptake and mitochondrial bioenergetics, respectively. RESULTS: The combination of the decoction of S. humilis or 2-hydroxy-destigloyl-6-deoxyswietenine acetate (mexicanolide 1) with glibenclamide resulted in a reduction of the antihyperglycemic effect while a significant increase was observed when they were dosed with metformin. These effects were related to KATP SUR blockade, insulin secretion in INSE1 cells, and modulation of 5-HT2 receptors. Furthermore, mexicanolides 1-3 inhibited glucose-phosphatase in H4IIE cells, and enhanced glucose uptake and spare respiratory capacity in C2C12 myotubes. CONCLUSION: S. humilis mexicanolides interact with pharmacological targets at pancreas (KATP channels), liver (glucose-6-phosphatase), and skeletal muscle (mitochondria and possibly glucose transporters) to modulate glucose homeostasis, and could be a promising resource to treat type 2 diabetes.


Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Hipoglicemiantes/farmacologia , Limoninas/farmacologia , Meliaceae/química , Animais , Linhagem Celular , Relação Dose-Resposta a Droga , Sinergismo Farmacológico , Teste de Tolerância a Glucose , Glibureto/farmacologia , Hipoglicemiantes/administração & dosagem , Fígado/efeitos dos fármacos , Fígado/metabolismo , Masculino , Metformina/farmacologia , México , Camundongos Endogâmicos ICR , Pâncreas/efeitos dos fármacos , Pâncreas/metabolismo , Plantas Medicinais/química
14.
Z Naturforsch C J Biosci ; 74(7-8): 175-182, 2019 Jul 26.
Artigo em Inglês | MEDLINE | ID: mdl-30903762

RESUMO

Three new limonoids, designated as rubescins F (1), G (2), and H (3), together with two known compounds of this type, TS1 (4) and trichirubine A (5), were isolated from methylene chloride/methanol extracts of Trichilia rubescens leaves. The structures of these compounds were elucidated based on 1D and 2D nuclear magnetic resonance (NMR) analysis and complemented by electrospray ionization high-resolution mass spectrometry results and by comparison to data of related compounds described in the literature and ab initio calculations. Rubescin F (1) is the first limonoid from Trichilia spp. with an oxetane ring between C-7 and C-14, which seems to be formed by the isomerization of TS1 (4). The γ-hydroxybutenolide rubescin G (2) is a potential precursor of trichirubine A (5), whereas rubescin H (3) is the first example of a triterpenoid with a single bond between C-7/C-14, forming a cyclopropane ring. The absolute configuration of these limonoids was derived from biosynthetic considerations and ab initio calculations of NMR and optical rotation dispersion data.


Assuntos
Limoninas/análise , Meliaceae/química , Ciclopropanos/química , Limoninas/química , Folhas de Planta/química
15.
Pak J Pharm Sci ; 32(1(Supplementary)): 241-245, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30829199

RESUMO

The leaf extract of Turraea vogelii Hook. f. ex. Benth. is used in ethnomedicine for the management of pain and inflammation. Anti-nociceptive activity was determined using acetic acid-induced mouse writhing model. The anti-inflammatory activity was investigated using in-vitro bovine serum albumin (BSA) denaturation assay and BSA-induced hind paw edema in rats. The extract (125-500 mg/kg) administered via the oral route produced a significant (p<0.005) inhibition of acetic acid-induced writhes. The percent inhibition of writhes for extract (500 mg/kg) and diclofenac (10 mg/kg) was 53.3 and 59.5% respectively. The methanol extract (10-6-1.0 µg/mL) inhibited protein denaturation with IC50values of (1.06 × 10-3 µg/mL and 2.58 × 10-3 µg/mL) for extract and diclofenac respectively. Furthermore, the leaf extract (62.5 mg/kg) significantly (p<0.05) inhibited BSA-induced paw edema in rats. The methanol leaf extract of T. vogelii has anti-nociceptive and anti-inflammatory activities. These findings justify the use of the plant in traditional medicine for the management of pain and inflammation.


Assuntos
Analgésicos/farmacologia , Anti-Inflamatórios não Esteroides/farmacologia , Meliaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Avaliação Pré-Clínica de Medicamentos/métodos , Inflamação/induzido quimicamente , Inflamação/tratamento farmacológico , Camundongos , Folhas de Planta/química , Plantas Medicinais/química , Ratos Wistar , Soroalbumina Bovina/administração & dosagem , Soroalbumina Bovina/toxicidade
16.
Fitoterapia ; 134: 188-195, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30826367

RESUMO

Ten undescribed phragmalin-type limonoids (Chuktabularoids A-J, 1-10) and four known compounds (11-14) were isolated from the fruit shells of Chukrasia tabularis A. Juss. Their chemical structures were elucidated through a combination of HRESIMS, NMR, and ECD experiments. Their frameworks differed mainly in D-ring, including C-15-acyl, 16-nor C-15 acyl, C-13/14/18-cyclopropane, and Δ14, 15 types. The majority of the isolated compounds were investigated for multidrug resistance (MDR) reversal activity against doxorubicin-resistant human breast carcinoma (MCF-7/DOX) cells, compounds 11 and 12 exhibited a 5.6-fold and 19.7-fold enhancing effect on doxorubicin susceptibility at 30 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Frutas/química , Limoninas/farmacologia , Meliaceae/química , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , China , Resistência a Múltiplos Medicamentos , Resistencia a Medicamentos Antineoplásicos , Humanos , Limoninas/isolamento & purificação , Células MCF-7 , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7
17.
Food Chem ; 282: 153-163, 2019 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-30711100

RESUMO

Toona sinensis (A. Juss.) M. Roem. (TS) possesses a unique and pleasant flavor and is consumed as a popular seasonal vegetable in certain parts of eastern and southeastern Asia. The potent odorants in raw and cooked TS were identified by combined sensory and instrumental analysis techniques, including sensory descriptive aroma profiling and two complimentary volatile isolation methods combined with gas chromatography-olfactometry (GC-O) techniques. Highly volatile odorants were determined by static headspace dilution analysis (SHDA)-GC-O, while those of intermediate- and semi-volatility were determined by solvent-assisted flavor evaporation-aroma extract dilution analysis (SAFE-AEDA). Among the numerous odorants identified by SHDA and SAFE-AEDA, (E,E)-bis-(1-propenyl) disulfide was found to be predominant in both raw and cooked TS. In agreement with results of sensory descriptive analysis, hexanal, (Z)-3-hexenal, (E)-2-hexenal and (Z)-3-hexen-1-ol contributed green, grassy and leafy aroma notes; while hydrogen sulfide, methyl thiirane, (E,E)-bis-(1-propenyl) disulfide and (E,Z)-bis-(1-propenyl) disulfide contributed pungent, sulfurous and alliaceous notes in TS.


Assuntos
Meliaceae/química , Odorantes/análise , Olfatometria/métodos , Cromatografia Gasosa , Cromatografia Gasosa-Espectrometria de Massas , Temperatura Alta , Técnicas de Diluição do Indicador , Meliaceae/metabolismo , Compostos Orgânicos Voláteis/análise , Volatilização
18.
J Org Chem ; 84(5): 2596-2606, 2019 03 01.
Artigo em Inglês | MEDLINE | ID: mdl-30719915

RESUMO

Two new 9,10- seco limonoids with a central 3,4-dihydro-2 H-pyran motif, named xylomolones A and B (1 and 2, respectively), possessing identical absolute configurations but reversed alignments of ring A, compared to the tricyclic core of rings B-D, were obtained from seeds of the Thai mangrove Xylocarpus moluccensis, together with a highly modified 1,2- seco limonoid, named xylomolone C (3), containing a novel 3-oxabicyclo[3.2.1]octane-2,7-dione motif, and a new C11-terpenic acid methyl ester (4). The relative and absolute configurations of 1-4 were evidenced by extensive nuclear magnetic resonance (NMR) investigations combined with density functional theory and time-dependent density functional theory calculations of electronic circular dichroism, specific optical rotation, and 13C NMR data. The co-isolation of 1-4 allowed us to propose a novel convergent strategy for limonoid biosynthesis for the first time. This study demonstrates that mangroves of the genus Xylocarpus harbor new limonoid biosynthetic routes.


Assuntos
Limoninas/biossíntese , Limoninas/química , Meliaceae/metabolismo , Meliaceae/química , Ressonância Magnética Nuclear Biomolecular , Estereoisomerismo
19.
Bioorg Chem ; 84: 177-185, 2019 03.
Artigo em Inglês | MEDLINE | ID: mdl-30502629

RESUMO

Recent studies have revealed that there is a close relationship between neuroinflammation and Alzheimer's disease (AD) and compounds with anti-neuroinflammatory effects are potentially useful for the treatment of AD. A phytochemical investigation to obtain new neuroinflammatory inhibitors resulted in the isolation of four new and three known limonoids from Swietenia mahagoni. The structures of these limonoids were established by NMR, MS, and electronic circular dichroism (ECD) data analysis. Compounds 1-3 feature complicated polycyclic caged structures of limonoid orthoester and represent new examples of phragmalin-type limonoids. All of the isolates showed anti-neuroinflammatory activities by inhibiting nitric oxide (NO) release in LPS-induced murine microglial BV-2 cells with compounds 1 and 3-6 having IC50 values of 26.8, 26.1, 26.0, 37.1, and 16.5 µM, respectively. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the inducible nitric oxide synthase (iNOS) protein.


Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Limoninas/farmacologia , Meliaceae/química , Óxido Nítrico/antagonistas & inibidores , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Linhagem Celular , Relação Dose-Resposta a Droga , Frutas/química , Limoninas/química , Limoninas/isolamento & purificação , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Simulação de Acoplamento Molecular , Estrutura Molecular , Óxido Nítrico/metabolismo , Relação Estrutura-Atividade
20.
J Asian Nat Prod Res ; 21(10): 1005-1012, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-29947263

RESUMO

Phytochemical investigation on the roots of Swietenia macrophylla yielded one new pharagmalin-type limonoid named 2-dehydroxyl-swietephragmin C (1) and one new xanthone, 1,5-dihydroxy-6-methoxy-6',6'-dimethyl-2H-pyrano[2',3':3,2]xanthone (2), in addition to three known compounds. The structures of the new compounds were unambiguously determined by comprehensive spectroscopic methods (NMR, UV, IR, MS), as well as by comparison with the reported data in the literature. Xanthones were reported from Swietenia genus for the first time.


Assuntos
Limoninas/isolamento & purificação , Limoninas/farmacologia , Meliaceae/química , Raízes de Plantas/química , Xantonas/isolamento & purificação , Xantonas/farmacologia , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Bactérias/efeitos dos fármacos , Linhagem Celular Tumoral , Inibidores da Colinesterase/farmacologia , Fungos/efeitos dos fármacos , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Espectrometria de Massas por Ionização por Electrospray
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