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1.
Fitoterapia ; 137: 104281, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31381957

RESUMO

Veratrum californicum is a rich source of steroidal alkaloids, many of which have proven to be antagonists of the Hedgehog (Hh) signaling pathway that becomes aberrant in over twenty types of cancer. These alkaloids first became known in the 1950's due to their teratogenic properties, which resulted in newborn and fetal lambs developing cyclopia as a result of pregnant ewes consuming Veratrum californicum. It was discovered that the alkaloids in V. californicum were concentrated in the root and rhizome of the plant with much lower amounts of the most active alkaloid, cyclopamine, present in the aerial plant, especially in the late growth season. Inspired by the limitations in analytical instrumentation and methods available to researchers at the time of the original investigation, we have used state-of-the-art instrumentation and modern analytical methods to quantitate four steroidal alkaloids based on study parameters including plant part, harvest location, and growth stage. The results of the current inquiry detail differences in alkaloid composition based on the study parameters, provide a detailed assessment for alkaloids that have been characterized previously (cyclopamine, veratramine, muldamine and isorubijervine), and identify at least six alkaloids that have not been previously characterized. This study provides insight into optimal harvest time, plant growth stage, harvest location, and plant part required to isolate, yet to be characterized, alkaloids of interest for exploration as Hh pathway antagonists with desirable medicinal properties.


Assuntos
Alcaloides/química , Esteroides/química , Veratrum/química , Alcaloides/isolamento & purificação , Proteínas Hedgehog/antagonistas & inibidores , Idaho , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Componentes Aéreos da Planta/química , Rizoma/química , Estações do Ano , Esteroides/isolamento & purificação , Alcaloides de Veratrum
2.
Ecotoxicol Environ Saf ; 182: 109448, 2019 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-31398781

RESUMO

The electrocoagulation (EC) technique is an alternative method of isolating natural products with the advantage of minimizing the amounts of organic solvents required for this process, which are often harmful to the environment. In this research, the EC and the conventional solvent extraction methods were used in the isolation of Stemona alkaloids from the aerial parts of Stemona aphylla. A comparison was made between the amounts of the isolated alkaloids and the solvents used. The isolated alkaloids were evaluated for their larvicidal, ovicidal and oviposition-deterrent activities against the dengue vector, Aedes aegypti. The morphology and histopatology of the alkaloid treated larvae were also investigated. Two Stemona alkaloids, (2'S)-hydroxystemofoline and stemofoline, were isolated from both the EC and the conventional method. The amounts of (2'S)-hydroxystemofoline from the EC method was about the same as that obtained from the conventional method. However, the amounts of stemofoline obtained from the EC method were about two times larger than those obtained from the conventional method. Importantly, the EC method required six times less total organic solvents. The larvicidal activity assays of (2'S)-hydroxystemofoline and stemofoline showed that these were highly effective against Aedes aegypti larvae with LC50 values of 3.91 µg/ml and 4.35 µg/ml, respectively. Whereas, the crude EC extract (LC50 = 11.86 µg/ml) showed greater larvicidal activity than the crude extract obtained from the conventional extraction method (LC50 = 53.40 µg/ml). The morphological observations of the (2'S)-hydroxystemofoline and the stemofoline treated larvae revealed that the anal gills were the sites of aberrations. A histopathological study showed that larvae treated with these alkaloids had cytopathological alterations to the epithelial cells of the midgut. At a concentration 40 µg/ml (2'S)-hydroxystemofoline showed 100% ovicidal activity on 24 h old eggs while stemofoline showed 97.2%. Furthermore, the oviposition-deterrent effects of (2'S)-hydroxystemofoline and stemofoline, at a concentration of 80 µg/ml were 99.5% and 97.2%, respectively.


Assuntos
Aedes/efeitos dos fármacos , Alcaloides/toxicidade , Controle de Mosquitos/métodos , Componentes Aéreos da Planta/química , Extratos Vegetais/toxicidade , Stemonaceae/química , Animais , Dengue/transmissão , Vetores de Doenças , Eletrocoagulação , Feminino , Compostos Heterocíclicos de 4 ou mais Anéis , Inseticidas/farmacologia , Larva/efeitos dos fármacos , Mosquitos Vetores , Oviposição/efeitos dos fármacos
3.
Phytochemistry ; 166: 112065, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31362147

RESUMO

Ten undescribed neo-clerodane diterpenoids, named hispanins A-J, together with six known ones, were isolated from the aerial parts of Salvia hispanica L. Their structures were established by extensive spectroscopic analysis. The absolute configurations of the undescribed compounds were determined by the ECD data and single crystal X-ray diffraction analysis. Hispanins B and C represented the first neo-clerodane diterpenoids with a unique oxygen bridge between C-19 and C-20. All isolated compounds were evaluated for their protective effects against H2O2-induced cardiomyocyte injury. Five of these compounds showed significant cardioprotective effects.


Assuntos
Cardiotônicos/química , Cardiotônicos/farmacologia , Diterpenos Clerodânicos/química , Diterpenos Clerodânicos/farmacologia , Componentes Aéreos da Planta/química , Salvia/química , Animais , Miócitos Cardíacos/citologia , Miócitos Cardíacos/efeitos dos fármacos , Miócitos Cardíacos/metabolismo , Ratos
4.
Planta Med ; 85(11-12): 1008-1015, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31266068

RESUMO

One new natural monoterpene, 5-O-ß-d-glucopyranosyl-2-hydroxy-p-cymene (1: ), and 11 known compounds were isolated through a biologically oriented approach from the aerial parts of Phagnalon sordidum L. The most active extract and fractions were selected using 3 complementary antioxidant activity assays. Results and the different methods were compared by relative antioxidant capacity index. In addition, the most active extract of P. sordidum was subjected to liquid chromatography coupled with electrospray ionization hybrid linear ion trap quadrupole Orbitrap mass spectrometry to quantify secondary metabolites. Antioxidant activities of ethyl acetate extract, and purified 3,4-dihydroxyacetophenone (3: ) and nebrodenside A (7: ) were demonstrated by in vitro cell free model assays, and their protective effect against H2O2-induced oxidative stress in a HepG2 (human hepatocellular carcinoma) cell line was established.


Assuntos
Antioxidantes/farmacologia , Asteraceae/química , Componentes Aéreos da Planta/química , Extratos Vegetais/farmacologia , Antioxidantes/isolamento & purificação , Células Hep G2/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/isolamento & purificação
5.
Bioengineered ; 10(1): 292-305, 2019 12.
Artigo em Inglês | MEDLINE | ID: mdl-31284815

RESUMO

In the present study, Probit, Cauchy Fractional and three types of Log methods, i.e., Logit, Log-log, and Complementary log-log were employed to model the feeding deterrence of the lesser grain borer, Rhyzopertha dominica (F) (Coleoptera: Bostrichidae), when fed latex protein, crude flavonoid fraction, 3-O-rutinosides of quercetin, kaempferol and isorhamnetin, isolated from Calotropis procera (Ait.) (Gentianales: Asclepiadaceae). A nutritional study with treated flour discs at sub-lethal concentrations indicated that the tested natural products negatively affected the feeding behavior of the lesser grain borer, causing high feeding deterrent indices. Our results assure that Probit, Logit and Clog-log model the feeding deterrent indices with high goodness of fit. The models aim to support the management of the test insect when fed grains treated with sub-lethal doses of the tested phytochemicals in order to develop a viable, precise and long-term strategy to minimize the excessive reliance on the chemical pesticides currently in use.


Assuntos
Produtos Biológicos/farmacologia , Calotropis/química , Besouros/efeitos dos fármacos , Quempferóis/farmacologia , Modelos Estatísticos , Quercetina/análogos & derivados , Quercetina/farmacologia , Animais , Besouros/fisiologia , Grão Comestível/parasitologia , Comportamento Alimentar/efeitos dos fármacos , Comportamento Alimentar/fisiologia , Glicosídeos/farmacologia , Larva/efeitos dos fármacos , Larva/fisiologia , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Triticum/parasitologia
6.
Fitoterapia ; 136: 104186, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31150769

RESUMO

Five new amide alkaloids, named delamide A-E (1-5), along with five known ones, methyl-N-(3-carboxy-2-methylpropanoyl) anthranilate (6), benzoic acid, 2-[(1-oxodecyl) amino]-methylester (7), puberline (8), benzoic acid, 2-[(4-methoxy-2-methyl-1, 4-dioxobutyl) amino]-methylester (9) and benzoic acid, 2-[(4-methoxy-3-methyl-1, 4-dioxobutyl) amino]-methylester (10) were isolated from the extract of Delphinium brunonianum. Their structures were elucidated by extensive spectroscopic analyses (including 1D-, 2D-NMR, and HR-ESI-MS). 1-10 were also evaluated for their acetylcholinesterase (AChE) inhibiting activity by the Ellman's method. Delamide A (1) showed highly selective AChE inhibition activity. The kinetic analysis revealed that 1 was a mixed-type reversible inhibitor of AChE.


Assuntos
Alcaloides/farmacologia , Inibidores da Colinesterase/farmacologia , Delphinium/química , Componentes Aéreos da Planta/química , Alcaloides/isolamento & purificação , Inibidores da Colinesterase/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Tibet
7.
Food Chem Toxicol ; 131: 110534, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31150781

RESUMO

Acute and subacute toxicities of the ethanol extract from Epigynum auritum (EAE) wereperformed by oral administration in pathogen-free mice. Acute toxicity study was performed at a single dose of 5000 mg/kg for 14 consecutive days, while subacute toxicity test was conducted by daily oral administration of EAE at doses of 312, 625, 1250, and 2500 mg/kg for 28 days. Acute toxicity study showed that LD50 of EAE was over 5000 mg/kg. The results of subacute toxicity showed no significant adverse effect of EAE at 312 mg/kg. Moreover, EAE exhibited toxicities to liver, spleen and kidney in mice determined by hematological, serum biochemical and histological analyses during daily oral administration of 1250 mg/kg and 2500 mg/kg EAE. The results revealed that the dose of EAE lower than 625 mg/kg can be regarded as safe.


Assuntos
Apocynaceae/química , Componentes Aéreos da Planta/química , Extratos Vegetais/toxicidade , Administração Oral , Animais , Relação Dose-Resposta a Droga , Etanol/química , Feminino , Rim/patologia , Fígado/patologia , Pulmão/patologia , Masculino , Camundongos Endogâmicos ICR , Extratos Vegetais/administração & dosagem , Extratos Vegetais/isolamento & purificação , Potássio/sangue , Sódio/sangue , Baço/patologia , Testes de Toxicidade Aguda , Testes de Toxicidade Subaguda
8.
Fitoterapia ; 137: 104188, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31158428

RESUMO

Repeated chromatographic purifications of aerial parts of the Tunisian plant Daucus virgatus led to the isolation of four new germacranolides, named daucovirgolides I-L (2-5), along with the Plasmodium transmission-blocking agent daucovirgolide G. The chemical structures of the new compounds were defined as mono- or di-angeloylated germacrane-type sesquiterpenoids by spectroscopic (mainly 1D and 2D NMR) and spectrometric methods (ESIMS). The low potency exhibited by daucovirgolides I-L further supports the observation that strict structural requirements do exist for the Plasmodium transmission blocking activity in the daucovirgolide series. In particular, the endocyclic double bond system seems to be crucial for bioactivity.


Assuntos
Antimaláricos/farmacologia , Apiaceae/química , Plasmodium berghei/efeitos dos fármacos , Sesquiterpenos de Germacrano/farmacologia , Antimaláricos/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/isolamento & purificação , Tunísia
9.
Planta Med ; 85(11-12): 947-956, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31163459

RESUMO

In this paper, the isolation of five new guaianolides (1:  - 5: ) and four (6:  - 9: ) known sesquiterpenes from Ormenis mixta aerial parts is reported. The structural determination of the guaianolides was obtained by NMR spectroscopic data, as well as MS experiments. Their relative configurations were assigned by a combined quantum mechanical/NMR approach, comparing the experimental 13C/1H NMR chemical shift data and 1 J H-H homonuclear coupling constants with the related predicted values. The isolates were assayed for their anti-inflammatory potential evaluating nitric oxide release and cyclooxygenase-2 expression in J774A.1 macrophages treated with lipopolysaccharide from Escherichia coli. Our results indicated that, among the tested compounds, 1:  - 3: , and 7: were able to inhibit nitric oxide release, while all were able to inhibit cyclooxygenase-2 expression with different potencies.


Assuntos
Anti-Inflamatórios/farmacologia , Camomila/química , Sesquiterpenos de Guaiano/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular , Ciclo-Oxigenase 2/metabolismo , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Óxido Nítrico/metabolismo , Componentes Aéreos da Planta/química , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/isolamento & purificação
10.
Chem Biodivers ; 16(8): e1900278, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31207097

RESUMO

Using synthetic chemicals in industry and agriculture has led to several environmental problems. Thus, plant products derived from volatile oils (VOs) could be a potential green source for bioherbicides. Little is known about the VOs of Lactuca serriola. Hence, the present study aimed to characterize the VOs chemical composition from the aerial parts of L. serriola, assessment of antioxidant activity, and evaluate allelopathic potential against the noxious weed Bidens pilosa. The VOs were extracted by hydrodistillation and analyzed by GC/MS. The VOs from the Egyptian ecospecies of L. serriola were found to comprise 34 compounds mainly oxygenated sesquiterpenes and diterpenes. The major compounds were isoshyobunone (64.22 %), isocembrol (17.35 %), and alloaromadendrene oxide-1 (7.32 %). So, L. serriola can be considered as a good source for isoshyobunone, considering that it has a much higher concentration than any other plants. Also, this plant has a high content of the oxygenated diterpene compound, isocembrol, which is rarely found in the VOs of most plants. The VOs expressed strong antioxidant activity. Also, for the first time, our results showed a strong allelopathic activity of VOs from L. serriola on germination and seedling growth of the noxious weed, B. pilosa. We suppose that the activity of the VOs from L. serriola could be attributed to these previously mentioned major compounds, as they represent about 89 % of the total identified oil constituents. Nevertheless, to evaluate these compounds as new allelochemicals, further study is needed to test the allelopathic activity of authenticated standard of these compounds either singular or in combination on several weeds as well as evaluate the safety, and improve the efficacy and stability at the field scale.


Assuntos
Antioxidantes/química , Asteraceae/química , Diterpenos/química , Óleos Voláteis/química , Sesquiterpenos/química , Asteraceae/metabolismo , Bidens/crescimento & desenvolvimento , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Germinação/efeitos dos fármacos , Óleos Voláteis/farmacologia , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
11.
Molecules ; 24(9)2019 May 04.
Artigo em Inglês | MEDLINE | ID: mdl-31060200

RESUMO

Leea asiatica (L.) Ridsdale (Leeaceae) is found in tropical and subtropical countries and has historically been used as a traditional medicine in local healthcare systems. Although L. asiatica extracts have been found to possess anthelmintic and antioxidant-related nephroprotective and hepatoprotective effects, little attention has been paid toward the investigation of phytochemical constituents of this plant. In the current study, phytochemical analysis of isolates from L. asiatica led to the identification of 24 compounds, including a novel phenolic glucoside, seven triterpenoids, eight flavonoids, two phenolic glycosides, four diglycosidic compounds, and two miscellaneous compounds. The phytochemical structures of the isolates from L. asiatica were elucidated using spectroscopic analyses including 1D- and 2D-NMR and ESI-Q-TOF-MS. The presence of triterpenoids and flavonoids supports the evidence for anthelmintic and antioxidative effects of L. asiatica.


Assuntos
Compostos Fitoquímicos/análise , Vitaceae/química , Anti-Helmínticos/química , Anti-Helmínticos/isolamento & purificação , Anti-Helmínticos/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Medicina Tradicional , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia
12.
Fitoterapia ; 137: 104174, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31100437

RESUMO

Five new phthalide dimers, chaxiongnolides C-G (1-5), the two enantiomers of riligustilide (6a and 6b) and tokinolide B (7) were isolated from the aerial parts of Ligusticum sinense Oliv cv. Chaxiong. The structures of 1-5 were elucidated through extensive spectroscopic analysis, and the relative configurations of compounds 2 and 3 were further confirmed by an X-ray diffraction experiment. The absolute configurations of 1-3 were assigned by comparing calculated and experimental ECD spectra. The ECD exciton chirality method was used to confirm the absolute configurations of compounds 4, 5, 6a and 6b. Compounds 1-3 are the first dimeric phthalides to be reported that are comprising a sedanolide unit. The compounds were evaluated in vitro for their cytotoxic activity against select human cell lines.


Assuntos
Benzofuranos/química , Ligusticum/química , Benzofuranos/isolamento & purificação , Linhagem Celular , China , Humanos , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Componentes Aéreos da Planta/química , Estereoisomerismo , Difração de Raios X
13.
Fitoterapia ; 137: 104182, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31145985

RESUMO

Three previously undescribed polyoxygenated cyclohexene derivatives named cherrevenol M (1), cherrevenol N (2), and cherrevenone (3), together with nine related known analogues 4-12 were isolated from the ethyl acetate fraction partitioned from the methanol extract of the aerial parts of Uvaria cherrevensis (Annonaceae). The determination of the structures and their relative configurations of the isolated compounds were established by spectroscopic techniques, electronic circular dichroism (ECD) analysis as well as comparison with the literature data. For cherrevenone (3), the relative and absolute configurations were also confirmed by using X-ray diffraction and ECD techniques, respectively. Compounds isolated except for compounds 8 and 10 were evaluated for their cytotoxic activity and cherrevenone (3) showed moderate cytotoxic activity against all cancerous cell lines except for ASK cell line with ED50 values ranging from 1.04 ±â€¯0.13 to 10.09 ±â€¯4.31 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacocinética , Cicloexenos/farmacologia , Uvaria/química , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Cicloexenos/isolamento & purificação , Humanos , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Ratos , Tailândia
14.
Zhongguo Zhong Yao Za Zhi ; 44(7): 1416-1424, 2019 Apr.
Artigo em Chinês | MEDLINE | ID: mdl-31090300

RESUMO

Ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry(UPLC-Q-TOF-MS) was used to establish the chromatography fingerprint for aerial parts of Angelica sinenis(AAS) from 10 different places. Acetyl-phenyl-hydrazine(APH) was used to duplicate the mouse model of blood deficiency. Then partial least squares regression was used to investigate the spectrum-effect relationship between the relative contents and the data of enriching blood pharmacodynamics efficacy. The results showed that the three groups of high, medium and low doses of AAS had certain enriching blood activities(P<0.05), and the high dose group had the best effect(P<0.01). The contribution degree of the AAS to enriching blood activities of each common peaks were determined by PLS regression coefficient. Among them, 7 common peaks, including P17(unknown), P18(unknown), P19(unknown), P28(alisol B 23-acetate or its isomer), N5(luteolin), N11(1-caffeoylquinicacid,1-O-caffeoylquinic acid) and N14(unknown), contributed significantly to the effect of enriching blood activities. This paper dealed with the investigation on the spectrum-effect relationship between enriching blood activities and LC-MS chromatography fingerprint of AAS, and determination of the effective compositions of AAS with enriching blood activities. It provided theoretical foundation for the comprehensive development and utilization of AAS.


Assuntos
Angelica/química , Medicamentos de Ervas Chinesas/farmacologia , Animais , Cromatografia Líquida de Alta Pressão , Espectrometria de Massas , Medicina Tradicional Chinesa , Camundongos , Componentes Aéreos da Planta/química
15.
Planta Med ; 85(9-10): 719-728, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31137047

RESUMO

Abnormal lipid metabolism, such as increased fatty acid uptake and esterification, is associated with nonalcoholic fatty liver disease (NAFLD). The aqueous extract of the aerial part of Angelica tenuissima Nakai (ATX) inhibited high-fat diet-induced hepatic steatosis in mice as well as oleic acid-induced neutral lipid accumulation in HepG2 cells. ATX decreased the mRNA and protein levels of CD36 and diglyceride acyltransferase 2 (DGAT2), the maturation of sterol regulatory element-binding proteins (SREBP), and the expression of the lipogenic target genes fasn and scd1. The ATX components, Z-ligustilide and n-butylidenephthalide, inhibited the expression of FATP5 and DGAT2 and thus oleic acid-induced lipid accumulation in HepG2 cells. These results suggest that ATX and its active components Z-ligustilide and n-butylidenephthalide inhibit fatty acid uptake and esterification in mice and have potential as therapeutics for NAFLD.


Assuntos
4-Butirolactona/análogos & derivados , Angelica/química , Metabolismo dos Lipídeos/efeitos dos fármacos , Hepatopatia Gordurosa não Alcoólica/tratamento farmacológico , Anidridos Ftálicos/farmacologia , 4-Butirolactona/isolamento & purificação , 4-Butirolactona/farmacologia , Animais , Dieta Hiperlipídica/efeitos adversos , Avaliação Pré-Clínica de Medicamentos/métodos , Regulação da Expressão Gênica/efeitos dos fármacos , Células Hep G2 , Humanos , Lipogênese/efeitos dos fármacos , Masculino , Camundongos Endogâmicos C57BL , Hepatopatia Gordurosa não Alcoólica/etiologia , Hepatopatia Gordurosa não Alcoólica/metabolismo , Ácido Oleico/farmacologia , Anidridos Ftálicos/isolamento & purificação , Componentes Aéreos da Planta/química , Extratos Vegetais/análise , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Proteína de Ligação a Elemento Regulador de Esterol 1/genética , Proteína de Ligação a Elemento Regulador de Esterol 1/metabolismo
16.
Chem Biodivers ; 16(6): e1900206, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31081987

RESUMO

Three new 4,5-seco-20(10→5)-abeo-abietane diterpenoids, 16-hydroxysalvilenone (1), 15-hydroxysalprionin (2), and 11ß,15-dihydroxysalprionin-12-one (3), and nine known abietane diterpenoids, 4-12, along with one known sempervirane diterpenoid, hispidanol A (13), were isolated from the aerial parts of Isodon lophanthoides var. graciliflorus. The structures of compounds 1-3 were determined on the basis of spectroscopic methods including extensive analysis of NMR and mass spectroscopic data. All diterpenoids were tested for their TNF-α inhibitory effects on LPS-induced RAW264.7 cells. Compound 9 (16-acetoxyhorminone) was the most potent with an IC50 value of 3.97±0.70 µm.


Assuntos
Anti-Inflamatórios/química , Diterpenos de Abietano/química , Isodon/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Diterpenos de Abietano/isolamento & purificação , Diterpenos de Abietano/farmacologia , Isodon/metabolismo , Lipopolissacarídeos/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Conformação Molecular , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Células RAW 264.7
17.
Chem Biodivers ; 16(7): e1900033, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30977279

RESUMO

Achillea alpina is widely distributed in Korea and is often used as a folk medicine for stomach disorders. Although a previous study isolated antioxidant compounds (flavonoid O-glucoside, sesquiterpene) from this plant, no systematic study of its chemical constituents had been reported. The present study aimed to identify the phytochemicals present in a methanol extract of A. alpina, assess their potential antioxidant activities in vitro, and determine their effects on melanogenesis in B16F10 melanoma cells. Column chromatographic separation of aqueous fractions of A. alpina led to the isolation of 17 compounds. The chemical structures of these compounds were determined using spectroscopic data from electrospray ionization-mass spectrometry and nuclear magnetic resonance. To the best of our knowledge, the present study is the first to identify compounds 2-10 and 12-17 in A. alpina. Furthermore, compound 6 possessed powerful antioxidant activity, while compound 15 suppressed intracellular tyrosinase activity and thus reduced melanogenesis in B16F10 cells. Therefore, our research suggested that these naturally occurring compounds have the potential to reduce oxidative stress and promote skin whitening. Further investigations will be required to elucidate the mechanisms underlying the antioxidant and antityrosinase activities of these compounds.


Assuntos
Achillea/química , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Picratos/antagonistas & inibidores , Componentes Aéreos da Planta/química , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Camundongos , Estrutura Molecular , Relação Estrutura-Atividade
18.
Molecules ; 24(8)2019 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-31022860

RESUMO

Carpesium divaricatum Sieb. & Zucc. has a long history of use as both a medicinal and a food plant. However, except for terpenoids, its chemical constituents have remained poorly investigated. The composition of hydroalcoholic extract from aerial parts of C. divaricatum was analyzed by HPLC-DAD-MSn, revealing the presence of numerous caffeic acid derivatives that were formerly unknown constituents of the plant. In all, 17 compounds, including commonly found chlorogenic acids and rarely occurring butyryl and methylbutyryl tricaffeoylhexaric acids, were tentatively identified. Fractionation of lipophilic extract from cultivated shoots led to the isolation of 12-oxo-phytodienoic acid (12-OPDA), which is a newly identified constituent of the plant. The compound, at concentrations of 0.5, 1.0, and 2.5 µM, significantly reduced IL-8, IL-1ß, TNFα, and CCL2 excretion by lipopolysaccharide (LPS)-stimulated human neutrophils. Reactive oxygen species (ROS) production induced by f-MLP was also significantly diminished in the neutrophils pretreated by 12-OPDA. The newly identified constituents of the plant seem to be partly responsible for its pharmacological activity and elevate the value of C. divaricatum as a potential functional food.


Assuntos
Asteraceae/química , Ácidos Cafeicos/química , Ácido Clorogênico/química , Ácidos Graxos Insaturados/química , Ácidos Cafeicos/isolamento & purificação , Ácidos Cafeicos/farmacologia , Quimiocina CCL2/genética , Ácido Clorogênico/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Ácidos Graxos Insaturados/isolamento & purificação , Ácidos Graxos Insaturados/farmacologia , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Interleucina-8/genética , Lipopolissacarídeos/farmacologia , Neutrófilos/efeitos dos fármacos , Componentes Aéreos da Planta/química , Brotos de Planta/química , Espécies Reativas de Oxigênio/química , Fator de Necrose Tumoral alfa/genética
19.
Fitoterapia ; 137: 104150, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-30995564

RESUMO

Schefflera kwangsiensis Merr. ex H.L. Li (Araliaceae) is a widely used traditional Chinese medicine for pain management in the clinic. In the present study, we isolated a previously undescribed lupane saponin, designated as schekwanglupaside C (Sch C) from the ethanolic extract of S. kwangsiensis. The structure of Sch C was determined by comprehensive spectroscopic and spectrometric analyses and chemical degradation. In primary cultured cortical neurons, Sch C altered the pattern of spontaneous Ca2+ oscillation (SCO) with a slight increase in the frequency of SCO right after addition and a gradual decrease in the frequency and amplitude of SCO, that dynamic change mimicked by an activator of sarcoplasmic reticulum Ca2+-ATPase (SERCA). The IC50 values for Sch C suppression of the frequency and amplitude of SCO were 1.75 and 2.51 µM, respectively. Furthermore, we demonstrated that Sch C is a potent SERCA activator (EC50 = 1.20 µM). Given the pivotal role of SERCA in the progression of neuropathic pain and neurodegenerative diseases, Sch C represents a new drug lead compound to develop the treatment of neuropathic pain and Alzheimer's disease.


Assuntos
Araliaceae/química , Neurônios/efeitos dos fármacos , Saponinas/farmacologia , ATPases Transportadoras de Cálcio do Retículo Sarcoplasmático/metabolismo , Triterpenos/farmacologia , Animais , Cálcio/metabolismo , Células Cultivadas , China , Feminino , Masculino , Camundongos Endogâmicos C57BL , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Saponinas/isolamento & purificação , Retículo Sarcoplasmático/enzimologia , Triterpenos/isolamento & purificação
20.
Molecules ; 24(8)2019 Apr 12.
Artigo em Inglês | MEDLINE | ID: mdl-31013828

RESUMO

Six new coumarin glycosides, genglycoside A-F (1-6), were isolated from the aerial parts of Gendarussa vulgaris, along with ten known analogues (7-16). Their structures were unambiguously established on the basis of extensive spectroscopic data and HPLC analysis. The cytotoxic activities of all isolated compounds were evaluated by MTT assay. Compound 12 showed the most potent cytotoxicity in Eca-109, MCF-7, and HepG2 cell lines. By the preliminary structure-activity relationships, it was firstly discovered that the glycosylation or esterification at 7,8-dihydroxy or 7-hydroxy drastically reduced the cytotoxic activity of the parent coumarin.


Assuntos
Antineoplásicos Fitogênicos , Cumarínicos , Glicosídeos , Lamiales/química , Componentes Aéreos da Planta/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Cumarínicos/química , Cumarínicos/isolamento & purificação , Cumarínicos/farmacologia , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Células Hep G2 , Humanos , Células MCF-7
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