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1.
Nat Prod Res ; : 1-8, 2019 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-31373230

RESUMO

Ten compounds (1-10) were purified from the extract of lichens C. faveomaculata, and among these one new triterpenoid, cryptothecin A (1) was characterized through mass spectrometric and 2D NMR spectroscopic analyses. Some of the isolated compounds were assessed for their antimicrobial (1, 6, and 8) and cytotoxic activity (1, 4-5, and 7-9), but only weak inhibitory effects were observed.

2.
Nat Prod Res ; : 1-6, 2019 Jun 10.
Artigo em Inglês | MEDLINE | ID: mdl-31180241

RESUMO

One new triterpenoid, hexagonin F (1) was characterized from the fruiting bodies of Hexagonia tenuis with the assistance of spectroscopic and spectrometric analytical methods. In addition, two triterpenoids and two steroids were also identified by comparison of their physical and spectroscopic data with those reported. The purified compounds were examined for their cytotoxicity against five tumor cell lines, however, only weak cytotoxicity was demonstrated.

3.
Molecules ; 24(2)2019 Jan 10.
Artigo em Inglês | MEDLINE | ID: mdl-30634658

RESUMO

Two new sesquiterpenoids peltopterins A and B (compounds 1 and 2) and fifty-two known compounds were isolated from the methanol extract of P. pterocarpum and their chemical structures were established through spectroscopic and mass spectrometric analyses. The isolates 40, 43, 44, 47, 48, 51 and 52 exhibited potential inhibitory effects of superoxide anion generation or elastase release.


Assuntos
Fabaceae/química , Sesquiterpenos/isolamento & purificação , Espectrometria de Massas , Estrutura Molecular , Elastase Pancreática/metabolismo , Extratos Vegetais/análise , Folhas de Planta/química , Sesquiterpenos/química , Superóxidos/metabolismo
4.
Molecules ; 23(10)2018 Oct 05.
Artigo em Inglês | MEDLINE | ID: mdl-30301176

RESUMO

Fifty-seven compounds were purified from the stems of Tinospora sinensis, including three new compounds characterized as a lignan (1), a pyrrole alkaloid (11), and a benzenoid (17), respectively. Their structures were elucidated and established by various spectroscopic and spectrometric analytical methods. Among the isolates, fifteen compounds were examined for their anti-inflammatory potential in vitro. The results showed that several compounds displayed moderate inhibition of N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release.

5.
Nat Prod Res ; 32(20): 2392-2397, 2018 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-29232973

RESUMO

A new tirucallane-type triterpenoid igniarine (1), and four known compounds meshimakobnol A (2), meshimakobnol B (3), ergosterol (4) and ergosterol peroxide (5), were purified from the methanol extracts of the fruiting bodies of Phellinus igniarius (DC. ex Fr.) Quél. The structure of 1 was elucidated using a combination of 1D and 2D NMR techniques and HR-ESI-MS analyses. In addition, the isolated compounds were examined for their cytotoxicity against several tumour cell lines and part of the tested compounds demonstrated weak cytotoxicity.


Assuntos
Antineoplásicos/farmacologia , Basidiomycota/química , Triterpenos/farmacologia , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Ergosterol/análogos & derivados , Ergosterol/isolamento & purificação , Carpóforos/química , Células Hep G2 , Humanos , Células MCF-7 , Estrutura Molecular , Triterpenos/isolamento & purificação , Vietnã
6.
J Nat Med ; 71(1): 96-104, 2017 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-27539584

RESUMO

Five new acyclic amides, clausenalansamides C-G (1-5), clausenaline G (6) and (±)-5-(4-methylphenyl)-γ-valerolactone (7) reported from the natural source for the first time, were characterized from the leaves of Clausena lansium. Their structures were established by spectroscopic and spectrometric methods, and the absolute configurations of new compounds 1-5 were determined by electronic circular dichroism and single-crystal X-ray diffraction analyses. Eighteen compounds were evaluated for their anti-inflammatory activity and only imperatorin (11) and wampetin (12) displayed significant inhibition of fMLP/CB-induced superoxide anion generation with IC50 values of 1.7 ± 0.3 and 6.8 ± 1.1 µM, respectively.


Assuntos
Anti-Inflamatórios/química , Clausena/química , Folhas de Planta/química , Anti-Inflamatórios/farmacologia , Estrutura Molecular
7.
Nat Prod Commun ; 12(3): 377-378, 2017 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30549889

RESUMO

A new cyclodepsipeptide, isarin (1), was isolated from the insect pathogenic fungus Isaria japonica Yasuda, together with one known compound, beauveriolide 1 (2). The structure of this new compound was characterized using a combination of spectroscopic and spectrometric analyses.


Assuntos
Ascomicetos/química , Depsipeptídeos/química , Micélio/química , Vietnã
8.
Sci Rep ; 6: 39251, 2016 12 21.
Artigo em Inglês | MEDLINE | ID: mdl-28000792

RESUMO

For past three decades, numerous studies have elucidated the antiproliferative effects of acetogenins in hopes of developing a new class of clinical anticancer agents. However, clear and definitive action mechanisms of acetogenins were less clarified. In the present study, three tetrahydrofuran (THF)-containing acetogenins were found to have potent and selective antiproliferative activity against human nasopharyngeal carcinoma (NPC) cell lines and their methotrexate-resistant counterparts. The THF-containing acetogenins induced G2/M phase arrest, mitochondrial damage and apoptosis, and increased cytosolic and mitochondrial Ca2+ in NPCs. Microarray analysis of NPC-TW01 cells treated with squamostatin A, a non-adjacent bis-THF acetogenin, demonstrated an increased endoplasmic reticulum (ER)-stress response (ESR). Enhanced ESR in squamostatin A-treated cells was confirmed by real-time PCR, Western blot and shRNA gene knockdown experiments. Although our results showed that squamostatin A-induced ESR was independent of extracellular Ca2+, the presence of extracellular Ca2+ enhanced the antiproliferative effect of acetogenins. In vivo analyses demonstrated that squamostatin A showed good pharmacokinetic properties and significantly retarded NPC tumor growth in the xenograft mouse model. Conclusively, our work demonstrates that acetogenins are effective and selective inducers of the ESR that can block NPC proliferation, and illustrate a previously unappreciated antitumor mechanism of acetogenins that is effective against nasopharyngeal malignancies.


Assuntos
Acetogeninas/toxicidade , Antineoplásicos/toxicidade , Apoptose/efeitos dos fármacos , Estresse do Retículo Endoplasmático/efeitos dos fármacos , Furanos/química , Acetogeninas/química , Acetogeninas/isolamento & purificação , Acetogeninas/uso terapêutico , Animais , Antineoplásicos/química , Antineoplásicos/uso terapêutico , Carcinoma/tratamento farmacológico , Carcinoma/metabolismo , Carcinoma/patologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Pontos de Checagem da Fase G2 do Ciclo Celular/efeitos dos fármacos , Proteínas de Choque Térmico/genética , Proteínas de Choque Térmico/metabolismo , Humanos , Pontos de Checagem da Fase M do Ciclo Celular/efeitos dos fármacos , Masculino , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Camundongos , Camundongos Endogâmicos BALB C , Camundongos Nus , Carcinoma Nasofaríngeo , Neoplasias Nasofaríngeas/tratamento farmacológico , Neoplasias Nasofaríngeas/metabolismo , Neoplasias Nasofaríngeas/patologia , Proteína Fosfatase 1/antagonistas & inibidores , Proteína Fosfatase 1/genética , Proteína Fosfatase 1/metabolismo , Transplante Heterólogo
9.
Phytochemistry ; 122: 184-192, 2016 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-26732672

RESUMO

The phytochemical investigation of the methanolic extract of Uvaria flexuosa (Annonaceae) leaves led to the isolation of seven compounds including, 3-methyl-4,5-dihydro-oxepine (flexuvaroxepine A), four polyoxygenated seco-cyclohexene (flexuvarin A-D) and two polyoxygenated cyclohexene (flexuvarol A-B) derivatives, together with four known flavones. The structures of the isolated compounds were elucidated using different spectroscopic techniques. A plausible biogenetic route of the new compounds was discussed. The anti-inflammatory activity of the isolated compounds was evaluated by superoxide anion generation and elastase release assays. Among the tested compounds, flexuvarol B and chrysin showed the most potent anti-inflammatory effect by inhibiting superoxide anion generation and elastase release from human neutrophils in response to fMLP with IC50 2.25-5.55µM. Moreover, 5-hydroxy-6,7-dimethoxy-flavone showed selective inhibitory activity on superoxide anion generation (IC50=1.19±0.34µM).


Assuntos
Annonaceae/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Cicloexenos/isolamento & purificação , Cicloexenos/farmacologia , Oxepinas/isolamento & purificação , Oxepinas/farmacologia , Uvaria/química , Anti-Inflamatórios/química , Cicloexenos/química , Flavonoides/farmacologia , Humanos , Estrutura Molecular , Oxepinas/química , Folhas de Planta/química
10.
J Nat Prod ; 78(11): 2521-30, 2015 Nov 25.
Artigo em Inglês | MEDLINE | ID: mdl-26523463

RESUMO

Eight new clausenamides, including three γ-lactams (1-3), four δ-lactams (4-7), and an amide (8), and seven known lactams, including compounds 9-11, which were purified from natural sources for the first time, were characterized from the leaves of Clausena lansium. Their structures were elucidated using spectroscopic methods, and the absolute configurations were determined using electronic circular dichroism and single-crystal X-ray diffraction analyses with Cu Kα radiation. Compound 2 (50 µM) protected 22.24% of cortical neurons against Aß25-35-induced cell death.


Assuntos
Clausena/química , Lactamas/isolamento & purificação , Lignanas/isolamento & purificação , Fármacos Neuroprotetores/isolamento & purificação , Peptídeos beta-Amiloides/farmacologia , Carbazóis , Lactamas/química , Lignanas/química , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/farmacologia , Ressonância Magnética Nuclear Biomolecular , Fragmentos de Peptídeos/farmacologia , Folhas de Planta/química , Estereoisomerismo , Vietnã
11.
J Nat Prod ; 78(11): 2552-8, 2015 Nov 25.
Artigo em Inglês | MEDLINE | ID: mdl-26575215

RESUMO

A chemical investigation of the fruiting bodies of Hexagonia apiaria resulted in the identification of nine compounds including five new triterpenoids, hexagonins A-E (1-5), along with four known compounds. The purified constituents were examined for their anti-inflammatory activity. Among the tested compounds, hexatenuin A displayed the most significant inhibition of superoxide anion generation and elastase release. These triterpenoids may have potentials as anti-inflammatory agents.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Carpóforos/química , Polyporaceae/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Anti-Inflamatórios/sangue , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Elastase Pancreática/efeitos dos fármacos , Elastase Pancreática/metabolismo , Superóxidos/metabolismo , Triterpenos/sangue , Triterpenos/química
12.
Bol. latinoam. Caribe plantas med. aromát ; 14(1): 60-66, ene.2015. tab
Artigo em Inglês | LILACS | ID: lil-795834

RESUMO

The chemical compositions of essential oils obtained by hydrodistillation of the leaves, stems and flowers of Euodia lepta and Euodia callophylla grown in Vietnam and then analysed by gas chromatography-flame ionization detector (GC-FID) and gas chromatography/mass spectrometry (GC-MS) were being reported. The main compounds of the leaves oil of E. lepta were (E)-beta-ocimene (24.4 percent), alpha-pinene (9.8 percent), (Z)-beta-ocimene (6.3 percent) and delta-cadinene (5.2 percent), while the stems oil comprised of spathulenol (26.0 percent), (E)-beta- ocimene (9.9 percent) and (Z)-9-octadecenamide (7.7 percent). However, ciscarane (19.2 percent), alpha-cadinol (10.8 percent), alpha-pinene (10.5 percent) and (E)-beta-ocimene (9.0 percent) were present in the flowers oil of E. lepta. On the other hand, alpha-pinene (8.3 percent), trans-alpha-bergamotene (7.5 percent), (E)-beta-ocimene (7.0 percent) and (E)-nerolidol (6.6 percent) were the major constituents of the leaves oil of E. calophylla. The quantitatively significant compounds of the stems oil were (E,E)-alpha-farnesene (11.9 percent), alpha-terpinolene (11.3 percent) and alpha-pinene (8.2 percent), while alpha-pinene (21.6 percent), limonene (19.0 percent) and sabinene (15.5 percent) were obtained from the flowers oil...


La composición químicas de los aceites esenciales obtenidos por hidrodestilación de las hojas, tallos y flores de Euodia lepta y Euodia callophylla cultivadas en Vietnam, fueron analizados por cromatografía de gases-detector de ionización de llama (GC-FID) y la cromatografía de gases/espectrometría de masas (GC-MS). Los principales compuestos del aceite de hojas de E. lepta fueron (E) -beta-ocimeno (24,4 por ciento), alfa-pineno (9,8 por ciento), (Z)-beta- ocimeno (6,3 por ciento) y delta-cadineno (5.2 por ciento), mientras que los tallos de aceite estaban compuestos de spatulenol (26,0 por ciento), (E) -beta-ocimeno (9,9 por ciento) y (Z) -9- octadecenamida (7,7 por ciento). Sin embargo, cis-carano (19,2 por ciento), alfa-cadinol (10,8 por ciento), alfa-pineno (10,5 por ciento) y (E) -beta-ocimeno (9,0 por ciento) estaban presentes en el aceite de flores de E. lepta. Por otro lado, alfa-pineno (8,3 por ciento), trans-alfa-bergamoteno (7,5 por ciento), (E) - beta-ocimeno (7,0 por ciento) y (E) -nerolidol (6,6 por ciento) fueron los principales constituyentes del aceite de las hojas de E. calophylla. Los compuestos cuantitativamente significativos del aceite de los tallos fueron (E, E)-farneseno -alfa (11,9 por ciento), alfa-terpinoleno (11,3 por ciento) y alfa-pineno (8,2 por ciento), mientras que alfa-pineno (21,6 por ciento), limoneno (19,0 por ciento) y sabineno (15,5 por ciento) se obtuvieron del aceite de las flores...


Assuntos
Óleos Voláteis/química , Evodia/química , Monoterpenos/análise , Sesquiterpenos/análise , Ionização de Chama , Cromatografia Gasosa-Espectrometria de Massas
13.
J Nat Prod ; 77(12): 2626-32, 2014 Dec 26.
Artigo em Inglês | MEDLINE | ID: mdl-25419616

RESUMO

Parvistones A-E (1-5), five new styryllactones possessing a rare α,ß-lactone moiety and a 6S configuration, were isolated from a methanolic extract of Polyalthia parviflora leaves. The structures and the absolute configuration of the isolates were elucidated using NMR spectroscopy, specific rotation, circular dichroism, and X-ray single-crystal analysis. Compounds 8, 9, 11, and 12 were isolated for the first time. The results were supported by comparing the data measured to those of 6R-styryllactones. Moreover, a plausible biogenetic pathway of the isolated compounds was proposed. The structure-activity relationship of the compounds in an in vitro anti-inflammatory assay revealed the 6S-styryllactones to be more potent than the 6R derivatives. However, the effect was opposite regarding their cytotoxic activity. In addition, 6S-styrylpyrones isolated showed more potent anti-inflammatory and cytotoxic activity when compared to the 1S-phenylpyranopyrones obtained.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Lactonas/isolamento & purificação , Lactonas/farmacologia , Polyalthia/química , Anti-Inflamatórios/química , Dicroísmo Circular , Cristalografia por Raios X , Lactonas/química , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Estereoisomerismo , Relação Estrutura-Atividade , Vietnã
14.
Molecules ; 19(9): 13577-86, 2014 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-25255757

RESUMO

In an effort to develop new antimicrobial agents, 3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazolidin-4-one (4) was synthesized by reaction of thiocarbonylbisthioglycolic acid with ethyl (4-methyl-2-oxo-2H-chromen-7-yloxy)aceto- hydrazide (3), which was prepared in turn from 7-hydroxy-4-methylcoumarin (1). The condensation of compound 4 with different aromatic aldehydes afforded a series of 5-(arylidene)-3-(4-methylcoumarin-7-yloxyacetyl-amino)-2-thioxo-1,3-thiozolidin-4-one analogs 5a-h. The structures of these synthetic compounds were elucidated on the basis of IR, 1H-NMR and 13C-NMR spectral data and ESI-MS spectrometric analysis. Compounds 5a-h were examined for their antibacterial activity against several strains of Gram-positive and Gram-negative bacteria.


Assuntos
Antibacterianos/química , Cumarínicos/química , Antibacterianos/síntese química , Antibacterianos/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Cumarínicos/síntese química , Cumarínicos/farmacologia , Testes de Sensibilidade Microbiana , Espectroscopia de Prótons por Ressonância Magnética , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Infravermelho
15.
J Nat Prod ; 77(5): 1215-23, 2014 May 23.
Artigo em Inglês | MEDLINE | ID: mdl-24798144

RESUMO

Eight new carbazole alkaloids, claulamines C (1), D (2), and E (5) and clausenalines B-F (3, 4, 6-8), four new coumarins, clausemarins A-D (9-12), and 43 known compounds were isolated from the roots of Clausena lansium. The structures of the new compounds were established on the basis of 2D-NMR spectroscopic analysis, and their absolute configurations were established from their ECD spectra. The configuration of wampetin was revised as E using a NOESY experiment. Most of the isolated compounds were evaluated for their potential anti-inflammatory activity. The results showed that compounds 9, 13-18, and 20-22 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 1.9 to 8.4 µM, while compounds 18, 19, and 21 inhibited elastase release with IC50 values in the range from 2.0 to 6.9 µM.


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Carbazóis/isolamento & purificação , Clausena/química , Cumarínicos/isolamento & purificação , Cumarínicos/farmacologia , Acidentes por Quedas , Alcaloides/química , Anti-Inflamatórios/química , Carbazóis/química , Carbazóis/farmacologia , Cumarínicos/química , Estrutura Molecular , Raízes de Plantas/química , Caules de Planta/química
16.
Molecules ; 18(11): 14285-92, 2013 Nov 19.
Artigo em Inglês | MEDLINE | ID: mdl-24256922

RESUMO

The methanol extracts of the fruiting bodies of Ganoderma mastoporum collected in Vietnam was purified to afford eight compounds, including three triterpenoids and five steroids. The purified compounds were examined for their inhibitory effects against superoxide anion generation and elastase release. Among the tested compounds, ergosta-4,6,8(14),22-tetraen-3-one (3) exhibited the most significant inhibition towards superoxide anion generation and elastase release with IC50 values of 2.30 ± 0.38 and 1.94 ± 0.50 µg/mL, respectively.


Assuntos
Ganoderma/química , Elastase Pancreática/metabolismo , Esteroides/química , Superóxidos/metabolismo , Triterpenos/química , Adulto , Células Cultivadas , Humanos , Estrutura Molecular , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Adulto Jovem
17.
Molecules ; 18(4): 4477-86, 2013 Apr 16.
Artigo em Inglês | MEDLINE | ID: mdl-23591927

RESUMO

In the present study, the chemical investigation of the leaves of Annona reticulata has resulted in the identification of nine compounds, including annonaretin A, a new triterpenoid. The purified compounds were subjected to the examination of their effects on NO inhibition in LPS-activated mouse peritoneal macrophages and most of them exhibited significant NO inhibition, with IC50 values in the range of 48.6 ± 1.2 and 99.8 ± 0.4 µM.


Assuntos
Annona/química , Anti-Inflamatórios/farmacologia , Óxido Nítrico/antagonistas & inibidores , Extratos Vegetais/farmacologia , Folhas de Planta/química , Animais , Anti-Inflamatórios/análise , Anti-Inflamatórios/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Concentração Inibidora 50 , Lipopolissacarídeos/efeitos adversos , Macrófagos/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Camundongos , Óxido Nítrico/biossíntese , Extratos Vegetais/química
18.
J Nat Prod ; 76(2): 230-6, 2013 Feb 22.
Artigo em Inglês | MEDLINE | ID: mdl-23347584

RESUMO

Phytochemical investigation of the methanolic extract of Croton tonkinensis afforded two known kauranes (1, 2), eight new ent-kauranes (3-10), and 16 known ent-kaurane-type diterpenoids (12-27). In addition, 30 known compounds were identified by comparison of their physical and spectroscopic data with reported data. Among the isolated compounds, ent-18-acetoxykaur-16-en-15-one (20) displayed the most significant inhibition of superoxide anion generation and elastase release.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Diterpenos de Caurano/isolamento & purificação , Diterpenos de Caurano/farmacologia , Anti-Inflamatórios/química , Croton/química , Diterpenos de Caurano/química , Estrutura Molecular , Elastase Pancreática/efeitos dos fármacos , Elastase Pancreática/metabolismo , Superóxidos/antagonistas & inibidores , Superóxidos/metabolismo , Vietnã
19.
Planta Med ; 79(3-4): 288-94, 2013 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-23345166

RESUMO

Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 µM. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.


Assuntos
Annonaceae/química , Anti-Inflamatórios não Esteroides/farmacologia , Cinamatos/síntese química , Cinamatos/isolamento & purificação , Cicloexanonas/síntese química , Cicloexanonas/isolamento & purificação , Adulto , Amidas/química , Anti-Inflamatórios não Esteroides/síntese química , Anti-Inflamatórios não Esteroides/química , Técnicas de Química Sintética , Cinamatos/farmacologia , Cristalografia por Raios X , Cicloexanonas/farmacologia , Inibidores Enzimáticos/farmacologia , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Neutrófilos/efeitos dos fármacos , Neutrófilos/enzimologia , Elastase Pancreática/antagonistas & inibidores , Fenóis/química , Folhas de Planta/química , Superóxidos/antagonistas & inibidores , Adulto Jovem
20.
Phytochemistry ; 82: 110-7, 2012 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-22818357

RESUMO

Glycosides, clausenosides A and B, and carbazole alkaloids, clausenaline A, claulamine A, and claulamine B, together with 50 known compounds, were isolated from the stems of Clausena lansium. Their structures were determined by means of spectroscopic methods, including that of CD and 1D/2D NMR analysis. Claulamine A has a 1-oxygenated carbazole skeleton with a rare 2,3-lactone ring, and claulamine B represents an hitherto unknown acetal carbazole alkaloid. Thirty-one of the isolated known compounds were evaluated in various assays for anti-inflammatory activity. Among them, imperatorin, isoheraclenin, and osthol exhibited selective and potent inhibition of formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation, and lansiumarin C also decreased nitric oxide (NO) and tumor necrosis factor-α (TNF-α) production in lipopolysaccharide (LPS)-induced macrophages. In addition, a modified HPLC method of pre-column derivatization was developed that is more practical for simultaneous analysis of aldose enantiomers as compared to the literature method. The absolute configurations of the sugar moieties in clausenosides A and B were determined with this modified method.


Assuntos
Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Clausena/química , Monossacarídeos/química , Monossacarídeos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Concentração Inibidora 50 , Camundongos , Monossacarídeos/isolamento & purificação , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Caules de Planta/química , Análise Espectral , Estereoisomerismo , Superóxidos/metabolismo
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