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1.
Molecules ; 24(23)2019 Nov 23.
Artigo em Inglês | MEDLINE | ID: mdl-31771241

RESUMO

Three previously undescribed compounds, two prenyleudesmanes (1 and 2), and one hexanorlanostane (3), were isolated from the roots of Lonicera macranthoides. Their structures were established based on 1D and 2D nuclear magnetic resonance (NMR) spectra and high-resolution electrospray ionization mass spectral (HR-ESI-MS) data. The absolute configurations of 1 and 3 were determined by X-ray diffraction. To the best of our knowledge, this is the first time that the absolute configuration of a prenyleudesmane with a trans-decalin system and a hexanorlanostane have been unambiguously confirmed by single-crystal X-ray diffraction with Cu Kα radiation. Thecompounds were tested for their antiproliferative activity on the cancer cell lines (HepG2 and HeLa). The compounds 1-3 exhibited moderate inhibitory effects against two human cancer cell lines.

2.
Molecules ; 24(20)2019 Oct 16.
Artigo em Inglês | MEDLINE | ID: mdl-31623197

RESUMO

The lindenane-type sesquiterpenoid chlojaponilactone B (1), isolated from Chloranthus japonicus, has been reported to possess anti-inflammatory properties. The present study aimed to further explore the molecular mechanisms underlying the anti-inflammatory activity of 1. RNA-seq analyses revealed the significant changes in the expression levels of genes related to multiple inflammatory pathways upon treatment of lipopolysaccharide (LPS)-induced RAW 264.7 murine macrophages with 1. Real time PCR (RT-PCR) and Western blotting were used to confirm the modulations in the expression of essential molecules related to inflammatory responses. Compound 1 inhibited toll like receptor 4 (TLR4) and myeloid differentiation factor 88 (MyD88) activation upon LPS stimulation, influencing the expression of NF-κB and pro-inflammatory mediators. Molecular docking studies showed that 1 bound to TLR4 in a manner similar to that of TAK-242, a TLR4 inhibitor. Moreover, our results showed that 1 suppressed inflammatory responses by inhibiting TLR4 and subsequently decreasing reactive oxygen species (ROS) generation, downregulating the NF-κB, thus reducing the expression of the pro-inflammatory cytokines iNOS, NO, COX-2, IL-6 and TNF-α; these effects were similar to those of TAK-242. We proposed that 1 should be considered as a potential anti-inflammatory compound in future research.

3.
J Nat Prod ; 82(2): 407-411, 2019 02 22.
Artigo em Inglês | MEDLINE | ID: mdl-30724564

RESUMO

Chloraserrtone A (1), a new sesquiterpenoid dimer with two lindenane-type sesquiterpenoid monomers bridged by two six-membered rings, was obtained from Chloranthus serratus. A combination of UV, IR, NMR, HRESIMS, and X-ray diffraction data were used to elucidate the structure of 1. Compound 1 represents the first lindenane-type sesquiterpenoid dimer with extremely unique C-15-C-15', C-4-C-6', and C-6-C-11' linkages to form two six-membered rings between the monomeric units. A plausible biosynthesis toward chloraserrtone A is proposed. This new compound (1), together with the known lindenane dimers (2-11), were assessed for their inhibitory effects on lipopolysaccharide-induced NO production in RAW264.7 cells. Compound 6 showed activity with an IC50 value of 3.7 µM.

4.
Nat Prod Res ; 32(8): 885-891, 2018 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-28817970

RESUMO

Four fractions were prepared from the crude extract of Caesalpinia minax Hance and the inhibitory activity of nitric oxide (NO) production release of RAW 264.7 cells stimulated by lipopolysaccharide (LPS) was evaluated. The ethyl acetate (EtOAc) fraction showed obvious inhibitory effect. Bioassay-guided fractionation led to the isolation of three new cassane diterpenes, caesalmin X (1), caesalmin Y (2) and caesalmin Z (3), together with 19 known cassane diterpenoids (4-22). Their structures were mainly characterised on the basis of extensive spectroscopic analyses and comparison with reported data. Moreover, three compounds (20-22) which possessed furanditerpenoid 7,17-lactone structures, displayed moderate activities, with IC50 value of 29.85, 27.38 and 25.40 µM, respectively.


Assuntos
Caesalpinia/química , Diterpenos/química , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Linhagem Celular , Diterpenos/farmacologia , Avaliação Pré-Clínica de Medicamentos/métodos , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Sementes/química , Espectrofotometria Infravermelho
5.
Nat Prod Res ; 31(7): 810-816, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-27809603

RESUMO

Solanerioside A (1), the first example of a diterpenoid glucoside featuring a 14,15-dinor-cyclophytane scaffold, together with three known terpene glucosides (2-4) were isolated from the methanol extract of the leaves of Solanum erianthum (Solanaceae). The structure of 1 was mainly characterised on the basis of extensive spectroscopic analyses, especially from the 2D NMR spectra. In addition, the spectroscopic data of (6E, 10E)-5,12-dihydroxy-ß-nerolidol 5-O-ß-D-glucopyranoside (3) were reported for the first time. However, these compounds did not display obvious inhibition of LPS-induced NO release in RAW264.7 cells and anti-tumour activity against A549, HepG2, Hela and MCF-7 cells in vitro.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Diterpenos/isolamento & purificação , Glucosídeos/isolamento & purificação , Folhas de Planta/química , Solanum/química , Animais , Linhagem Celular Tumoral , Diterpenos/química , Diterpenos/farmacologia , Glucosídeos/química , Glucosídeos/farmacologia , Humanos , Lipopolissacarídeos/farmacologia , Espectroscopia de Ressonância Magnética , Camundongos , Óxido Nítrico/metabolismo , Extratos Vegetais/química , Células RAW 264.7 , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Infravermelho
6.
Chirality ; 28(3): 259-63, 2016 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-26781827

RESUMO

One pair of new C-8-C-3'/C-7-O-C-4' linked neolignan enantiomers (1a/1b) and one new guaiane sesquiterpene (2) first featuring the 1(2),9(10)-conjugated double bond were isolated from the stems of Solanum erianthum (Solanceae). Their structures were characterized on the basis of extensive spectroscopic analyses, especially from their 2D nuclear magnetic resonance (NMR) spectra. The absolute configurations of 1a/2b were rigorously elucidated by electronic circular dichroism (ECD) experiments combined with the reversed helicity rule for the 2,3-dihydrobenzo[b]furan chromophore, and compound 2 is the first report on the sterochemical assignment of a guaiane sesquiterpene by using the allylic axial chirality rule for the conjugated diene chromophore in combination with the calculated ECD spectrum.


Assuntos
Lignanas/química , Sesquiterpenos/química , Solanum/química , Benzofuranos/química , Dicroísmo Circular , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Sesquiterpenos de Guaiano/química , Estereoisomerismo
7.
Zhong Yao Cai ; 38(3): 518-20, 2015 Mar.
Artigo em Chinês | MEDLINE | ID: mdl-26495652

RESUMO

OBJECTIVE: To study chemical constituents of petroleum ether fraction of the roots of Lonicera macranthoides. METHODS: The chemical constituents were isolated and purified by several separation and purification techniques and their structures were elucidated by physicochemical properties and spectroscopic methods. RESULTS: Six compounds were isolated from petroleum ether fraction of the roots of Lonicera macranthoides as 3α, 16ß-dihydroxyaphidicolane (1), (22E,24R)-ergosta-6,9,22-trien-3ß,5α,8α-triol (2), (22E)-5α,8α-epidioxyergosta-6,22-dien-3ß-ol (3), (24S)-stigmast-4-en-3-one (4), ß-amyrin (5) and ß-amyrin acetate (6). CONCLUSION: Compounds 1 ~ 3 and 6 are isolated from this genus for the first time. All the compounds are isolated from this plant for the first time. Compound 1 is a new natural product.


Assuntos
Lonicera/química , Compostos Fitoquímicos/química , Raízes de Plantas/química , Ergosterol/análogos & derivados , Compostos Fitoquímicos/isolamento & purificação , Estigmasterol/análogos & derivados
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