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1.
Mar Drugs ; 18(3)2020 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-32244866

RESUMO

The chemical examination of the marine soft coral Lemnalia sp., collected at the Xisha islands in the South China Sea, resulted in the isolation of four new nardosinane-type sesquiterpenoids, namely clavukoellians G-J (1-4), and one new aristolane sesquiterpene, namely clavukoellian K (5), together with five known compounds, 6-10. The structure elucidation of the isolated natural products was based on various spectroscopic techniques including HRESIMS and NMR, while their absolute configurations were resolved on the basis of comparisons of the ECD spectra with the calculated ECD data. The isolated new compounds 1-5 were evaluated for their anti- and pro- angiogenesis activities in a transgenic fluorescent zebrafish (Tg(vegfr2:GFP)) model. Quantitative analysis revealed that compound 5 displayed pro-angiogenesis activity in a PTK787-induced vascular injury zebrafish model at 2.5 µM. Data showed that compound 5 significantly promoted the angiogenesis in a dose-dependent manner.

2.
Mar Drugs ; 18(4)2020 Mar 31.
Artigo em Inglês | MEDLINE | ID: mdl-32244363

RESUMO

Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells.

3.
Molecules ; 25(6)2020 Mar 19.
Artigo em Inglês | MEDLINE | ID: mdl-32204524

RESUMO

Five 8,17-epoxybriaranes, including three new compounds-briarenols I-K (1-3), along with two known analogues, briaexcavatolide P (4) and briaexcavatin P (5), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1-3 were elucidated by spectroscopic methods, including 1D and 2D NMR studies and (+)-HRESIMS. Briarane 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7.

4.
Phytochemistry ; 173: 112326, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-32120117

RESUMO

Four undescribed alkaloids, 7-ethoxy-6-methoxy-2-methylisoquinolin-1(2H)-one, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, and 5,6-dihydroxy-N-methylphthalimide, were obtained from the root bark of Hernanadia nymphaeifolia, along with fourteen known compounds. The structures of these compounds were determined through spectroscopic and MS analyses. 7,8-Dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, 5,6-dihydroxy-N-methylphthalimide, oxohernagine, hernandonine, and N-trans-feruloylmethoxytyramine inhibited the superoxide anion (O2-) production (IC50 values ≤ 6.23 µg/mL) by neutrophils stimulated with formyl-L-methionyl-L-leuckyl-L-phenyl-alanine/cytochalasin B (fMLP/CB). Furthermore, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, 5,6-dihydroxy-N-methylphthalimide, oxohernagine, and N-trans-feruloylmethoxytyramine inhibited fMLP/CB-induced elastase release with IC50 values ≤ 7.41 µg/mL. In addition, 7,8-dihydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one, N-formylhernagine, oxohernagine, and N-trans-feruloylmethoxytyramine showed potent inhibition with IC50 values ≤ 28.55 µM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation.


Assuntos
Alcaloides , Hernandiaceae , Anti-Inflamatórios , N-Formilmetionina Leucil-Fenilalanina , Neutrófilos , Elastase Pancreática , Casca de Planta , Superóxidos
5.
Mar Drugs ; 18(2)2020 Jan 24.
Artigo em Inglês | MEDLINE | ID: mdl-31991544

RESUMO

In the current study, an NMR spectroscopic pattern-based procedure for probing scalarane derivatives was performed and four new 24-homoscalaranes, lendenfeldaranes A-D (1- 4), along with three known compounds, 12α-acetoxy-22-hydroxy-24-methyl-24-oxoscalar-16-en- 25-al (5), felixin F (6), and 24-methyl-12,24,25-trioxoscalar-16-en-22-oic acid (7) were isolated from the sponge Lendenfeldia sp. The structures of scalaranes 1-7 were elucidated on the basis of spectroscopic analysis. Scalaranes 1-7 were further evaluated for their cytotoxicity toward a series of human cancer cell lines and the results suggested that 5 and 7 dominated in the anti- proliferative activity of the extract. The 18-aldehyde functionality was found to play a key role in their activity.

6.
Mar Drugs ; 17(12)2019 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-31847481

RESUMO

Three new 11,20-epoxybriaranes-fragilides U-W (1-3), as well as two known metabolites, junceellonoid D (4) and junceellin (5), were obtained from the octocoral Junceella fragilis. The structures of briaranes 1-3 were elucidated by spectroscopic methods and briaranes 3 and 5 displayed inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW264.7.

7.
Nat Prod Res ; : 1-9, 2019 Sep 09.
Artigo em Inglês | MEDLINE | ID: mdl-31496280

RESUMO

One new naturally occurring quinone, 3',4'-dihydroxy-1,2,6-trimethoxy-[1,1'-biphenyl]-4(1H)-one (1), one new diarylpropane, emarginone A (2), and one new neolignan, emarginone B (3), along with eighteen known compounds have been isolated from the chemical investigation of the EtOAc-soluble fraction of the Vaccinium emarginatum whole plant methanolic extract. The new structures were elucidated by combined analysis of spectroscopic analytical methods and comparison with the literature data obtained from known analogues. In addition, the cytotoxicity of compounds 2, 4, and 14-20 against Du145 and PC-3 prostate cancer cell lines using MTT cell proliferation assay was evaluated. Compounds 2 and 19 showed most potent cytotoxicity against Du145 with IC50 values of 7.53 and 6.63 µg/mL, respectively. Furthermore, compounds 2, 17, and 19 also exhibited significant cytotoxicity against PC-3 with IC50 values ranging from 3.44-6.64 µg/mL.

8.
Mar Drugs ; 17(9)2019 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-31514359

RESUMO

Two new steroids, dendronesterones D (1) and E (2), featuring with 1,4-dienone moiety, along with three known steroids, methyl 3-oxochola-4,22-diene-24-oate (3), 5α,8α-epidioxy-24(S)- methylcholesta-6,22-dien-3ß-ol (4), and 5α,8α-epidioxy-24(S)-methylcholesta-6,9(11),22-trien-3ß-ol (5), were isolated from an octocoral Dendronephthya sp. The structures of steroids 1 and 2 were elucidated by using spectroscopic methods and steroid 1 was found to exhibit significant in vitro anti-inflammatory activity in lipopolysaccharides (LPS)-induced RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Esteroides/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Células RAW 264.7 , Esteroides/isolamento & purificação
9.
Mar Drugs ; 17(9)2019 Sep 14.
Artigo em Inglês | MEDLINE | ID: mdl-31540107

RESUMO

Three new 8-hydroxybriaranes-fragilides R-T (1-3) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 1-3 were elucidated by using spectroscopic methods, including 1D (1H and 13C NMR), 2D (COSY, HSQC, HMBC, and NOESY experiments) NMR studies, and (+)-HRESIMS. Fragilides S and T (2 and 3) are the only briaranes known to possess 8α-hydroxy and 17ß-methyl groups, respectively. Briarane 2 exerted an inhibition effect on iNOS release from RAW264.7; a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/metabolismo , Espectroscopia de Prótons por Ressonância Magnética , Células RAW 264.7 , Relação Estrutura-Atividade
10.
Br J Pharmacol ; 2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31368509

RESUMO

Traditional chemotherapy is being considered due to hindrances caused by systemic toxicity. Currently, the administration of multiple chemotherapeutic drugs with different biochemical/molecular targets, known as combination chemotherapy, has attained numerous benefits like efficacy enhancement and amelioration of adverse effects that has been broadly applied to various cancer types. Additionally, seeking natural-based alternatives with less toxicity has become more important. Experimental evidence suggests that herbal extracts such as Solanum nigrum and Claviceps purpurea and isolated herbal compounds (e.g., curcumin, resveratrol, and matairesinol) combined with antitumoral drugs have the potential to attenuate resistance against cancer therapy and to exert chemoprotective actions. Plant products are not free of risks: Herb adverse effects, including herb-drug interactions, should be carefully considered.

11.
Molecules ; 24(13)2019 Jul 07.
Artigo em Inglês | MEDLINE | ID: mdl-31284657

RESUMO

Two new 11,20-epoxybriaranes, fragilides P (1) and Q (2), as well as two known analogues, robustolide F (3) and juncin Z (4), were obtained from the gorgonian coral Junceella fragilis. The structures, including the absolute configurations of briaranes 1 and 2, were elucidated by using spectroscopic methods and comparing the spectroscopic and rotation data with those of known related analogues. Briarane 4 decreased the generation of superoxide anions by human neutrophils. The propionate group in 1 is rarely found.


Assuntos
Antozoários/química , Diterpenos/química , Proteínas de Plantas/química , Animais , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Modelos Moleculares , Conformação Molecular , Estrutura Molecular , Proteínas de Plantas/isolamento & purificação , Proteínas de Plantas/farmacologia , Análise Espectral
12.
Oxid Med Cell Longev ; 2019: 6342104, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31205586

RESUMO

Lung cancer is the leading cause of cancer deaths in the world, with a five-year survival rate of less than 30%. Clinically effective chemotherapeutic treatments at the initial stage may eventually face the dilemma of no drug being effective due to drug resistance; therefore, finding new effective drugs for lung cancer treatment is a necessary and important issue. Compounds capable of further increasing the oxidative stress of cancer cells are considered to have anticancer potential because they possessed the ability to induce apoptosis. This study mainly investigated the effects of BA6 (heteronemin), the marine sponge sesterterpene, on lung cancer cell apoptosis, via modulation of mitochondrial reactive oxygen species (mtROS) and oxidative phosphorylation (OXPHOS). BA6 has cellular cytotoxic activities against a variety of cancer cell lines, but it has no effect on nontumor cells. The BA6-treated lung cancer cells show a significant increase in both cellular ROS and mtROS, which in turn caused the loss of mitochondrial membrane potential (MMP). The increase of oxidative stress in lung cancer cells treated with BA6 was accompanied by a decrease in the expression of antioxidant enzymes Cu/Zn SOD, MnSOD, and catalase. In addition, OXPHOS performed in the mitochondria and glycolysis in the cytoplasm were inhibited, which subsequently reduced downstream ATP production. Pretreatment with mitochondria-targeted antioxidant MitoTEMPO reduced BA6-induced apoptosis through the mitochondria-dependent apoptotic pathway, which was accompanied by increased cell viability, decreased mtROS, enhanced MMP, and suppressed expression of cleaved caspase-3 and caspase-9 proteins. In conclusion, the results of this study clarify the mechanism of BA6-induced apoptosis in lung cancer cells via the mitochondrial apoptotic pathway, suggesting that it is a potentially innovative alternative to the treatment of human lung cancer.


Assuntos
Apoptose/efeitos dos fármacos , Neoplasias Pulmonares/patologia , Mitocôndrias/efeitos dos fármacos , Fosforilação Oxidativa/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo , Terpenos/farmacologia , Sobrevivência Celular , Humanos , Neoplasias Pulmonares/tratamento farmacológico , Neoplasias Pulmonares/metabolismo , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Mitocôndrias/metabolismo , Mitocôndrias/patologia , Superóxido Dismutase/metabolismo , Células Tumorais Cultivadas
13.
Mar Drugs ; 17(6)2019 May 29.
Artigo em Inglês | MEDLINE | ID: mdl-31146323

RESUMO

Pharmaceutical agents for halting the progression of Parkinson's disease (PD) are lacking. The current available medications only relieve clinical symptoms and may cause severe side effects. Therefore, there is an urgent need for novel drug candidates for PD. In this study, we demonstrated the neuroprotective activity of stellettin B (SB), a compound isolated from marine sponges. We showed that SB could significantly protect SH-SY5Y cells against 6-OHDA-induced cellular damage by inhibiting cell apoptosis and oxidative stress through PI3K/Akt, MAPK, caspase cascade modulation and Nrf2/HO-1 cascade modulation, respectively. In addition, an in vivo study showed that SB reversed 6-OHDA-induced a locomotor deficit in a zebrafish model of PD. The potential for developing SB as a candidate drug for PD treatment is discussed.


Assuntos
Apoptose/efeitos dos fármacos , Heme Oxigenase-1/metabolismo , Fator 2 Relacionado a NF-E2/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Poríferos/química , Triterpenos/farmacologia , Animais , Organismos Aquáticos/química , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Modelos Animais de Doenças , Humanos , Locomoção/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Oxidopamina/toxicidade , Doença de Parkinson/tratamento farmacológico , Triterpenos/química , Triterpenos/isolamento & purificação , Peixe-Zebra
14.
Molecules ; 24(11)2019 Jun 10.
Artigo em Inglês | MEDLINE | ID: mdl-31185647

RESUMO

Three new dimeric abietane-type diterpenoids, abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7α-yl peroxide (1), abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7ß-yl peroxide (2), and 12-hydroxyabieta-8,11,13-trien-7ß-yl 7-oxoabieta-5,8,11,13-tetraen-12-yl peroxide (3), together with four known abietane-type diterpenoids (4-7) were isolated from the methanol extract of the bark of Cryptomeria japonica. Their structures were elucidated on the basis of spectroscopic analysis and comparison of NMR data with those of known analogues. At a concentration of 50 µM, compounds 1, 2, and 3 showed 26.2%, 23.6%, and 35.7% inhibition towards xanthine oxidase enzyme, respectively. In addition, compound 3 also showed 24.9% inhibition toward angiotensin-converting enzyme (ACE).


Assuntos
/farmacologia , Cryptomeria/química , Dimerização , Peróxidos/farmacologia , Casca de Planta/química , /química , Inibidores da Enzima Conversora de Angiotensina , Animais , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Espectroscopia de Ressonância Magnética , Peptidil Dipeptidase A/metabolismo , Peróxidos/química , Peróxidos/isolamento & purificação , Coelhos , Xantina Oxidase/antagonistas & inibidores
15.
Mar Drugs ; 17(4)2019 Apr 05.
Artigo em Inglês | MEDLINE | ID: mdl-30959843

RESUMO

Three new furanocembranoids-briaviodiol F (1) and briaviotriols A (2) and B (3)-along with a known analogue, briaviodiol A (4), were obtained from a cultured-type octocoral Briareum violaceum. The structures of cembranoids 1⁻3 were elucidated by using spectroscopic methods. In vitro study demonstrated that compounds 2 and 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW 264.7, a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Camundongos , Modelos Moleculares , Estrutura Molecular , Células RAW 264.7
16.
Mar Drugs ; 17(3)2019 Feb 27.
Artigo em Inglês | MEDLINE | ID: mdl-30818790

RESUMO

Gingival recession (GR) potentially leads to the exposure of tooth root to the oral cavity microenvironment and increases susceptibility to dental caries, dentin hypersensitivity, and other dental diseases. Even though many etiological factors were reported, the specific mechanism of GR is yet to be elucidated. Given the species richness concerning marine biodiversity, it could be a treasure trove for drug discovery. In this study, we demonstrate the effects of a marine compound, (+)-rhodoptilometrin from crinoid, on gingival cell migration, wound healing, and oxidative phosphorylation (OXPHOS). Experimental results showed that (+)-rhodoptilometrin can significantly increase wound healing, migration, and proliferation of human gingival fibroblast cells, and it does not have effects on oral mucosa fibroblast cells. In addition, (+)-rhodoptilometrin increases the gene and protein expression levels of focal adhesion kinase (FAK), fibronectin, and type I collagen, changes the intracellular distribution of FAK and F-actin, and increases OXPHOS and the expression levels of complexes I~V in the mitochondria. Based on our results, we believe that (+)-rhodoptilometrin might increase FAK expression and promote mitochondrial function to affect cell migration and promote gingival regeneration. Therefore, (+)-rhodoptilometrin may be a promising therapeutic agent for GR.


Assuntos
Antraquinonas/farmacologia , Equinodermos/química , Fibroblastos/efeitos dos fármacos , Regeneração/efeitos dos fármacos , Cicatrização/efeitos dos fármacos , Animais , Linhagem Celular , Movimento Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos , Fibroblastos/citologia , Fibroblastos/fisiologia , Proteína-Tirosina Quinases de Adesão Focal/metabolismo , Gengiva/citologia , Gengiva/efeitos dos fármacos , Gengiva/fisiologia , Retração Gengival/tratamento farmacológico , Humanos , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Mucosa Bucal/citologia , Mucosa Bucal/efeitos dos fármacos , Mucosa Bucal/fisiologia , Fosforilação Oxidativa/efeitos dos fármacos
17.
Cancers (Basel) ; 11(2)2019 Feb 14.
Artigo em Inglês | MEDLINE | ID: mdl-30769863

RESUMO

Angiogenesis and invasion are highly related with tumor metastatic potential and recurrence prediction in the most aggressive brain cancer, glioblastoma multiforme (GBM). For the first time, this study reveals that marine-sponge-derived stellettin B reduces angiogenesis and invasion. We discovered that stellettin B reduces migration of glioblastoma cells by scratch wound healing assay and invasion via chamber transwell assay. Further, stellettin B downregulates Akt/Mammalian Target of Rapamycin (Akt/mTOR) and Signal transducer and activator of transcription 3 (Stat3) signaling pathways, which are essential for invasion and angiogenesis in glioblastoma. This study further demonstrates that stellettin B affects filamentous actin (F-actin) rearrangement by decreasing the cross-linkage of phosphor-Girdin (p-Girdin), which attenuates glioblastoma cell invasion. Moreover, stellettin B blocks the expression and secretion of a major proangiogenic factor, vascular endothelial growth factor (VEGF), in glioblastoma cells. Stellettin B also reduces angiogenic tubule formation in human umbilical vein endothelial cells (HUVECs). In vivo, we observed that stellettin B decreased blood vesicle formation in developmental zebrafish and suppressed angiogenesis in Matrigel plug transplant assay in mice. Decreased VEGF transcriptional expression was also found in stellettin B⁻treated zebrafish embryos. Overall, we conclude that stellettin B might be a potential antiangiogenic and anti-invasion agent for future development of therapeutic agents for cancer therapy.

18.
Molecules ; 23(10)2018 Oct 10.
Artigo em Inglês | MEDLINE | ID: mdl-30308951

RESUMO

Two new acylphloroglucinol derivatives, 13,14-didehydroxygarcicowin C (1) and 13,14-didehydroxyisoxanthochymol (2), have been isolated from the stems of Garcinia multiflora, together with seven known compounds (3⁻9). The structures of new compounds 1 and 2 were elucidated by MS and extensive 1D/2D NMR spectroscopic analyses. Among the isolates, 13,14-didehydroxy-isoxanthochymol (2) and sampsonione B (3) exhibited inhibition against lipopolysaccharide (LPS)-induced NF-κB activation in macrophages at 30 µM with relative luciferase activity values (inhibitory %) of 0.75 ± 0.03 (24 ± 4%) and 0.12 ± 0.03 (88 ± 4%), respectively. Additionally, sampsonione B (3) reduced LPS-induced nitric oxide (NO) production in murine RAW264.7 macrophages and did not induce cytotoxicity against RAW 264.7 cells after 24 h treatment. Compound 3 is worth further investigation and may be expectantly developed as an anti-inflammatory drug candidate.


Assuntos
Anti-Inflamatórios/farmacologia , Garcinia/química , Floroglucinol/farmacologia , Animais , Anti-Inflamatórios/química , Benzofenonas/química , Benzofenonas/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Lipopolissacarídeos , Camundongos , NF-kappa B/metabolismo , Óxido Nítrico/biossíntese , Floroglucinol/química , Espectroscopia de Prótons por Ressonância Magnética , Células RAW 264.7
19.
Molecules ; 23(9)2018 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-30205430

RESUMO

A new aporphine, 3-hydroxyhernandonine (1) and a new lignin, 4'-O-demethyl-7-O-methyldehydropodophyllotoxin (2), have been isolated from the root wood of Hernanadia nymphaeifolia, together with thirteen known compounds (3⁻15). The structures of these compounds were determined through mass spectrometry (MS) and spectroscopic analyses. The known isolate, 2-O-methyl-7-oxolaetine (3), was first isolated from natural sources. Among the isolated compounds, 3-hydroxyhernandonine (1), 4'-O-demethyl-7-O-methyldehydropodophyllotoxin (2), hernandonine (4), oxohernangerine (5), and oxohernagine (6) displayed inhibition (IC50 values ≤5.72 µg/mL) of superoxide anion production by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). In addition, 3-hydroxyhernandonine (1), 4'-O-demethyl-7-O-methyldehydropodophyllotoxin (2), oxohernangerine (5), and oxohernagine (6) suppressed fMLP/CB-induced elastase release with IC50 values ≤5.40 µg/mL.


Assuntos
Anti-Inflamatórios não Esteroides/isolamento & purificação , Aporfinas/isolamento & purificação , Hernandiaceae/química , Lignanas/isolamento & purificação , Raízes de Plantas/química , Madeira/química , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Aporfinas/química , Aporfinas/farmacologia , Cromatografia Líquida , Humanos , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Neutrófilos/efeitos dos fármacos , Neutrófilos/enzimologia , Neutrófilos/metabolismo , Elastase Pancreática/metabolismo , Análise Espectral/métodos , Superóxidos/metabolismo
20.
Molecules ; 23(9)2018 Sep 08.
Artigo em Inglês | MEDLINE | ID: mdl-30205569

RESUMO

Three new iridoids, namely neonanin A (1), neonanin B (2) and neoretinin A (3), as well as twelve known compounds, 6-hydroxy-7-methyl-1-oxo-4-carbomethoxyoctahydrocyclopenta[c]pyran (4), 4-epi-alyxialactone (5), loganetin (6), loganin (7), phenylcoumaran-α'-aldehyde (8), cleomiscosin A (9), ficusal (10), balanophonin (11), vanillic acid (12), p-coumaric acid (13), cis,trans-abscisic acid (14), and trans,trans-abscisic acid (15) were isolated from the stems of Neonauclea reticulata (Havil.) Merr. These new structures were determined by the detailed analysis of spectroscopic data and comparison with the data of known analogues. Compounds 1⁻13 were evaluated using an in-vitro MTT cytotoxic assay for hepatocellular carcinoma (HCC) cells, and the preliminary results showed that ficusal (10), balanophonin (11), and p-coumaric acid (13) exhibited moderate cytotoxic activity, with EC50 values of 85.36 ± 4.36, 92.63 ± 1.41, and 29.18 ± 3.48 µg/mL against Hep3B cells, respectively.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Iridoides/farmacologia , Extratos Vegetais/análise , Rubiaceae/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Carcinoma Hepatocelular/tratamento farmacológico , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Células Hep G2 , Humanos , Iridoides/química , Iridoides/isolamento & purificação , Neoplasias Hepáticas/tratamento farmacológico , Estrutura Molecular , Caules de Planta/química
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