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1.
Molecules ; 28(4)2023 Feb 04.
Artigo em Inglês | MEDLINE | ID: mdl-36838513

RESUMO

An investigation of the chemical composition of a Formosan soft coral Cespitularia sp. led to the discovery of one new verticillene-type diterpenoid, cespitulactam M (1); one new eudesmane sesquiterpenoid, cespilamide F (2); and three new hydroperoxysteroids (3-5) along with twelve known analogous metabolites (6-17). In addition, one new derivative, cespitulactam M-6,2'-diacetate (1a), was prepared from compound 1. The structures were determined by detailed spectroscopic analyses, particularly HRESIMS and NMR techniques. Moreover, the in vitro cytotoxicity, anti-inflammatory, and antibacterial activity of 1-17 and 1a were evaluated.


Assuntos
Antozoários , Diterpenos , Sesquiterpenos de Eudesmano , Sesquiterpenos , Animais , Antozoários/química , Sesquiterpenos de Eudesmano/química , Espectroscopia de Ressonância Magnética , Diterpenos/química , Sesquiterpenos/química , Estrutura Molecular
2.
Molecules ; 28(2)2023 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-36677699

RESUMO

The present chemical investigation on the organic extract of the soft coral Sarcophyton cinereum has contributed to the isolation of four new cembranoids: 16ß- and 16α-hydroperoxyisosarcophytoxides (1 and 2), 16ß- and 16α-methoxyisosarcophytoxides (3 and 4), and a known cembranoid, lobocrasol (5). The structures of all isolates were elucidated by detailed spectroscopic analysis. Their structures were characterized by a 2,5-dihydrofuran moiety, of which the relative configuration was determined by DU8-based calculation for long-range coupling constants (4JH,H). The cytotoxicity and immunosuppressive activities of all isolates were evaluated in this study.


Assuntos
Antozoários , Diterpenos , Animais , Antozoários/química , Diterpenos/química , Estrutura Molecular
3.
Mar Drugs ; 20(5)2022 Apr 27.
Artigo em Inglês | MEDLINE | ID: mdl-35621948

RESUMO

A persistent study on soft coral Sarcophyton tortuosum resulted in the characterization of two new cembranolides, tortuolides A and B (1 and 2), and a new related diterpene, epi-sarcophytonolide Q. Their structures were determined not only by extensive spectroscopic analysis but also by DFT calculations of ECD and NMR data, the latter of which was combined with statistical analysis methods, e.g., DP4+ and J-DP4 approaches. Anti-inflammatory and cytotoxicity activities were evaluated in this study.


Assuntos
Antozoários , Diterpenos , Animais , Antozoários/química , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Espectroscopia de Ressonância Magnética
4.
Molecules ; 27(6)2022 Mar 08.
Artigo em Inglês | MEDLINE | ID: mdl-35335127

RESUMO

In an attempt to explore the bioactive metabolites of the soft coral Sarcophyton cinereum, three new cembranolides, cinerenolides A-C (1-3), and 16 known compounds were isolated and identified from the EtOAc extract. The structures of the new cembranolides were elucidated on the basis of spectroscopic analysis, and the NOE analysis of cinerenolide A (1) was performed with the assistance of the calculated lowest-energy molecular model. The relative configuration of cinerenolide C (3) was determined by the quantum chemical NMR calculation, followed by applying DP4+ analysis. In addition, the cytotoxic assays disclosed that some compounds exhibited moderate to potent activities in the proliferation of P388, DLD-1, HuCCT-1, and CCD966SK cell lines.


Assuntos
Antozoários , Antineoplásicos , Diterpenos , Animais , Antozoários/química , Antineoplásicos/química , Diterpenos/química , Ensaios de Seleção de Medicamentos Antitumorais , Estrutura Molecular
5.
Molecules ; 26(11)2021 May 28.
Artigo em Inglês | MEDLINE | ID: mdl-34071660

RESUMO

Three new polyoxygenated diterpenoids with a rare 4-isopropyl-1,5,8a-trimethylperhydrophenanthrane structure of the klysimplexane skeleton, briarols A‒C (1‒3), and one eunicellin-based diterpenoid, briarol D (4), were isolated from Briareum violaceum, a gorgonian inhabiting Taiwanese waters. The chemical structures of these compounds were determined by employing extensive analyses of NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) data. Metabolites 1‒3 were found to possess the rarely found skeleton of the diterpenoid klysimplexin T. All isolated compounds showed very weak cytotoxic activity against the growth of three cancer cell lines. A plausible biosynthetic pathway for briarols A‒C from the coexisting eunicellin diterpenoid briarol D (4) was postulated.


Assuntos
Antozoários/metabolismo , Diterpenos/química , Animais , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Química Farmacêutica/métodos , Desenho de Fármacos , Células HT29 , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Neoplasias/tratamento farmacológico , Pós , Prótons , Espectrometria de Massas por Ionização por Electrospray , Taiwan , Poluentes Químicos da Água/análise , Purificação da Água
6.
Mar Drugs ; 18(9)2020 Aug 29.
Artigo em Inglês | MEDLINE | ID: mdl-32872418

RESUMO

Chemical examination from the cultured soft coral Sarcophyton digitatum resulted in the isolation and structural identification of four new biscembranoidal metabolites, sardigitolides A-D (1-4), along with three previously isolated biscembranoids, sarcophytolide L (5), glaucumolide A (6), glaucumolide B (7), and two known cembranoids (8 and 9). The chemical structures of all isolates were elucidated on the basis of 1D and 2D NMR spectroscopic analyses. Additionally, in order to discover bioactivity of marine natural products, 1-8 were examined in terms of their inhibitory potential against the upregulation of inflammatory factor production in lipopolysaccharide (LPS)-stimulated murine macrophage J774A.1 cells and their cytotoxicities against a limited panel of cancer cells. The anti-inflammatory results showed that at a concentration of 10 µg/mL, 6 and 8 inhibited the production of IL-1ß to 68 ± 1 and 56 ± 1%, respectively, in LPS-stimulated murine macrophages J774A.1. Furthermore, sardigitolide B (2) displayed cytotoxicities toward MCF-7 and MDA-MB-231 cancer cell lines with the IC50 values of 9.6 ± 3.0 and 14.8 ± 4.0 µg/mL, respectively.


Assuntos
Antozoários/metabolismo , Anti-Inflamatórios/farmacologia , Antineoplásicos/farmacologia , Macrófagos/efeitos dos fármacos , Neoplasias/tratamento farmacológico , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Feminino , Células HeLa , Células Hep G2 , Humanos , Mediadores da Inflamação/metabolismo , Interleucina-1beta/metabolismo , Lipopolissacarídeos/farmacologia , Células MCF-7 , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Neoplasias/patologia , Relação Estrutura-Atividade
7.
Mar Drugs ; 17(2)2019 Feb 17.
Artigo em Inglês | MEDLINE | ID: mdl-30781569

RESUMO

Three new eunicellin-derived diterpenoids of briarellin type, briarenones A‒C (1‒3), were isolated from a Formosan gorgonian Briareum violaceum. The chemical structures of the compounds were elucidated on the basis of extensive spectroscopic analyses, including two-dimensional (2D) NMR. The absolute configuration of 1 was further confirmed by a single crystal X-ray diffraction analysis. The in vitro cytotoxic and anti-inflammatory potentialities of the isolated metabolites were tested against the growth of a limited panel of cancer cell lines and against the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenyl-alanine and cytochalasin B (fMLF/CB)-stimulated human neutrophils, respectively.


Assuntos
Cnidários/química , Diterpenos/química , Animais , Anti-Inflamatórios não Esteroides/farmacologia , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Citocalasinas/farmacologia , Diterpenos/isolamento & purificação , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Conformação Molecular , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Elastase Pancreática/metabolismo , Superóxidos/metabolismo , Difração de Raios X
8.
Mar Drugs ; 17(8)2019 Aug 07.
Artigo em Inglês | MEDLINE | ID: mdl-31394844

RESUMO

Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral Klyxum flaccidum, collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus Klyxum for the first time. The cytotoxicity of compounds 1 to 7 against the proliferation of a limited panel of cancer cell lines was assayed. The isolated diterpenoids also exhibited anti-inflammatory activity through suppression of superoxide anion generation and elastase release in the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-stimulated human neutrophils. Furthermore, 1 and 7 also exhibited cytotoxicity toward the tested cancer cells, and 7 could effectively inhibit elastase release. It is worth noting that the biological activities of 7 are reported for the first time in this paper.


Assuntos
Antozoários/química , Fatores Biológicos/farmacologia , Diterpenos/farmacologia , Animais , Anti-Inflamatórios/farmacologia , Linhagem Celular , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Citocalasina B/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais/métodos , Humanos , Espectroscopia de Ressonância Magnética/métodos , N-Formilmetionina Leucil-Fenilalanina/metabolismo , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Elastase Pancreática/metabolismo , Superóxidos/metabolismo
9.
Mar Drugs ; 16(8)2018 Aug 06.
Artigo em Inglês | MEDLINE | ID: mdl-30082637

RESUMO

Six new cembranoids, cherbonolides A-E (1⁻5) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by detailed spectroscopic analysis and chemical methods. Compound 6 was discovered to be the first example of a molecular skeleton formed from two cembranoids connected by a peroxide group. Compounds 1⁻7 were shown to have the ability of inhibiting the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLF/CB)-induced human neutrophils.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Neutrófilos/efeitos dos fármacos , Peróxidos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular Tumoral , Citocalasina B/farmacologia , Diterpenos/química , Diterpenos/isolamento & purificação , Humanos , Estrutura Molecular , N-Formilmetionina Leucil-Fenilalanina/farmacologia , Neutrófilos/metabolismo , Elastase Pancreática/metabolismo , Peróxidos/química , Peróxidos/isolamento & purificação , Superóxidos/metabolismo
10.
Mar Drugs ; 16(8)2018 Aug 09.
Artigo em Inglês | MEDLINE | ID: mdl-30096866

RESUMO

Five new cembranoid-related diterpenoids, namely, flexibilisins D and E (1 and 2), secoflexibilisolides A and B (3 and 4), and flexibilisolide H (5), along with nine known compounds (6⁻14), were isolated from the soft coral Sinularia flexibilis. Their structures were established by extensive spectral analysis. Compound 3 possesses an unusual skeleton that could be biogenetically derived from cembranoids. The cytotoxicity and anti-inflammatory activities of the isolates were investigated, and the results showed that dehydrosinulariolide (7) and 11-epi-sinulariolide acetate (8) exhibited cytotoxicity toward a limited panel of cancer cell lines and 14-deoxycrassin (9) displayed anti-inflammatory activity by inhibition of superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophils.


Assuntos
Antozoários/metabolismo , Anti-Inflamatórios/farmacologia , Antineoplásicos/farmacologia , Diterpenos/farmacologia , Neutrófilos/efeitos dos fármacos , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/metabolismo , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/metabolismo , Linhagem Celular Tumoral , Citocalasina B/farmacologia , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/metabolismo , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , N-Formilmetionina Leucil-Fenilalanina/farmacologia , Neutrófilos/metabolismo , Elastase Pancreática/metabolismo , Superóxidos/metabolismo
11.
Mar Drugs ; 16(6)2018 Jun 14.
Artigo em Inglês | MEDLINE | ID: mdl-29903990

RESUMO

Six new polyoxygenated cembrane-based diterpenoids, stellatumolides A⁻C (1⁻3), stellatumonins A and B (4 and 5), and stellatumonone (6), were isolated together with ten known related compounds (7⁻16) from the ethyl acetate (EtOAc) extract of soft coral Sarcophyton stellatum. The structures of the new compounds were established by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and data comparison with related structures. Compounds 8 and 14 were isolated from a natural source for the first time. The isolated metabolites were shown to be not cytotoxic against a limited panel of cancer cells. Compound 9 showed anti-inflammatory activity by reducing the expression of proinflammatory cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) proteins in lipopolysaccharide (LPS)-stimulated mouse leukaemic monocyte macrophage (RAW 264.7) cells.


Assuntos
Antozoários/química , Inibidores de Ciclo-Oxigenase 2/química , Diterpenos/química , Animais , Linhagem Celular Tumoral , Ciclo-Oxigenase 2/metabolismo , Inibidores de Ciclo-Oxigenase 2/isolamento & purificação , Inibidores de Ciclo-Oxigenase 2/farmacologia , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/metabolismo
12.
Mar Drugs ; 16(3)2018 Mar 13.
Artigo em Inglês | MEDLINE | ID: mdl-29534040

RESUMO

Three new polyoxygenated steroids, michosterols A-C (1-3), and four known compounds (4-7) were isolated from the ethyl acetate (EtOAc) extract of the soft coral Lobophytum michaelae, collected off the coast of Taitung. The structures of the new compounds were elucidated on the basis of spectroscopic analyses and comparison of the nuclear magnetic resonance (NMR) data with related steroids. The cytotoxicity of compounds 1-3 against the proliferation of a limited panel of cancer cell lines was assayed. Compound 1 was found to display moderate cytotoxicity against adenocarcinomic human alveolar basal epithelial (A549) cancer cells. It also exhibited potent anti-inflammatory activity by suppressing superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-stimulated human neutrophils. Furthermore, 3 could effectively inhibit elastase release, as well.


Assuntos
Antozoários/química , Anti-Inflamatórios/química , Esteroides/química , Células A549 , Animais , Anti-Inflamatórios/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Citocalasina B/farmacologia , Citotoxinas/química , Citotoxinas/farmacologia , Humanos , Espectroscopia de Ressonância Magnética/métodos , N-Formilmetionina Leucil-Fenilalanina/farmacologia , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Elastase Pancreática/metabolismo , Esteroides/farmacologia , Superóxidos/metabolismo
13.
Bioorg Med Chem Lett ; 27(15): 3267-3271, 2017 08 01.
Artigo em Inglês | MEDLINE | ID: mdl-28648460

RESUMO

Continuing study of the ethyl acetate (EtOAc) extract of the cultured soft coral Sinularia brassica afforded five new withanolides, sinubrasolides H-L (1-5). The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The cytotoxicities of new compounds 1-5 and a known compound sinubrasolide A (6) against the proliferation of a limited panel of cancer cell lines were assayed. The anti-inflammatory activities of compounds 1-6 were evaluated by measuring their ability to suppress N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release in human neutrophils.


Assuntos
Antozoários/química , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Vitanolídeos/química , Vitanolídeos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Citocalasina B/imunologia , Humanos , Modelos Moleculares , Neoplasias/tratamento farmacológico , Neutrófilos/efeitos dos fármacos , Elastase Pancreática/imunologia , Superóxidos/imunologia , Vitanolídeos/isolamento & purificação
14.
Bioorg Med Chem Lett ; 27(5): 1220-1224, 2017 03 01.
Artigo em Inglês | MEDLINE | ID: mdl-28159416

RESUMO

New steroids, klyflaccisteroids K-M (1-3), were isolated from a soft coral Klyxum flaccidum. Their structures were elucidated on the basis of extensive spectroscopic analysis. Klyflaccisteroid K (1) is the unique 9,11-secosteroid with a 5,8-epidioxy-9-ene functional group. Klyflaccisteroid L (2) has an unusual 11-norsteroid skeleton and is the first example of 11-oxasteroid isolated from natural sources. Cytotoxicity assay showed that 1 and 3 possessed moderate to weak cytotoxicity against these cancer cells. Compound 1 was also found to display significant anti-inflammatory activity of suppressing superoxide anion generation (O2-) and elastase release, and compound 3 was found to show notable anti-inflammatory activity toward inhibition of elasstase release, too.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Neutrófilos/efeitos dos fármacos , Esteroides/química , Animais , Anti-Inflamatórios/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Esteroides/farmacologia , Superóxidos/antagonistas & inibidores
15.
Mar Drugs ; 15(10)2017 Sep 29.
Artigo em Inglês | MEDLINE | ID: mdl-28961211

RESUMO

New lobane-based diterpenoids lobovarols A-D (1-4) and a prenyleudesmane-type diterpenoid lobovarol E (5) along with seven known related diterpenoids (6-12) were isolated from the ethyl acetate extract of a Taiwanese soft coral Lobophytum varium. Their structures were identified on the basis of multiple spectroscopic analyses and spectral comparison. The absolute configuration at C-16 of the known compound 11 is reported herein for the first time. The anti-inflammatory activities of compounds 1-12 were assessed by measuring their inhibitory effect on N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release in human neutrophils. Metabolites 2, 5, and 11 were found to show moderate inhibitory activity on the generation of superoxide anion, while compounds 5, 8, 11, and 12 could effectively suppress elastase release in fMLP/CB-stimulated human neutrophil cells at 10 µM. All of the isolated diterpenoids did not exhibit cytotoxic activity (IC50 > 50 µM) towards a limited panel of cancer cell lines.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Linhagem Celular Tumoral , Citocalasina B/farmacologia , Diterpenos/química , Humanos , N-Formilmetionina Leucil-Fenilalanina/farmacologia , Neoplasias/tratamento farmacológico , Neoplasias/metabolismo , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Elastase Pancreática/metabolismo , Superóxidos/metabolismo
16.
Mar Drugs ; 15(7)2017 Jun 27.
Artigo em Inglês | MEDLINE | ID: mdl-28653983

RESUMO

Five new isoprenoids, 3,4,8,16-tetra-epi-lobocrasol (1), 1,15ß-epoxy-deoxysarcophine (2), 3,4-dihydro-4α,7ß,8α-trihydroxy-Δ²-sarcophine (3), ent-sarcophyolide E (4), and 16-deacetyl- halicrasterol B (5) and ten known compounds 6‒15, were characterized from the marine soft coral Sarcophyton glaucum, collected off Taitung coastline. Their structures were defined by analyzing spectra data, especially 2D NMR and electronic circular dichroism (ECD). The structure of the known compound lobocrasol (7) was revised. Cytotoxicity potential of the isolated compounds was reported, too.


Assuntos
Antozoários/química , Antineoplásicos/isolamento & purificação , Terpenos/isolamento & purificação , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Dicroísmo Circular , Humanos , Espectroscopia de Ressonância Magnética , Terpenos/química , Terpenos/farmacologia
17.
Mar Drugs ; 15(9)2017 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-28862648

RESUMO

A continuing chemical investigation of the ethyl acetate (EtOAc) extract of a reef soft coral Sinularia brassica, which was cultured in a tank, afforded four new steroids with methyl ester groups, sinubrasones A-D (1-4) for the first time. In particular, 1 possesses a ß-D-xylopyranose. The structures of the new compounds were elucidated on the basis of spectroscopic analyses. The cytotoxicities of compounds 1-4 against the proliferation of a limited panel of cancer cell lines were assayed. The anti-inflammatory activities of these new compounds 1-4 were also evaluated by measuring their ability to suppress superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced human neutrophils. Compounds 2 and 3 were shown to exhibit significant cytotoxicity, and compounds 3 and 4 were also found to display attracting anti-inflammatory activities.


Assuntos
Antozoários/química , Esteroides , Acetatos/química , Animais , Anti-Inflamatórios não Esteroides/farmacologia , Humanos , N-Formilmetionina Leucil-Fenilalanina/química , Neutrófilos/efeitos dos fármacos , Elastase Pancreática/efeitos dos fármacos , Esteroides/química , Esteroides/isolamento & purificação , Esteroides/farmacologia , Superóxidos/metabolismo , Xilose/análogos & derivados , Xilose/química
18.
Bioorg Med Chem Lett ; 26(14): 3253-3257, 2016 07 15.
Artigo em Inglês | MEDLINE | ID: mdl-27256910

RESUMO

Four new steroids, namely klyflaccisteroids G-J (1-4) were isolated from the Formosan soft coral Klyxum flaccidum. The structures of compounds 1-4 were established by spectral data analysis (IR, MS, 1D and 2D NMR) and comparison of spectral data with those of the related known compounds. Cytotoxicity assay revealed that 4 exhibited inhibition activity against the growth of HT-29, P388 and K562 cancer cell lines, whereas 2 showed selective cytotoxicity toward P388 cells. Compound 4 was also found to display significant anti-inflammatory activity for suppressing superoxide anion generation (O2(-)) and elastase release.


Assuntos
Antozoários/química , Anti-Inflamatórios não Esteroides/farmacologia , Antineoplásicos/farmacologia , Elastase Pancreática/antagonistas & inibidores , Esteroides/farmacologia , Superóxidos/antagonistas & inibidores , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Camundongos , Estrutura Molecular , Elastase Pancreática/metabolismo , Esteroides/química , Esteroides/isolamento & purificação , Relação Estrutura-Atividade , Superóxidos/metabolismo
19.
J Nat Prod ; 79(5): 1339-46, 2016 05 27.
Artigo em Inglês | MEDLINE | ID: mdl-27142697

RESUMO

Four new isoprenoids, including two norcembranoids sinulerectols A and B (1 and 2), a cembranoid sinulerectol C (3), and a degraded cembranoid sinulerectadione (4), along with three known isoprenoids, an unnamed norcembrene (5), sinularectin (6), and ineleganolide (7), and a known nitrogen-containing compound (Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide (8), were isolated from an extract of the marine soft coral Sinularia erecta. The structure of sinularectin (6) was revised, too. Compounds 3, 4, and 8 exhibited inhibitory activity against the proliferation of a limited panel of cancer cell lines, whereas 1, 2, and 8 displayed potent anti-inflammatory activity in fMLP/CB-stimulated human neutrophils.


Assuntos
Antozoários/química , Produtos Biológicos , Terpenos , Animais , Anti-Inflamatórios/farmacologia , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Ciclo-Oxigenase 2/metabolismo , Diterpenos/química , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Macrófagos/metabolismo , Biologia Marinha , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologia
20.
Mar Drugs ; 14(8)2016 Aug 09.
Artigo em Inglês | MEDLINE | ID: mdl-27517938

RESUMO

Two new cubitanoids, nanoculones A and B (1 and 2), and three new cembranoids, nanolobols A-C (3-5), as well as six known compounds, calyculone I (6), sinulariuol A (7), sinulariols C, D, H, and J (8-11), were isolated from the soft coral Sinularia nanolobata, collected off the coast of the eastern region of Taiwan. Their structures were elucidated on the basis of extensive spectroscopic analysis. Cytotoxicity of compounds 1-11 was evaluated. The nitric oxide (NO) inhibitory activity of selected compounds was further measured by assay of lipopolysaccharide (LPS)-stimulated NO production in activated RAW264.7 cells. The results showed that none of 1-11 exhibited cytotoxicity against the tested cancer cell lines, whereas compound 8 was found to significantly reduce NO production.


Assuntos
Antozoários/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Diterpenos/farmacologia , Óxido Nítrico/metabolismo , Animais , Antineoplásicos/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Células HT29 , Humanos , Células K562 , Lipopolissacarídeos/metabolismo , Camundongos , Estrutura Molecular , Células RAW 264.7
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