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1.
J Asian Nat Prod Res ; 26(10): 1254-1260, 2024 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-38945154

RESUMO

A new steroid, 2a-oxa-2-oxo-5ß-hydroxy-3,4-dinor-24-methylcholesta-22E-ene (1), together with 10 known ones (2-11), was isolated from the marine sponge Cliona sp. The structures of these compounds were determined by the spectroscopic methods (UV, IR, MS, and NMR) and X-ray diffraction analysis. Compound 1 was the third example of 3,4-dinorsteroid with a hemiketal at C-5 that was isolated from the natural source. In addition, the antibacterial activities of these compounds were also evaluated. However, none of them exhibited significant inhibition effects.


Assuntos
Antibacterianos , Biologia Marinha , Poríferos , Animais , Poríferos/química , Estrutura Molecular , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Testes de Sensibilidade Microbiana , Ressonância Magnética Nuclear Biomolecular , Esteroides/química , Esteroides/farmacologia , Esteroides/isolamento & purificação , Cristalografia por Raios X
2.
J Asian Nat Prod Res ; 26(3): 328-333, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-37602427

RESUMO

(+)- and (-)-Tedanine [(+)-1 and (-)-1], a pair of new enantiomeric indolone alkaloids, along with nine compounds (2-10) were isolated from the marine sponge Tedania sp. The structures of (+)-1 and (-)-1 including absolute configurations were determined by spectroscopic analysis and quantum chemical calculation. Compounds (+)-1 and (-)-1 were the first examples of indolone alkaloids isolated from this genus. In addition, the cytotoxic and antibacterial activities of these compounds were also evaluated.


Assuntos
Alcaloides , Antineoplásicos , Poríferos , Animais , Poríferos/química , Alcaloides/química , Antibacterianos/química , Antineoplásicos/química , Estrutura Molecular
3.
Chem Biodivers ; 20(8): e202300950, 2023 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-37477082

RESUMO

Two new pairs of enantiomeric butenolides, (+)- and (-)-suberiteslide A, (+)- and (-)-subertieslide B had been obtained from the marine sponge Suberties sp. The structures with absolute configurations of these compounds were unequivocally determined by spectroscopic analyses and ECD (Electronic Circular Dichroism) method. It was the first separation of butenolides from the marine sponges of genus Suberites. Additionally, the anti-inflammatory, antibacterial and cytotoxic activities of these compounds were evaluated. The result indicated that only (-)-subertieslide B showed weak anti-inflammatory activity with the IC50 value of 40.8 µM.


Assuntos
Poríferos , Animais , Poríferos/microbiologia , 4-Butirolactona/química , Antibacterianos/farmacologia , Dicroísmo Circular , Estrutura Molecular
4.
J Asian Nat Prod Res ; 25(9): 899-904, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-36587815

RESUMO

A new chlorobenzoate derivative, solieriate (1), together with six known compounds (2-7), were isolated from the red alga Solieria sp. The structures of 1-7 were determined by comprehensive spectroscopic methods and X-ray diffraction analysis. Compound 1 is the first example of halogenated derivative isolated from this genus. In addition, 1 exhibited moderate antibacterial activity on A. baumannii with MIC value of 64 µg/ml.


Assuntos
Rodófitas , Rodófitas/química , Cristalografia por Raios X , Antibacterianos/química , Clorobenzoatos , Estrutura Molecular
5.
J Asian Nat Prod Res ; 25(11): 1044-1050, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37042722

RESUMO

Two new alkaloids, spongimides A (1) and B (2), along with five known ones (3-7), were isolated from the marine sponge Spongia sp. The structures of 1 and 2 were determined by the spectroscopic methods (UV, IR, MS, and NMR) and X-ray diffraction analysis. Compounds 1, 3, and 4 were the first examples of 2,4-imidazolidinediones isolated from this genus. In addition, the cytotoxic and antibacterial activities of compounds 1 and 2 were also evaluated.


Assuntos
Alcaloides , Antineoplásicos , Poríferos , Animais , Estrutura Molecular , Poríferos/química , Antineoplásicos/química , Alcaloides/química , Espectroscopia de Ressonância Magnética
6.
J Asian Nat Prod Res ; 25(1): 61-67, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-35352584

RESUMO

Two new halogenated metabolites, laurenhalogens A (1) and B (2), along with four known ones (3-6), were isolated from the red alga Laurencia sp. The structures of 1 and 2 were determined by the means of UV, IR, MS, NMR and X-ray diffraction analysis. In addition, the antibacterial activities of 1-6 were also evaluated.


Assuntos
Laurencia , Sesquiterpenos , Laurencia/química , Estrutura Molecular , Espectroscopia de Ressonância Magnética , Antibacterianos/química , Cristalografia por Raios X , Sesquiterpenos/química
7.
Chem Biodivers ; 17(5): e2000022, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-32166904

RESUMO

Three new butenolides, caulerpalide A and a pair of enantiomers, (+)-caulerpalide B and (-)-caulerpalide B, together with seven known compounds, have been isolated from the green alga Caulerpa racemosa var. turbinata. All these structures were determined by spectroscopic techniques. The absolute configurations of caulerpalide A, (+)-caulerpalide B and (-)-caulerpalide B were elucidated by the method of ECD calculation. This is the first separation of butenolides from the algae of genus Caulerpa. Additionally, the antibacterial activities of the nine isolated compounds were also evaluated.


Assuntos
4-Butirolactona/análogos & derivados , Antibacterianos/farmacologia , Caulerpa/química , 4-Butirolactona/química , 4-Butirolactona/isolamento & purificação , 4-Butirolactona/farmacologia , Acinetobacter baumannii/efeitos dos fármacos , Antibacterianos/química , Antibacterianos/isolamento & purificação , Relação Dose-Resposta a Droga , Enterococcus faecalis/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Conformação Molecular , Pseudomonas aeruginosa/efeitos dos fármacos , Relação Estrutura-Atividade
8.
J Asian Nat Prod Res ; 21(5): 494-501, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-29595069

RESUMO

A novel valerenane sesquiterpenoid sinulaspirolactam A (1), together with five known compounds, was isolated from the soft coral Sinularia sp. Their structures were determined by spectroscopic analyses. The absolute configuration of 1 was established by ECD calculation. Compound 1 was the first example of valerenane sesquiterpenoid bearing an aza-spiro[4.5] ring moiety, the plausible biogenetic pathway of which was proposed. Cytotoxic activities of these compounds were also evaluated.


Assuntos
Antozoários/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Modelos Moleculares , Estrutura Molecular
9.
Anticancer Drugs ; 29(6): 503-512, 2018 07.
Artigo em Inglês | MEDLINE | ID: mdl-29697412

RESUMO

Galaxamide is a rare cyclic homopentapeptide composed of three leucines and two N-methyl leucines isolated from marine algae Galaxaura filamentosa. The strong antitumor activity of this compound makes it a promising candidate for tumor therapy. The synthesis of galaxamide, however, is a complex process, and it has poor water solubility. On the basis of its special chemical composition, we designed a series of linear leucine homopeptides. Among seven dipeptide derivatives, five compounds with terminal protection groups and methyl substitution of the hydrogen in the amido group showed remarkable inhibitory effects against various cancer cells. N-tertbutyl-D-leucine-N-methyl-D-leucinebenzyl (A7), the only stereomer condensed by two D-leucines, showed the highest antineoplastic activity. A7-treated cells showed cell cycle arrest and morphological changes typical of cells undergoing apoptosis. The population of Annexin-V positive/propidium iodide-negative cells also increased, indicating the induction of early apoptosis. A7 promoted the cleavage of caspase-9 and caspase-3, as well as increased intracellular Ca levels and decreased the mitochondrial membrane potential. Collectively, certain linear leucine dipeptides derived from cyclic pentapeptide are able to inhibit tumor cell proliferation through cell cycle arrest and apoptosis induction. The N-methyl group in the side chain and the D/L conformation of the amino-acid residue are critical for their activity.


Assuntos
Dipeptídeos/química , Dipeptídeos/farmacologia , Neoplasias/tratamento farmacológico , Células A549 , Antineoplásicos/síntese química , Antineoplásicos/química , Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Compostos de Benzil/síntese química , Compostos de Benzil/química , Compostos de Benzil/farmacologia , Ciclo Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Ésteres/síntese química , Ésteres/química , Ésteres/farmacologia , Células HeLa , Células Hep G2 , Humanos , Células MCF-7 , Neoplasias/patologia
10.
J Asian Nat Prod Res ; 19(12): 1232-1238, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-28349726

RESUMO

A new α-pyrone, nocapyrone S (1), together with five known compounds (2-6), were isolated from the deep-sea actinomycete Nocardiopsis dassonvillei subsp. dassonvillei DSM 43111(T). Their structures were determined by spectroscopic analyses. The absolute configuration of 1 was established by quantum approaches. Cytotoxic activity of 1 was evaluated against K562, MCF-7, SGC7901, A375, Hela, and HepG2 cell lines.


Assuntos
Actinomycetales/química , Antineoplásicos/isolamento & purificação , Nocardia/química , Pironas/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Células Hep G2 , Humanos , Células K562 , Células MCF-7 , Biologia Marinha , Estrutura Molecular , Pironas/química , Pironas/farmacologia
11.
J Asian Nat Prod Res ; 19(7): 684-690, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28276769

RESUMO

Two new polyketides, aspergchromones A (1) and B (2), together with five known compounds, secalonic acid D (3), noreugenin (4), (3S)-5-hydroxymellein (5), (4S)-6-hydroxyisosclerone (6), and (-)-regiolone (7), were isolated from the ethyl acetate extract of marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. Their structures were elucidated by means of spectroscopic techniques (1D and 2D NMR, MS, UV, and IR). The absolute configurations of the new compounds were established by ECD calculations. Compound 3 showed moderate antimicrobial activity.


Assuntos
Aspergillus/química , Policetídeos/isolamento & purificação , Poríferos/microbiologia , Xantonas/isolamento & purificação , Animais , Biologia Marinha , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Policetídeos/química , Xantonas/química
12.
J Nat Prod ; 79(8): 2045-52, 2016 08 26.
Artigo em Inglês | MEDLINE | ID: mdl-27489998

RESUMO

Three new cyclohexadepsipeptides, oryzamides A-C (1-3), two isolation artifacts, oryzamides D (4) and E (5), and the known congener scopularide A (6), all possessing a rare 3-hydroxy-4-methyldecanoic acid (HMDA) substructure, were isolated from the mycelial extract of the sponge-derived fungus Nigrospora oryzae PF18. Their planar structures were elucidated by spectroscopic analysis and comparison with the literature data. The absolute configurations were determined using the advanced Marfey's method and single-crystal X-ray diffraction analysis. Among them, oryzamides D (4) and E (5) were a pair of diastereomers at the sulfur atom of the l-methionine sulfoxide residue, which showcased the possible separation of a pair of methionine sulfoxide diastereomers. The X-ray crystal structure of scopularide A (6) was obtained for the first time, thereby establishing its relative and absolute configuration at C-4 of the HMDA residue. Oryzamides A-C (1-3) did not display cytotoxic, antibacterial, antiparasitic, and NF-κB inhibitory activities.


Assuntos
Ascomicetos/química , Poríferos/microbiologia , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Cristalografia por Raios X , Depsipeptídeos/química , Depsipeptídeos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Biologia Marinha , Metionina/análogos & derivados , Metionina/química , Fungos Mitospóricos , Conformação Molecular , Estrutura Molecular , NF-kappa B/efeitos dos fármacos
13.
Mar Drugs ; 13(9): 5579-92, 2015 Aug 26.
Artigo em Inglês | MEDLINE | ID: mdl-26343687

RESUMO

Two new furan derivatives, hypofurans A and B (1 and 2), and three new cyclopentenone derivatives, hypocrenones A-C (3-5), along with seven known compounds (6-12), were isolated from a marine fungus Hypocrea koningii PF04 associated with the sponge Phakellia fusca. Among them, compounds 10 and 11 were obtained for the first time as natural products. The planar structures of compounds 1-5 were elucidated by analysis of their spectroscopic data. Meanwhile, the absolute configuration of 1 was determined as 2R,3R by the comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. All the isolates were evaluated for their antibacterial and antioxidant activity. Compounds 1, 10, and 12 all showed modest antibacterial activity against Staphylococcus aureus ATCC25923 (MIC, 32 µg/mL). In addition, compounds 1, 10 and 11 exhibited moderate DPPH radical scavenging capacity with IC50 values of 27.4, 16.8, and 61.7 µg/mL, respectively.


Assuntos
Ciclopentanos/metabolismo , Furanos/metabolismo , Hypocrea/metabolismo , Poríferos/microbiologia , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Ciclopentanos/química , Furanos/química , Estrutura Molecular
14.
J Asian Nat Prod Res ; 17(8): 851-5, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25732799

RESUMO

A new alkaloid named N-(3-aminopropyl)subergorgamide (1), along with nine known nitrogen-containing compounds (2-10), was isolated from the organic extract of gorgonian Paraplexaura sp. collected from Zhanjiang in Naozhou Island, South China Sea. Their structures were established by detailed MS and NMR spectroscopic analyses, as well as by comparison with literature data.


Assuntos
Alcaloides/isolamento & purificação , Antozoários/química , Alcaloides/química , Animais , China , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Oceanos e Mares
15.
Zhong Yao Cai ; 37(2): 266-9, 2014 Feb.
Artigo em Zh | MEDLINE | ID: mdl-25095349

RESUMO

OBJECTIVE: To study the chemical constituents from Dichotella gemmacea. METHODS: Chemical constituents were isolated by silica gel and Sephadex LH-20 column chromatography. The structures of the isolated compounds were elucidated through spectroscopic analysis. RESULTS: Eight compounds were identified as fragilide J(I), junceelldide D(II), junceellin A (IlI), juncin P(IV), dichotellides A (V), cerevisterol (VI), 1,2-diphenyldiselane (VII) and 5H-pyrido[4,3-b] indole (VIII). CONCLUSION: Compounds VI, VII and VIII are isolated from Dichotella gemmacea for the first time.


Assuntos
Antozoários/química , Carbolinas/química , Fitosteróis/química , Animais , Carbolinas/isolamento & purificação , China , Diterpenos/química , Diterpenos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Estrutura Molecular , Oceanos e Mares , Fitosteróis/isolamento & purificação
16.
Nat Prod Res ; : 1-6, 2024 Apr 09.
Artigo em Inglês | MEDLINE | ID: mdl-38591101

RESUMO

A chemical investigation on the marine sponge Dysidea sp. resulted in the isolation of a series of diketopiperazines, including two new compounds, dysidines A (1) and B (2) as well as six known ones (3-8). Their structures with absolute configurations were determined on the basis of UV, IR, HRMS, NMR and calculated ECD method. Additionally, the cytotoxic, anti-inflammatory, antibacterial and antiviral activities of 1-8 were also tested. However, none of them exhibited significant bioactivities.

17.
Bioorg Med Chem Lett ; 23(4): 1079-82, 2013 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-23294699

RESUMO

A novel unusual pentacyclic hemiacetal sterol nephthoacetal (1), was isolated from soft coral Nephthea sp. The structure of this sterol was inferred from its two acetyl derivatives (2) and (3), by means of spectroscopic methods, and quantum chemical calculations. Anti-fouling activity of compounds 1-3 against Bugula neritina larvae was evaluated, sterol (1) exhibited significant inhibitory effect with EC(50) value of 2.5 µg/mL, while having low toxicity with LC(50)>25.0 µg/mL. The in vitro cytotoxic activity of compounds 1-3 against HeLa cells was also evaluated, all of them exhibited moderate cytotoxicity with IC(50) values of 12.3 (1), 10.1 (2), and 19.6 µg/mL (3), respectively.


Assuntos
Acetais/química , Acetais/farmacologia , Antozoários/química , Esteróis/química , Esteróis/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Briozoários/efeitos dos fármacos , Células HeLa , Humanos , Larva/efeitos dos fármacos , Estereoisomerismo
18.
Zhong Yao Cai ; 36(6): 919-21, 2013 Jun.
Artigo em Zh | MEDLINE | ID: mdl-24380275

RESUMO

OBJECTIVE: To study the secondary metabolites from marine sponge Phakellia fusca. METHODS: The compounds were isolated by column chromatography over silica gel and purified by Sephadex LH-20 column chromategraphy and preparative TLC. The structures were elucidated by means of physiochemical properties and spectroscopic analysis. RESULTS: Ten compounds were separated and identified as: p-hydroxybenzoic acid (1), cetanic acid (2), batyl alcohol (3), cety ethers of glycerol (4), (E)-N-2-(1,3-dihydroxy octadecan-4-en)-hexade-camide (5), thymidine (6), cyclo-(L-Tyr-L-Pro) (7), phenyl acetylamine (8), uracil (9),4-hydroxybenzamide (10). CONCLUSION: Compound 5, 7 and 10 are isolated from Phakellia fusca for the first time.


Assuntos
Benzamidas/isolamento & purificação , Peptídeos Cíclicos/isolamento & purificação , Poríferos/química , Animais , Benzamidas/química , Cromatografia Líquida de Alta Pressão , Dipeptídeos/química , Dipeptídeos/isolamento & purificação , Biologia Marinha , Estrutura Molecular , Peptídeos Cíclicos/química , Poríferos/metabolismo
19.
Nat Prod Res ; 37(1): 1-7, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34180744

RESUMO

A new amide, baeriamide (1), along with nine known diketopiperazines (2-10), was isolated from the marine sponge Haliclona baeri. Their structures were identified by the means of UV, IR, MS and NMR. The absolute configuration of 1 was established by Marfey's method and comparing the specific optical rotation with the known compound HCO-Val-Gly methyl ester. Compound 1 was derived from dehydration of formylated L-valine with γ-amino-butanoic acid methyl ester. Compounds 2-10 were isolated from the genus of Haliclona for the first time. The absolute confirmation of 7 was confirmed first by the means of single-crystal X-ray diffraction. The cytotoxic, antibacterial, antiviral and antifouling activities of these compounds were also tested. However, none of them exhibited significant bioactivities.


Assuntos
Haliclona , Animais , Haliclona/química , Amidas/farmacologia , Espectroscopia de Ressonância Magnética , Antibacterianos/farmacologia , Antibacterianos/química , Dicetopiperazinas
20.
mSphere ; 8(5): e0034623, 2023 10 24.
Artigo em Inglês | MEDLINE | ID: mdl-37642418

RESUMO

Type III secretion system (T3SS) facilitates survival and replication of Edwardsiella piscicida in vivo. Identifying novel T3SS effectors and elucidating their functions are critical in understanding the pathogenesis of E. piscicida. E. piscicida T3SS effector EseG and EseJ was highly secreted when T3SS gatekeeper-containing protein complex EsaB-EsaL-EsaM was disrupted by EsaB deficiency. Based on this observation, concentrated secretomes of ΔesaB strain and ΔesaBΔesaN strain were purified by loading them into SDS-PAGE gel for a short electrophoresis to remove impurities prior to the in-the gel digestion and mass spectrometry. Four reported T3SS effectors and two novel T3SS effector candidates EseQ (ETAE_2009) and Trx2 (ETAE_0559) were unraveled by quantitative comparison of the identified peptides. EseQ and Trx2 were revealed to be secreted and translocated in a T3SS-dependent manner through CyaA-based translocation assay and immunofluorescent staining, demonstrating that EseQ and Trx2 are the novel T3SS effectors of E. piscicida. Trx2 was found to suppress macrophage apoptosis as revealed by TUNEL staining and cleaved caspase-3 of infected J774A.1 monolayers. Moreover, Trx2 has been shown to inhibit the p65 phosphorylation and p65 translocation into the nucleus, thus blocking the NF-κB pathway. Furthermore, depletion of Trx2 slightly but significantly attenuates E. piscicida virulence in a fish infection model. Taken together, an efficient method was established in unraveling T3SS effectors in E. piscicida, and Trx2, one of the novel T3SS effectors identified in this study, was demonstrated to suppress apoptosis and block NF- κB pathway during E. piscicida infection. IMPORTANCE Edwardsiella piscicida is an intracellular bacterial pathogen that causes intestinal inflammation and hemorrhagic sepsis in fish and human. Virulence depends on the Edwardsiella type III secretion system (T3SS). Identifying the bacterial effector proteins secreted by T3SS and defining their role is key to understanding Edwardsiella pathogenesis. EsaB depletion disrupts the T3SS gatekeeper-containing protein complex, resulting in increased secretion of T3SS effectors EseG and EseJ. EseQ and Trx2 were shown to be the novel T3SS effectors of E. piscicida by a secretome comparison between ∆esaB strain and ∆esaB∆esaN strain (T3SS mutant), together with CyaA-based translocation assay. In addition, Trx2 has been shown to suppress macrophage apoptosis and block the NF-κB pathway. Together, this work expands the known repertoire of T3SS effectors and sheds light on the pathogenic mechanism of E. piscicida.


Assuntos
Edwardsiella , Sistemas de Secreção Tipo III , Animais , Humanos , Sistemas de Secreção Tipo III/metabolismo , Fatores de Virulência/metabolismo , NF-kappa B , Edwardsiella/metabolismo , Peixes
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