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1.
J Nat Prod ; 87(4): 1209-1216, 2024 04 26.
Artigo em Inglês | MEDLINE | ID: mdl-38394380

RESUMO

Seven new 4-hydroxy-6-phenyl-2H-pyran-2-one (HPPO) derived meroterpenoids, 1-methyl-12a,12b-epoxyarisugacin M (1), 1-methyl-4a,12b-epoxyarisugacin M (2), 2,3-dihydroxy-3,4a-epoxy-12a-dehydroxyisoterreulactone A (3), 2-hydroxy-12a-dehydroxyisoterreulactone A (4), 3'-demethoxyterritrems B' (5), 4a-hydroxyarisugacin P (6), and 1-epi-arisugacin H (7), together with two known analogues (8 and 9), were isolated from the marine-derived fungal strain Penicillium sp. SCSIO 41691. Their structures were elucidated by spectroscopic methods, and the absolute configurations of compounds 1 and 3 were determined by single-crystal X-ray diffraction. Among them, 1 and 2 had a unique methyl migration in the basic meroterpenoid skeleton with a 12a,12b-epoxy or 4a,12b-epoxy group, and 3 was a highly oxygenated HPPO-derived meroterpenoid featuring a rare 6/5/6/6/6/6 hexacyclic system with a 3,4a-epoxy group. Biologically, 5 exhibited inhibitory activity against lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells with an IC50 value of 21 µM, more potent than the positive control indomethacin.


Assuntos
Penicillium , Terpenos , Penicillium/química , Terpenos/farmacologia , Terpenos/química , Terpenos/isolamento & purificação , Estrutura Molecular , Animais , Camundongos , Células RAW 264.7 , Óxido Nítrico/biossíntese , Cristalografia por Raios X , Biologia Marinha , Lipopolissacarídeos/farmacologia
2.
J Nat Prod ; 87(4): 810-819, 2024 04 26.
Artigo em Inglês | MEDLINE | ID: mdl-38427823

RESUMO

Eight new decahydrofluorene-class alkaloids, microascones A and B (1 and 2), 2,3-epoxyphomapyrrolidone C (3), 14,16-epiascomylactam B (4), 24-hydroxyphomapyrrolidone A (5), and microascones C-E (6-8), along with five known analogs (9-13) were isolated from the marine-derived fungus Microascus sp. SCSIO 41821. Compounds 1 and 2 have an unprecedented complex macrocyclic alkaloid skeleton with a 6/5/6/5/6/5/13 polycyclic system. Their structures and absolute configurations were determined by spectroscopic analysis, quantum chemical calculations of ECD spectra, and 13C NMR chemical shifts. Compounds 10-13 showed selective enzyme inhibitory activity against PTPSig, PTP1B, and CDC25B, and 4, 9, and 10 exhibited strong antibacterial activity against seven tested pathogens. Their structure-bioactivity relationship was discussed, and a plausible biosynthetic pathway for 1-8 was also proposed.


Assuntos
Alcaloides , Antibacterianos , Testes de Sensibilidade Microbiana , Alcaloides/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Estrutura Molecular , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Relação Estrutura-Atividade , Biologia Marinha , Ascomicetos/química , Fluorenos/farmacologia , Fluorenos/química , Fluorenos/isolamento & purificação , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores
3.
Mar Drugs ; 21(11)2023 Oct 31.
Artigo em Inglês | MEDLINE | ID: mdl-37999399

RESUMO

Six new thiodiketopiperazine-class alkaloids lecanicilliums A-F were isolated from the mangrove sediment-derived fungus Lecanicillium kalimantanense SCSIO41702, together with thirteen known analogues. Their structures were determined by spectroscopic analysis. The absolute configurations were determined by quantum chemical calculations. Electronic circular dichroism (ECD) spectra and the structure of Lecanicillium C were further confirmed by a single-crystal X-ray diffraction analysis. Lecanicillium A contained an unprecedented 6/5/6/5/7/6 cyclic system with a spirocyclic center at C-2'. Biologically, lecanicillium E, emethacin B, and versicolor A displayed significant cytotoxicity against human lung adenocarcinoma cell line H1975, with IC50 values of 7.2~16.9 µM, and lecanicillium E also showed antibacterial activity against four pathogens with MIC values of 10~40 µg/mL. Their structure-activity relationship is also discussed.


Assuntos
Alcaloides , Hypocreales , Humanos , Alcaloides/farmacologia , Antibacterianos/química , Linhagem Celular , Estrutura Molecular
4.
J Asian Nat Prod Res ; 25(10): 941-948, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-36916424

RESUMO

Two new linear peptides, penicamides A and B (1 and 2), together with four known analogous were isolated from the extracts of the marine-derived fungus Penicillium sp. SCSIO 41512. Their structures were elucidated by analysis of 1D/2D NMR data and HRESI-MS. Their absolute configurations were established by Marfey's methods and quantum chemical calculations.


Assuntos
Penicillium , Estrutura Molecular , Penicillium/química , Espectroscopia de Ressonância Magnética , Fungos/química , Peptídeos
5.
J Nat Prod ; 85(8): 2071-2081, 2022 08 26.
Artigo em Inglês | MEDLINE | ID: mdl-35930265

RESUMO

Seven new decahydrofluorene-class alkaloids, pyrrospirones K-Q (1-7), together with six known analogues (8-13) were isolated from the marine-derived fungal strain Penicillium sp. SCSIO 41512. Their structures were determined by extensive spectroscopic analysis, and their absolute configurations were established by single-crystal X-ray diffraction analysis and quantum chemical calculations of electronic circular dichroism spectra. Compounds 1 and 3 possess a novel decahydrofluorene-class alkaloid skeleton with a 6/5/6/8/5/6/13 and a 6/5/6/5/6/13 polycyclic system, respectively. Biologically, 13 displayed significant inhibitory activity against protein tyrosine phosphatases CD45, TCPTP, SHP1, and PTP1B with IC50 values of 8.1-17.8 µM, and 1, 2, 5, 8-10, 12, and 13 showed antibacterial activity against six pathogens. Their structure-activity relationship is also discussed.


Assuntos
Alcaloides , Penicillium , Alcaloides/química , Antibacterianos/química , Dicroísmo Circular , Fungos/química , Estrutura Molecular , Penicillium/química
6.
Mar Drugs ; 20(1)2022 Jan 17.
Artigo em Inglês | MEDLINE | ID: mdl-35049933

RESUMO

Puniceusines A-N (1-14), 14 new isoquinoline alkaloids, were isolated from the extracts of a deep-sea-derived fungus, Aspergillus puniceus SCSIO z021. Their structures were elucidated by spectroscopic analyses. The absolute configuration of 9 was determined by ECD calculations, and the structures of 6 and 12 were further confirmed by a single-crystal X-ray diffraction analysis. Compounds 3-5 and 8-13 unprecedentedly contained an isoquinolinyl, a polysubstituted benzyl or a pyronyl at position C-7 of isoquinoline nucleus. Compounds 3 and 4 showed selective inhibitory activity against protein tyrosine phosphatase CD45 with IC50 values of 8.4 and 5.6 µM, respectively, 4 also had a moderate cytotoxicity towards human lung adenocarcinoma cell line H1975 with an IC50 value of 11.0 µM, and 14, which contained an active center, -C=N+, exhibited antibacterial activity. An analysis of the relationship between the structures, enzyme inhibitory activity and cytotoxicity of 1-14 revealed that the substituents at C-7 of the isoquinoline nucleus could greatly affect their bioactivity.


Assuntos
Alcaloides/farmacologia , Antibacterianos/farmacologia , Antineoplásicos/farmacologia , Aspergillus , Isoquinolinas/farmacologia , Proteínas Tirosina Fosfatases/antagonistas & inibidores , Alcaloides/química , Animais , Antibacterianos/química , Antineoplásicos/química , Organismos Aquáticos , Linhagem Celular Tumoral/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Isoquinolinas/química , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana
7.
Int J Mol Sci ; 23(16)2022 Aug 09.
Artigo em Inglês | MEDLINE | ID: mdl-36012099

RESUMO

An effective method was developed to improve the interfacial interaction between Mutiwalled carbon nanotubes (MWCNTs) and epoxy matrix. The performance of thermal conductivity and strength of the epoxy vitrimer were enhanced by polydopamine (PDA) coating. Polydopamine is a commonly used photothermal agent, which of course, was effective in modifying MWCNTs used in photoresponsive epoxy resin. The surface temperature of the epoxy composite with 3% MWCNTs@PDA fillers added increased from room temperature to 215 °C in 48 s. The metal-catechol coordination interactions formed between the catechol groups of PDA and Zn2+ accelerated the stress relaxation of epoxy vitrimer. Moreover, the shape memory, repairing, and recycling of epoxy vitrimer were investigated. Therefore, dopamine coating is a multifunctional approach to enhance the performance of epoxy vitrimer.


Assuntos
Resinas Epóxi , Nanotubos de Carbono , Catecóis , Condutividade Térmica
8.
J Org Chem ; 86(18): 12831-12839, 2021 09 17.
Artigo em Inglês | MEDLINE | ID: mdl-34477382

RESUMO

(+)- and (-)-talaromyoxaones A and B (1 and 2, respectively), two new oxaphenalenone derivatives with a hemiacetal frame and an unprecedented spirolactone frame of a 2'H,3H,4'H-spiro[isobenzofuran-1,3'-pyran]-3-one unit that show biosynthetic enantiodivergence, and two new oxaphenalenone analogues (±)-11-apopyrenulin (3) and (+)- or (-)-abeopyrenulin (4) were isolated from the marine-derived fungus Talaromyces purpureogenus SCSIO 41517. Their structures were elucidated by spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical calculations of ECD spectra. Compounds 1 and 2 showed selective inhibitory activity against phosphatases SHP1, SHP2, and MEG2 with IC50 values of 1.3-3.4 µM, and the potential modes of action for 1 were investigated by a preliminary molecular docking study.


Assuntos
Talaromyces , Simulação de Acoplamento Molecular , Monoéster Fosfórico Hidrolases , Espironolactona
9.
J Nat Prod ; 84(10): 2727-2737, 2021 10 22.
Artigo em Inglês | MEDLINE | ID: mdl-34596414

RESUMO

Nine new highly oxygenated 3,5-dimethylorsellinic acid-derived meroterpenoids, talaromynoids A-I (1-9), were isolated from the marine-derived fungus Talaromyces purpureogenus SCSIO 41517. Their structures including absolute configurations were elucidated by HRMS, NMR, single-crystal X-ray diffraction analysis, and electronic circular dichroism calculations. Compounds 1 and 7-9 possessed unprecedented 5/7/6/5/6/6, 6/7/6/6/6/5, 6/7/6/5/6/5/4, and 7/6/5/6/5/4 polycyclic systems, respectively. Biologically, compound 5 showed selective inhibitory activity against phosphatase CDC25B with an IC50 value of 13 µM. Moreover, 7-9 and 12 exhibited the activity of reducing triglyceride in 3T3-L1 adipocytes in a dosage-dependent manner.


Assuntos
Metabolismo dos Lipídeos/efeitos dos fármacos , Talaromyces/química , Terpenos/farmacologia , Células 3T3-L1 , Animais , Organismos Aquáticos/química , China , Humanos , Camundongos , Estrutura Molecular , Oxigênio , Terpenos/isolamento & purificação , Triglicerídeos/metabolismo , Fosfatases cdc25/antagonistas & inibidores
10.
J Nat Prod ; 84(11): 2945-2952, 2021 11 26.
Artigo em Inglês | MEDLINE | ID: mdl-34755511

RESUMO

Simplifusidic acids A-K (1-11), 11 new fusidane-type nortriterpenoids, were isolated from the marine-derived fungus Simplicillium sp. SCSIO 41513. Compound 1 possessed an unprecedented fusidane triterpene skeleton with a 6/6/7/5/5 polycyclic system. Their structures were elucidated by spectroscopic methods, and their absolute configurations were further determined by quantum chemical calculations of ECD spectra, comparison of experimental ECD spectra, and single-crystal X-ray diffraction analysis. Compound 9 showed strong antibacterial activity toward Staphylococcus aureus with an MIC value of 0.078 µg/mL. Their structure-bioactivity relationship was also discussed.


Assuntos
Antibacterianos/isolamento & purificação , Hypocreales/metabolismo , Triterpenos/isolamento & purificação , Antibacterianos/química , Antibacterianos/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Relação Estrutura-Atividade , Triterpenos/química , Triterpenos/farmacologia
11.
Bioorg Chem ; 107: 104571, 2021 02.
Artigo em Inglês | MEDLINE | ID: mdl-33373758

RESUMO

Nine new xanthone-type and anthraquinone-type mycotoxins including austocystins J-N (1-5), 7-chloro versicolorin A (6), 3'-hydroxy-8-O-methyl versicolorin B (7), 8-O-methyl versiconol (8) and 2',3'-dihydroxy versiconol (9), together with 17 known analogues (10-26) were isolated from an extract of the deep-sea-derived fungus Aspergillus puniceus SCSIO z021. Their structures were elucidated by detailed analysis of spectroscopic data, and their absolute configurations were further determined by quantum chemical calculations of ECD spectra or comparison of the experimental ECD spectra. Eleven hydrogenated austocystins were synthesized from 1-2, 10-15 and 17 by catalytic hydrogenation for bioactivities evaluation. Totally, 18 of the all 37 compounds showed strong toxicity against brine shrimps or Vero cell, and the toxicity of 8-O-methyldemethylsterigmatocystin (18) (LC50 = 0.020 µM) against brine shrimps was higher than those of three positive controls. In addition, 22 of the isolated compounds also exhibited significant inhibitory activity against seven different protein tyrosine phosphatases (PTPs), among them austocystin H (15) and methyl-averantin (24) were the most potent inhibitors with IC50 values of 0.20-3.0 µM. Their structure-bioactivity relationship was also discussed.


Assuntos
Aspergillus/metabolismo , Micotoxinas/química , Proteínas Tirosina Fosfatases/antagonistas & inibidores , Água do Mar/microbiologia , Animais , Artemia/crescimento & desenvolvimento , Aspergillus/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Chlorocebus aethiops , Dicroísmo Circular , Conformação Molecular , Micotoxinas/metabolismo , Micotoxinas/farmacologia , Óvulo/efeitos dos fármacos , Óvulo/crescimento & desenvolvimento , Isoformas de Proteínas/antagonistas & inibidores , Isoformas de Proteínas/metabolismo , Proteínas Tirosina Fosfatases/metabolismo , Relação Estrutura-Atividade , Células Vero
12.
Virol J ; 17(1): 45, 2020 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-32238179

RESUMO

Following publication of the original article [1], we have been notified that there is a typo in the title of this article.

13.
Virol J ; 17(1): 41, 2020 03 19.
Artigo em Inglês | MEDLINE | ID: mdl-32192525

RESUMO

BACKGROUND: Herpes simplex virus 1, an enveloped DNA virus belonging to the Herpesviridae family, spreads to neurons and causes pathological changes in the central nervous system. The purpose of this study was to investigate the potency and mechanism of antiviral activity of Aspergillipeptide D, a cyclic pentapeptide isolated from a culture broth of marine gorgonian-derived fungus Aspergillus sp. SCSIO 41501, At present, there are many studies on the anti-tumor, anti-clotting, anti-oxidant and immunoinflammatory effects of Aspergillipeptide D, but little research has been done on the anti-HSV-1 activity of Aspergillipeptide D. METHODS: The anti-HSV-1 activity of Aspergillipeptide D was evaluated by plaque reduction assay. The mechanism of action against HSV-1 was determined from the effective stage. Then we assayed the viral DNA replication, viral RNA synthesis and protein expression, respectively. We also identified the proteins that interact with gB by mass spectrometry, and assayed the effect of Aspergillipeptide D on the interaction between the virus gB protein and cell proteins. RESULTS: Plaque reduction experiments showed that Aspergillipeptide D did not affect HSV-1 early infection events, including viral inactivation, attachment and penetration. Interestingly, Aspergillipeptide D dramatically reduced both the gene and protein levels of viral late protein gB, and suppressed its location in the endoplasmic reticulum and Golgi apparatus. In contrast, overexpression of gB restored viral production. Finally, proteomic analysis revealed that the numbers of cellular proteins that interacted with gB protein was largely decreased by Aspergillipeptide D. These results suggested that Aspergillipeptide D inhibited gB function to affect HSV-1 intercellular spread. CONCLUSIONS: Our results indicated that Aspergillipeptide D might be a potential candidate for HSV-1 therapy, especially for ACV-resistant strains.


Assuntos
Antivirais/farmacologia , Aspergillus/química , Herpesvirus Humano 1/efeitos dos fármacos , Peptídeos Cíclicos/farmacologia , Animais , Antivirais/isolamento & purificação , Chlorocebus aethiops , Meios de Cultura , Herpesvirus Humano 1/fisiologia , Humanos , Inibidores da Síntese de Ácido Nucleico/isolamento & purificação , Inibidores da Síntese de Ácido Nucleico/farmacologia , Peptídeos Cíclicos/isolamento & purificação , Proteômica , RNA Viral/biossíntese , Células Vero , Inativação de Vírus/efeitos dos fármacos , Replicação Viral/efeitos dos fármacos
14.
Bioorg Med Chem Lett ; 30(11): 127168, 2020 06 01.
Artigo em Inglês | MEDLINE | ID: mdl-32273216

RESUMO

Fourteen ansamycin derivatives including seven new herbimycins G-L (1-6) and divergolide O (7), and seven known analogues were isolated from a culture broth of the marine-derived Streptomyces sp. SCSGAA 0027. Their complete structures were determined by detailed analysis of spectroscopic data and quantum chemical calculations. Compounds 1-5 and 7 featured an additional eight-membered O-heterocycle that has rarely been reported for ansamycins, and the Z,Z- and E,E-configurations for Δ2,Δ4 were reported for the first time in geldanamycin analogues. Compound 1 exhibited weak inhibition activity towards Hsp90α with an IC50 value of 96 µM, 2-5 showed mild cytotoxicity against four human cancer cell lines with IC50 values ranging from 13 µM to 86 µM, and 7 had moderate anti-HSV-1 activity with an IC50 value of 19 µM and very weak cytotoxicity towards Vero cell. The possible biosynthetic pathways for 1-5 were proposed. And their structure-bioactivity relationship was also discussed.


Assuntos
Antivirais/química , Rifabutina/análogos & derivados , Streptomyces/química , Antivirais/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Proteínas de Choque Térmico HSP90/antagonistas & inibidores , Proteínas de Choque Térmico HSP90/metabolismo , Herpesvirus Humano 1/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Rifabutina/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Estereoisomerismo , Streptomyces/metabolismo , Relação Estrutura-Atividade
15.
J Asian Nat Prod Res ; 22(4): 338-345, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30835537

RESUMO

A new isopentylated dibenzodioxocinone, canescenin A (1), and a new isopentylated pyran-3,5-dione derivative, canescenin B (2), were isolated from an extract of the deep-sea-derived fungus Penicillium canescens SCSIO z053. Their structures were elucidated by spectroscopic analysis. It was rare to obtain pyran-3,5-dione derivatives from nature. Antibacterial, cytotoxic, and antiviral activities of 1 and 2 were also evaluated.


Assuntos
Antineoplásicos , Penicillium , Antibacterianos , Estrutura Molecular , Piranos
16.
J Nat Prod ; 82(6): 1558-1564, 2019 06 28.
Artigo em Inglês | MEDLINE | ID: mdl-31095389

RESUMO

Eight new diketopiperazine-type alkaloids including four oxepin-containing diketopiperazine-type alkaloids, oxepinamides H-K (1-4), and four 4-quinazolinone alkaloids, puniceloids A-D (5-8), together with two known analogues (9 and 10), were isolated from the culture broth extracts of the deep-sea-derived fungus Aspergillus puniceus SCSIO z021. Their structures were elucidated by spectroscopic analyses, and their absolute configurations were determined by Marfey's method along with comparison of their specific rotations and ECD spectra. The absolute configurations of 4 and 5 were further confirmed by a single-crystal X-ray diffraction analysis. Compounds 1-8 showed significant transcriptional activation of liver X receptor α with EC50 values of 1.7-50 µM, and 7 and 8 were the most potent agonists.


Assuntos
Alcaloides/química , Aspergillus/química , Dicetopiperazinas/química , Fungos/química , Receptores X do Fígado/efeitos dos fármacos , Oxepinas/química , Piperazinas/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Cristalografia por Raios X , Dicetopiperazinas/isolamento & purificação , Dicetopiperazinas/farmacologia , Estrutura Molecular , Oxepinas/sangue , Oxepinas/isolamento & purificação , Oxepinas/farmacologia , Piperazinas/isolamento & purificação , Piperazinas/farmacologia
17.
Appl Microbiol Biotechnol ; 102(3): 1417-1427, 2018 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-29189900

RESUMO

Several ansamycins have been reported to inhibit bacterial biofilm formation and accelerate the eradication of developed biofilms, but little is known about the effect of hygrocin C, an ansamycin, on bacterial biofilm formation. Here, hygrocin C was isolated from the marine-derived Streptomyces sp. SCSGAA 0027 and reported for the first time to be capable of inhibiting the biofilm formation of Staphylococcus aureus and Bacillus amyloliquefaciens SCSGAB0082 with the production of anti-microbial lipopeptides from South China Sea gorgonian Subergorgia suberosa at concentrations of less than minimum inhibitory concentrations. Moreover, hygrocin C also promoted the eradication of developed biofilms, affected the biofilm architecture, and lowered the extracellular polymeric matrix formation, cell motility, and surface hydrophobicity in B. amyloliquefaciens, which was in accordance with the inhibition of biofilm formation. Furthermore, transcriptome analysis revealed that hygrocin C altered the transcripts of several genes associated with bacterial chemotaxis and flagellar, two-component system and the synthesis of arginine and histidine, which are important for bacterial biofilm formation. In conclusion, hygrocin C could be used as a potential biofilm inhibitor against S. aureus and B. amyloliquefaciens. But further genetic investigations are needed to provide more details for elucidation of the molecular mechanisms responsible for the effects of hygrocin C on B. amyloliquefaciens biofilm formation.


Assuntos
Antozoários/microbiologia , Bacillus amyloliquefaciens/efeitos dos fármacos , Biofilmes/efeitos dos fármacos , Lactamas Macrocíclicas/farmacologia , Streptomyces/química , Animais , Bacillus amyloliquefaciens/crescimento & desenvolvimento , Proteínas de Bactérias/genética , China , Perfilação da Expressão Gênica , Lactamas Macrocíclicas/isolamento & purificação , Lipopeptídeos/metabolismo , Testes de Sensibilidade Microbiana , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus aureus/crescimento & desenvolvimento
18.
Mar Drugs ; 16(11)2018 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-30445739

RESUMO

Seven new unstable tetramic acid derivatives, cladosporiumins I-O (1⁻7), together with the known analogue cladodionen (8) were isolated from the extract of the deep-sea-derived fungus Cladosporium sphaerospermum EIODSF 008. Their structures were elucidated by spectroscopic analysis, quantum chemical calculations and ECD spectra. Compound 4 was a Mg complex of tetramic acid derivative. In acidic solvent, 4 could change to 1 and 6, and 7 could change to 5. In addition, 1, 5 and 8 existed as two exchangeable isomers, respectively. The structures of cladosporiumins E-H were reassigned as their Na complexes. The antibacterial and cytotoxic activities of 1⁻8 were also evaluated. However, because of their instability, all of the isolated compounds did not show significant antibacterial activity as the preliminary EtOAc extracts of the fungal strain.


Assuntos
Organismos Aquáticos/química , Cladosporium/química , Pirrolidinonas/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Bactérias/efeitos dos fármacos , Estabilidade de Medicamentos , Células HL-60 , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Pirrolidinonas/isolamento & purificação , Pirrolidinonas/farmacologia , Solventes/química
19.
Bioorg Med Chem Lett ; 27(4): 787-791, 2017 02 15.
Artigo em Inglês | MEDLINE | ID: mdl-28129981

RESUMO

Chemical investigation of the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502 resulted in the isolation of three new anthraquinones, aspergilols G-I (1-3), one new diphenyl ether, 4-carbglyceryl-3,3'-dihydroxy-5,5'-dimethyldiphenyl ether (4), and one new benzaldehyde derivative, 2,4-dihydroxy-6-(4-methoxy-2-oxopentyl)-3-methylbenzaldehyde (5), along with 23 known phenolic compounds (6-28). The structures of new compounds were elucidated by extensive spectroscopic analysis. The absolute configuration of 3 was established by CD spectrum and the modified Mosher method. Compounds 2, 3 and 9 had evident antiviral activity towards HSV-1 with EC50 values of 4.68, 6.25, and 3.12µM, respectively. Compounds 15, 18, 20 and 22-24 showed more potent antioxidant activity than l-ascorbic acid with IC50 values of 18.92-52.27µM towards DPPH radicals. Comparison of the structures and antioxidant activities of 1-28 suggests that the number of phenolic hydroxyl group that can freely rotate can significantly affect the antioxidant activity of phenolic compounds. In addition, 4, 22-24 and 27 had significant antifouling activity against Bugula neritina larval settlement with EC50 values of 1.28, 2.61, 5.48, 1.59, and 3.40µg/ml, respectively.


Assuntos
Antioxidantes/química , Antivirais/química , Aspergillus/química , Fenóis/química , Animais , Antraquinonas/química , Antraquinonas/isolamento & purificação , Antraquinonas/farmacologia , Antioxidantes/isolamento & purificação , Antivirais/isolamento & purificação , Antivirais/farmacologia , Aspergillus/metabolismo , Incrustação Biológica/prevenção & controle , Briozoários/efeitos dos fármacos , Briozoários/crescimento & desenvolvimento , Dicroísmo Circular , Larva/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Fenóis/isolamento & purificação , Fenóis/farmacologia , Água do Mar/microbiologia , Estereoisomerismo
20.
Mar Drugs ; 15(9)2017 Aug 28.
Artigo em Inglês | MEDLINE | ID: mdl-28846623

RESUMO

In this review, a comprehensive overview about the antifouling compounds from marine invertebrates is described. In total, more than 198 antifouling compounds have been obtained from marine invertebrates, specifically, sponges, gorgonian and soft corals.


Assuntos
Incrustação Biológica/prevenção & controle , Invertebrados/química , Biologia Marinha , Animais , Antozoários , Poríferos
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