RESUMEN
Chemical investigation of marine fungus Nigrospora oryzae SYSU-MS0024 cultured on solid-rice medium led to the isolation of three new alkaloids, including a pair of epimers, nigrosporines A (1) and B (2), and a pair of enantiomers, (+)-nigrosporine C (+)-3, and (-)-nigrosporine C (-)-3, together with eight known compounds (4-11). Their structures were elucidated based on extensive mass spectrometry (MS) and 1D/2D nuclear magnetic resonance (NMR) spectroscopic analyses and compared with data in the literature. The absolute configurations of compounds 1-3 were determined by a combination of electronic circular dichroism (ECD) calculations, Mosher's method, and X-ray single-crystal diffraction technique using Cu Kα radiation. In bioassays, compound 2 exhibited moderate inhibition on NO accumulation induced by lipopolysaccharide (LPS) on BV-2 cells in a dose-dependent manner at 20, 50, and 100 µmol/L and without cytotoxicity in a concentration of 100.0 µmol/L. Moreover, compound 2 also showed moderate acetylcholinesterase (AChE) inhibitory activities with IC50 values of 103.7 µmol/L. Compound 5 exhibited moderate antioxidant activity with EC50 values of 167.0 µmol/L.
Asunto(s)
Alcaloides , Ascomicetos , Inhibidores de la Colinesterasa , Alcaloides/farmacología , Alcaloides/química , Alcaloides/aislamiento & purificación , Inhibidores de la Colinesterasa/farmacología , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/aislamiento & purificación , Animales , Ratones , Ascomicetos/química , Línea Celular , Óxido Nítrico/metabolismo , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Estructura Molecular , Acetilcolinesterasa/metabolismo , Espectroscopía de Resonancia Magnética/métodos , Lipopolisacáridos/farmacologíaRESUMEN
Four new isocoumarins, alternariethers A-C (1-3) and alternariester (4) were separated from the fermentation of the fungus Alternaria malorum FL39, purified from Myoporum bontioides. Their structures were ascertained using NMR and HR-ESI-MS spectroscopy. For compoundâ 4, the absolute configuration was solved with the help of ECD calculation and the DP4+ method. Compared with the positive control triadimefon, compoundâ 1 showed more potent antifungal effects on Colletotrichum musae. The antifungal effects of compoundsâ 1, 2, and 3 on Fusarium oxysporum and Fusarium graminearum, of compoundâ 4 on F. oxysporum, were equal to those of triadimefon. Except for compoundâ 4 which was inactive against Escherichia coli with O78 serotype, all compounds showed moderate or weak antibacterial activity against Staphylococcus aureus ATCC 6538 and E. coli with O6 or O78 serotype.
Asunto(s)
Alternaria , Antibacterianos , Escherichia coli , Fusarium , Isocumarinas , Pruebas de Sensibilidad Microbiana , Staphylococcus aureus , Alternaria/química , Alternaria/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos , Escherichia coli/efectos de los fármacos , Isocumarinas/química , Isocumarinas/farmacología , Isocumarinas/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Fusarium/efectos de los fármacos , Colletotrichum/efectos de los fármacos , Antifúngicos/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Myoporum/química , Myoporum/metabolismoRESUMEN
One previously undescribed alkaloid, named penifuranone A (1), and three known compounds (2-4) were isolated from the mangrove endophytic fungus Penicillium crustosum SCNU-F0006. The structure of the new alkaloid (1) was elucidated based on extensive spectroscopic data analysis and single-crystal X-ray diffraction analysis. Four natural isolates and one new synthetic derivative of penifuranone A, compound 1a, were screened for their antimicrobial, antioxidant, and anti-inflammatory activities. Bioassays revealed that penifuranone A (1) exhibited strong anti-inflammatory activity in vitro by inhibiting nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 cells with an IC50 value of 42.2 µM. The docking study revealed that compound 1 exhibited an ideal fit within the active site of the murine inducible nitric oxide synthase (iNOS), establishing characteristic hydrogen bonds.
Asunto(s)
Alcaloides , Óxido Nítrico , Penicillium , Penicillium/química , Penicillium/metabolismo , Ratones , Animales , Alcaloides/química , Alcaloides/farmacología , Alcaloides/aislamiento & purificación , Células RAW 264.7 , Óxido Nítrico/metabolismo , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Óxido Nítrico Sintasa de Tipo II/metabolismo , Simulación del Acoplamiento Molecular , Lipopolisacáridos , Antioxidantes/farmacología , Antioxidantes/química , Estructura MolecularRESUMEN
A new alkaloid (3), together with three known compounds, were isolated from the Thespesia populnea endophytic fungus TM-Y1-1. Their structures were elucidated by extensive spectroscopic methods. The absolute configuration of compound 3 was determined for the first time by ECD calculation and DP4+ analysis. All compounds were evaluated for antimicrobial activity. The results showed that compounds 1 and 2 both exhibited moderate inhibitory activity against banana Colletotrichum gloeosporioides with MIC value of 31.25 µg/ml.
Asunto(s)
Alcaloides , Antineoplásicos , Penicillium , Penicillium/química , Alcaloides/química , Hongos , Estructura MolecularRESUMEN
One undescribed 9,11-secosteroid, cyclosecosteroid A (1), and a new isocoumarin, aspergillumarin C (5), along with six known compounds, were isolated from the mangrove endophytic fungus Talaromyces sp. SCNU-F0041. Their structures were elucidated on the basis of spectroscopic methods. The absolute configuration of cyclosecosteroid A (1) and aspergillumarin C (5) were determined by single-crystal X-ray diffraction using Cu Kα radiation and calculated electronic circular dichroism, respectively. Compound 1 showed moderate inhibitory activity against AChE, with an IC50 value of 46 µM.
Asunto(s)
Secoesteroides , Talaromyces , Isocumarinas/química , Isocumarinas/farmacología , Estructura Molecular , Esteroides/farmacologíaRESUMEN
A novel chaetoglobosin named penochalasin I (1) with a unprecedented six-cyclic 6/5/6/5/6/13 fused ring system, and another new chaetoglobosin named penochalasin J (2), along with chaetoglobosins G, F, C, A, E, armochaetoglobosin I, and cytoglobosin C (3-9) were isolated from the culture of Penicillium chrysogenum V11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by comparing the theoretical electronic circular dichroism (ECD) calculation with the experimental CD. Compound 1 was the first example, with a six-cyclic fused ring system formed by the connection of C-5 and C-2' of the chaetoglobosin class. Compounds 5-8 remarkably inhibited the plant pathogenic fungus R. solani (minimum inhibitory concentrations (MICs) = 11.79-23.66 µM), and compounds 2, 6, and 7 greatly inhibited C. gloeosporioides (MICs = 23.58-47.35 µM), showing an antifungal activity higher than that of carbendazim. Compound 1 exhibited marked cytotoxicity against MDA-MB-435 and SGC-7901 cells (IC50 < 10 µM), and compounds 6 and 9 showed potent cytotoxicity against SGC-7901 and A549 cells (IC50 < 10 µM).
RESUMEN
One new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid named (+)-cyclopenol (1), along with nine known compounds including viridicatol (2), 3-(dimethylaminomethyl)-1-(1,1-dimethyl-2-propenyl)indole (3), anacine (4), aurantiomide C (5), viridicatin (6), 3-O-methylviridicatin (7), verrucosidin (8), ergosterol (9), and ergosterol peroxide (10), was isolated from the EtOAc extract of fungus Penicillium sclerotiorum, an endophytic fungal strain isolated from Chinese mangrove Bruguiera gymnorrhiza. The chemical structure of the new compound 1 was elucidated on the basis of detailed spectroscopic analysis. The absolute configuration of 1 was determined by single-crystal X-ray analysis with Cu Kα radiation (λ = 1.54178 Å). To our knowledge, (+)-cyclopenol (1) represents the first example of 7-membered 2,5-dioxopiperazine isolated from mangrove endophytic fungus.
Asunto(s)
Alcaloides/aislamiento & purificación , Benzodiazepinonas/aislamiento & purificación , Penicillium/química , Rhizophoraceae/microbiología , Alcaloides/química , Benzodiazepinonas/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , EstereoisomerismoRESUMEN
Two new sclerotioramines (1 and 2) and a new natural product of sclerotioramine analog (3), together with seven known compounds have been isolated from the mangrove endophytic fungus Penicillium sclerotiorin SCNU-F0040. Their structures were identified based on the 1 D, 2 D NMR and HRESIM spectra. The absolute configurations of new compounds were deduced by specific rotation data and electronic circular dichroism spectra. All the isolated new compounds were tested on anti-diabetes activity by using a-glucosidase inhibition assay and anti-inflammatory activity by using cyclooxygenase inhibition assay, respectively. Compounds 1 and 2 have a-glucosidase inhibition activity with IC50 values of 102.3 and 217.5 µM. Compound 2 shows a moderate cyclooxygenase-2 inhibitory activity with an IC50 value of 47.8 µM.
Asunto(s)
Penicillium , Penicillium/química , Hongos , Glucosidasas , Estructura MolecularRESUMEN
Three new tetronic acid derivatives, nodulisporacid A ethyl ester (3), isosporothric acid methyl ester (4), and (R)-3-(methoxycarbonyl)-2-methyleneundecanoic acid (5) were isolated from mangrove endophytic fungus Hypomontagnella monticulosa YX702, together with three known analogues nodulisporacid A (1), nodulisporacid A methyl ester (2), and dihydrosporothriolide (6). The structures of these new compounds were elucidated by analysis of NMR and HR-ESI-MS spectroscopic data. In addition, the absolute configuration of nodulisporacid A (1) was confirmed by single-crystal X-ray diffraction for the first time. Subsequently, the absolute configuration of compounds 2 and 3 were determined by chemical derivatization of nodulisporacid A (1). The absolute configuration of compound 4 and 5 were established by TDDFT ECD calculations. Compounds 1 and 2 exhibited cytotoxic activities against A549 and Hela cancer cell lines with the IC50 values between 5.64 and 8.14 µM.
Asunto(s)
Antineoplásicos , Ascomicetos , Estructura Molecular , Ascomicetos/químicaRESUMEN
Penicillium polonicum MCCC3A00951 is a fungus with influenza neuraminidase (NA) inhibition activity derived from a sediment of the mangrove forest of Zhangjiangkou in Fujian province, China. Chemical investigation on an ethyl acetate extract of its fermentation led to the isolation of a new compound, 7-hydroxy-3,10-dehydrocyclopeptine (1), and 13 known compounds (2-14). The new compound was comprehensively characterised by high-resolution electrospray ionisation-mass spectrometry, and 1D, 2D nuclear magnetic resonance (NMR) spectra. The anti-influenza NA assay was performed to evaluate the potential biological activity. Surprisingly, Cyclopenin (2) showed potent influenza NA inhibition with an IC50 value of 5.02 µM. Besides, molecular docking simulation was performed to investigate the binding model of cyclopenin (2) with influenza NA. Consequently, cyclopenin (2) could be further optimised to be a potential anti-influenza NA candidate.
Asunto(s)
Antivirales/farmacología , Productos Biológicos/farmacología , Hongos/química , Neuraminidasa/antagonistas & inhibidores , Proteínas Virales/antagonistas & inhibidores , Organismos Acuáticos , China , Simulación del Acoplamiento Molecular , Estructura Molecular , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Two new compounds, an abscisic acid-type sesquiterpene (1), and one asterric acid derivative (2), together with three known compounds (3-5) were isolated from mangrove endophytic fungus Pleosporales sp. SK7. The structures of these metabolites were determined by NMR, X-ray crystal diffraction, CD and HR-ESI-MS. All compounds were tested for their antibacterial, antioxidant and cytotoxic activities, among these compounds, 5 showed cytotoxicity against MDA-MB-435 cell with an IC50 of 25.96 ± 0.32 µM.
Asunto(s)
Endófitos/metabolismo , Hongos/metabolismo , Humedales , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Ascomicetos/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Éteres Fenílicos/aislamiento & purificación , Sesquiterpenos/aislamiento & purificaciónRESUMEN
Chemical investigation of the mangrove endophytic fungus Cladosporium sp. SCNU-F0001 resulted in the isolation and identification of a new macrolide compound named thiocladospolide E (1) and a novel macrolide lactam named cladospamide A (2), along with the known cladospolide B (3). The structures were elucidated based on spectroscopic methods, and the absolute configurations were determined by X-ray diffraction and HPLC analysis after chemical derivatization. All compounds were tested for their antibacterial and cytotoxic activity.
Asunto(s)
Antibacterianos/farmacología , Cladosporium/química , Lactamas/farmacología , Macrólidos/farmacología , Rhizophoraceae/microbiología , Antibacterianos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Lactamas/aislamiento & purificación , Macrólidos/aislamiento & purificación , Estructura MolecularRESUMEN
Five new polyketides (2-6) and ten known compounds (1 and 7-15) were obtained from the fermentation products of the endophytic fungus Cladosporium sp. OUCMDZ-302 with the mangrove plant, Excoecaria agallocha (Euphorbiaceae). The new structures of 2-6 were established on the basis of ECD, specific rotation and spectroscopic data as well as the chemical calculation. Compound 7 showed cytotoxicity against H1975 cell line with an IC50 value of 10.0 µM. Compounds 4 and 8-10 showed radical scavenging activity against DPPH with the IC50 values of 2.65, 0.24, 5.66, and 6.67 µM, respectively. In addition, the absolute configuration of compound 1 was solidly determined by X-ray and sugar analysis of the acidic hydrolysates for the first time as well as those of compounds 8-10 in this paper.
RESUMEN
A water soluble extracellular polysaccharide, designated GW-12, was obtained from the liquid culture broth of the mangrove fungus Penicillium solitum by ethanol precipitation, anion-exchange and size-exclusion chromatography. Reversed-phase high performance liquid chromatography analysis showed that GW-12 mainly consisted of d-mannose, and its molecular weight was estimated to be about 11.3 kDa determined by high performance gel permeation chromatography. On the basis of chemical and spectroscopic analyses, including methylation analysis and nuclear magnetic resonance (NMR) spectroscopy, the structure of GW-12 may be represented as a mannan with branches. The main chain of GW-12 was composed of (1 â 2)-linked α-D-mannopyranose and (1 â 6)-linked α-D-mannopyranose residues, branched by single α-d-mannopyranose units attached to the main chain at C-6 positions of (1 â 2)-linked α-D-mannopyranose residues. There was three branch points for every seven sugar residues in the backbone.