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1.
Fitoterapia ; 177: 106104, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-38950637

RESUMEN

Four undescribed polyketides, beshanzones A (1) and B (2) as well as beshanhexanols A (3) and B (4), along with three known ones (5-7) were isolated from the rice fermentation of two endophytic fungi associated with the critically endangered Chinese endemic conifer Abies beshanzuensis. γ-Butyrolactone derivatives 1, 2, and 5 were isolated from Phomopsis sp. BSZ-AZ-2, an interesting strain that drawn our attention this time. The cyclohexanol derivatives 3, 4, 6, and 7 were obtained during a follow-up investigation on Penicillium commune BSZ-P-4-1. The chemical structures including absolute configurations of compounds 1-4 were determined by spectroscopic methods, Mo2(OAc)4 induced electronic circular dichroism (IECD), GIAO NMR calculations and DP4+ probability analyses. In particular, compound 2 contains a novel 5/5 bicyclic ring system, which might be biogenetically derived from the known compound 5 through hydrolysis followed by an Aldol reaction. All isolates were evaluated for their antimicrobial activities against a small panel of bacterial and fungal pathogens. Compounds 6 and 7 showed moderate inhibitory activities against Candida albicans, with MIC values of 16 and 32 µg/mL, respectively.


Asunto(s)
Abies , Especies en Peligro de Extinción , Endófitos , Policétidos , Endófitos/química , Policétidos/farmacología , Policétidos/aislamiento & purificación , Policétidos/química , Estructura Molecular , China , Abies/química , Phomopsis/química , Pruebas de Sensibilidad Microbiana , Penicillium/química , Bacterias/efectos de los fármacos , Antibacterianos/farmacología , Antibacterianos/aislamiento & purificación , 4-Butirolactona/análogos & derivados , 4-Butirolactona/aislamiento & purificación , 4-Butirolactona/farmacología , 4-Butirolactona/química
2.
Bioorg Chem ; 143: 107073, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-38176375

RESUMEN

Six new highly oxygenated and polycyclic andrastin-type meroterpenoids, namely, bialorastins A-F (1-6), were discovered from the culture of Penicillium bialowiezense CS-283, a fungus isolated from the deep-sea cold seep squat lobster Shinkaia crosnieri. The planar structures and absolute configurations of these compounds were determined by detailed analysis of spectroscopic data, single crystal X-ray diffraction, and TDDFT-ECD calculations. Structurally, bialorastin A (1) represents a rare 17-nor-andrastin that possesses an unusual 2-oxaspiro[4.5]decane-1,4-dione moiety with a unique 6/6/6/6/5 polycyclic system, while bialorastin B (2) is also a 17-nor-andrastin featuring a gem-propane-1,2-dione moiety. Additionally, bialorastins C-E (3-5) possess a 6/6/6/6/5/5 fused hexacyclic skeleton, characterized by distinctive 3,23-acetal/lactone-bridged functionalities. All isolated compounds were evaluated for their proangiogenic activities in transgenic zebrafish. Compound 3 exhibited significant proangiogenic activity, which notably increased the number and length of intersegmental blood vessels in model zebrafish in a dose-dependent manner at concentrations of 20 and 40 µM. On a molecular scale, the tested compounds were modeled through molecular docking to have insight into the interactions with the possible target VEGFR2. Mechanistically, RT-qPCR results revealed that compound 3 could promote angiogenesis via activating VEGFR2 and subsequently activating the downstream PI3K/AKT and MAPK signaling pathways. These findings indicate that 3 could be a potential lead compound for developing angiogenesis agents.


Asunto(s)
Penicillium , Terpenos , Pez Cebra , Animales , Hongos , Simulación del Acoplamiento Molecular , Estructura Molecular , Penicillium/química , Fosfatidilinositol 3-Quinasas , Terpenos/química , Terpenos/farmacología
3.
Nat Prod Rep ; 40(12): 1874-1900, 2023 Dec 13.
Artículo en Inglés | MEDLINE | ID: mdl-37642299

RESUMEN

Covering: up to the end of July, 20231,2-Oxazine is a heterocyclic scaffold rarely found in natural products and is characterized by a directly connected N-O bond in a six-membered ring. Since the discovery of geneserine, the first 1,2-oxazine-containing natural product (1,2-oxazine NP) being isolated from Calabar bean (Physostigma venenosum) in 1925, a total of 76 naturally occurring 1,2-oxazine NPs have been isolated and identified from various sources, which have attracted the attention of researchers in the field of natural product chemistry, organic synthesis, biosynthesis, and pharmacology. This review summarizes the chemical family of 1,2-oxazine NPs, focusing on their source organisms, structural diversities, chemical synthesis, and biosynthesis.


Asunto(s)
Productos Biológicos , Productos Biológicos/farmacología , Productos Biológicos/química , Oxazinas/farmacología , Oxazinas/química
4.
Mar Drugs ; 21(3)2023 Mar 22.
Artículo en Inglés | MEDLINE | ID: mdl-36976244

RESUMEN

A large body of fungal secondary metabolites has been discovered to exhibit potent antibacterial activities with distinctive mechanisms and has the potential to be an untapped resource for drug discovery. Here, we describe the isolation and characterization of five new antibacterial indole diketopiperazine alkaloids, namely 24,25-dihydroxyvariecolorin G (1), 25-hydroxyrubrumazine B (2), 22-chloro-25-hydroxyrubrumazine B (3), 25-hydroxyvariecolorin F (4), and 27-epi-aspechinulin D (5), along with the known analogue neoechinulin B (6) from a fungal strain of deep-sea cold seep-derived Aspergillus chevalieri. Among these compounds, 3 and 4 represented a class of infrequently occurring fungal chlorinated natural products. Compounds 1-6 showed inhibitory activities against several pathogenic bacteria with MIC values ranging from 4 to 32 µg/mL. It was revealed that compound 6 could induce structural damage to the Aeromonas hydrophila cells based on the observation by scanning electron microscopy (SEM), which led to the bacteriolysis and death of A. hydrophila, suggesting that neoechinulin B (6) might be a potential alternative to novel antibiotics development.


Asunto(s)
Alcaloides , Dicetopiperazinas , Dicetopiperazinas/química , Estructura Molecular , Antibacterianos/química , Alcaloides Indólicos/química , Alcaloides/química , Hongos/química
5.
J Clin Apher ; 38(1): 4-15, 2023 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-36151902

RESUMEN

BACKGROUND: The treatment of acute pancreatitis (AP) induced by hypertriglyceridemia (HTG) remains controversial with regard to plasmapheresis vs conventional treatment. We reviewed relevant articles to explore the efficacy of plasmapheresis in the management of HTG-induced AP. METHODS: We systematically reviewed studies that compared plasmapheresis with conventional treatment for HTG-induced AP using three databases: PubMed, Embase, and Cochrane Library, as well as relevant references. The primary outcomes were 24 h triglyceride reduction rate and in-hospital mortality. RESULTS: A total of 791 articles were retrieved. Finally, 15 observational studies (1080 participants) were included, most of which were historical cohort studies. Compared with conventional treatment, plasmapheresis assisted in the reduction of serum triglyceride (TG) levels in the first 24 h after hospital admission (standardized mean difference [SMD]: 0.58; 95% confidence interval [CI]: 0.17 to 0.99; P = 0.005). However, it resulted in increased hospitalization costs (thousand yuan) (weighted mean difference [WMD]: 24.32; 95% CI: 12.96 to 35.68; P < 0.001). With regard to in-hospital mortality, although the mortality rate in the plasmapheresis group was higher than that in the conventional treatment group (relative risk [RR]: 1.74; 95% CI: 1.03 to 2.94; P = 0.038), the result was disturbed by confounding factors as per the subgroup and sensitivity analysis, as well as trial sequential analysis (TSA). No significant differences were found in other outcomes, including systematic complications, local complications, the requirement for surgery, and hospitalization duration. CONCLUSION: The effect of plasmapheresis in HTG-induced AP is not superior to that of conventional treatment, even resulting in a greater economic burden to patients and health care system. High quality randomized control trials are required to obtain a more a definitive understanding of this issue.


Asunto(s)
Hipertrigliceridemia , Pancreatitis , Humanos , Pancreatitis/complicaciones , Pancreatitis/terapia , Enfermedad Aguda , Plasmaféresis/métodos , Hipertrigliceridemia/complicaciones , Hipertrigliceridemia/terapia , Triglicéridos , Estudios Retrospectivos
6.
Org Lett ; 24(14): 2684-2688, 2022 04 15.
Artículo en Inglés | MEDLINE | ID: mdl-35389665

RESUMEN

Chevalinulins A (1) and B (2), two indole diketopiperazine alkaloids containing an unprecedented spiro[bicyclo[2.2.2]octane-diketopiperazine] skeleton, together with a known analogue neoechinulin B (3), were isolated from the deep-sea cold-seep-derived fungus Aspergillus chevalieri CS-122. Their structures were determined by spectroscopic analysis, single-crystal X-ray diffraction, specific rotation (SR), and NMR calculations. Compounds 1 and 2 exhibited significant in vivo proangiogenic activity in transgenic zebrafish.


Asunto(s)
Alcaloides , Dicetopiperazinas , Alcaloides/química , Animales , Aspergillus , Dicetopiperazinas/química , Hongos , Alcaloides Indólicos/química , Estructura Molecular , Octanos , Esqueleto , Pez Cebra
7.
Mar Drugs ; 20(1)2021 Dec 21.
Artículo en Inglés | MEDLINE | ID: mdl-35049858

RESUMEN

Six new metabolites, including a pair of inseparable mixtures of secofumitremorgins A (1a) and B (1b), which differed in the configuration of the nitrogen atom, 29-hydroxyfumiquinazoline C (6), 10R-15-methylpseurotin A (7), 1,4,23-trihydroxy-hopane-22,30-diol (10), and sphingofungin I (11), together with six known compounds (2-5 and 8-9), were isolated and identified from the deep-sea sediment-derived fungus Aspergillus fumigatus SD-406. Their structures were determined by detailed spectroscopic analysis of NMR and MS data, chiral HPLC analysis of the acidic hydrolysate, X-ray crystallographic analysis, J-based configuration analysis, and quantum chemical calculations of ECD, OR, and NMR (with DP4+ probability analysis). Among the compounds, 1a/1b represent a pair of novel scaffolds derived from indole diketopiperazine by cleavage of the amide bond following aromatization to give a pyridine ring. Compounds 1, 4, 6, 7, 10 and 11 showed inhibitory activities against pathogenic bacteria and plant pathogenic fungus, with MIC values ranging from 4 to 64 µg/mL.


Asunto(s)
Antibacterianos/farmacología , Aspergillus fumigatus , Microbiología del Suelo , Animales , Antibacterianos/química , Organismos Acuáticos , Cristalografía por Rayos X , Fusarium/efectos de los fármacos , Sedimentos Geológicos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Pseudomonas aeruginosa/efectos de los fármacos
8.
Huan Jing Ke Xue ; 34(1): 51-60, 2013 Jan.
Artículo en Chino | MEDLINE | ID: mdl-23487918

RESUMEN

The distribution and estuarine behavior of fluorescent components of chromophoric dissolved organic matter in the seawater of outer Yangtze Estuary were determined by fluorescence excitation emission matrix spectra combined with parallel factor analysis. Six individual fluorescent components were identified by PARAFAC models, including three terrestrial humic-like components C1 [330 nm/390(430) nm], C2 (390 nm/480 nm), C3 (360 nm/440 nm), marine biological production component C5 (300 nm/400 nm) and protein-like components C4 (290 nm/350 nm) and C6 (275 nm/300 nm). The results indicated that C1, C2, and C3 showed a conservative mixing behavior in the whole estuarine region, especially in high-salinity region. And the fluorescence intensity proportion of C1 and C3 decreased with increase of salinity and fluorescence intensity proportion of C2 kept constant with increase of salinity in the whole estuarine region. While C4 showed conservative mixing behavior in low-salinity region and non-conservative mixing behavior in high-salinity region, and fluorescence intensity proportion of C4 increased with increase of salinity. However, C5 and C6 showed a non-conservative mixing behavior and fluorescence intensity proportion increased with increase of salinity in high-salinity region. Significantly spatial difference was recorded for CDOM absorption coefficient in the coastal region and in the open water areas with the highest value in coastal region and the lowest value in the open water areas. The scope of absorption coefficient and absorption slope was higher in coastal region than that in the open water areas. Significantly positive correlations were found between CDOM absorption coefficient and the fluorescence intensities of C1, C2, C3, and C4, but no significant correlation was found between C5 and C6, suggesting that the river inputs contributed to the coastal areas, while CDOM in the open water areas was affected by terrestrial inputs and phytoplankton degradation.


Asunto(s)
Monitoreo del Ambiente/métodos , Compuestos Orgánicos/análisis , Espectrometría de Fluorescencia/métodos , Contaminantes Químicos del Agua/análisis , China , Estuarios , Océanos y Mares , Ríos , Estaciones del Año , Agua de Mar/análisis , Contaminantes Químicos del Agua/metabolismo
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