scholarly journals 20-Nor-Isopimarane Epimers Produced by Aspergillus wentii SD-310, a Fungal Strain Obtained from Deep Sea Sediment

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 440 ◽  
Author(s):  
Xiao-Dong Li ◽  
Xin Li ◽  
Xiao-Ming Li ◽  
Gang-Ming Xu ◽  
Yang Liu ◽  
...  

Four new uncommon 20-nor-isopimarane diterpenoid epimers, aspewentins I−L (1–4), together with a new methylated derivative of 3, aspewentin M (5), were isolated from the deep sea sediment-derived fungus Aspergillus wentii SD-310. The very similar structures of these epimers made the separation and purification procedures difficult. The structures of compounds 1–5 were illustrated based on spectroscopic analysis, and the absolute configurations of compounds 1–5 were unambiguously determined by the combination of NOESY, time-dependent density functional (TDDFT)-ECD calculations, and X-ray crystallographic analysis. These metabolites represented the rare examples of 20-nor-isopimarane analogues possessing a cyclohexa-2,5-dien-1-one moiety. These compounds were tested for antimicrobial activities against human and aquatic pathogenic bacteria, as well as plant-pathogenic fungi. While compounds 1 and 2 exhibited inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli, Edwardsiella tarda, Vibrio harveyi, and V. parahaemolyticus, compound 5 showed potent activity against the plant pathogen Fusarium graminearum.

Marine Drugs ◽  
2019 ◽  
Vol 17 (10) ◽  
pp. 563 ◽  
Author(s):  
Xiao-Dong Li ◽  
Xiao-Ming Li ◽  
Xiu-Li Yin ◽  
Xin Li ◽  
Bin-Gui Wang

Two new antimicrobial bisabolane-type sesquiterpenoid derivatives, ent-aspergoterpenin C (compound 1) and 7-O-methylhydroxysydonic acid (2), and two new butyrolactone-type monoterpenoids, pestalotiolactones C (3) and D (4), along with a known monoterpenoid pestalotiolactone A (5) and four known bisabolane sesquiterpenoids (6−9), were isolated and identified from the deep-sea sediment-derived fungus Aspergillus versicolor SD-330. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the absolute configurations of the new compounds 1−4 were determined by the combination of NOESY and TDDFT-ECD calculations and X-ray crystallographic analysis. Additionally, we first determined and reported the absolute configuration of the known monoterpenoid pestalotiolactone A (5) through the X-ray crystallographic experiment. All of these isolated compounds were evaluated for antimicrobial activities against human and aquatic pathogenic bacteria. Compounds 1, 2, 6 and 9 exhibited selective inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli, Edwardsiella tarda, Vibrio anguillarum and V. harveyi, with MIC values ranging from 1.0 to 8.0 μg/mL.


Marine Drugs ◽  
2021 ◽  
Vol 20 (1) ◽  
pp. 4
Author(s):  
Li-Hong Yan ◽  
Xiao-Ming Li ◽  
Lu-Ping Chi ◽  
Xin Li ◽  
Bin-Gui Wang

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.


Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 553
Author(s):  
Yan-He Li ◽  
Xiao-Ming Li ◽  
Xin Li ◽  
Sui-Qun Yang ◽  
Xiao-Shan Shi ◽  
...  

Nine secondary metabolites (1–9), including two new polyketide derivatives 9-dehydroxysargassopenilline A (4) and 1,2-didehydropeaurantiogriseol E (5), along with seven known related secondary metabolites (1–3 and 6–9), were isolated and identified from the deep sea-derived fungus Penicilliumcyclopium SD-413. Their structures were elucidated on the basis of 1D/2D NMR spectroscopic and mass spectrometric analysis and the absolute configurations were determined by the combination of NOESY correlations and time-dependent density functional (TDDFT) ECD calculations. Compounds 1–9 inhibited some pathogenic bacteria including Escherichia coli, E. ictaluri, Edwardsiella tarda, Micrococcus luteus, Vibrio anguillarum, and V. harveyi, with MIC (minimum inhibitory concentration) values ranging from 4 to 32 μg/mL.


Planta Medica ◽  
2016 ◽  
Vol 82 (09/10) ◽  
pp. 877-881 ◽  
Author(s):  
Xiao-Dong Li ◽  
Xin Li ◽  
Xiao-Ming Li ◽  
Gang-Ming Xu ◽  
Peng Zhang ◽  
...  

RSC Advances ◽  
2016 ◽  
Vol 6 (79) ◽  
pp. 75981-75987 ◽  
Author(s):  
Xin Li ◽  
Xiao-Ming Li ◽  
Xiao-Dong Li ◽  
Gang-Ming Xu ◽  
Yang Liu ◽  
...  

Five new 20-nor-isopimaranes, asperethers A–E (1–5), were isolated from the deep-sea derived fungus Aspergillus wentii SD-310. These compounds possess a unique 6/6/6/5 tetracyclic system and exhibited cytotoxicity against several tumor cell lines.


2014 ◽  
Vol 37 (2) ◽  
pp. 145-158 ◽  
Author(s):  
Sarkar MA Kawsar ◽  
Abul K MS Kabir ◽  
Mohammad M R Bhuiyan ◽  
Jannatul Ferdous ◽  
Mohammad S Rahman

Regioselective pentanoylation of methyl 4,6-O-(4-methoxybenzylidene)-?-D-glucopyranoside by the direct acylation method provided the methyl 4,6-O-(4-methoxybenzylidene)-2-O-pentanoyl- ?-D-glucopyranoside in good yield. A number of 3-O-acyl derivatives of this 2-O-pentanoylation product were also prepared in order to obtain new compounds and also gather additional information for structure elucidation. The chemical structure of the newly synthesized compounds was characterized by analytical and spectral methods. Synthesized acylated derivatives of Dglucopyranoside were screened for in vitro antimicrobial activities against ten human pathogenic bacteria and four plant pathogenic fungi. The study revealed that the acylated products exhibited moderate to good antimicrobial activities. It was interesting to observe that the selected compounds were more sensitive against fungal phytopathogens than those of the bacterial strains. DOI: http://dx.doi.org/10.3329/jbas.v37i2.17554 Journal of Bangladesh Academy of Sciences, Vol. 37, No. 2, 145-158, 2013


RSC Advances ◽  
2017 ◽  
Vol 7 (8) ◽  
pp. 4387-4394 ◽  
Author(s):  
Xin Li ◽  
Xiao-Dong Li ◽  
Xiao-Ming Li ◽  
Gang-Ming Xu ◽  
Yang Liu ◽  
...  

Wentinoids A–F (1–6), presented as the first examples of isopimarane analogues from the fungus Aspergillus wentii, were isolated and identified.


Author(s):  
Kwang Seung Park ◽  
Myoung-Ki Hong ◽  
Jin Wan Jeon ◽  
Ji Hwan Kim ◽  
Jeong Ho Jeon ◽  
...  

Metallo-β-lactamases (MBLs) are present in major Gram-negative pathogens and environmental species, and pose great health risks because of their ability to hydrolyze the β-lactam rings of antibiotics such as carbapenems. PNGM-1 was the first reported case of a subclass B3 MBL protein that was identified from a metagenomic library from deep-sea sediments that predate the antibiotic era. In this study, PNGM-1 was overexpressed, purified and crystallized. Crystals of native and selenomethionine-substituted PNGM-1 diffracted to 2.10 and 2.30 Å resolution, respectively. Both the native and the selenomethionine-labelled PNGM-1 crystals belonged to the monoclinic space group P21, with unit-cell parameters a = 122, b = 83, c = 163 Å, β = 110°. Matthews coefficient (V M) calculations suggested the presence of 6–10 molecules in the asymmetric unit, corresponding to a solvent content of ∼31–58%. Structure determination is currently in progress.


2013 ◽  
Vol 5 (3) ◽  
pp. 515-525 ◽  
Author(s):  
M. M. Matin ◽  
M. M. H. Bhuiyan ◽  
A. Afrin ◽  
D. C. Debnath

A number of furanose (2,4) and pyranose (5,7,9,11,13) acetates were prepared by direct acetylation method. For comparative antimicrobial studies sucrose octaacetate (14) was also prepared. All the compounds (1-14) were screened for in vitro antibacterial activity against ten human pathogenic bacteria viz. Bacillus subtilis, Bacillus cereus, Bacillus megaterium, Staphylococcus aureus, Escherichia coli, INABA ET (Vibrio), Pseudomonas species, Salmonella paratyphi, Salmonella typhi and Shigella dysenteriae. These compounds were also screened for in vitro antifungal activity against four pathogenic fungi viz. Aspergillus niger, Alternaria alternata, Curvularia lunata and Fusarium equiseti. The study revealed that the pyranose acetate derivatives (5,7,9,11,13) are more prone towards antimicrobial functionality than those of the furanose acetates (2,4) and sucrose octaacetate (14).  Keywords: Glucofuranose; Glucopyranose; Acetylation; Antimicrobial activity; Structure activity relationship (SAR).  © 2013 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved.  doi: http://dx.doi.org/10.3329/jsr.v5i3.15695 J. Sci. Res. 5 (3), 515-525 (2013)


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