scholarly journals Novel Antimicrobial Indolepyrazines A and B from the Marine-Associated Acinetobacter sp. ZZ1275

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 89 ◽  
Author(s):  
Komal Anjum ◽  
Sidra Kaleem ◽  
Wenwen Yi ◽  
Guowan Zheng ◽  
Xiaoyuan Lian ◽  
...  

Two new alkaloids indolepyrazines A (1) and B (2) were isolated from the marine-derived Acinetobacter sp. ZZ1275. Their structures were elucidated through extensive nuclear magnetic resonance (NMR) spectroscopic analyses, high resolution electrospray ionization mass spectroscopy (HRESIMS) data, and electronic circular dichroism (ECD) calculation. Indolepyrazine A represents the first example of alkaloids with an indole-pyrazine-oxindole skeleton. Both 1 and 2 showed antimicrobial activities against methicillin-resistant Staphylococcus aureus, Escherichia coli, and Candida albicans with minimum inhibitory concentration (MIC) values of 12 μg/mL, 8–10 μg/mL, and 12–14 μg/mL, respectively.

Marine Drugs ◽  
2019 ◽  
Vol 17 (5) ◽  
pp. 292 ◽  
Author(s):  
Tengfei Song ◽  
Mingmin Tang ◽  
Hengju Ge ◽  
Mengxuan Chen ◽  
Xiaoyuan Lian ◽  
...  

The marine-sourced fungus Penicillium sp. ZZ380 was previously reported to have the ability to produce a series of new pyrrospirone alkaloids. Further investigation on this strain resulted in the isolation and identification of novel penicipyrroether A and pyrrospirone J. Each of them represents the first example of its structural type, with a unique 6/5/6/5 polycyclic fusion that is different from the 6/5/6/6 fused ring system for the reported pyrrospirones. Their structures were elucidated by extensive nuclear magnetic resonance (NMR) and high resolution electrospray ionization mass spectroscopy (HRESIMS) spectroscopic analyses, electronic circular dichroism (ECD) and 13C NMR calculations and X-ray single crystal diffraction. Penicipyrroether A showed potent antiproliferative activity against human glioma U87MG and U251 cells with half maximal inhibitory concentration (IC50) values of 1.64–5.50 μM and antibacterial inhibitory activity with minimum inhibitory concentration (MIC) values of 1.7 μg/mL against methicillin-resistant Staphylococcus aureus and 3.0 μg/mL against Escherichia coli.


2019 ◽  
Vol 14 (12) ◽  
pp. 1934578X1989343
Author(s):  
Li Jiang ◽  
Yang Wang ◽  
Min-Hui Zhu ◽  
Lin Zheng ◽  
Lin-Zhen Li ◽  
...  

Two new compounds, rel-(3 S,4a R,10b R)-3-(4′-methoxyphenyl)-8-hydroxy-9-methoxy-4a,5,6,10b-tetrahydro-3 H-naphtho[2,1-b]pyran (1), 7-hydroxy- 2-phenylnaphthalene-1-carboxylic acid ethyl ester (2), were isolated from the 70% ethanol extract of the rhizomes of Musa basjoo. Their structures were determined on the basis of spectroscopic analysis including 1-dimensional (1D), 2D nuclear magnetic resonance and high-resolution electrospray ionization mass spectroscopy.


Marine Drugs ◽  
2020 ◽  
Vol 18 (5) ◽  
pp. 258 ◽  
Author(s):  
Sidra Kaleem ◽  
Le Qin ◽  
Wenwen Yi ◽  
Xiao-Yuan Lian ◽  
Zhizhen Zhang

Mariana Trench sediments are enriched in microorganisms, however, the structures and bioactivities of their secondary metabolites are not very known. In this study, a fungus Penicillium sp. SY2107 was isolated from a sample of Mariana Trench sediment collected at a depth of 11000 m and an extract prepared from the culture of this fungus in rice medium showed antimicrobial activities. Chemical investigation on this active extract led to the isolation of 16 compounds, including one novel meroterpenoid, named andrastone C. Structure of the new compound was elucidated based on high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses and a single crystal X-ray diffraction. The crystal structure of a known meroterpenoid andrastone B was also reported in this study. Both andrastones B and C exhibited antimicrobial activities against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, and Candida albicans with minimum inhibitory concentration (MIC) values in a range from 6 to 13 μg/mL.


2019 ◽  
Vol 14 (7) ◽  
pp. 1934578X1985997
Author(s):  
Huiyou Xu ◽  
Yatie Qiu ◽  
Jingxin Chen ◽  
Yan Shi ◽  
Xiaoqin Zhang ◽  
...  

A new cytisine-like alkaloid, hosimonoal (1), with a fused monoterpene group, and 6 known compounds (2-6) were isolated from the seeds of Ormosia hosiei Hemsl. et Wils. The structure of the new compound was confirmed by high resolution electrospray ionization mass spectroscopy (HRESIMS), 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and electronic circular dichroism, and the others by 1H and 13C NMR spectroscopy and comparison with the literature data. In addition, compounds 1, 2, 3, and 6 showed moderate cytotoxic effects against A2780, A-549, HepG2, and MCF-7 cell lines with IC50 values ranging from 5.7 to 36.5 μM.


2019 ◽  
Vol 38 (1) ◽  
pp. 29
Author(s):  
Joshua A Obaleye ◽  
Olufunso Olumide Abosede

Three new iron(III) complexes of doxycycline viz: [Fe(dox)2Cl]Cl2 (1), [Febpy(dox)Cl]Cl2 (2) and [Fephen(dox)Cl]Cl2 (3), where dox is doxycycline, bpy is 2,2ʹ-bipyridine and phen is 1,10-phenanthroline, were synthesized and characterized by elemental analysis, electronic absorption, FT-IR, and electrospray ionization mass spectroscopy. Doxycycline and the polypyridyl ligands behave as bidendate ligands; the polypyridyl ligands coordinate through the two diimine nitrogen atoms and doxycycline through enolate and diketoamide oxygen atoms of ring A in a five-coordinate system with chloride atom in the axial position. Their antibacterial and antiplasmodial activities against chloroquine-sensitive Plasmodium falciparum NF54 and their interaction with calf thymus (CT) DNA using electronic titration were investigated. The three complexes showed good activity against strains of Staphylococcus aureus and Klebsiella pneumonia. The complexes bind moderately to CT DNA with binding constants of 5.6 × 104 and 4.8 × 104 for complexes 2 and 3, respectively.


2013 ◽  
Vol 25 (1) ◽  
pp. 293 ◽  
Author(s):  
M. Bionaz ◽  
C. R. Ferreira ◽  
E. Monaco ◽  
R. G. Cooks ◽  
M. B. Wheeler

The measurement of end products of metabolism in combination with the dynamic measurement of the transcriptome can be a valuable approach to study complex processes, such as adipogenesis. For this purpose, we have combined the analysis of metabolic pathways using transcriptomics data with in situ lipid imaging obtained by desorption electrospray ionization–mass spectroscopy (DESI-MS). The transcriptome data was obtained from a previous experiment where adipose-derived stem cells (ASC) from 3 individual pigs were induced to differentiate into adipocytes for 21 days. The metabolic pathway analysis of transcriptomics data was performed using the dynamic impact approach (DIA) to determine the directional impact of pathways and gene categories. For the DESI-MS, porcine ASC were induced towards adipogenic differentiation (Monaco et al. 2009 Open Tissue Eng. Regen. Med. J. 2, 20–33) for 2 weeks in 24-well plates over round coverslips. Direct lipid profile of fatty acids and phospholipids in 3 different locations in undifferentiated and differentiated ASC was performed. Relative values of ion counts in each location were used for statistical analysis by means of a two-tailed t-test with unequal variance and false discovery rate (FDR) correction. The DIA uncovered amino acid and lipid metabolism as being the most affected pathways during adipogenesis. Among lipid-related pathways, the DIA indicated a strong induction during differentiation of unsaturation of fatty acids (FA) and metabolism of lipids, particularly triacylglycerol formation (TAG). The metabolism of tryptophan, phenylalanine, and histidine was strongly induced among amino acid-related metabolism. Among the lipid molecules identified in the mass-to-charge ratio (m/z) range of 250–1000 by the DESI-MS, >200 had significantly (FDR <0.01) lower abundance and ~30 lipids had higher abundance in differentiated compared with undifferentiated ASC. The lipid profile of undifferentiated cells was featured by a large amount of lipid molecules in the lower (m/z 780) mass range but with almost no signal in the intermediate range. The differentiated cells had a consistent large increase in amount of molecules in the range from m/z 500 to 650 and a decreased amount in the lower and upper ranges. Among the lipid molecules that decreased during differentiation, we identified several phospholipids, particularly phosphoserine and phosphoinositol species, but also linoleic, linolenic, arachidic, and eicosapentaenoic acids. The unsaturated FA oleate and docosahexaenate increased >10-fold and 2.2-fold, respectively, due to adipogenic differentiation. High-resolution experiments are being performed in order to annotate more, if not all, lipid species identified in the samples by DESI-MS. The DIA indicated greater unsaturation of FA during adipogenesis, confirmed by DESI-MS, which corresponds to the characteristic increase in lipid fractions with intermediate molecular mass. This can be considered a signature of adipogenesis in porcine ASC and essential for TAG formation. The DESI-MS appears to be a valuable tool for rapid lipid profile of cells and with the potential to be used to identify cell differentiation.


2019 ◽  
Vol 14 (8) ◽  
pp. 1934578X1986837
Author(s):  
Kazuki Tani ◽  
Takashi Kamada ◽  
Chin-Soon Phan ◽  
Charles S. Vairappan

A new cembranolide diterpene, sarcophytonolide V (1), along with 6 known compounds, isosarcophytonolide D (2), (4 Z,8 S*,9 R*,12 E,14 E)-9-hydroxy-1-(prop-1-en-2-yl)-8,12-dimethyl-oxabicyclo[9.3.2]-hexadeca-4,12,14-trien-18-one (3), (7 E,11 E)-3,4-epoxy-7,11,15-cembratriene (4), (1 S*,3 S*,4 S*,7 E,11 E)-3,4-epoxy-13-oxo-7,11,15-cembratriene (5), (-)-eunicenone (6), and 2-[( E, E, E)-7′,8′-epoxy-4′,8′,12′-trimethylcyclotetradeca-1′,3′,11′-trienyl]propan-2-ol (7) were isolated from the Bornean soft coral Sarcophyton sp. Their structures were elucidated based on spectroscopic data, such as nuclear magnetic resonance (NMR) and high resolution electron spray ionization mass spectroscopy (HRESIMS). These compounds were evaluated for their biological activity against marine pathogenic fungi.


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