scholarly journals Antimicrobial Sesquiterpenoid Derivatives and Monoterpenoids from the Deep-Sea Sediment-Derived Fungus Aspergillus versicolor SD-330

Marine Drugs ◽  
2019 ◽  
Vol 17 (10) ◽  
pp. 563 ◽  
Author(s):  
Xiao-Dong Li ◽  
Xiao-Ming Li ◽  
Xiu-Li Yin ◽  
Xin Li ◽  
Bin-Gui Wang
Keyword(s):  
Deep Sea ◽  
Pathogenic Bacteria ◽  
Vibrio Anguillarum ◽  
Antimicrobial Activities ◽  
Crystallographic Analysis ◽  
Edwardsiella Tarda ◽  
Aspergillus Versicolor ◽  
Deep Sea Sediment ◽  
X Ray ◽  
The Absolute

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.

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 ◽  
...  
Keyword(s):  
Deep Sea ◽  
Density Functional ◽  
Pathogenic Bacteria ◽  
Pathogenic Fungi ◽  
Antimicrobial Activities ◽  
Crystallographic Analysis ◽  
Edwardsiella Tarda ◽  
Separation And Purification ◽  
Deep Sea Sediment ◽  
Aspergillus Wentii

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.

scholarly journals Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 160 ◽  
Author(s):  
Lu-Ping Chi ◽  
Xiao-Ming Li ◽  
Li Li ◽  
Xin Li ◽  
Bin-Gui Wang
Keyword(s):  
Deep Sea ◽  
Disulfide Bridge ◽  
Positive Control ◽  
Crystallographic Analysis ◽  
X Ray ◽  
Spectrometric Data ◽  
Epicoccum Nigrum ◽  
Culture Extract ◽  
The Absolute ◽  
Detailed Interpretation

Four new thiodiketopiperazine alkaloids, namely, 5’-hydroxy-6’-ene-epicoccin G (1), 7-methoxy-7’-hydroxyepicoccin G (2), 8’-acetoxyepicoccin D (3), and 7’-demethoxyrostratin C (4), as well as a pair of new enantiomeric diketopiperazines, (±)-5-hydroxydiphenylalazine A (5), along with five known analogues (6–10), were isolated and identified from the culture extract of Epicoccum nigrum SD-388, a fungus obtained from deep-sea sediments (−4500 m). Their structures were established on the basis of detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis confirmed the structures and established the absolute configurations of compounds 1–3, while the absolute configurations for compounds 4 and 5 were determined by ECD calculations. Compounds 4 and 10 showed potent activity against Huh7.5 liver tumor cells, which were comparable to that of the positive control, sorafenib, and the disulfide bridge at C-2/C-2’ is likely essential for the activity.

scholarly journals Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus Aspergillus fumigatus SD-406

Marine Drugs ◽  
2021 ◽  
Vol 20 (1) ◽  
pp. 4
Author(s):  
Li-Hong Yan ◽  
Xiao-Ming Li ◽  
Lu-Ping Chi ◽  
Xin Li ◽  
Bin-Gui Wang
Keyword(s):  
Aspergillus Fumigatus ◽  
Deep Sea ◽  
Pathogenic Bacteria ◽  
Pathogenic Fungus ◽  
Crystallographic Analysis ◽  
Amide Bond ◽  
Chiral Hplc ◽  
Deep Sea Sediment ◽  
Ring Compounds ◽  
Antimicrobial Metabolites

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.

scholarly journals Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus Penicillium cyclopium SD-413

Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 553
Author(s):  
Yan-He Li ◽  
Xiao-Ming Li ◽  
Xin Li ◽  
Sui-Qun Yang ◽  
Xiao-Shan Shi ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Deep Sea ◽  
Density Functional ◽  
Pathogenic Bacteria ◽  
Micrococcus Luteus ◽  
Vibrio Anguillarum ◽  
2D Nmr ◽  
Edwardsiella Tarda ◽  
Spectrometric Analysis ◽  
Mic Minimum Inhibitory Concentration

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.

scholarly journals The novel metallo-β-lactamase PNGM-1 from a deep-sea sediment metagenome: crystallization and X-ray crystallographic analysis

2018 ◽  
Vol 74 (10) ◽  
pp. 644-649 ◽  
Author(s):  
Kwang Seung Park ◽  
Myoung-Ki Hong ◽  
Jin Wan Jeon ◽  
Ji Hwan Kim ◽  
Jeong Ho Jeon ◽  
...  
Keyword(s):  
Deep Sea ◽  
Metagenomic Library ◽  
Crystallographic Analysis ◽  
Monoclinic Space Group ◽  
The Novel ◽  
Unit Cell Parameters ◽  
Deep Sea Sediment ◽  
X Ray ◽  
Cell Parameters ◽  
Great Health

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.

scholarly journals Novel Harziane Diterpenes from Deep-Sea Sediment Fungus Trichoderma sp. SCSIOW21 and Their Potential Anti-Inflammatory Effects

Marine Drugs ◽  
2021 ◽  
Vol 19 (12) ◽  
pp. 689
Author(s):  
Hongxu Li ◽  
Xinyi Liu ◽  
Xiaofan Li ◽  
Zhangli Hu ◽  
Liyan Wang
Keyword(s):  
Deep Sea ◽  
2D Nmr ◽  
Crystallographic Analysis ◽  
Spectroscopic Methods ◽  
2D Nmr Spectroscopy ◽  
Deep Sea Sediment ◽  
X Ray ◽  
Trichoderma Sp ◽  
Anti Inflammatory ◽  
Inflammatory Effect

Five undescribed harziane-type diterpene derivatives, namely harzianol K (1), harzianol L (4), harzianol M (5), harzianol N (6), harzianol O (7), along with two known compounds, hazianol J (2) and harzianol A (3) were isolated from the deep-sea sediment-derived fungus Trichoderma sp. SCSIOW21. The relative configurations were determined by meticulous spectroscopic methods including 1D, 2D NMR spectroscopy, and HR-ESI-MS. The absolute configurations were established by the ECD curve calculations and the X-ray crystallographic analysis. These compounds (1, and 4–7) contributed to increasing the diversity of the caged harziane type diterpenes with highly congested skeleton characteristics. Harzianol J (2) exhibited a weak anti-inflammatory effect with 81.8% NO inhibition at 100 µM.

THE REACTION OF UNSATURATED CARBOHYDRATES WITH CARBON MONOXIDE AND HYDROGEN: V. ABSOLUTE STEREOCHEMISTRY OF ANHYDRODEOXYHEPTITOLS FROM 3,4,6-TRI-O-ACETYL-D-GLUCAL. STEREOCHEMISTRY OF HYDROFORMYLATION. CONFORMATIONAL ANALYSIS

1965 ◽  
Vol 43 (5) ◽  
pp. 1375-1381 ◽  
Author(s):  
Alex Rosenthal ◽  
Hans J. Koch
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Carbon Monoxide ◽  
Absolute Configuration ◽  
Sodium Iodide ◽  
Crystallographic Analysis ◽  
X Ray ◽  
Dicobalt Octacarbonyl ◽  
The Absolute ◽  
Compound Ii ◽  
Absolute Stereochemistry

3,4,6-Tri-O-acetyl-D-glucal reacted with carbon monoxide and hydrogen in the presence of dicobalt octacarbonyl to yield a mixture of two epimeric anhydrodeoxyheptitols, namely, 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-manno-heptitol (I) and 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-gluco-heptitol (II). De-O-acetylation of the mixture, followed by chromatographic separation, yielded crystalline 2,6-anhydro-3-deoxy-D-manno-heptitol (III) and 2,6-anhydro-3-deoxy-D-gluco-heptitol (IV). Reaction of the mixture of heptitols (I) and (II) with p-bromobenzenesulfonyl chloride, followed by fractional crystallization of the brosylates, gave pure 4,5,7-tri-O-acetyl-2,6-anhydro-1-O-(p-bromophenylsulfonyl)-3-deoxy-D-gluco-heptitol (VII). The absolute configuration of (VII) has been previously established by X-ray crystallographic analysis. The absolute configuration of (III) was established by correlation with that of (VII). The conversion of compound (II) into various derivatives is described.Reaction of 3,4,6-tri-O-acetyl-D-glucal with carbon monoxide and deuterium afforded 2,6-anhydro-3-deoxy-D-manno-heptitol-1,1,3-2H3 (XIII) and 2,6-anhydro-3-deoxy-D-gluco-heptitol-1,1,3-2H3 (XIV). Examination of the nuclear magnetic resonance (n.m.r.) spectra of the normal and deuterated anhydrodeoxyheptitols confirmed the structural assignments and showed that cis addition to the double bond took place to give (XIV).Comparison of the exchange reaction of sodium iodide with 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-1-O-tosyl-D-gluco-heptitol (VIII) and with 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-1-O-tosyl-D-manno-heptitol (XV) revealed that the equatorial primary tosyloxy group of (VIII) was exchanged by iodine twice as readily as the axial primary tosyloxy group of (XV).

scholarly journals Highly Substituted Benzophenone Aldehydes and Eremophilane Derivatives from the Deep-Sea Derived Fungus Phomopsis lithocarpus FS508

Marine Drugs ◽  
2018 ◽  
Vol 16 (9) ◽  
pp. 329 ◽  
Author(s):  
Jian-Lin Xu ◽  
Hong-Xin Liu ◽  
Yu-Chan Chen ◽  
Hai-Bo Tan ◽  
Heng Guo ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
A549 Cell ◽  
Marine Sediment ◽  
Deep Sea ◽  
Crystallographic Analysis ◽  
X Ray ◽  
Naturally Occurring ◽  
Ic50 Values ◽  
New Compounds

Five new benzophenone derivatives named tenellones D–H (1–5), sharing a rare naturally occurring aldehyde functionality in this family, and a new eremophilane derivative named lithocarin A (7), together with two known compounds (6 and 8), were isolated from the deep marine sediment-derived fungus Phomopsis lithocarpus FS508. All of the structures for these new compounds were fully characterized and established on the basis of extensive spectroscopic interpretation and X-ray crystallographic analysis. Compound 5 exhibited cytotoxic activity against HepG-2 and A549 cell lines with IC50 values of 16.0 and 17.6 μM, respectively.

scholarly journals 2,4-Dimethyl-3,4-O-isopropylidene-L-arabinono-1,5-lactone

2007 ◽  
Vol 63 (3) ◽  
pp. o1128-o1130 ◽  
Author(s):  
Kathrine V. Booth ◽  
David J. Watkin ◽  
Sarah F. Jenkinson ◽  
George W. J. Fleet
Keyword(s):  
Absolute Configuration ◽  
Crystallographic Analysis ◽  
Starting Material ◽  
Relative Configuration ◽  
X Ray ◽  
Boat Form ◽  
The Absolute

The relative configuration at C-2 of 2,4-dimethyl-3,4-O-isopropylidene-L-arabinono lactone, C10H16O5, which exists in the boat form, was unequivocally established by X-ray crystallographic analysis. The absolute configuration was determined by the use of 2-C-methyl-D-ribonolactone as a starting material.

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