scholarly journals Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213

Marine Drugs ◽  
2020 ◽  
Vol 18 (10) ◽  
pp. 513
Author(s):  
Hirotaka Matsuo ◽  
Rei Hokari ◽  
Aki Ishiyama ◽  
Masato Iwatsuki ◽  
Mayuka Higo ◽  
...  
Keyword(s):  
Optical Rotation ◽  
Hybrid Structure ◽  
Culture Broth ◽  
Nmr Data ◽  
1H Nuclear Magnetic Resonance ◽  
Ic50 Values ◽  
Hela S3 ◽  
Hydrolysis Of ◽  
Fcr3 Strain ◽  
New Metabolites

Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicilliumsteckii FKJ-0213 together with the known compounds tanzawaic acid B (3) and trichodermamide C (4) by physicochemical (PC) screening. The structures of 1 and 2 were determined as a tanzawaic acid B-trichodermamide C hybrid structure and a new analog of aspergillazines, respectively. The absolute configuration of 1 was determined by comparing the values of tanzawaic acid B and trichodermamide C in the literatures, such as 1H-nuclear magnetic resonance (1H-NMR) data and optical rotation, after hydrolysis of 1. Compounds 1–4 were evaluated for cytotoxicity and anti-malarial activities. Compounds 1 and 3 exhibited weak anti-malarial activity at half-maximal inhibitory concentration (IC50) values of 27.2 and 78.5 µM against the K1 strain, and 27.9 and 79.2 µM against the FCR3 strain of Plasmodium falciparum, respectively. Furthermore, 1 exhibited cytotoxicity against HeLa S3, A549, Panc1, HT29 and H1299 cells, with IC50 values of 15.0, 13.7, 12.9, 6.8, and 18.7 μM, respectively.

scholarly journals Two New Phomaligols from the Marine-Derived Fungus Aspergillus flocculosus and Their Anti-Neuroinflammatory Activity in BV-2 Microglial Cells

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 65
Author(s):  
Byeoung-Kyu Choi ◽  
Duk-Yeon Cho ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
Hee Jae Shin
Keyword(s):  
Nitric Oxide ◽  
Mass Spectrometry ◽  
Optical Rotation ◽  
Chemical Oxidation ◽  
Culture Broth ◽  
Membered Ring ◽  
Microglial Cells ◽  
No Production ◽  
Nmr Data ◽  
Ic50 Value

Two new phomaligols, deketo-phomaligol A (1) and phomaligol E (2), together with six known compounds (3–8) were isolated from the culture broth of the marine-derived fungus Aspergillus flocculosus. Compound 1 was first isolated as a phomaligol derivative possessing a five-membered ring. The structures and absolute configurations of the new phomaligols were determined by detailed analyses of mass spectrometry (MS), nuclear magnetic resonance (NMR) data, optical rotation values and electronic circular dichroism (ECD). In addition, the absolute configurations of the known compounds 3 and 4 were confirmed by chemical oxidation and comparison of optical rotation values. Isolated compounds at a concentration of 100 μM were screened for inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells. Among the compounds, 4 showed moderate anti-neuroinflammatory effects with an IC50 value of 56.6 μM by suppressing the production of pro-inflammatory mediators in activated microglial cells without cytotoxicity.

scholarly journals A Degradation Product from Hydrolysate of Imipenem with Imis Broad-Spectrum Inhibits Metallo-β-Lactamases

2020 ◽  
Vol 13 (10) ◽  
Author(s):  
Ying Ge ◽  
Li-Wei Xu ◽  
Jian-Bin Zhen ◽  
Cheng Chen ◽  
Miao Lv ◽  
...  
Keyword(s):  
Broad Spectrum ◽  
Degradation Product ◽  
Substrate Inhibition ◽  
Resistant Bacteria ◽  
Drug Resistant ◽  
Antibiotic Resistant Bacteria ◽  
Antibiotic Resistant ◽  
Leaving Group ◽  
Ic50 Values ◽  
Hydrolysis Of

Background: Infections caused by metallo-β-lactamases (MβLs)-producing antibiotic-resistant bacteria pose a severe threat to public health. The synergistic use of current antibiotics in combination with MβL inhibitors is a promising therapeutic mode against these antibiotic-resistant bacteria. Objectives: The study aimed to probe the inhibition of MβLs and obtain the active component, P1, in the degradation product after imipenem was hydrolyzed by ImiS. Methods: The hydrolysis of two carbapenems with MβL ImiS was monitored by UV-Vis in real-time, and the degradation product from the leaving group produced after imipenem was hydrolyzed (but not for faropenem) was purified by HPLC to give one component, P1. Results: Kinetic assays revealed that P1 exhibited a broad-spectrum inhibition against VIM-2, NDM-1, ImiS, and L1, from three sub-classes of MβLs, with IC50 values of 8 - 32, 13.8 - 29.3, and 14.2 - 19.2 µM, using imipenem, cefazolin, and nitrocefin as substrates, respectively. Also, P1 showed synergistic antibacterial efficacy against drug-resistant Escherichia coli producing VIM-2, NDM-1, ImiS, and L1, in combination with antibiotics, restoring 16 to 32-fold and 32 to 128-fold efficacies of imipenem and cefazolin, respectively. Spectroscopic and Ellman's reagent analyses suggested that P1, a mercaptoethyl-form imidamide, is a mechanism-based inhibitor, while faropenem has no substrate inhibition, due to the lack of a leaving group. Conclusions: This work reveals that the hydrolysate of imipenem, a carbapenem with a good leaving group, can be used in screening for broad-spectrum inhibitors of MβLs.

scholarly journals Restricticin B from the Marine Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

2020 ◽  
Author(s):  
Byeonung-Kyu Choi ◽  
Shin-Young Park ◽  
Song-Hee Jo ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Optical Rotation ◽  
2D Nmr ◽  
Marine Fungus ◽  
No Production ◽  
Spectroscopy Data ◽  
Penicillium Janthinellum ◽  
Etoac Extract ◽  
Data Comparison ◽  
Nmr Data

A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2-5) were obtained from the EtOAc extract of the marine fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via analyses of NOESY spectroscopy data, comparison of optical rotation values with those of restricticin derivatives reported and electronic circular dichroism (ECD). All the compounds were screened for their anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced BV-2 microglia cells. Restricticin B (1) and N-acetyl restricticin (2) exhibited anti-neuroinflammatory effects by suppressing the production of pro-inflammatory mediators in activated microglial cells.

scholarly journals Chemical Constituents from Scindapsus officinalis (Roxb.) Schott. and Their Anti–Inflammatory Activities

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2577 ◽  
Author(s):  
Hongjing Dong ◽  
Yanling Geng ◽  
Xueyong Wang ◽  
Xiangyun Song ◽  
Xiao Wang ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
2D Nmr ◽  
No Production ◽  
Inhibitory Effects ◽  
Nmr Data ◽  
Extensive Analysis ◽  
Ic50 Values ◽  
Monoterpene Glycoside ◽  
Anti Inflammatory

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4–7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 ± 0.8 and 18.9 ± 0.3 μM, respectively.

scholarly journals THE INTERRELATION OF THE SURVIVING HEART AND PANCREAS OF THE DOG IN SUGAR METABOLISM

1917 ◽  
Vol 26 (5) ◽  
pp. 721-744 ◽  
Author(s):  
Admont H. Clark
Keyword(s):  
Optical Rotation ◽  
Reducing Power ◽  
Sugar Metabolism ◽  
Weak Acid ◽  
Perfused Pancreas ◽  
Melting Points ◽  
Optical Rotations ◽  
Normal Utilization ◽  
Hydrolysis Of ◽  
Reducing Properties

When the pancreas of a dog is perfused aseptically with a Locke's solution containing dextrose in physiological concentrations, the optical rotation of the perfusate is diminished, but its reducing power is unaltered. This change also occurs if dextrose is added to a sugarfree pancreatic perfusate and the mixture incubated. These perfusates yield osazones with lower melting points than glucosazone, but when the perfusates are hydrolyzed with weak acid their optical, rotations and the melting points of their osazones are increased. These changes do not occur with levulose, or with an extract of the pancreas and dextrose. When the heart, spleen, or kidneys are perfused with dextrose solutions hydrolysis of the perfusates does not increase their optical rotation or power of reduction. When a pancreatic perfusate containing dextrose is circulated through a living heart not only do the above changes take place but, in addition, the reducing properties of the perfusate are altered. Hydrolysis of such a perfusate increases its reducing power, its optical rotation, and the melting point of its osazone. A heart does not cause this effect either alone or when perfused together with the spleen or kidneys. Levulose perfused through the heart and pancreas is unchanged. These phenomena are believed to be due to an enzyme or enzymes obtained from the perfused pancreas. The changes in optical rotation, in reduction, and in the osazones are accounted for by different degrees of dextrose condensation. While the living heart can destroy both dextrose and levulose to some extent, the experimental results suggest that the enzyme or enzymes derived from the perfused pancreas have a specific action on dextrose and are responsible for certain essential steps by which dextrose is prepared for normal utilization.

scholarly journals Chemical and physical properties of an arabinogalactan-peptide from wheat endosperm

1974 ◽  
Vol 139 (3) ◽  
pp. 535-545 ◽  
Author(s):  
G. B. Fincher ◽  
W. H. Sawyer ◽  
B. A. Stone
Keyword(s):  
Optical Rotation ◽  
Subcellular Location ◽  
Successive Treatment ◽  
Partial Acid Hydrolysis ◽  
Wheat Endosperm ◽  
Anomeric Configuration ◽  
Molecular Core ◽  
Tentative Model ◽  
And Function ◽  
Hydrolysis Of

1. An arabinogalactan-peptide from wheat endosperm was studied by using physicochemical techniques and some aspects of its chemical structure were determined. 2. The arabinogalactan-peptide is a non-associating, polydisperse macromolecule ([unk]=22000) which exhibits only minor non-ideal effects in aqueous solution. 3. Examination of the products of partial acid hydrolysis of the polysaccharide component showed that arabinose is present in the α-l-arabinofuranosyl configuration, and i.r.-absorption spectroscopy and optical-rotation studies suggest that the d-galactopyranose residues are linked by glycosidic linkages in the β-anomeric configuration. 4. The arabinogalactan is linked to a peptide which represents 8% (w/w) of the arabinogalactan-peptide and which may be present as a molecular core. Partial degradation of the polymer by successive treatment with oxalic acid and NaOH showed that the linkage between polysaccharide and peptide involves galactose and hydroxyproline residues and is glycosidic in nature. A tentative model is proposed for the structure of the wheat endosperm arabinogalactan-peptide. 5. The subcellular location and function of the arabinogalactan-peptide is discussed in relation to previous work with related molecules.

scholarly journals Cytotoxic Polyketides from the Marine Sponge-Derived Fungus Pestalotiopsis heterocornis XWS03F09

Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2655 ◽  
Author(s):  
Lei ◽  
Lei ◽  
Zhou ◽  
Hu ◽  
Niu ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Fermentation Broth ◽  
Human Cancer ◽  
Optical Rotation ◽  
Cytotoxic Activities ◽  
Human Cancer Cell Lines ◽  
Chemical Structures ◽  
Ic50 Values ◽  
New Compounds

Four new compounds, including two new polyketides, heterocornols M and N (1, 2), and a pair of epimers, heterocornols O and P (3, 4), were isolated from the fermentation broth of the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09, together with three known compounds (5–7). The new chemical structures were established on the basis of a spectroscopic analysis, optical rotation, experimental and calculated electronic circular dichroism (ECD). All of the compounds (1–7) were evaluated for their cytotoxic activities, and heterocornols M-P (1–4) exhibited cytotoxicities against four human cancer cell lines with IC50 values of 20.4–94.2 μM.

Organophosphorverbindungen mit tertiären Alkylsubstituenten. III*: Synthese und Reaktionen Di-1-adamantylsubstituierter Phosphorverbindungen; Kristallstruktur von Di-1-Adamantylphosphinsäurechlorid / Organophosphorus Compounds with Tertiary Alkyl Substituents. Ill: Synthesis and Reactions of Di-1-adam antyl-Substituted Phosphorus Compounds; Crystal Structure of Di-1-adam antylphosphinic Chloride

1994 ◽  
Vol 49 (6) ◽  
pp. 801-811 ◽  
Author(s):  
Jens R. Goerlich ◽  
Axel Fischer ◽  
Peter G. Jones ◽  
Reinhard Schmutzler
Keyword(s):  
Organophosphorus Compounds ◽  
Phosphorus Compounds ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
X Ray ◽  
Dry Air ◽  
Nmr Data ◽  
Standard Procedures ◽  
Hydrolysis Of ◽  
Tertiary Alkyl

The reaction of adamantane with PCl3/A1Cl3, followed by hydrolysis, gave (1-Ad)2P(:O)Cl 1, which was converted to (1-Ad)2P(:O)F 2 and (1-Ad)2P(:S)Cl 3 by standard procedures. The structure of 1 was confirmed by a single crystal X-ray structure determination; despite the bulky substituents the P-C bond lengths are normal (184.0(3), 185.0(3) pm). Whereas chlorine-fluorine exchange in 3 with AsF3 furnished (1-Ad)2P(:S)F 4, desulfuration of 3 with Ph3P to give (1-Ad)2PCl 5 failed. The secondary phosphine oxides R 1R2P(:O)H (R1, R2 = 1-Ad: 6; R1 = 1-Ad, R2 = tBu: 7; R1, R2 = tBu: 8) were synthesized by reaction of 1, 1-AdP(:O)Cl2 and tBuP(:0)Cl2 with tBuLi. 6 and 8 reacted readily with chloral to give the adducts R2P(:O)CH(OH)CCl3 (R = 1-Ad: 9; R = tBu: 10). Silylation of 6 with Me2NSiMe3 in the presence of dry air led to (1-Ad)2P(:O)OSiMe3 11, which was hydrolyzed to give (1-Ad)2P(:O)OH 12. (1-Ad)2POSiMe3 13 was obtained by the reaction of 6 with n-BuLi, followed by Me3SiCl. No reaction took place upon heating 6 with Mo(CO)6. (1-Ad)2PCl 5 was synthesized in low yield by the reaction of 6 with PCl3. The action of tetrachloro-obenzoquinone (TOB) upon 6 furnished (1-Ad)2P(:O)(o-OH)C6Cl4 15, whereas the tbutyl analogue of 15, 16, was synthesized by hydrolysis of the TOB-adduct of di-tbutylfluorophosphine. Analogous 1-adamantyl- and tbutyl-phosphorus compounds are compared with regard to their 31P NMR data

THE PREPARATION OF L-α-GLYCERYLPHOSPHORYLCHOLINE FROM LECITHINS

1955 ◽  
Vol 33 (5) ◽  
pp. 761-766 ◽  
Author(s):  
N. H. Tattrie ◽  
C. S. McArthur
Keyword(s):  
Cadmium Chloride ◽  
Inorganic Salt ◽  
Optical Rotation ◽  
Chloride Complex ◽  
Ion Exchange Resins ◽  
Aqueous Alcohol ◽  
Synthetic Compound ◽  
Exchange Resins ◽  
Hydrolysis Of ◽  
Crude Lecithin

Investigation of the hydrolysis of phosphatidylcholines (lecithins) in hot aqueous alcohol under the influence of mercuric chloride has shown that glycerylphosphorylcholine is formed and that neither racemization nor migration of the phosphorylcholine moiety occurs. The fatty acids are split off much more rapidly than is choline and as a consequence appreciable amounts of glycerylphosphorylcholine are formed. On the basis of these observations a procedure was devised for the hydrolysis of crude lecithin and the isolation of glycerylphosphorylcholine in a yield of 69%. The product was identified as L-α-glycerylphosphorylcholine by analysis of its cadmium chloride complex, and comparison of its optical rotation with that of the synthetic compound of known configuration. Recovery of the diester from this complex was accomplished through removal of the inorganic salt by ion-exchange resins and the free L-α-glycerylphosphorylcholine was crystallized from 99% ethanol.

Synthesis of anisomycin. Part I. The stereospecific synthesis of N-benzoyl-2-(p-methoxybenzyl)-3-hydroxy-4-carboxamido pyrrolidine and the absolute configuration of anisomycin

1968 ◽  
Vol 46 (7) ◽  
pp. 1101-1104 ◽  
Author(s):  
C. M. Wong
Keyword(s):  
Infrared Spectra ◽  
Absolute Configuration ◽  
Optical Rotation ◽  
Specific Rotation ◽  
Stereospecific Synthesis ◽  
Specific Optical Rotation ◽  
Synthetic Compound ◽  
The Absolute ◽  
Hydrolysis Of ◽  
Absolute Stereochemistry

L-Tyrosine was converted stereospecifically to N-benzoyl-2-(p-methoxybenzyl)-3-hydroxy-4-cyanopyrrolidine (10) which had a specific optical rotation [Formula: see text]. Anisomycin was converted also to N-benzoyl-2-(p-methoxybenzyl)-3-hydroxy-4-cyanopyrrolidine (16) which had a specific rotation [Formula: see text]. The infrared spectra of the synthetic compound and the derivative of anisomycin were superimposable with each other. This result showed that the absolute configuration of the three asymmetric centers in (10) of synthetic origin were 2S, 3S, 4S, and those in (16) were 2R, 3R, 4R. Thus, anisomycin should have the absolute stereochemistry 2R, 3S, 4S as depicted in the structure (2). Hydrolysis of the hydroxy nitriles (8) and (10) gave an identical amide (3) which should have the absolute stereochemistry 2S, 3S, 4R as shown in structure (3).

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