Structure Elucidation of Azotobactin 87, Isolated from Azotobacter vinelandii ATCC 12837*, **

1996 ◽  
Vol 51 (3-4) ◽  
pp. 139-150 ◽  
Author(s):  
E. M. Schaffner ◽  
R. Hartmann ◽  
K. Taraz ◽  
H. Budzikiewicz
Keyword(s):  
Structure Elucidation ◽  
Culture Medium ◽  
Azotobacter Vinelandii ◽  
2D Nmr ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Hydroxybutyric Acid ◽  
Iron Deficient ◽  
N Terminus ◽  
Sequential Information

Abstract Chromopeptide siderophores (azotobactin 87-1 and -II) were isolated from an iron deficient culture medium of Azotobacter vinelandii ATCC 12837 (=DSM 87). Their structures were elu­ cidated by chemical degradation studies and spectroscopic methods, especially 2D-NMR-tech-niques. Total assignments of 1H-, 13C-, and 15N-resonances based on 2D-HOHAHA-, 1H/13C-HMQC-, 1H /13C-HMBC-, 1H /15N-HMQC/TOCSY-, and 1H/15N-HMBC-experiments are given as well as sequential information derived from 1H/1H-NOESY-, 1H /13C-HMBC-and 1H/ 13N-HMBC-experiments. Both Az 87-1 and Az 87-11 consist of a tetracyclic chromophore -(1S)8,9-dihydroxy-4-oxo-2,3,4,5-tetrahydro-1H,10cH-3a,5,10b-triazaacephenantrylene-1-carb-oxylic acid -and a decapeptide chain linked with the N-terminus to the carboxy group of the chromophore containing also modified, non-proteinogenic amino acids. The sequence L-Ser-D-Ser-L-Hse-Gly-D-threo-OHAsp-Hse-Hse-Hse-D-N5OH-N5-R-Hbu-Om-L-Hse was determined for Az 87-1, while Az 87-11 contains a C-terminal L-Hse-lactone instead. Iron is chelated by the catecholic group of the chromophore, the β-hydroxy aspartic acid, and the hydroxamate function formed by N5-hydroxyornithine and R-β-hydroxybutyric acid.

Catecholate Siderophores from Chryseomonas luteola

1996 ◽  
Vol 51 (5-6) ◽  
pp. 281-285 ◽  
Author(s):  
M. Adolphs ◽  
K. Taraz ◽  
H. Budzikiewicz
Keyword(s):  
Culture Medium ◽  
2D Nmr ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Iron Deficient ◽  
Nmr Techniques ◽  
Degradation Studies ◽  
Chryseomonas Luteola

Abstract Two catecholate siderophores (chrysobactin and chryseomonin) were isolated from an iron-deficient culture medium of Chryseomonas luteola. Their structures were elucidated by chemical degradation studies and spectroscopic methods, especially 2D-NMR techniques, and confirmed by synthesis. Chryseomonin constitutes a novel type of catecholate siderophore.

New Pyoverdin-Type Siderophores from Pseudomonas fluorescens

1990 ◽  
Vol 45 (10) ◽  
pp. 1437-1450 ◽  
Author(s):  
G. Mohn ◽  
K. Taraz ◽  
H. Budzikiewicz
Keyword(s):  
Carboxylic Acid ◽  
Pseudomonas Fluorescens ◽  
Carboxy Group ◽  
Culture Medium ◽  
Spectroscopic Methods ◽  
Amino Group ◽  
N Terminus ◽  
Short Hand ◽  
Degradation Studies

The structures of two new pyoverdins (GM-I and GM-II) isolated from the culture medium of Pseudomonas fluorescens have been elucidated by spectroscopic methods and degradation studies. The pyoverdins consist of a chromophore which could be identified as (1 S)-5-amino-2,3-dihydro-8,9-dihydroxy-1 H-pyrimido[1,2-a]quinoline-1-carboxylic acid substituted at the amino group with a 3-carboxypropanoyl or a succinamoyl residue and at the carboxy group with the N-terminus of D-Ala-D-Lys-Gly-Gly-D-threo-(OH)Asp-D-Glu-D-Ser-L-Ala-D-Ala-D-Ala-L-Ala-L-N5-(OH)Orn.According to the “short-hand” nomenclature proposed in [2]*** the two compounds should be characterized as pyoverdin-Q-akGGd'qsAaaAO′*-SUCA and pyoverdin-Q-akGGd'qsAaaAO′ *-SUC

The Structure Elucidation and Antimicrobial Activities of Nonsterol Triterpenoids from Ixeris chinensis

2014 ◽  
Vol 69 (9-10) ◽  
pp. 1021-1025 ◽  
Author(s):  
Qing-Hu Wang ◽  
Na-Ren-Chao-Ke-Tu Han ◽  
Na-Yin-Tai Dai ◽  
Xiao-Lan Wu ◽  
Wen-Quan Tai ◽  
...  
Keyword(s):  
Petroleum Ether ◽  
Structure Elucidation ◽  
Petroleum Ether Extract ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Spectroscopic Methods ◽  
Ether Extract ◽  
Esi Ms ◽  
Nmr Techniques ◽  
First Time

Abstract An investigation of the petroleum ether extract from Ixeris chinensis Nakai has led to the isolation of a new compound, 3-O-acetyl-22,28-cyclobauer-7-en-3β-ol (1), together with four known compounds which have been isolated from this plant for the first time, namely taraxast-20-en-3β-ol (2), 3-O-acetyl-taraxast-20-en-3β-ol (3), taraxast-20(30)-en-3β-ol (4), and 3-O-acetyl-taraxast-20(30)- en-3β-ol (5). The structures of the isolated compounds have been elucidated on the basis of spectroscopic methods including UV, IR, ESI-MS, 1D NMR, 2D NMR techniques, and by comparison with data reported in the literature. All compounds have been evaluated for their activity against various bacteria and shown to give good results

Staphyloferrin B, a Citrate Siderophore of Ralstonia eutropha

1999 ◽  
Vol 54 (11) ◽  
pp. 867-875 ◽  
Author(s):  
Maik Münzinger ◽  
Kambiz Taraz ◽  
Herbert Budzikiewicz
Keyword(s):  
Culture Medium ◽  
New Genus ◽  
Ralstonia Eutropha ◽  
Alcaligenes Eutrophus ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Relationship Of ◽  
The Relationship

Abstract The structure and stereochemistry of the siderophore isolated from the culture medium of Ralstonia eutropha (formerly Alcaligenes eutrophus) could be elucidated as staphyloferrin B by spectroscopic methods and chemical degradation. The relationship of the three species of the new genus Ralstonia is reflected in the observation that all three form citrate sidero-phores.

Achromobactin, a New Citrate Siderophore of Erwinia chrysanthemi

2000 ◽  
Vol 55 (5-6) ◽  
pp. 328-332 ◽  
Author(s):  
Maik Münzinger ◽  
Herbert Budzikiewicz ◽  
Dominique Expert ◽  
Corine Enard ◽  
Jean-Marie Meyer
Keyword(s):  
Culture Medium ◽  
Chemical Degradation ◽  
Erwinia Chrysanthemi ◽  
Spectroscopic Methods

The structure of a citrate siderophore named achromobactin isolated from the culture medium of Erwinia chrysanthemi was elucidated by spectroscopic methods and chemical degradation.

scholarly journals The Antitumor Antibiotics Complex of Aureolic Acids from the Marine Sediment-associated Strain of Streptomyces sp. KMM 9048

2017 ◽  
Vol 12 (4) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Nataliya I. Kalinovskaya ◽  
Lyudmila A. Romanenko ◽  
Anatoly I. Kalinovsky ◽  
Svetlana P. Ermakova ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Marine Sediment ◽  
Colony Formation ◽  
Structure Elucidation ◽  
Antimicrobial Agents ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Antitumor Antibiotics ◽  
Inhibitory Effects ◽  
Streptomyces Sp ◽  
Strong Antimicrobial Activity

A new antibiotic complex of six aureolic acids was isolated from the marine sediment-associated strain Streptomyces sp. KMM 9048. Four of the compounds (3–6) were found to be similar but not identical to the known chromomycins A2, A3, demethyl chromomycin A3 and A4. The two remaining compounds, A2–1 (1) and A3–1 (2), were established as novel chromomycin analogs, which did not contain sugar B. Spectroscopic methods including 1D and 2D NMR, and HRMS and MS/MS were applied for structure elucidation. Compounds 1-5 showed strong antimicrobial activity against Gram-positive indicatory bacteria Enterococcus faecium, Staphylococcus aureus, S. epidermidis, and Bacillus subtilis. Antitumor assay indicated that all tested compounds, in different manners, inhibited colony formation of RPMI-7951 and SK-Mel-28 cancer cells. This is the first study reporting the inhibitory effects of chromomycin analogs 1–5 on the colony formation of the investigated cancer cell lines. Compound 3, in a concentration of 5 nM, inhibited colony formation of RPMI-7951 and SK-Mel-28 cells by 82 % and 72 %, respectively. Our finding indicated that, of the compounds tested, 3 and 4 are promising anticancer and antimicrobial agents.

Pyoverdins with a Lys ε-Amino Link in the Peptide Chain?§

1999 ◽  
Vol 54 (12) ◽  
pp. 1021-1026 ◽  
Author(s):  
Herbert Budzikiewicz ◽  
Diana Uría Fernández ◽  
Regine Fuchs ◽  
Roland Michalke ◽  
Kambiz Taraz ◽  
...  
Keyword(s):  
Pseudomonas Putida ◽  
Structure Elucidation ◽  
Chemical Degradation ◽  
Peptide Chain ◽  
Spectroscopic Methods ◽  
Amino Group ◽  
Amine Group

For a pyoverdin isolated from Pseudomonas putida it could be shown that Lys is incorporated into the peptide chain by its ε-amine group in contrast to the normally observed connection by the α-amino group. The structure elucidation of the pyoverdin by chemical degradation and spectroscopic methods is reported and the criteria for the distinction between α-and ε-connection in the case of Lys are discussed.

scholarly journals New Haloterpenes from the Marine Red Alga Laurencia papillosa: Structure Elucidation and Biological Activity

Marine Drugs ◽  
2021 ◽  
Vol 19 (1) ◽  
pp. 35
Author(s):  
Mohamed Shaaban ◽  
Ghada S. E. Abou-El-Wafa ◽  
Christopher Golz ◽  
Hartmut Laatsch
Keyword(s):  
Biological Activity ◽  
Crude Extract ◽  
Structure Elucidation ◽  
Antimicrobial Activities ◽  
Red Alga ◽  
Spectroscopic Methods ◽  
X Ray Diffraction ◽  
X Ray ◽  
Chemical Structures ◽  
Terpene Derivatives

Analysis of the air-dried marine red alga Laurencia papillosa, collected near Ras-Bakr at the Suez gulf (Red Sea) in Egypt delivered five new halogenated terpene derivatives: aplysiolic acid (1), 7-acetyl-aplysiol (2), aplysiol-7-one (3), 11,14-dihydroaplysia-5,11,14,15-tetrol (5a), and a new maneonene derivative 6, named 5-epi-maneolactone. The chemical structures of these metabolites were characterized employing spectroscopic methods, and the relative and absolute configurations were determined by comparison of experimental and ab initio-calculated NMR, NOE, ECD, and ORD data, and by X-ray diffraction of 2 and 6. The antimicrobial activities of the crude extract and compounds 1–3, 5a and 6 were studied.

scholarly journals Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 305
Author(s):  
Guangyuan Luo ◽  
Li Zheng ◽  
Qilin Wu ◽  
Senhua Chen ◽  
Jing Li ◽  
...  
Keyword(s):  
Fusarium Solani ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Raw264.7 Cells ◽  
Spectroscopic Methods ◽  
X Ray ◽  
X Ray Crystallography ◽  
Structure Activity ◽  
Ic50 Values ◽  
New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

scholarly journals 30-Normedicagenic Acid Glycosides from Chenopodium Foliosum

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701
Author(s):  
Paraskev T. Nedialkov ◽  
Zlatina Kokanova-Nedialkova ◽  
Daniel Bücherl ◽  
Georgi Momekov ◽  
Jörg Heilmann ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Cell Lines ◽  
Interleukin 2 ◽  
Leukemic Cell ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Dioic Acid ◽  
Leukemic Cell Lines ◽  
Aerial Parts

Two new glycosides of 30-normedicagenic acid, namely 3- O-[ β-D-glucuronopyranosyl methyl ester]-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-D-glucopyranosyl ester, and 3- O-β-D-glucopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid, together with the known 3- O-β-glucopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-glucopyranosyl ester, and 3- O-β-glucuronopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-glucopyranosyl ester were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR) and HRMS-ESI. The compounds were tested for cytotoxicity on three leukemic cell lines (BV-173, SKW-3, HL-60). In addition, the saponins showed moderate stimulatory effects on interleukin-2 production in PHA/PMA stimulated Jurkat E6.1 cells.

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