New Anthraquinones from a Marine Streptomyces sp. – Isolation, Structure Determination and Biological Activities

2006 ◽  
Vol 61 (11) ◽  
pp. 1450-1454 ◽  
Author(s):  
Hervé M. P. Poumale ◽  
Bonaventure T. Ngadjui ◽  
Elisabeth Helmke ◽  
Hartmut Laatscha
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Biological Activities ◽  
Acid Methyl Ester ◽  
Streptomyces Sp ◽  
Spectroscopic Analyses ◽  
Acid Methyl ◽  
Marine Streptomyces ◽  
New Compounds ◽  
Indole 3 Acetic Acid

Two new anthraquinones were isolated from the marine Streptomyces sp. B8000, in addition to the known metabolites 3,8-dihydroxy-1-propylanthraquinone-2-carboxylic acid (1a), indole-3- carboxylic acid, 2-desoxythymidin, indole-3-acetic acid methyl ester, N-acetyltyramine, and nicotinic acid. The structures of the new compounds were established as 8-hydroxy-3-methoxy-1- propylanthraquinone (2a) and 3,8-dihydroxy-1-propylanthraquinone (2c) on the basis of extensive spectroscopic analyses. Some derivatives were prepared and their biological activities were studied.

scholarly journals Isolation and Structural Elucidation of Nitrogenous Secondary Metabolites from Terrestrial and Marine Streptomyces spp

2017 ◽  
Vol 12 (3) ◽  
pp. 1934578X1701200
Author(s):  
Mohamed Shaaban ◽  
Khaled A. Shaaban ◽  
Elisabeth Helmke ◽  
Iris Grün-Wollny ◽  
Hartmut Laatsch
Keyword(s):  
Carboxylic Acid ◽  
Nmr Spectra ◽  
Acid Methyl Ester ◽  
2D Nmr ◽  
Benzene Derivatives ◽  
Streptomyces Spp ◽  
Acid Methyl ◽  
2D Nmr Spectra ◽  
New Compounds ◽  
Related Compounds

Screening and chromatography of extracts from a terrestrial and a marine-derived streptomycete yielded two new nitrogenous benzene derivatives, namely ( S)- N-[3-hydroxy-1-(4-hydroxyphenyl)-propyl]-acetamide (1a), and ( R)-2-(1-methyl-2-oxopropylamino)-benzoic acid (2). Additionally, eight known compounds were isolated, 2-acetamidophenol, phenazine-1-carboxylic acid, phenazine-1-carboxylic acid methyl ester, perlolyrin, tyrosol, uracil, and anthranilic acid. The structures of the new compounds were deduced from high resolution mass, 1D and 2D NMR spectra and by comparison with related compounds from the literature. The absolute configuration of 1a and 2 was determined by comparison of experimental and calculated CD and ORD data.

scholarly journals Generation of Unusual Aromatic Polyketides by Incorporation of Phenylamine Analogues into a C-Ring-Cleaved Angucyclinone

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1959
Author(s):  
Hua Xiao ◽  
Guiyang Wang ◽  
Zhengdong Wang ◽  
Yi Kuang ◽  
Juan Song ◽  
...  
Keyword(s):  
Natural Products ◽  
Biological Activities ◽  
Structural Diversity ◽  
Related Factor ◽  
Nuclear Factor ◽  
Streptomyces Sp ◽  
Mild Conditions ◽  
Aromatic Polyketides ◽  
Marine Streptomyces ◽  
New Compounds

Angucyclinones are aromatic polyketides that possess impressive structural diversity and significant biological activities. The structural diversity of these natural products is attributed to various enzymatic or nonenzymatic modifications on their tetracyclic benz(a)anthracene skeleton. Previously, we discovered an unusual phenylamine-incorporated angucyclinone (1) from a marine Streptomyces sp. PKU-MA00218, and identified that it was produced from the nonenzymatic conversion of a C-ring-cleaved angucyclinone (2) with phenylamine. In this study, we tested the nonenzymatic conversion of 2 with more phenylamine analogues, to expand the utility of this feasible conversion in unusual angucyclinones generation. The (3-ethynyl)phenylamine and disubstituted analogues including (3,4-dimethyl)phenylamine, (3,4-methylenedioxy)phenylamine, and (4-bromo-3-methyl)phenylamine were used in the conversion of 2, which was isolated from the fermentation of Streptomyces sp. PKU-MA00218. All four phenylamine analogues were incorporated into 2 efficiently under mild conditions, generating new compounds 3–6. The activation of 3–6 on nuclear factor erythroid 2-related factor 2 (Nrf2) transcription were tested, which showed that 4 possessing a dimethyl-substitution gave most potent activity. These results evidenced that disubstitutions on phenylamine can be roughly tolerated in the nonenzymatic reactions with 2, suggesting extended applications of more disubstituted phenylamines incorporation to generate new bioactive angucyclinones in the future.

Identification of Potential Antimicrobial Compounds from A Marine Streptomyces Sp. SM2.4 Strain (MH752437) Isolated from Rachgoun Island in Western Algeria

2021 ◽  
Vol 17 ◽  
Author(s):  
Nesrine Boublenza ◽  
Nadir Boudjlal Dergal ◽  
Larbi Belyagoubi ◽  
Noujoud Gabed ◽  
Djamel-Eddine Abdelouahid ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Bioactive Compounds ◽  
Crude Extract ◽  
Acid Methyl Ester ◽  
Bioactive Metabolites ◽  
Streptomyces Sp ◽  
Acid Methyl ◽  
Ms Analysis ◽  
Western Algeria ◽  
Marine Streptomyces

Background: Marine actinobacteria are a potential resource for natural products; their secondary bioactive metabolites have shown several biological activities. Most of the isolated and identified actinobacteria in Algeria were usually explored from caves, Saharan soil or palm groves. The marine ecosystem is poorly explored and documented. Methods: Five Streptomyces strains producing bioactive compounds were isolated from Rachgoun Island located in Western Algeria and characterised phenotypically and genotypically using microbiological and 16S rRNA sequencing methods, respectively. The crude extract of the most representative strain “Streptomyces sp. strain SM2.4” and its seven active fractions were characterised by GC/MS analysis. Results: Streptomyces sp. strain SM2.4 revealed the strongest activity against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, the fungus Aspergillus niger and was inactive against Gram-negative bacteria. GC/MS analysis of the methylated crude extract of Streptomyces sp. strain SM2.4 revealed the presence of 11 major compounds including fatty acids methyl ester (12-methyltridecanoic acid methyl ester, 9-hexadecenoic acid methyl ester, hexadecanoic acid methyl ester, 14-methylhexadecanoic acid methyl ester and 16-methylheptadecanoic acid methyl ester), 2,4-di-tert-butylphenol, (4S,4aS,8aR)-4,8a-dimethyloctahydro-4a(2H)-naphthalenol (geosmin), 2,4-dimethylbenzaldehyde, 3,4-difluorobenzaldehyde, dimethylfuran-2,4-dicarboxylate and pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-. Partial purification of the crude extract by Thin-layer chromatography provided seven active fractions which were tested by radial diffusion assay. GC/MS analysis of the active TLC-fractions revealed the presence of a mixture of active compounds from which 2-(bromomethyl)-2-(2-methylphenyl)-1,3-dioxolane was found to be a new 1,3 dioxolane derivative. Furthermore, 3,4-dimethylbenzamide and pyrido[2,3-d] pyridazine-1,4-dione, hexahydro-3-(2-methylpropyl)-, were extracted for the first time from a natural source. Conclusion: Our study reveals that marine Streptomyces sp. strain SM2.4 has an interesting antimicrobial potential due to its panel of bioactive compounds.

The possible action mechanisms of indole-3-acetic acid methyl ester in Arabidopsis

2007 ◽  
Vol 27 (3) ◽  
pp. 575-584 ◽  
Author(s):  
Linchuan Li ◽  
Xianhui Hou ◽  
Tomohiko Tsuge ◽  
Maoyu Ding ◽  
Takashi Aoyama ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Methyl Ester ◽  
Acid Methyl Ester ◽  
Action Mechanisms ◽  
Acid Methyl ◽  
Indole 3 Acetic Acid

scholarly journals Thermodynamic Properties of Three Pyridine Carboxylic Acid Methyl Ester Isomers

2007 ◽  
Vol 52 (2) ◽  
pp. 580-585 ◽  
Author(s):  
Maria D. M. C. Ribeiro da Silva ◽  
Vera L. S. Freitas ◽  
Luís M. N. B. F. Santos ◽  
Michal Fulem ◽  
M. J. Sottomayor ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Methyl Ester ◽  
Thermodynamic Properties ◽  
Acid Methyl Ester ◽  
Pyridine Carboxylic Acid ◽  
Acid Methyl ◽  
Pyridine Carboxylic

scholarly journals Azukisapogenol Triterpene Glycosides from Oxytropis chiliophylla Royle

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2448
Author(s):  
Jun Wang ◽  
Hongshuai Yang ◽  
Yang Liu ◽  
Kelsang Norbo ◽  
Kewu Zeng ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Glucuronic Acid ◽  
Acid Methyl Ester ◽  
Triterpene Glycosides ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Acid Methyl ◽  
Potent Inhibition ◽  
New Compounds ◽  
First Time

Eight azukisapogenol triterpene glycosides, including five new compounds, oxychiliotriterpenosides A–E (1–5), two new methyl glucuronide derivatives that proved to be artifacts, oxychiliotriterpenoside E-glucuronic acid methyl ester (6) and myrioside B-glucuronic acid methyl ester (7), and a known one, myrioside B (8), was isolated from the aerial part of Oxytropis chiliophylla Royle. Their structures were elucidated based on extensive spectroscopic analyses and chemical methods. Triterpene glycosides were first obtained from O. chiliophylla, and those containing a galactose unit (1, 2, 5 and 6) and diglucosidic or triglucosidic linkage at C-29 (1–4), were reported from Oxytropis species for the first time, which might be recognized as a chemotaxonomic feature of O. chiliophylla. All isolated compounds were evaluated for their anti-inflammatory activities against NO production using lipopolysaccharide (LPS)-induced RAW 264.7 cells, but no compounds showed potent inhibition on NO production.

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