Stoffwechselprodukte von Actinomyceten. 19. Mitteilung N‐Acetyl‐tyramin

Comin, J.; Keller‐Schierlein, W.

doi:10.1002/hlca.19590420537

Cited by 13 publications

(9 citation statements)

References 4 publications

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“…The fragment at m/z 78 is could be attributed to a pyridinium ion and the ion at m/z 45 is indicative for a carboxylic acid group. These spectral data are matching nicely with the 1 H NMR spectrum and allowed us to elucidate the compound as pyridine-3-carboxylic acid (190). Nicotinic acid (190) has been reported as a fungal metabolite from Phycomyces blakesleeanu [241] and is an important plant intermediate.…”

supporting

confidence: 62%

“…These spectral data are matching nicely with the 1 H NMR spectrum and allowed us to elucidate the compound as pyridine-3-carboxylic acid (190). Nicotinic acid (190) has been reported as a fungal metabolite from Phycomyces blakesleeanu [241] and is an important plant intermediate. It is used as vitamin, enzyme cofactor, vasodilator and antihyperglycemic agent and widely used in treatment of lipid disorders [24] .…”

supporting

confidence: 62%

“…S. griseus [190] , as well as from plants [191] . It was found also as metabolite from pathogenic fungi, Mycobacteria, Enterobacteria and from Bombyx mori at the chrysalis stage [24] .…”

Section: P-hydroxyphenethyl Acetamide; N-acetyl-tyraminementioning

confidence: 99%

“…Comparison with authentic spectra and the literature [233, * ] afforded uridine (187), which is widely distributed in nature in free state or in nucleic acid and can be produced by hydrolysis thereof [24] . pyridine carboxylic acid (190), 2-acetamidophenol (192), indolyl-3-carbaldehyde (194) and cytoxazone (195), in addition to other known compounds (Figure 82).…”

Section: Isoxanthohumolmentioning

confidence: 99%

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Bioactive Secondary Metabolites from Marine and Terrestrial Bacteria: Isoquinolinequinones, Bacterial Compounds with a Novel Pharmacophor

Mahmoud¹

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Antibiotics are defined [5,6] as low-molecular weight (MW < 2000 Dalton) secondary metabolites from natural sources including their chemically or biosynthetically produced derivatives, which show inhibition of the growth of higher organisms (e.g. tumour cells) or pathogens (e.g. bacteria, fungi, viruses) at low concentration, and subsequently can be used to cure the infectious diseases. Not all natural products serve as antibiotics, many of them function as signalling substances between micro- 4Recently, chemists on a worldwide basis have paid attention towards the potential of marine microorganisms (e.g. bacteria, fungi, blue green algae, dinoflagellates etc.), as an alternative source for isolation of novel metabolites with interesting biological and pharmaceutical properties [20,21] . Most metabolites of bacterial origin come from one group, Gram-positive soil bacteria of the order Actinomycetes.1993 [4] .It was expected that marine bacteria might produce compounds, which differ basically from terrestrial products, as it is known from spongial metabolites. Many metabolites of marine microorganisms, especially those of Streptomycetes are, however, similar to or identical with those of terrestrial origin, and it is not easy to decide if a microorganism is truly marine. One of the principal difficulties appears to be therefore the definition of a marine microorganism. It was reported recently, that the marine microbial Picoplankton contains a high abundance of rare species, virtually none of which has ever been isolated and chemically investigated [27] . It can be expected that truly marine bacteria can be found in this or related sources. Fenical postulated that the newly described genus Salinospora is a rare Actinomycete restricted to the Pentabromopseudilin (9), an antibiotic and cytotoxic brominated marine natural product, was isolated from Alteromonas luteoviolaceus. 70 % of the compound's molecular weight consists of bromine [44][45][46] . Due to its highly toxic effects, it could not be used as medicine. The chloro analogue 10 was isolated in 1978 from the terrestrial Actinoplanes sp. ATCC 33002 [47] . A recent study carried out on 136 marine 19 1.6 The Phylogenetic Tree of Bacteria Bioactive compounds have been reported from marine bacteria belonging to the genus Pseudoalteromonas, Cytophaga, Alteromonas, Micrococcus, Bacillus, Acinetobacter, Agrobacterium, Pseudomonas [40] as well as Streptomycetes. Presently, there are two microbial phylogenetic hot spots known for the production of secondary metabolites: 24Zeeck and co-workers [69] have isolated 3-(4'-hydroxyphenyl)-4-phenylpyrrole-2, 5-dicarboxylic acid (25a), 3,4-di(4'-hydroxyphenyl)pyrrole-2,5-dicarboxylic acid (25b) and 7-hydroxy-2H-benzo [1,4]thiazin-3-one (26) from the culture broth of the North Sea strain RK377 fermented on MB medium with artificial sea water. From the same strain on SJ medium, two new imidazole and pyrimidin derivatives, namely glusun I ( 27) and glusun II (28), were isolated. Continuing these investigations, the same group...

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supporting

confidence: 62%

supporting

confidence: 62%

“…S. griseus [190] , as well as from plants [191] . It was found also as metabolite from pathogenic fungi, Mycobacteria, Enterobacteria and from Bombyx mori at the chrysalis stage [24] .…”

Section: P-hydroxyphenethyl Acetamide; N-acetyl-tyraminementioning

confidence: 99%

Section: Isoxanthohumolmentioning

confidence: 99%

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Bioactive Secondary Metabolites from Marine and Terrestrial Bacteria: Isoquinolinequinones, Bacterial Compounds with a Novel Pharmacophor

Mahmoud¹

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“…Due to the small quantity of the mixture (~1 mg), we have not attempted to separate both compounds in order to avoid any loss of material. Since we have been also able to isolate a pure sample of 4, 7 we could analyse the MS and NMR data of 3 and 4, in order to assign the H COSY spectrum, which showed sequencial couplings from H-5 (δ 4.38) to H-4a (δ 1.93) and H-4b (δ 2.02), from these two hydrogens to H-3 (δ 4.27), which was in turn coupled with both H-2a (δ 3.21, overlapped by the H 2 O signal in DMSO-d 6 ) and H-2b (δ 3.47). Since the spectra were obtained in DMSO-d 6 , we have been able to observe a vicinal coupling between H-3 and the hydroxyl proton at δ 5.08 (d, J 3 Hz).…”

Section: Resultsmentioning

confidence: 99%

Dipeptide metabolites from the marine derived bacterium Streptomyces acrymicini

Hernandez¹,

Macedo²,

Berlinck³

et al. 2004

J. Braz. Chem. Soc.

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A investigação química do extrato bruto obtido a partir do meio de crescimento do actinomiceto Streptomyces acrimycini isolado de sedimentos marinhos levou ao isolamento de dois dipeptídeos: a 8-amino-[1,4]diazonano-2,5-diona (1) e leucil-4-hidroxiprolina (3). Os compostos foram isolados a partir do seu meio de crescimento por uma série de etapas cromatográficas e identificados pela análise de seus dados espectroscópicos. O esqueleto macrocíclico da 8-amino-[1,4]diazonano-2,5-diona foi descrito apenas uma vez nas marinobactinas, sideróforos isolados a partir de uma bactéria marinha do gênero Marinobacter.The chemical investigation of the crude extract obtained from the growth media of the marinederived actinomycete Streptomyces acrimycini isolated from marine sediments led to the isolation of two new dipeptide derivatives: 8-amino-[1,4]diazonane-2,5-dione (1) and leucyl-4-hydroxyproline (3). The dipeptides were isolated from the growth media by a series of chromatographic steps, and identified by analysis of spectroscopic data. The macrocyclic carbon backbone of 8-amino-[1,4]diazonane-2,5-dione has been previously reported only once in marinobactins, siderophores isolated from the marine bacterium Marinobacter sp.

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The production, isolation, and characterization of a grisein‐like sideromycin complex

Maehr¹,

Berger²

1969

Biotech & Bioengineering

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SummaryStreptomyces griseus var. X-2455 produces an antibiotic complex which is active in vitro against a number of gram-positive and gram-negative bacteria and in mice against systemic infections caused by K . pneumoniae and D. pneumoniae. In view of the favorable chemotherapeutic index and the broad in oitro spectrum of crude concentrates, isolation of the pure antibiotic complex and the individual constituents ww undertaken. The antibiotics referred to as Ro 5-2667, Ro 7-7730, and Ro 7-7731 can be differentiated by tlc, ultraviolet light absorption spectra, and in vitro antibacterial activities. They all contain iron and may be classified as sideromycins.From antibiotic concentrates an antibacterially inactive substance was isolated and identified as N-acetyltyramine.

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Stoffwechselprodukte von Actinomyceten. 19. Mitteilung N‐Acetyl‐tyramin

Cited by 13 publications

References 4 publications

Bioactive Secondary Metabolites from Marine and Terrestrial Bacteria: Isoquinolinequinones, Bacterial Compounds with a Novel Pharmacophor

Bioactive Secondary Metabolites from Marine and Terrestrial Bacteria: Isoquinolinequinones, Bacterial Compounds with a Novel Pharmacophor

Dipeptide metabolites from the marine derived bacterium Streptomyces acrymicini

The production, isolation, and characterization of a grisein‐like sideromycin complex

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