scholarly journals Antimicrobial Chlorinated 3-Phenylpropanoic Acid Derivatives from the Red Sea Marine Actinomycete Streptomyces coelicolor LY001

Marine Drugs ◽  
2020 ◽  
Vol 18 (9) ◽  
pp. 450 ◽  
Author(s):  
Lamiaa A. Shaala ◽  
Diaa T. A. Youssef ◽  
Torki A. Alzughaibi ◽  
Sameh S. Elhady

The actinomycete strain Streptomyces coelicolor LY001 was purified from the sponge Callyspongia siphonella. Fractionation of the antimicrobial extract of the culture of the actinomycete afforded three new natural chlorinated derivatives of 3-phenylpropanoic acid, 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid (1), 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid methyl ester (2), and 3-(3-chloro-4-hydroxyphenyl)propanoic acid (3), together with 3-phenylpropanoic acid (4), E-cinnamic acid (5), and the diketopiperazine alkaloids cyclo(l-Phe-trans-4-OH-l-Pro) (6) and cyclo(l-Phe-cis-4-OH-d-Pro) (7) were isolated. Interpretation of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HRESIMS) data of 1–7 supported their assignments. Compounds 1–3 are first candidates of the natural chlorinated phenylpropanoic acid derivatives. The production of the chlorinated derivatives of 3-phenylpropionic acid (1–3) by S. coelicolor provides insight into the biosynthetic capabilities of the marine-derived actinomycetes. Compounds 1–3 demonstrated significant and selective activities towards Escherichia. coli and Staphylococcus aureus, while Candida albicans displayed more sensitivity towards compounds 6 and 7, suggesting a selectivity effect of these compounds against C. albicans.

Fuel ◽  
2019 ◽  
Vol 243 ◽  
pp. 133-141 ◽  
Author(s):  
Razieh Razavi ◽  
Amin Bemani ◽  
Alireza Baghban ◽  
Amir H. Mohammadi ◽  
Sajjad Habibzadeh

1978 ◽  
Vol 33 (7-8) ◽  
pp. 465-471
Author(s):  
Franz Daliacker ◽  
Volker Mues ◽  
In-O Kim

Abstract We describe the possibilities of formation and preparation of the “natural” 1,3-benzodioxolecarboxylic acids 1, 2, 4, 6 b, and 7, already mentioned in literature. Myristic acid (3e) was prepared in good yield from 3-methoxy-4,5-dihydroxy-benzoic acid ester (3c) , which could be easily made from 3-methoxy-2,3-carbonyldioxy-benzoic acid methylester (3b). Myristicic acid methylester (3d) could be subjected to methylation and hydrolysis leading to 3e without any difficulties. 4.6-dimethoxy-1,3-benzodioxole-5-carboxylic acid (5b) was prepared in good yields by oxidation of 4,6-dimethoxy-1,3-benzodioxole-5-aldehyde (5a). 5.7-dimethoxy-1,3-benzodioxole-carboxylic acid (13f), one of the “unnatural” 1,3-benzodioxolecarboxylic acids, derivatives of o-ipiperonylic acid (8), was prepared from 5-amino-7-methoxy-1,3- benzodioxole-4carboxylic acid methyl ester (13b) by diazotisation, elimination of nitrogen, methylation, and hydrolysis. A comparison of our measured pkA-values showed the strongest acidity belonging to 5,6-dimethoxy-1,3-benzodioxole-4-carbocylic acid (11).


2017 ◽  
Vol 9 (26) ◽  
pp. 3949-3955
Author(s):  
Rodrigo V. P. Leal ◽  
Gabriel F. Sarmanho ◽  
Luiz H. Leal ◽  
Bruno C. Garrido ◽  
Lucas J. Carvalho ◽  
...  

Fatty acid methyl ester (FAME) intensities, by ESI-MS, used to their quantification in biodiesel.


2008 ◽  
Vol 14 (1) ◽  
pp. 27-35 ◽  
Author(s):  
Grazyna Bartkowiak

Electron ionization mass spectra of 12 derivatives of 2-thioorotic acid have been discussed and general fragmentation routes of their molecular ions have been proposed. The compounds under discussion were three groups of four chemical species (2-alkylthioorotic acid, methyl 2-alkylthioorotate, ethyl 2-alkylthioorotate and 2-alkylthioorotic hydrazide) each with the same relative molecular mass. The comparison of selected ions relative abundances and their correlation with the abundance of molecular ions enable differentiation between isomeric or isobaric species in this class of compounds.


1971 ◽  
Vol 122 (4) ◽  
pp. 503-508 ◽  
Author(s):  
R. Nery

1. Tritiation of arecoline hydrochloride by catalytic exchange in aqueous media (done by The Radiochemical Centre) gave arecaidine hydrochloride of high specific radioactivity; this on treatment with diazomethane gave [3H]arecoline, which was oxidized with peroxyacetic acid to [3H]arecoline 1-oxide. 2. Arecoline 1-oxide gave arecaidine 1-oxide on acid hydrolysis and 1,2-dihydro-1-methylnicotinic acid methyl ester on thermal decomposition. 3. [3H]Arecoline hydrochloride was metabolized in the rat into the 3H-labelled derivatives of arecoline 1-oxide, arecaidine 1-oxide, arecaidine, N-acetyl-S-(3-carboxy-1-methylpiperid-4-yl)-l-cysteine and an unidentified metabolite; some unchanged arecoline was also excreted. [3H]Arecoline 1-oxide gave the same metabolities, but in different amounts. 4. The possible relevance of these findings to betel-nut carcinogenesis is discussed.


2018 ◽  
Vol 54 (12) ◽  
pp. 1868-1870
Author(s):  
A. D. Zorina ◽  
V. L. Polozova ◽  
S. A. Marchenko ◽  
S. I. Selivanov ◽  
R. E. Trifonov

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