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

Abstract

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.

Magnificines A and B, Antimicrobial Marine Alkaloids Featuring a Tetrahydrooxazolo[3,2-a]azepine-2,5(3H,6H)-dione Backbone from the Red Sea Sponge Negombata magnifica

“…The optical rotations and spectral data of 1 - 5 including UV, ECD, NMR and MS are acquired as previously reported [ 27 , 28 , 29 ].…”

“…As a part of our growing interest to discover biologically active leads from marine resources [ 27 , 28 , 29 ], the organic extract of the sponge Negombata magnifica was examined. Two alkaloids, magnificines A and B ( 1 and 2 ), with a previously unreported tetrahydrooxazolo[3,2- a ]azepine-2,5( 3H,6H )-dione skeleton were purified.…”

A Review: Halogenated Compounds from Marine Actinomycetes

“…Compound 3 also inhibited the growth of Chlamydia trachomatis with an IC 50 value of 9.54 μM [ 7 ]. New 3-phenylpropanoic acids 3-(3,5-dichloro-4-hydroxyphenyl) propanoic acid ( 4 ), 3-(3,5-dichloro-4-hydroxyphenyl) propanoic acid methyl ester ( 5 ) and 3-(3-chloro-4-hydroxyphenyl) propanoic acid ( 6 ) were isolated from Streptomyces coelicolor LY001, which demonstrated a broad spectrum of antibacterial activities with MIC values ranging from 16 to 250 μg/mL [ 8 ].…”

Pseudoceratonic Acid and Moloka’iamine Derivatives from the Red Sea Verongiid Sponge Pseudoceratina arabica

“…NMR spectra were obtained on Bruker Avance DRX 400 and 600 MHz (Bruker, Rheinstetten, Germany). The UV spectra were measured on a Hitachi 300 spectrometer (Hitachi High-Technologies Corporation, Kyoto, Japan) and as reported earlier [34]. Liquid-Liquid partitions, C18 Sep-Pak and Sephadex LH-20 were used for fractionation of the extract and successive fractions.…”