Antimicrobial Chlorinated 3-Phenylpropanoic Acid Derivatives from the Red Sea Marine Actinomycete <i>Streptomyces</i> <i>coelicolor</i> LY001
2020
Lamiaa A. Shaala | Diaa T. A. Youssef | Torki A. Alzughaibi | Sameh S. Elhady
The actinomycete strain <i>Streptomyces coelicolor</i> LY001 was purified from the sponge <i>Callyspongia siphonella</i>. 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 (<b>1</b>), 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid methyl ester (<b>2</b>), and 3-(3-chloro-4-hydroxyphenyl)propanoic acid (<b>3</b>), together with 3-phenylpropanoic acid (<b>4</b>), <i>E</i>-cinnamic acid (<b>5</b>), and the diketopiperazine alkaloids cyclo(<span style="font-variant: small-caps;">l</span>-Phe-<i>trans</i>-4-OH-<span style="font-variant: small-caps;">l</span>-Pro) (<b>6</b>) and cyclo(<span style="font-variant: small-caps;">l</span>-Phe-<i>cis</i>-4-OH-<span style="font-variant: small-caps;">d</span>-Pro) (<b>7</b>) were isolated. Interpretation of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HRESIMS) data of <b>1</b>–<b>7</b> supported their assignments. Compounds <b>1</b>–<b>3</b> are first candidates of the natural chlorinated phenylpropanoic acid derivatives. The production of the chlorinated derivatives of 3-phenylpropionic acid (<b>1</b>–<b>3</b>) by <i>S. coelicolor</i> provides insight into the biosynthetic capabilities of the marine-derived actinomycetes. Compounds <b>1</b>–<b>3</b> demonstrated significant and selective activities towards <i>Escherichia. coli</i> and <i>Staphylococcus aureus</i>, while <i>Candida albicans</i> displayed more sensitivity towards compounds <b>6</b> and <b>7</b>, suggesting a selectivity effect of these compounds against <i>C. albicans</i>.
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