3-Hydroxypropionic Acid as an Antibacterial Agent from Endophytic Fungi Diaporthe phaseolorum

Abstract

Endophytic fungi are considered a rich source of active compounds resulting from their secondary metabolism. Fungi from marine environment grow in a habitat with unique conditions that can contribute to the activation of metabolic pathways of synthesis of different unknown molecules. The production of these compounds may support the adaptation and survival of the fungi in the marine ecosystem. Mangroves are ecosystems situated between land and sea. They are frequently found in tropical and subtropical areas and enclose approximately 18.1 million hectares of the planet. The great biodiversity found in these ecosystems shows the importance of researching them, including studies regarding new compounds derived from the endophytic fungi that inhabit these ecosystems. 3-hydroxypropionic acid (3-HPA) has been isolated from the mangrove endophytic fungus Diaporthe phaseolorum, which was obtained from branches of Laguncularia racemosa. The structure of this compound was elucidated by spectroscopic methods, mainly 1D and 2D NMR. In bioassays, 3-HPA showed antimicrobial activities against both Staphylococcus aureus and Salmonella typhi. The structure of this antibiotic was modified by the chemical reaction of Fischer-Speier esterification to evaluate the biologic activity of its chemical analog. The esterified product, 3-hydroxypropanoic ethyl ester, did not exhibit antibiotic activity, suggesting that the free carboxylic acid group is important to the pharmacological activity. The antibiotic-producing strain was identified with internal transcribed spacer sequence data. To the best of our knowledge, this is the first report of antibacterial activity by 3-HPA against the growth of medically important pathogens.

An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds

“…Molecular mass conformed GC-MS library data. This 1 H and 13 C-NMR, GC-MS mass data matched to reported data (Sebastianes et al 2012). We obtained a yield of 6.5 mg of 3-HPA per liter of the culture broth (Supplementary material).…”

“…3-HPA has also been isolated from Diaporthe phaseolorum, a strain obtained from the branches of Laguncularia racemosa (Sebastianes et al 2012). It possesses antimicrobial as well as nematicidal activities against (Schwarz et al 2004;Sebastianes et al 2012). Other volatiles, limonene, trichloromethane, 3-pentanone, 1-pentanol, toluene, 2,4-di-tert-butyl phenol are also useful metabolites as these have been reported as potential alternate fuel molecules (Lide 1995;Dellomonaco et al 2010;AlonsoGutierrez et al 2013).…”

“…There is an increasing demand for the production of 3-HPA through environment friendly and sustainable biological processes ). 3-HPA has also been isolated from Diaporthe phaseolorum, a strain obtained from the branches of Laguncularia racemosa (Sebastianes et al 2012). It possesses antimicrobial as well as nematicidal activities against (Schwarz et al 2004;Sebastianes et al 2012).…”

Diversity of Lactobacillus reuteri Strains in Converting Glycerol into 3-Hydroxypropionic Acid

“…Among the products of this metabolic pathway, only the toxicity of 3-HPA towards the producing strains has been studied in details [28][29][30][31]. Concerning 3-HP, one recent study [32] displayed that this organic acid produced by an endophytic marine fungi exerted an antibacterial activity against Staphylococcus aureus and Salmonella typhi, which was attributed to its free carboxylic acid group. In another work [33], minimum inhibitory concentration (MIC) for 3-HP on E. coli was estimated to be 15 g.L −1 .…”

Endophytic Fungi from Brazilian Tropical Hosts and Their Biotechnological Applications

“…Recently some endophytic fungi producing apparently new antimicrobials were isolated from mangroves (Sebastianes et al 2012). Additionally, some endophytes from petrol-contaminated mangroves were found to be able to reduce oil contamination.…”