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New ikarugamycin derivatives with antifungal and antibacterial properties from Streptomyces zhaozhouensis.

Lacret R, Oves-Costales D, Gómez C, Díaz C, de la Cruz M, Pérez-Victoria I, Vicente F, Genilloud O, Reyes F - Mar Drugs (2014)

Bottom Line: All the new compounds were structurally related to the known Streptomyces metabolite ikarugamycin (4).Their structural elucidation was accomplished using a combination of electrospray-time of flight mass spectrometry (ESI-TOF MS) and 1D and 2D NMR analyses.Compounds 1-3 showed antifungal activity against Aspergillus fumigatus, Candida albicans and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA).

View Article: PubMed Central - PubMed

Affiliation: Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, Armilla, Granada 18016, Spain. rodney.lacret@medinaandalucia.es.

ABSTRACT
A bioassay guided fractionation of the ethyl acetate extract from culture broths of the strain Streptomyces zhaozhouensis CA-185989 led to the isolation of three new polycyclic tetramic acid macrolactams (1-3) and four known compounds. All the new compounds were structurally related to the known Streptomyces metabolite ikarugamycin (4). Their structural elucidation was accomplished using a combination of electrospray-time of flight mass spectrometry (ESI-TOF MS) and 1D and 2D NMR analyses. Compounds 1-3 showed antifungal activity against Aspergillus fumigatus, Candida albicans and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA).

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Chromatographic UV trace (210 nm) from the LC-UV-MS analysis of aqueous crude extract (ACE) where compounds 1–4 were detected.
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marinedrugs-13-00128-f002: Chromatographic UV trace (210 nm) from the LC-UV-MS analysis of aqueous crude extract (ACE) where compounds 1–4 were detected.

Mentions: The producing strain, S. zhaozhouensis CA-185989, was fermented at 28 °C in 1 L of APM9-modified medium during 6 days. Extraction with an equal volume of acetone and evaporation of the solvent afforded an aqueous crude extract (ACE), which was subsequently subjected to liquid-liquid extraction with ethyl acetate. LC-UV-MS analysis of the ACE (Figure 2) revealed the presence of ikarugamycin and some related PTMs which were not included in our internal microbial natural products library [15,16,17] and whose molecular formulae suggested the presence in the extract of new natural products. The resulting aqueous and organic extracts were assayed against A. fumigatus and C. albicans, with the organic extract being the most active one. This extract was chromatographed on silica gel using hexane/ethyl acetate mixtures of increasing polarity.


New ikarugamycin derivatives with antifungal and antibacterial properties from Streptomyces zhaozhouensis.

Lacret R, Oves-Costales D, Gómez C, Díaz C, de la Cruz M, Pérez-Victoria I, Vicente F, Genilloud O, Reyes F - Mar Drugs (2014)

Chromatographic UV trace (210 nm) from the LC-UV-MS analysis of aqueous crude extract (ACE) where compounds 1–4 were detected.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4306928&req=5

marinedrugs-13-00128-f002: Chromatographic UV trace (210 nm) from the LC-UV-MS analysis of aqueous crude extract (ACE) where compounds 1–4 were detected.
Mentions: The producing strain, S. zhaozhouensis CA-185989, was fermented at 28 °C in 1 L of APM9-modified medium during 6 days. Extraction with an equal volume of acetone and evaporation of the solvent afforded an aqueous crude extract (ACE), which was subsequently subjected to liquid-liquid extraction with ethyl acetate. LC-UV-MS analysis of the ACE (Figure 2) revealed the presence of ikarugamycin and some related PTMs which were not included in our internal microbial natural products library [15,16,17] and whose molecular formulae suggested the presence in the extract of new natural products. The resulting aqueous and organic extracts were assayed against A. fumigatus and C. albicans, with the organic extract being the most active one. This extract was chromatographed on silica gel using hexane/ethyl acetate mixtures of increasing polarity.

Bottom Line: All the new compounds were structurally related to the known Streptomyces metabolite ikarugamycin (4).Their structural elucidation was accomplished using a combination of electrospray-time of flight mass spectrometry (ESI-TOF MS) and 1D and 2D NMR analyses.Compounds 1-3 showed antifungal activity against Aspergillus fumigatus, Candida albicans and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA).

View Article: PubMed Central - PubMed

Affiliation: Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, Armilla, Granada 18016, Spain. rodney.lacret@medinaandalucia.es.

ABSTRACT
A bioassay guided fractionation of the ethyl acetate extract from culture broths of the strain Streptomyces zhaozhouensis CA-185989 led to the isolation of three new polycyclic tetramic acid macrolactams (1-3) and four known compounds. All the new compounds were structurally related to the known Streptomyces metabolite ikarugamycin (4). Their structural elucidation was accomplished using a combination of electrospray-time of flight mass spectrometry (ESI-TOF MS) and 1D and 2D NMR analyses. Compounds 1-3 showed antifungal activity against Aspergillus fumigatus, Candida albicans and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA).

Show MeSH
Related in: MedlinePlus