Butremycin, the 3-hydroxyl derivative of ikarugamycin and a protonated aromatic tautomer of 5'-methylthioinosine from a Ghanaian Micromonospora sp. K310

Kwaku Kyeremeh; Kojo Sekyi Acquah; Anil Sazak; Wael Houssen; Jioji Tabudravu; Hai Deng; Marcel Jaspars

doi:10.3390/md12020999

Butremycin, the 3-hydroxyl derivative of ikarugamycin and a protonated aromatic tautomer of 5'-methylthioinosine from a Ghanaian Micromonospora sp. K310

Mar Drugs. 2014 Feb 14;12(2):999-1012. doi: 10.3390/md12020999.

Authors

Kwaku Kyeremeh¹, Kojo Sekyi Acquah², Anil Sazak³, Wael Houssen⁴, Jioji Tabudravu⁵, Hai Deng⁶, Marcel Jaspars⁷

Affiliations

¹ Marine and Plant Laboratory of Ghana, Department of Chemistry, University of Ghana, Accra, P.O. Box LG 56, Ghana. kkyeremeh@ug.edu.gh.
² Marine and Plant Laboratory of Ghana, Department of Chemistry, University of Ghana, Accra, P.O. Box LG 56, Ghana. ksaquah@yahoo.com.
³ Department of Biology, Faculty of Art and Science, Ondokuz Mayis University, Kurupelit Samsun 55139, Turkey. asazak@omu.edu.tr.
⁴ Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UK. w.houssen@abdn.ac.uk.
⁵ Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UK. j.tabudravu@abdn.ac.uk.
⁶ Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UK. h.deng@abdn.ac.uk.
⁷ Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UK. m.jaspars@abdn.ac.uk.

Abstract

A new actinomycete strain Micromonospora sp. K310 was isolated from Ghanaian mangrove river sediment. Spectroscopy-guided fractionation led to the isolation of two new compounds from the fermentation culture. One of the compounds is butremycin (2) which is the (3-hydroxyl) derivative of the known Streptomyces metabolite ikarugamycin (1) and the other compound is a protonated aromatic tautomer of 5'-methylthioinosine (MTI) (3). Both new compounds were characterized by 1D, 2D NMR and MS data. Butremycin (2) displayed weak antibacterial activity against Gram-positive S. aureus ATCC 25923, the Gram-negative E. coli ATCC 25922 and a panel of clinical isolates of methicillin-resistant S. aureus (MRSA) strains while 3 did not show any antibacterial activity against these microbes.

Publication types

Comparative Study
Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology*
Escherichia coli / drug effects
Fermentation
Geologic Sediments / microbiology
Ghana
Lactams, Macrocyclic / chemistry
Lactams, Macrocyclic / isolation & purification
Lactams, Macrocyclic / pharmacology*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Methicillin-Resistant Staphylococcus aureus / drug effects
Methylthioinosine / analogs & derivatives*
Methylthioinosine / chemistry
Methylthioinosine / isolation & purification
Methylthioinosine / pharmacology
Microbial Sensitivity Tests
Micromonospora / chemistry*
Rivers / microbiology
Staphylococcus aureus / drug effects

Substances

Anti-Bacterial Agents
Lactams, Macrocyclic
butremycin
5'-methylthioinosine
Methylthioinosine