An N-acyl homolog of mycothiol is produced in marine actinomycetes

Gerald L. Newton, Paul R. Jensen, John B. MacMillan, William Fenical, Robert C. Fahey

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Marine actinomycetes have generated much recent interest as a potentially valuable source of novel antibiotics. Like terrestrial actinomycetes the marine actinomycetes are shown here to produce mycothiol as their protective thiol. However, a novel thiol, U25, was produced by MAR2 strain CNQ703 upon progression into stationary phase when secondary metabolite production occurred and became the dominant thiol. MSH and U25 were maintained in a reduced state during early stationary phase, but become significantly oxidized after 10 days in culture. Isolation and structural analysis of the monobromobimane derivative identified U25 as a homolog of mycothiol in which the acetyl group attached to the nitrogen of cysteine is replaced by a propionyl residue. This N-propionyl-desacetyl- mycothiol was present in 13 of the 17 strains of marine actinomycetes examined, including five strains of Salinispora and representatives of the MAR2, MAR3, MAR4 and MAR6 groups. Mycothiol and its precursor, the pseudodisaccharide 1-O-(2-amino-2-deoxy-α-d-glucopyranosyl)-d-myo-inositol, were found in all strains. High levels of mycothiol S-conjugate amidase activity, a key enzyme in mycothiol-dependent detoxification, were found in most strains. The results demonstrate that major thiol/disulfide changes accompany secondary metabolite production and suggest that mycothiol-dependent detoxification is important at this developmental stage.

Original languageEnglish (US)
Pages (from-to)547-557
Number of pages11
JournalArchives of Microbiology
Volume190
Issue number5
DOIs
StatePublished - Nov 2008

Fingerprint

Actinobacteria
Sulfhydryl Compounds
Detoxification
Metabolites
Melanocyte-Stimulating Hormones
Inositol
Structural analysis
Disulfides
Cysteine
mycothiol
Nitrogen
Anti-Bacterial Agents
Derivatives
Enzymes

Keywords

  • Marine actinomycetes
  • Mca
  • Mycothiol
  • N-propionyl-desacetyl-mycothiol
  • Salinispora arencola

ASJC Scopus subject areas

  • Microbiology
  • Molecular Biology
  • Biochemistry
  • Genetics

Cite this

An N-acyl homolog of mycothiol is produced in marine actinomycetes. / Newton, Gerald L.; Jensen, Paul R.; MacMillan, John B.; Fenical, William; Fahey, Robert C.

In: Archives of Microbiology, Vol. 190, No. 5, 11.2008, p. 547-557.

Research output: Contribution to journalArticle

Newton, Gerald L. ; Jensen, Paul R. ; MacMillan, John B. ; Fenical, William ; Fahey, Robert C. / An N-acyl homolog of mycothiol is produced in marine actinomycetes. In: Archives of Microbiology. 2008 ; Vol. 190, No. 5. pp. 547-557.
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