Nat Prod Sci.  2015 Dec;21(4):261-267. 10.20307/nps.2015.21.4.261.

Deuteromethylactin B from a Freshwater-derived Streptomyces sp.

• Shaikh AF
• Elfeki M
• Landolfa S
• Tanouye U
• Green SJ
• Murphy BT

• KMID: 2312907
• DOI: http://doi.org/10.20307/nps.2015.21.4.261

Abstract

Compared to their terrestrial and marine counterparts, little is known about the capacity of freshwater-derived actinomycete bacteria to produce novel secondary metabolites. In the current study, we highlight the disparities that exist between cultivation-independent and -dependent analyses of actinomycete communities from four locations in Lake Michigan sediment. Furthermore, through phylogenetic analysis of strains isolated from these locations, we identified a Streptomyces sp., strain B025, as being distinct from other Streptomyces spp. isolated from sediment. Upon fermentation this strain produced a rare class of eight-membered lactone secondary metabolites, which have been for their antitumor properties. We used spectroscopic and chemical derivitization techniques to characterize octalactin B (1) in addition to its corresponding novel, unnatural degradation product (2).

Keyword

Actinomycete; Freshwater; Streptomyces; Octalactin

MeSH Terms

Bacteria
Fermentation
Fresh Water
Lakes
Michigan
Streptomyces*

Figure

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  Fig. 1. Composition of bacterial community in collected Lake Michigan sediment.

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  Fig. 2. Phylogenetic analysis of cultivatable actinomycete strains from Lake Michigan.

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  Fig. 3. Structure of octalactin B (1), and deuteromethylactin B (2).

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  Fig. 4. CD Spectrum of 1.

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  Fig. 5. Key 2D NMR correlations of 2.

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