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Shaikh, Elfeki, Landolfa, Tanouye, J.Green, and Murphy: Deuteromethylactin B from a Freshwater-derived Streptomyces sp.
Original Article

Natural Product Sciences 2015;21(4):261-267.

Published online: 17 January 2015

DOI: https://doi.org/10.20307/nps.2015.21.4.261

Deuteromethylactin B from a Freshwater-derived Streptomyces sp.

Anam F. Shaikh1, 2, Maryam Elfeki1, 2, Samantha Landolfa1, Urszula Tanouye1, 2, Stefan J.Green3, 4, Brian T. Murphy1, 2, ∗

1 Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL 60612, USA

2 Center for Biomolecular Sciences, University of Illinois at Chicago, Chicago, IL 60607, USA

3 Department of Biological Sciences, University of Illinois at Chicago, Chicago, IL 60607, USA

4 DNA Services Facility, University of Illinois at Chicago, Chicago, IL, 60612, USA

∗Author for correspondence Brian T. Murphy, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL 60612, USA Tel: +1-312-413-9057; E-mail: btmurphy@uic.edu

      Revised 4 July 201512 August 2015       Accepted 13 August 2015

Copyright © 2015 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

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).

Keywords: Actinomycete, Freshwater, Streptomyces, Octalactin

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Fig. 1.
Composition of bacterial community in collected Lake Michigan sediment.
nps-21-261f1.tif
Fig. 2.
Phylogenetic analysis of cultivatable actinomycete strains from Lake Michigan.
nps-21-261f2.tif
Fig. 3.
Structure of octalactin B (1), and deuteromethylactin B (2).
nps-21-261f3.tif
Fig. 4.
CD Spectrum of 1.
nps-21-261f4.tif
Fig. 5.
Key 2D NMR correlations of 2.
nps-21-261f5.tif
Table 1.
1H and 13C NMR data of 2.
Position 13Ca,b 13Ca,c 1H mult. (J, Hz)b,d
-OCD3 49.0 52.0
1 173.9 174.2
2 39.8 38.1 2.36 dd (15.1, 9.4)
2.51 dd (15.1, 3.4)
3 73.4 72.7 3.88 ddd (9.4, 5.2, 3.4)
4 39.9 38.3 1.55 m
5 28.9 28.6 1.32 m, 1.54 m
6 32.5 32.7 1.32 m, 1.48 m
7 74.7 74.6 3.74 ddd (3.0, 7.3, 8.0)
8 46.2 43.4 3.46 p (7.3)
9 207.7 207.6
10 139.4 138.5
11 142.5 141.2 6.91 t (7.2)
12 35.2 34.1 2.48 m
2.40 dd (16.0, 7.2)
13 76.7 76.0 3.49 m
14 35.0 34.1 1.70 m
15 19.3 18.9 0.96 d (7.0)
16 15.4 15.3 0.90 d (6.7)
17 14.8 16.3 1.02 d (7.3)
18 11.9 11.7 1.79 s
19 18.0 17.6 0.97 d (7.0)

a 226.2 MHz;

b experiment performed in CD3 OD;

c experiment performed in CDCl3;

d 600 MHz. s = singlet; d = doublet; t = triplet; p = pentet; dd = doublet of doublets; ddd = doublet of doublet of doublets; m = multiplet.

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