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. 2017 Apr 28;80(4):1141-1149.
doi: 10.1021/acs.jnatprod.7b00108. Epub 2017 Mar 30.

Bi- and Tetracyclic Spirotetronates from the Coal Mine Fire Isolate Streptomyces sp. LC-6-2

Affiliations

Bi- and Tetracyclic Spirotetronates from the Coal Mine Fire Isolate Streptomyces sp. LC-6-2

Xiachang Wang et al. J Nat Prod. .

Abstract

The structures of 12 new "enantiomeric"-like abyssomicin metabolites (abyssomicins M-X) from Streptomyces sp. LC-6-2 are reported. Of this set, the abyssomicin W (11) contains an unprecedented 8/6/6/6 tetracyclic core, while the bicyclic abyssomicin X (12) represents the first reported naturally occurring linear spirotetronate. Metabolite structures were determined based on spectroscopic data and X-ray crystallography, and Streptomyces sp. LC-6-2 genome sequencing also revealed the corresponding putative biosynthetic gene cluster.

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Conflict of interest statement

Notes

The authors declare the following competing financial interest(s): JST is a co-founder of Centrose (Madison, WI).

Figures

Figure 1
Figure 1
New metabolites (112) isolated from Streptomyces sp. LC-6-2 and representative prototypical abyssomicin comparators.
Figure 2
Figure 2
Structure of abyssomicin M (1).
Figure 3
Figure 3
1H,1H–COSY, key HMBC, and NOESY correlations for compounds 11 and 12.
Figure 4
Figure 4
Equilibrium mixtures and acetylation of 57.
Figure 5
Figure 5
ΔδSR values for MTPA esters of 11.

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References

    1. Bister B, Bischoff D, Strobele M, Riedlinger J, Reicke A, Wolter F, Bull AT, Zahner H, Fiedler HP, Sussmuth RD. Angew Chem, Int Ed. 2004;43:2574–2576. - PubMed
    1. Keller-Schierlein W, Muntwyle R, Pache W, Zähner H. Helv Chim Acta. 1969;52:127–142.
    1. Ding WD, Williams DR, Northcote P, Siegel MM, Tsao R, Ashcroft J, Morton GO, Alluri M, Abbanat D, Maiese WM, Ellestad GA. J Antibiot. 1994;47:1250–1257. - PubMed
    1. Kellerjuslen C, King HD, Kuhn M, Loosli HR, Pache W, Petcher TJ, Weber HP, Vonwartburg A. J Antibiot. 1982;35:142–150. - PubMed
    1. Park HR, Furihata K, Hayakawa Y, Shin-ya K. Tetrahedron Lett. 2002;43:6941–6945.

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