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. 2006 Jun 8;8(12):2471-4.
doi: 10.1021/ol060630r.

Azamerone, a terpenoid phthalazinone from a marine-derived bacterium related to the genus Streptomyces (Actinomycetales)

Ji Young Cho  1 , Hak Cheol Kwon, Philip G Williams, Paul R Jensen, William Fenical
Affiliations

Azamerone, a terpenoid phthalazinone from a marine-derived bacterium related to the genus Streptomyces (Actinomycetales)

Ji Young Cho et al. Org Lett. .

Abstract

A novel meroterpenoid, azamerone, was isolated from the saline culture of a new marine-derived bacterium related to the genus Streptomyces. Azamerone is composed of an unprecedented chloropyranophthalazinone core with a 3-chloro-6-hydroxy-2,2,6-trimethylcyclohexylmethyl side chain. The structure was rigorously determined by NMR spectroscopy and X-ray crystallography. A possible biosynthetic origin of this unusual ring system is proposed. [structure: see text]

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Figures

Figure 1
Figure 1
Partial structures and possible structures of azamerone
Figure 2
Figure 2
ORTEP Representation of 1
Figure 3
Figure 3
Hypothetical Biosynthesis of Azamerone
See this image and copyright information in PMC

References

    1. Williams PG, Buchanan GO, Feling RH, Kauffman CA, Jensen PR, Fenical W. J Org Chem. 2005;70:6196–6203. and references therein. - PubMed
    1. Jensen PR, Mincer TJ, Williams PG, Fenical W. Antonie van Leeuwenhoek. 2005;87:43–48. - PubMed
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    2. Jensen PR, Fenical W. In: Natural Products: Drug Discovery and Therapeutic Medicine. Zhang L, Demain AL, editors. Humana Press; New Jersey: 2005. pp. 315–328.

    1. For examples see Soria-Mercado IE, Prieto-Davo A, Jensen PR, Fenical W. J Nat Prod. 2005;68:904–910.Pathirana C, Jensen PR, Fenical W. Tetrahedron Lett. 1992;33:7663–7666.Hardt IH, Jensen PR, Fenical W. Tetrahedron Lett. 2000;41:2073–2076. This structure has been recently revised based on stable isotope feeding studies, see Moore 2003 (Ref 15).

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