4.8 Article

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

Journal

ORGANIC LETTERS
Volume 8, Issue 12, Pages 2471-2474

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol060630r

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Funding

  1. NCI NIH HHS [CA 44848, R37 CA044848, R37 CA044848-21, R01 CA044848] Funding Source: Medline
  2. NCRR NIH HHS [S10 RR 017768] Funding Source: Medline

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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.

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