Marinopyrones A-D, α-pyrones from marine-derived actinomycetes of the family Nocardiopsaceae

Jihye Lee, Chulkyeong Han, Tae Gu Lee, Jungwook Chin, Hyukjae Choi, Wonjae Lee, Man Jeong Paik, Dong Hwan Won, Gyusang Jeong, Jaeyoung Ko, Yeo Joon Yoon, Sang Jip Nam, William Fenical, Heonjoong Kang

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Two actinomycetes, a member of the rare halophilic genus Streptomonospora and a Nocardiopsis sp. (Nocardiopsaceae), strains CNQ-082 and CNQ-675, respectively, were isolated from marine sediments collected off shore near La Jolla, California. HPLC-UV guided fractionations of the extracts of these strains yielded marinopyrones A-D (1-4), the structures of which were elucidated by interpretation of 1D and 2D NMR and HRMS spectroscopic data. Oxidative ozonation, followed by conversion of the acid product to an α-naphthyl amide, provided the absolute configuration at the chiral center on the side-chain. Marinopyrones A-D were examined for the inhibitory activity on nitric oxide production in LPS-activated mouse macrophage cells (RAW 264.7); marinopyrone D (4) was inhibitory with an IC50 value of 13 μM. To our knowledge, marinopyrones A-C are only the second reported natural products from the rare halophilic genus Streptomonospora.

Original languageEnglish
Pages (from-to)1997-2000
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number18
DOIs
StatePublished - 4 May 2016

Keywords

  • Anti-inflammatory activity
  • Nocardiopsis sp.
  • Streptomonospora sp.
  • α-Pyrone

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