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

Citation:
Lee, J, Han C, Lee TG, Chin J, Choi H, Lee W, Paik MJ, Won DH, Jeong G, Ko J, Yoong YJ, Nam SJ, Fenical W, Kang H.  2016.  Marinopyrones A-D, alpha-pyrones from marine-derived actinomycetes of the family Nocardiopsaceae. Tetrahedron Letters. 57:1997-2000.

Date Published:

2016/05

Keywords:

activity, alpha-Pyrone, anti-inflammatory, discovery, diversity, mechanism, metabolites, Nocardiopsis sp., resistance, sediments, sp-nov, Streptomonospora sp.

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 alpha-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 mu M. To our knowledge, marinopyrones A-C are only the second reported natural products from the rare halophilic genus Streptomonospora. (C) 2016 Elsevier Ltd. All rights reserved.

Notes:

n/a

Website

DOI:

10.1016/j.tetlet.2016.03.084